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DEAR PRIORITIZING CSAT IN AN AI-WORLD: Every founder and support leader is feeling this tension right now.

You see the opportunity. Automate repetitive tickets. Free up your team. Reallocate headcount to strategic work. Improve margins.

But you also know one bad automated experience can undo months of goodwill with a customer.

We asked Mary-Beth Donovan, former Chief Customer Officer at EDB and Stage 2 LP, to share her take on how operators should think about automation without compromising trust. Her framing was simple and practical. There are three lenses to evaluate every automation decision: operational efficiency, customer experience, and product value.

Here is how to approach it thoughtfully.

Start with capacity, not cost savings

The cleanest use case for automation is not eliminating people. It is reallocating their time.

Mary-Beth emphasized that the first win most teams should chase is freeing up one full-time equivalent from low-value interactions. If AI can consistently handle repetitive, predictable questions, your team can move upstream into more proactive and strategic conversations.

This shift matters. Customers will tolerate automation if it leads to better human engagement where it counts.

Before setting an automation target, ask:

• Which interactions are repetitive and rules-based?

• Which conversations require judgment and context?

• What higher-value work would we do if we reclaimed this time?

If automation does not unlock a better customer experience somewhere else, it is the wrong goal.

Trust and tolerance are the real metrics

Mary-Beth introduced a powerful framing around trust and tolerance.

You do not need 100 percent perfection to automate. In many environments, good enough is acceptable if you preserve trust. The danger is over-automation that traps customers in loops or prevents escalation when they need it.

Every automated workflow should clearly answer one question. When does a human step in? That moment should not feel hidden or punitive. It should feel seamless.

Practical guardrails include:

• A clear path to escalate to a human

• Monitoring negative feedback patterns

• Regular review of cases that required escalation

Automation without a visible safety net erodes confidence quickly.

You cannot automate bad documentation

One of the most common surprises teams encounter is that their knowledge base is not ready for automation.Outdated documentation, inconsistent articles, or unclear processes will surface immediately once AI begins referencing them. Automation does not fix weak foundations. It amplifies them.

As an aside, I recently had a pretty funny intersection with an AI chatbot. I asked a “how to” question, and was immediately told it wasn’t possible. After playing around for 5 minutes, I found a way to do it and replied to that effect in the chat. The AI asked “can you walk me through how you did it so I can give better feedback to the next question?”. Rather than insisting I was wrong, I was surprised and delighted to see that the company had thoughtfully architected this moment for learning and growth.

Before increasing your automation rate, invest in tightening your knowledge base and documenting edge cases. The quality of your answers will determine whether customers view automation as helpful or frustrating.

This is often less about technology and more about discipline.

Set targets, and revisit them quarterly

There is no universal “right” automation percentage. The correct level depends on your customer base, complexity of product, and support model.

Mary-Beth cautions against chasing an arbitrary number like 80 percent automation without considering the downstream impact. Instead, set a goal tied to a clear business outcome. For example, freeing up capacity for proactive outreach or improving time to resolution on complex cases.

Then measure not only deflection rates, but also customer satisfaction and expansion indicators. If satisfaction drops or renewal conversations become harder, reassess.

Automation is not a one-time project. It is an evolving balance between efficiency and experience. When done well, it does not replace your team. It elevates them.

Until next week!

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DEAR OUTBOUND FATIGUE: It’s only March, and I’ve heard this sentence more times than I can count this year: “Outbound is dead.” And yet, I continue to see teams making it work.

What’s actually happening isn’t the death of outbound. It’s the death of high-volume, low-ownership outbound. The spray-and-pray motion popularized by the “sequence is the strategy” approach.

We recently got a group of GTM operators from our portfolio together to discuss what is actually working. These teams are all actively running outbound motions and had A LOT of advice to share.

Read on for my favorites:

Get Creative With Your Use of AI

One of the most actionable ideas was how they’re using AI behind the scenes. Not to crank out more generic emails, but to sharpen their thinking.

One company is feeding AI with transcripts from sales calls, customer support tickets, and closed-lost notes. Then they’re asking it to extract patterns: How does this segment describe the problem? What language do CFOs use versus operators? What objections show up repeatedly before deals stall?

The output isn’t copy-and-paste messaging, but phrasing grounded in how customers actually talk. This context is a shortcut as you lean into deeply personalized messages.

A few other ideas in this vein…

• Extract common language patterns from real customer conversations

• Identify recurring objections by segment

• Surface vertical-specific pain points from historical notes

• Draft contextual summaries that reps can refine, not blindly send

In other words, use AI to accelerate pattern recognition, not replace critical thinking.

Dramatically Narrow Focus

Instead of handing reps hundreds of accounts and calling it coverage, reduce books to a manageable number and force prioritization. When a rep owns 40–60 accounts, not 600, the dynamic changes. There’s room for planning. There’s space for research and personalization. There’s accountability to break in.

I am a huge supporter of removing decision fatigue, using data to select the right accounts, and letting reps focus on only the top-tier opportunities. Some leaders are even defining a hard cap (eg 75 accounts max) and maintaining weekly or biweekly book hygiene where reps can add/drop accounts based on engagement and fit. “One in one out” is a good rule to get started and ensure the list doesn’t grow out of control.

When you have a narrow focus, weekly reviews become less about activity volume and more about account rationale and strategy. Why this company? Why now? What’s the trigger? What will you say first?

Increased ownership will drive increased performance.

Coordinate channels tightly

Multi-channel isn’t new, but coordination is more critical than ever.

Rather than scattering touches over 60 days, several teams are running concentrated outreach sprints over a few weeks. Calls, emails, LinkedIn messages, executive outreach, physical mail, and digital follow-ups are tightly grouped. The goal isn’t to overwhelm. It’s to create a sense of momentum and urgency.

Phone calls and emails from a BDR or AE remain the baseline, but top-tier accounts are getting:

• FedEx package (category-specific materials)

• Within 24 hours: digital follow-up

• Within a week: executive LinkedIn message

Ultimately, it doesn’t matter which channel breaks through. The prospect may respond to the third touch or the seventh, to an email or a package. But the clustered timing creates cohesion that random outreach simply doesn’t.

A final note on the unglamorous but critical layer: infrastructure.

Deliverability is harder than it was even a year ago (thanks AI!) and high-performing teams are treating inbox health as a core metric. They’re monitoring bounce rates, domain reputation, reply rates by segment, and volume per sender. If your email isn’t landing, debating messaging strategy is irrelevant.

Outbound still works. But only when it’s deliberate.

Until next week!

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DEAR DROWNING IN EDGE CASES: I hear you! If your health score keeps crying wolf, your team stops listening. And once that happens, it’s all just noise.

We called on Parker Chase-Corwin, Stage 2 LP and fractional CS leader and advisor who has built CS, support, and services teams from Series A through Fortune 50 to shed some light on this question. His perspective? “Health scores aren’t meant to confirm what you already know. They’re meant to surface the blind spots.” The challenge, of course, is doing that when your customer base isn’t uniform.

Here’s how he recommends tackling this challenge:

Define “healthy” separately before you try to score it

Most health score problems are actually definition problems, especially if you are leveraging AI to help you with diagnostics.

If you serve SMB, mid-market, and enterprise customers, you likely have three different definitions of success (whether you’ve written them down or not). An enterprise account may be perfectly healthy with modest usage but strong executive alignment and a clear roadmap. An SMB account may only be healthy if usage is frequent and consistent. When you force those realities into one uniform red/yellow/green model, you create false positives.

Parker put it well: “You want the smallest number of inputs that reliably point to risk. Not the largest number of signals you can collect.” In practice, if you’ve got a lot of edge cases, that means creating segment-specific scorecards, even if 70% of the inputs are shared. Adjust thresholds by segment. Allow for nuance. Keep the number of signals intentionally small so you can interpret movement over time.

Account for seasonality by shifting the lens, not lowering the bar

Seasonality breaks a lot of early health score models. If you work with construction, education, retail, or any industry with predictable slow periods, your “usage = health” logic will collapse at least once a year.

Instead of letting the model panic every off-season, treat those periods as a different operating mode. When activity is expected to dip, shift what you’re measuring. During slower months, product usage may matter less than planning, responsiveness, stakeholder stability, and readiness for the busy season.

In other words, during hibernation you aren’t measuring “how much they’re doing.” You’re measuring “are we aligned and ready.”

That shift preserves signal integrity without creating noise. It also forces your team to be thoughtful about what really indicates risk versus what’s simply expected behavior.

Protect trust with simplicity and transparency

As your model evolves, resist the urge to throw in 50 signals just because you can. It’s tempting, especially with new tooling and AI layers, but more variables often create more volatility, not more accuracy.

Parker cautioned against over-complication: “When you have too many variables, it’s going to ping-pong all over the place. You want trending you can trust.” If your score is constantly bouncing because minor inputs shift daily, your team won’t know what actually matters or how to take the next best action.

Four principles help maintain trust:

1. Keep your core signals precise and stable.

2. Iterate intentionally (quarterly or semi-annually), not impulsively.

3. Keep the inputs visible so team members can reverse-engineer the score to determine which signals need to be prioritized and addressed.

4. Allow a “human override” so those employees closest to the customer can adjust based on their unique qualitative context that isn’t showing up in the signals

You can absolutely use AI to mine sentiment or identify anomalies in transcripts and emails, but the foundational rules still need to be understandable and defensible. Especially if you’re presenting health to your board, the model must clearly connect to observable behaviors, not the qualitative “they seem happy.”

A health score people understand is far more valuable than a sophisticated one no one believes.

Design the health score to trigger action

A red account without a defined motion is…nothing.

The most underutilized part of health scoring is intervention. When an account dips, how quickly do you respond? What changes? Who gets involved? One metric I love tracking is time to first intervention after a score change. If you can consistently respond within a defined window, you’ve turned a passive report into an operational lever.

This is also where Stage 2’s concept of a single behavioral anchor (the Leading Indicator of Retention from the Science of Scaling framework) becomes useful. If you can name one core behavior that healthy customers consistently demonstrate within a given timeframe, your model becomes dramatically easier to manage. The health score becomes a system that asks, “Are they building the habit that leads to renewal?” And when that habit breaks, you intervene.

Health scoring at this stage shouldn’t be about perfection. It should help your CSMs prioritize, give leadership a credible read on the base, and surface blind spots early enough to do something about them.

Until next week!

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Landing your first paying customers is a big moment. It’s validating, energizing… and let’s be honest, a little overwhelming.

You’re not just building product anymore, you’re running a business. And for product-led teams, that shift raises a classic tension:

We know we should be tracking metrics, but we don’t have time to track everything, and we’re not sure what actually matters.

Here’s the good news: most early-stage companies try to track too much, too soon. The ones who scale well? They focus on a tiny handful of metrics that actually answer one question: Is the business working before revenue scales?

Let’s break that down.

The Early-Stage Trap

At Stage 2 Capital, we see early-stage teams fall into two common traps when it comes to metrics:

1. Tracking nothing, because “we’ll worry about metrics later.”

2. Tracking everything, filling dashboards with vanity numbers that feel productive but rarely change decisions.

Neither approach works.

Before you chase growth, before you optimize for efficiency, before you worry about CAC or LTV, you need to validate one thing: Are customers getting real, repeatable value from your product?

The Three Metrics That Matter

In your first 12–18 months, success = value delivery. That’s it.

So let’s keep it simple. Here’s what we recommend tracking:

1. Leading Indicator of Retention (LIR)

The best proxy for long-term value

You don’t have enough time (or customer volume) to wait for churn numbers. Instead, define a leading indicator. This is an observable behavior that signals a customer is likely to stick around.

Examples:

• For Slack: teams sending 2,000+ messages

• For a data tool: weekly active users pulling reports

• For a workflow product: creating and reusing 3+ workflows in the first 30 days

Your LIR should be:

• Measurable (yes/no per customer)

• Tied to value (not just usage)

• Predictive of retention (even if directionally at first)

Pro tip: Don’t wait for perfect. Pick a hypothesis, measure it, and refine.

2. Time-to-Value

How quickly are new customers seeing impact?

Once you know your LIR, track how long it takes new customers to get there. This is your time-to-value, and it’s an early pulse on product clarity, onboarding, and customer experience.

Early warning sign? If it takes too long for customers to get value (even if they eventually do), you’re already at risk of churn.

Shorten time-to-value before you scale. It pays dividends later.

3. Customer Health Rollup

A simple weekly gut check (in a spreadsheet is fine)

You don’t need a full analytics stack. But you do need a way to consistently ask:

• Who’s healthy?

• Who’s stuck?

• Who’s at risk?

This is less about reporting and more about confronting reality before problems compound.

What Not to Optimize (Yet)

Feeling pressure to track CAC, LTV, gross margin, burn multiple?

Ignore it. Seriously.

Those metrics matter a lot. But only later, after you’ve nailed value creation and retention first.

Optimizing too early = polishing a funnel that doesn’t work yet.

First: make it work. Then: make it efficient.

A Final Thought

Right now, your job isn’t managing a dashboard.

It’s learning faster than your problems grow.

That means choosing a few high-signal metrics, revisiting them often, and using them to drive smart decisions before growth masks the truth.

This approach is core to how we think at Stage 2 and baked into the Science of Scaling framework. Define value clearly. Measure it early. Then build on what works.

If you get this right, everything downstream gets easier.

Until next week!

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DEAR STAGE 2: I'm the CEO of a Series B company, and my board is pushing me to uplevel two of the leaders on my team as we review plans for the year. How should I think about growing talent internally versus hiring from the outside? ~WEIGHING MY OPTIONS

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DEAR WEIGHING MY OPTIONS: This one hits close to home for a lot of founders. Upleveling your team is one of the hardest (and necessary!) parts of scaling. It’s deeply personal. You’ve built something from the ground up, often shoulder to shoulder with these early leaders. But as the business grows, so do the requirements of each role on the team.

I recently had the chance to hear Henry Schuck, founder and CEO of ZoomInfo, speak candidly about this very topic during our annual summit and was wowed by the learnings. Henry built ZoomInfo from a bootstrapped, two-person operation into a public company and navigated all the common inflection points along the way. His perspective? You owe it to the business to make the hard calls when it’s time.

Henry shared that every executive on his team was a first-timer in their role when he promoted them. That gave him a front-row seat to the strengths and limitations of internal talent as the business matured. He didn’t hesitate to get close to the business when things weren’t working. And more importantly, he didn’t shy away from making leadership changes when needed.

So how should you think about internal growth vs. external hires?

Assess what the business needs next

When you’re at the Series B stage, you’re no longer just looking for people who can “figure it out.” You need leaders who can execute at the next level, with increasing scale, complexity, and scrutiny from stakeholders.

Ask yourself:

• What do we need from this function over the next 12–24 months?

• Are we trying to mature a motion, break into enterprise, stand up international, etc.?

• Does this person know what great looks like in this phase, or are they learning alongside you?

It’s OK if the answer is “they’re not there yet.” The real question is whether they can get there fast enough.

Have the courage to act when it’s clear

Henry said it best: “The minute I realized someone was no longer right for the job, every day after that was a grueling day.”

The longer you wait to make a change, the more you’re asking your company, customers, and other team members to bear the cost of that delay. And ironically, you’re not doing that exec any favors either. If they’re struggling, they feel it too.

When it’s time to make a move:

• Be clear and respectful. They helped you get here, and deserve thoughtful communication.

• Give them the dignity of a clean transition and support finding what’s next.

• Use it as an opportunity to signal your standards to the broader team.

Don’t assume external = better

External hires can bring experience, playbooks, and credibility, but only if they’re truly a fit for your company. Some common pitfalls:

• Over-hiring from large companies (they expect infrastructure that doesn’t exist yet)

• Misalignment on values or leadership style

• A lack of startup muscle (scrappy, fast, hands-on)

Internal promotions can work if:

• The leader is self-aware and eager to learn

• You’re willing to stay close and coach them through the growth curve

• You can invest in advisors, coaches or mentors to support them through the transition

• They’ve earned trust across the org

Just know that internal bets often require more hands-on support in the short term.

Hope these lessons from Henry help you make the call on what’s in store for your own team this year.

Until next week!

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DEAR NEW TO PARTNERING: The tension you’re feeling is real. When you’re early, and every dollar counts, supporting indirect channels can feel like a gamble, especially if it threatens to pull energy and resources from your direct sales engine. But when partnerships are approached with intention, even a lean partner motion can become a force multiplier.

I had the chance to discuss this with Theresa Caragol, founder and CEO of AchieveUnite and a long‑time ecosystem leader who has spent decades helping companies design, launch, and scale successful partnership strategies across technology, services, and global markets. Her perspective is grounded in one core belief: partnerships are not an add‑on. They are a deliberate go‑to‑market choice. Here’s how she thinks about laying the right foundation for partnerships early on:

Not All Partners Are Equal. Treat Them Accordingly

The first mistake early‑stage companies make is engaging partners without a clear strategy. Before you invest time, enablement, or executive attention, you need clarity on three things:

• Your ideal customer profile

• Your ideal partner profile

• The business motion you need from those partners (influence, co‑sell, services, revenue, or market access)

The degree to which you get this strategy right upfront is directly tied to the success you’ll see down the road (we’re talking 12-18 months later).

Included in that strategy must be a clear answer to a question many companies overlook: What’s in it for the partner? There is a value proposition for the customer, and there is a distinct business proposition for the partner. If the partner cannot clearly articulate why working with you helps their business, momentum will stall.

Only after this foundation is in place should you begin partner segmentation. Segmentation is not a nice‑to‑have or a side exercise. It is how you decide where to place your limited bets. Leading indicators of potential and indicators of performance must be defined, measured, and understood across the organization. Segmentation and success metrics go hand in hand.

Partnering is not a sales initiative

This is where many seed‑stage companies get tripped up. Partnering is not a sales experiment or a side channel; it is a fundamental way the company goes to market.

When partnering is treated as “sales versus channel,” internal conflict follows. When partnering is aligned as a go‑to‑market motion across leadership, companies are significantly more successful over time. Organizations that align early avoid the friction that slows growth and dilutes trust between teams.

Every executive should understand how partnerships fit into the company’s strategy from the beginning.

Build the Strategy and Playbook Early

You do not need a large partner program at the seed stage, but you do need a repeatable motion. Theresa recommends documenting learnings as you go:

• Who is the buyer?

• Where does the partner add influence or access?

• What does a strong introduction or co‑sell motion look like?

• What behaviors consistently move deals forward?

Ownership matters here. Someone must be accountable for the partner motion, or sellers must be enabled from the start to leverage partners effectively. In today’s era of influence‑driven selling, teaching sellers how to work with partners is often the stronger path.

Balance Short and Long Term Goals

Every company should have a partner strategy from the onset. That strategy does not need to be complex, but it does need to be intentional.

For some early‑stage companies, the partner bet may focus on influence. For others, it may be revenue, services, or supplier leverage. The key is to place two to three deliberate bets where partnerships can act as a force multiplier.

In a world driven by digital, social, and ecosystem influence, direct sales and direct marketing alone cannot reach every buyer. Partners extend reach, credibility, and context, but only when they are chosen and engaged deliberately.

This is why success should be evaluated using both leading indicators (engagement, influence, access) and lagging indicators (revenue). Remember: revenue confirms success, but it rarely tells the whole story early on.

From Direct Sales to Leverage Selling

We are moving from a world dominated by pure direct sales to one defined by co‑selling and leverage. The most successful AEs are those who understand how to use partnerships for influence, new logos, service wrap, and long‑term stickiness. Alignment is the key. Compensation, engagement timing, and clarity around who leads and who supports at each stage of the sales cycle must be explicit.

Misalignment creates confusion. Alignment creates leverage.

Partnerships at the seed stage are less about scale and more about leverage. If you place a few intentional bets early, validate them with both leading and lagging indicators, and document what works, you will know exactly when it’s time to double down.

And when that moment comes, you’ll be scaling from clarity, not guesswork.

Until next week!

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As we kick off 2026 and shake off the holiday break after a couple of quieter weeks, I’ve been thinking about where go-to-market is headed. This year has been marked by a mix of sober budgeting, team recalibrations, and pressure to do more with less. But it’s also been a year of strong GTM fundamentals rising to the top and some unprecedented and explosive growth - Lovable anyone??

So what’s around the corner? Here are three GTM trends I’m watching closely and believe will be at the forefront of GTM in 2026. I hope they help you plan ahead as you enter the new year.

“No Decision” Becomes Your Biggest Competitor

In 2026, the biggest threat to your pipeline won’t be a head-to-head competitor. Instead, it will be the customer doing nothing. The shift isn’t about product quality or pricing. It’s about internal buyer dynamics and growing risk aversion after a year of testing AI products. Even the best-fit prospects are stalling because they’re overwhelmed, under pressure, and afraid to make the wrong call.

We’re seeing this firsthand across the Stage 2 portfolio: longer sales cycles, more CFO involvement, and an uptick in “pushed” close dates with no clear next step or real sense of urgency. Tactical shifts to help close deals in a no-decision world:

• Reframe your discovery to uncover internal blockers. Ask, “What happens if this problem goes unsolved for another quarter?” Or, “What’s the internal approval process like for initiatives like this?”

• Arm your champion with real-deal materials. Think: short business cases, ROI models (without the buzzwords), internal pitch decks, and a TL;DR for the CFO.

• Introduce “anti-decision” language. Make it clear that “waiting” isn’t risk-free. Use customer examples where inaction caused pain like missed goals, headcount cuts, or churn risk.

Remember: It’s not enough to sell the solution; you now have to highlight the cost of doing nothing.

Buyer Journeys Will Become Decentralized

The days of a single champion leading the charge from discovery to decision are (mostly) behind us. In 2026, expect more fragmented buying journeys with:

• Multiple stakeholders entering the process earlier

• Uncoordinated research happening across teams

• A growing appetite for asynchronous evaluations (think: videos, sandbox environments, AI-assisted demos)

Founders often ask why their pipeline is “ghosting” even when the problem fit is clear. The truth? You may be selling to a single contact while the broader team is self-educating in parallel, and no one’s syncing internally.

What to do:

• Arm champions with materials they can easily forward and share, with value propositions tailored to each buyer, not feature lists

• Assume the deal is never a one-person decision, even if your contact says otherwise.

• Track signals across the buying group and build processes internally to ensure your team is multi-threading and getting to the right contacts, not just your main POC.

Revenue Leaders Will Need to Be Cross-Functional Operators

The best-performing revenue leaders in 2026 will look less like traditional sales VPs and more like mini-COOs for the go-to-market engine. In the past, you could get away with a CRO who focused almost exclusively on the sales number…and maybe lead gen. That’s no longer true.

Today’s CRO must:

• Eat, sleep, and breathe data - it’s all about the numbers

• Constantly think about how the tech stack and systems should evolve with AI

• Collaborate with product to influence roadmap

• Work hand-in-hand with marketing on buyer education and lead quality

• Build a retention strategy with customer success

• Translate GTM metrics into board-level conversations with finance

We’re seeing this evolution clearly inside Stage 2 companies. The sales leaders who thrive are deeply aligned with product strategy and customer health metrics, not just the forecast. One founder told us: “Our CRO became the glue between product and revenue, and that’s what helped us land our first enterprise expansion.”

If you’re hiring GTM leadership in 2026:

• Prioritize strategic range and ability/willingness to learn and evolve

• Look for candidates who’ve owned revenue across new sales, expansion, and retention

• Ask how they’ve partnered cross-functionally, and what broke when they didn’t

Founder-Led Prospecting Makes a Comeback

2026 is the year we see a clear divide emerge in outbound strategy. In vertical software the, SDR-led motions are working. Why? Because they go to events, they (often) answer the phone and you can write a compelling outbound email when:

• You know exactly who to target

• Their pain is well-defined

• There’s a clear reason to take the meeting

• Your messaging is consistent and value prop well defined

Outbound is flourishing in these vertical motions because the buyer sees themselves in the message, the ROI is easy to understand, and you can quickly build name recognition.

But if you’re building a horizontal product? Or a new category? Or targeting a generalist buyer? You need a different play.

In those cases, founder-led prospecting is your best weapon.

• You bring the credibility that no SDR can fake.

• You can spark real curiosity because you’re not selling, you’re exploring.

• You can open doors that templated outbound simply can’t.

• You can cross channels and mediums - LinkedIn, podcasts, email, etc…

2025 was a year when many founders invested in building their personal brands. 2026 is when we are going to see this pay off. Our advice to get started:

• Move beyond investor intros as the primary top-of-funnel and commit to a regular cadence of posting to build a founder-brand.

• Send 1:1 highly personalized messages. Ditch automation entirely in the early days. AI is great for research, but you need the human touch.

• Show up with a learning mindset: “We’re building X, and I’d love your input on how you handle Y…”

Reach out and let me know what trends you’re watching and what you believe 2026 has in store for GTM teams.

Until next week!

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DEAR FINDING THE RIGHT METRIC: Welcome to one of the most misunderstood (and most important) parts of early go-to-market: picking a value metric.

It sounds simple in theory. Just charge based on the value your customer gets. But when you’re still validating your product and have only a handful of customers, it can feel like trying to spot constellations with a flashlight. I asked Kyle Hart, CEO of Juicer, founder of Rowan Insights and the former pricing lead at Toast, how he advises early-stage founders to approach this exact challenge.

Here’s what Kyle recommends.

Stop Searching for the “Perfect” Metric

Kyle’s first piece of advice? Let go of the idea that you’ll find the one magic metric that correlates to value for every customer.

• You don’t need a perfect answer. You need a useful approximation that works today and can evolve.

• A solid value metric doesn’t just reflect value; it needs to be measurable, understandable, and trusted by your customers.

• In early-stage deals, sometimes the “metric” you anchor around is a proxy for value: number of users, reports generated, or workflows completed.

Kyle shares, “You’re looking for the clearest line between what you charge for and what your customer cares about. If it takes three mental steps to get there, it’s probably too indirect.” –

Use Your Existing Customers as a Testing Ground

Even if you have just a few enterprise customers, there’s gold to be mined:

• Look at how those customers are using your product, and ask:

  • Where are they spending the most time?

  • What features or actions do they say drive value?

  • What would break their workflow if removed?
    

• Run customer interviews focused on outcomes. Ask:

  • “What would you say this product helps you accomplish?”

  • “How do you explain the benefit to your CFO?”

  • “What’s the most valuable thing this helps you do faster or better?”

Try a Two-Part Validation Approach

Kyle shared a practical research trick you can run even with a small user base:

• Step 1: Ask customers to rank the value propositions that resonate most with them (e.g. faster workflows, better visibility, reduced errors).

• Step 2: Then ask them to rank the metrics that would best correlate with that value (e.g. # of workflows automated, # of reports delivered).

If the same value prop and metric show up together across multiple interviews, you may be onto something. This also helps you avoid the biggest trap in value-based pricing — anchoring to something you care about instead of something the customer sees as a win.

If You Can’t Charge on It, Measure It Anyway

You may not be ready to price on outcomes, but you can start tracking them today.

• Collect usage and outcome data over time and watch for patterns.

• Kyle recommends segmenting by customer type and watching how usage maps to success signals (e.g. retention, renewals, expansion).

• When trends emerge, you’ll be better equipped to pilot new pricing strategies with confidence.

Kyle noted “I often create a pricing page mock-up as a hypothesis, and then test how prospects and customers react, even if it’s not live yet.”

Design for Flexibility, Not Perfection

The best pricing models evolve. Early on, your goal is to create a structure that helps you learn, not lock yourself in:

• Start with broad tiers tied to basic metrics.

• Bake in options to test add-ons, usage-based upsells, or outcome-aligned modules.

• Use qualitative feedback and actual usage to validate

You don’t need a giant customer base to find your first strong value metric. You need tight customer relationships, thoughtful interviews, and a willingness to iterate. Trust what your customers are telling you and what they’re doing in your product.

Thanks again to Kyle Hart for the frameworks and tactical advice. If you’re in the early stages of your pricing journey, Kyle’s one of the most practical minds in the game.

Have a wonderful holiday! I’ll be back with more Dear Stage 2 on January 3rd.

DEAR STAGE 2: We just brought on our first Head of Sales and want to set them up for success. What can we do as a founding team to help them hit the ground running? ~READY TO RAMP

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DEAR READY TO RAMP: Bringing on a Head of Sales is a pivotal moment. You’ve likely been running founder-led sales up to this point, or maybe have hired 1-2 AEs to join you on the founder-led journey, but now you’re “handing over the reins” to someone with deep sales experience. But here’s the thing: even the best sales leader can’t perform in a vacuum.

I spoke with Terry Lee, a Stage 2 LP, CRO at Arkitechture and seasoned go-to-market operator. His advice centers around creating clarity, building trust, and ensuring alignment between the new sales leader and the rest of the organization.

Here’s how to set your Head of Sales up to thrive:

Clarify What Good Looks Like

Your Head of Sales needs a clear mandate. What are they being hired to do? Build the team, grow the top of funnel, mature the sales process, or just hit this year’s revenue target? Terry advised:

“Aligning around goals and priorities is very important at this stage. A new Head of Sales is often eager to start building a team and scalable processes, but someone needs to transition the pipeline from the founders, ensure that the pipeline is accurate, current, and properly documented, and that deals are closing or you are in trouble from day one. Then, once you are closing deals or helping to deliver on that first forecast, you can worry more about additional processes, tools, new hires, etc. There is no better first board meeting than communicating that the forecast is being achieved. ”

Get on the same page early about:

• Your expectations for the next 30/60/90 days.

• The state of the current pipeline, team, and forecast.

• What success looks like in the next 12–18 months.

This is especially critical if you’re moving from founder-led sales to a formal sales function. Your new hire needs to know where the handoff starts and ends.

2. Get Them into Deals Immediately

Your new sales leader doesn’t need a two-week onboarding course. They need to get in front of customers and prospects, hear how your customers talk about your product, see how your sales team runs a call, etc…

Encourage shadowing and participation in current deals for at least the first 30–45 days. This helps them absorb:

• How you’ve positioned the product.

• Where buyers get stuck.

• What’s been working (and maybe more importantly, what hasn’t).

“Don’t fall into the trap of “needing to understand the business or understand the market” before you jump into sales calls. Start participating in sales calls immediately. Customers don’t expect you to know that much and your goal should be to just listen anyway. Also participate in Customer Success calls, what do happy customers sound like, go to events. You need to hear what the market is saying directly as quickly as possible.”

Early exposure will help them quickly spot patterns, build credibility with the team, and start shaping the playbook for what’s next.

Share Your ‘Sales Math’

A successful sales leader can’t operate without context. Share your current funnel math, including conversion rates, average deal size, sales cycles, and win/loss data. If you don’t have all of this buttoned up yet, give them what you can and then make it a joint effort to define and track it together.

• What’s your historical lead-to-close conversion rate?

• What kind of pipeline coverage do you expect?

• How have reps historically hit quota (if anyone has)?

Terry recommends every new sales leader leans in here. If you understand the historical performance and the goals of the business, you can start working (quickly) to improve performance:

“Once you understand the goal you can set a corresponding KPI. Is it bookings or ARR, is it NDR or GDR, new leads or conversion, etc? And then you need to understand whether the data in your CRM is worth anything. Most likely you need to clean that up and improve your sales process so that whatever KPIs you choose are being accurately monitored and reported going forward.”

This baseline becomes the foundation for forecast accuracy and performance reviews.

Let Them Lead (but Don’t Disappear)

You hired this person to lead sales, so let them. But don’t vanish.

Be available. Provide air cover and remove blockers. Help them build cross-functional trust with marketing, product, and customer success. And coach them on how decisions get made at your company.

The most effective founders don’t just delegate a function. Instead they stay close, ask smart questions, and give feedback frequently in the first 90 days. Terry advises:

“It is incredibly important to make sure the CEO, the CFO and the CRO spend a lot of time aligning, getting to know each other and creating a cadence for reporting and checking in. Too often, everyone breathes a sigh of relief when the CRO comes on board and expects them to take it from there.”

Align the Board Early

Your Head of Sales will likely join the next board meeting. Don’t let that be the first interaction. Set up intro calls with key board members early on and brief your new hire on:

• What the board cares about (beyond just “hitting the number”).

• Any landmines to avoid in presenting or forecasting.

• What questions they’re likely to get asked.

A confident, informed first impression goes a long way in earning board trust and buying time if things get bumpy.

A successful sales leader is a multiplier, but only if you set them up with the right tools, trust, and time to lead. We hope this helps as you bring on your newest executive team member.

Until next year!

That’s right, we’re taking next week off - enjoy the last few days of 2025 and we’ll see you in 2026!

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DEAR CEO LOOKING AHEAD: A startup CEO has the loneliest job in the company. When your company is growing fast, the job you had last year isn’t the job you have now. It’s important to zoom out and ensure you are focused on the right initiatives. Easier said than done.

I turned to Scott Berg for advice on evolving as a CEO during crucial growth periods. Scott is the former CEO of ServiceMax, a Stage 2 Capital LP, and a Partner at 10X CEO, a leadership program where he’s coached over a hundred venture-backed CEOs. Here’s Scott’s advice for avoiding the “busy trap” and making sure your time is pointed at what matters.

He started by sharing his thought process behind “3 Leveraged Priorities”. To paraphrase: anyone can accomplish 3 things in 3 months. The challenge lies in choosing the right 3 things, removing the primary constraint, and doing only the things a CEO could do.

Take a look at your own priorities through this lens:

1. Re-center on the Picture of the Future

The biggest mistake founders make as they scale? They stop pausing to ask: What am I actually building?

Scott pushes his CEOs to write a “picture of the future,” a 3-year vision that’s clear, specific, and revisited multiple times a year. Not a mission statement. A press-release-style summary of what success actually looks like. Think: “We’ll be the #1 provider of XYZ, touching 30% of global transactions over $5.”

You need to document this and revisit it quarterly. Why? Because without it, every day becomes about fire drills, not forward momentum. If you’re busy, but you’re off course, you’re just moving faster in the wrong direction.

2. Find the Kink in the Hose

Every startup has a primary constraint, the single biggest bottleneck that’s holding back growth.

Scott uses the “garden hose” metaphor: “You turn on the water, but nothing’s coming out. It’s not the faucet, it’s the kink.”

Your job as the CEO isn’t to solve every problem. It’s to solve the right one. You need to identify the kink that, if resolved, unlocks the most downstream impact. Don’t get distracted by noise. Focus your time on that single issue.

Examples of primary constraints:

• You’ve got demand but can’t scale onboarding

• Pipeline is strong, win rate is tanking

• Product is sticky but no longer differentiated

Scott advised taking the time to reflect on this regularly and ensuring that you are ruthless about aligning your calendar around fixing it.

3. Set 3 Leverage Priorities (and Actually Do Them)

Most CEOs make two mistakes with goal setting: too many priorities, and not enough priority on things that solve my primary constraint. Scott asks the CEOs he coaches to set 3 quarterly “leverage priorities”. These are things that only the CEO can do. No delegation. No multi-part lists. Just 3 big swings.

Typical examples:

• Making a critical exec hire

• Leading a fundraising round

• Fixing company narrative or market positioning

When you’re spending time on something that doesn’t map back to one of those three, stop and ask yourself why. Reclaim your time and reassign the task. Your job is to move these big boulders and surround yourself with a team that can manage the day to day.

If you do just one thing after reading this, block an hour this weekend to reflect and ask yourself these 3 questions:

• What’s our 3-year picture?

• What’s the ‘kink in the hose’?

• What 3 things should I really be doing this quarter?

Then go do them. And protect your time like the company’s future depends on it (because it does).

Until next week!

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Happy Thanksgiving!

No questions or answers or answers this week, just a heartfelt thank you.

First, a thank you to the 50+ Stage 2 LPs who have joined me in answering questions over the last year. This incredible group of operators continues to astound me with their knowledge, experience and willingness to dive in and help.

Second, a thank you to my partner, Mandy Cole, for jumping on the substack bandwagon and contributing a whole new series - GTM AI. The rate at which we are learning in GTM right now is unprecedented and her real-world AI examples have quickly become a favorite read for both me and our readers.

And speaking of readers…THANK YOU! Thank you for another year of reading, engaging, asking questions and sharing our content!

If you are looking to dig into some content this holiday weekend, here are 5 of my favorite posts from this year:

1. Should My Company Invest in a Reddit Strategy?

2. How to Build an AI Agent for Account Selection

3. Credits Aren’t a Strategy: Rethinking AI Pricing Models

4. Track This Metrics Before Your AI Customers Churn

5. The 25-Day Plan to Revive Closed-Lost Opportunities

Have a question? Interested in contributing? I’d love to hear from you - liz@stage2.capital!

Until next week!

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DEAR SLOW TO FIRE: A lot of founders hesitate to pull the trigger on Performance Improvement Plans (PIPs) because they’re afraid it will demoralize the team. But handled well, a PIP signals that you’re building a team where expectations are clear and performance is respected.

I recently dug into this topic with my Partner, Mark Roberge, who happens to be the founding CRO at HubSpot. He shared his philosophy and advice on using PIPs to strengthen the sales culture. Read on for his take on how to think about it.

PIPs Set the Standard

Too often, terminations happen based on a “gut feel” from leadership, and that’s where culture takes a hit. If someone is let go without a clear process or feels ambushed or surprised by the decision, even your top performers will start to question their own job security.

Key Takeaway #1: Standardize the PIP process

• Everyone should know the rules of the road; it should be a standard part of onboarding..

• The process should be quantitative, consistent, and repeatable.

• Avoid “behind-the-scenes” decisions that erode trust.

At HubSpot, Mark was running a team where the average rep closed ~10 deals/mo. That transactional sales environment is a great place to implement one consistent PIP process across the entire org. Their standard is six mos of ramp time followed by monthly check-ins. Each month, reps were evaluated on their rolling four-month quota attainment. If the average fell below 90%, then you’re on a 30-day PIP.

“It was the same for everyone, regardless of team or tenure. That consistency is what built a performance-first culture.”

Don’t Fear the Morale Hit, Fear Ambiguity

Contrary to what many assume, Mark argues that putting someone on a clear, fair PIP can actually improve team morale. Why? Because it shows there’s no place to hide.

When someone who’s clearly underperforming sticks around indefinitely, it frustrates everyone, especially your top performers. Clear guidelines on performance set the standard and ensure everyone works to earn their place on the team.

Key Takeaway #2: A clear bar motivates and aligns the team.

• Public PIP processes show the team that you’re serious about outcomes.

• They eliminate favoritism and politics.

• They reinforce the idea that performance earns your seat at the table.

Building a high-performance culture in sales should feel like assembling a professional sports team. Mark compared it to baseball: “You don’t stay on the Red Sox because people like you. If you’re batting.125 with 200 strikeouts, you’re not going to last. If you do, it tarnishes the whole team.”

Focus PIPs on Outcomes, Not Activity

Mark was clear: PIPs should be based on results. If someone’s missing their number, check the inputs. But if they’re hitting quota, don’t micromanage them.

I couldn’t agree more. The reality is that some reps find creative ways to drive results - maybe we can learn from them, maybe they are outliers. Like comp plans, you want to ensure that your performance plans incentivize the right behavior – healthy revenue contribution.

Key Takeaway #3: PIPs are about outcomes

• Don’t PIP someone for low activity if they’re hitting their number.

• Don’t avoid a PIP because someone is “trying hard.” If they’re not closing, they’re not succeeding.

It’s easier to focus on outcomes in a transactional sales environment, but even in longer sales cycles you can still compare pipeline growth and progress. With an enterprise motion, you need a longer ramp time to build pipeline and close deals. Consider adjusting your expectations on measurement for these folks, but again…be clear up front. An example for an enterprise rep might be something like four quarters of ramp, with the expectation of hitting quota by the fifth quarter in seat. Ultimately, PIPs are a tool to maintain performance, not avoid turnover. If someone’s not improving despite coaching, it’s time to open the slot. If you want to dig deeper on building sales culture, check out the Science of Scaling YouTube channel.

Until next week!

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DEAR PRICING IN THE AGE OF AI: When it comes to monetizing AI, the stakes are high for both your revenue model and customer trust. No one has been deeper in the pricing trenches than Kyle Poyar, author of Growth Unhinged and longtime pricing strategist. Kyle joined us in NYC last week for our annual summit and shared some incredible insights on making the shift to value-based pricing.

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He covered a lot of ground, but we’re going to go deep on this one question of hybrid pricing today. Hybrid pricing models (think “$X/month + Y credits”) have exploded recently, especially for products embedding AI. Companies like Clay, Intercom, and Salesforce are layering credit models into traditional SaaS plans to balance cost control with flexibility. They work because:

• You can meter usage and protect your margins.

• You can give customers a taste of AI functionality without forcing a full commitment.

• You can scale spend with value delivered.

But Kyle cautioned that these models aren’t magic. If you’re just copying what others are doing, you’re probably not thinking deeply enough about how it aligns with your own product and customer base.

Read on for his advice!

1. Design for Expansion, Not Confusion

While customers are willing to manage credits and take on some risk for their top vendors, “no one wants to manage 20 different credit systems,” Kyle warned. Your model should feel intuitive. If customers can’t predict what their bill will be, or if credits are so abstract they can’t understand them, they are far more likely to churn.

What to do:

• Use credit models to mirror your product’s natural usage pattern.

• Clearly define what each credit gets the user (e.g., 1 credit = 1 document processed).

• Offer visibility into usage in-app, in real time.

What not to do:

• Don’t bury definitions in fine print.

• Don’t mix too many pricing levers - it will feel chaotic and hard to control.

2. Avoid Flat Fees Unless You Have Sky-High Margins

Flat-rate AI pricing? That’s a trap for most early-stage companies. Kyle compared it to MoviePass (an incredible non-SaaS example of pricing gone wrong - MoviePass went under with their initial flat rate offering losing tens of millions every month, but has now reemerged with higher prices and a credit-based model): great for customer adoption, but a death spiral if your power users start racking up heavy compute costs.

Instead:

• Cap usage to protect yourself from power users (usage tiers with overage). In Kyle’s experience, the top 10% of users might account for 70-80% of your AI costs.

• Use hybrid pricing to give customers predictable spend with room to grow.

• Treat AI usage as a variable cost center to align pricing with margin reality.

• Put in place discounting rules to minimize pricing leakage and unprofitable customers.

3. Credits Aren’t the End Game

Hybrid pricing with credits are a stepping stone toward more value-based models. In Kyle’s words: “The real opportunity is value-based pricing. Credits are the bridge.” Today’s customers will tolerate credits, but as AI matures, they’ll want pricing that reflects outcomes or the work delivered by AI. That could mean tying pricing to support cases resolved, tasks automated, or chargeback revenue recovered. Until you get there:

• Use credits to train your buyers on usage patterns.

• Monitor which features deliver the most ROI.

• Start gathering data you’ll need for future pricing changes.

4. Don’t Set It and Forget It: Build a Pricing Review Cadence

Most early-stage companies treat pricing like a one-time decision and you are leaving money on the table. Build the muscle early of reviewing, experimenting, and changing pricing as your product evolves. Kyle recommends:

• Monthly pricing working sessions, especially at early stage.

• Pricing post-mortems after any changes.

• Giving someone (anyone is better than noone!) ownership of pricing metrics and strategy. And if you’re under $5M ARR, that someone is probably still you, the founder/CEO.

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PRIORITIZING IMPACT: Bringing on a Head of Marketing is a huge milestone, and also a big shift for the rest of the team. I can guarantee there is a whole host of pent up demands and a backlog of needs across the org. Suddenly you’ve got someone owning one of your most visible functions, and it’s tempting to try and solve everything right away.

To help make sense of this transition, I sat down with Paramita Bhattacharya, a seasoned marketing leader and Stage 2 LP. Her advice? Help your new leader find their footing quickly by aligning on strategy, narrowing focus, and securing a few early wins.

Here’s how:

Set the Guardrails

Before any campaigns get launched or assets are designed, step back and create clarity. Paramita recommends:

• CEO alignment: Sit down together and get honest about what outcomes matter most? What does “success” look like in the next 90 days?

• Cross-functional discovery: Encourage your Head of Marketing to meet with leaders across sales, product, and customer success. These sessions help surface opportunities, challenges, and dependencies.

• Use the data you have: Funnel metrics, conversion data, and campaign results to assess what’s working and what’s not.

• Define success: What matters for your business? Is it pipeline? Site traffic? Better qualified leads? Agreeing on KPIs up front reduces later friction.

• Define AI’s remit/span of control: this is critical as you enter a new org. You need to get a pulse on where AI fits today within the marketing org and set the roadmap for broader adoption.

Balance Learning and Doing

The first 30-60 days are about balancing exploration with execution. It’s easy to over-index on either:

• All action, no context → Risk of misfires and wasted effort.

• All listening, no movement → Teams get anxious, wondering what’s getting done.

Paramita suggests developing an onboarding plan that includes both learning goals and deliverables. Critically that plan cannot be private. You want to share it broadly (especially with exec peers!) and use it as a tool to manage expectations. With this plan as the backdrop, schedule regular check-ins with both you (the CEO) and cross-functional leaders to keep information flowing and everyone aligned.

AI adoption is a great place to starter! Run an AI audit to identify existing AI initiatives that are running, and evaluate risk/challenges/success and in parallel, identify a few use cases that can be piloted. Paramita shared a great idea for immediate action: “Invite team members across the org to share prompts and build a prompt library. Mark this as an early win. You can also start to formalize running a prompt hackathon every month or 6 weeks”.

Focus Matters

Your new marketing leader is going to be tempted to touch everything. Don’t let them. Instead, work together to identify the top 2–3 must-dos:

• What’s generating pipeline now? Secure and optimize it.

• What’s broken in the funnel? Fix that first.

• What’s a strategic bet that needs a little momentum? Start scoping it now.

Revisit this list often and be their partner in saying “no” to nice-to-haves. You can empower them to say “no” and more importantly, you should step in to support that decision as new asks arise that can derail focus. “A great Head of Marketing balances short- and long-term priorities. It’s not just about campaigns, it’s about business outcomes,” says Paramita.

Show Early Wins

Great leaders earn the trust of their teams and that’s usually through action, which means the first 45 days are all about showing impact. As the CEO you can help identify a few quick win areas and point your new hire in the right direction. A few ideas from Paramita’s experience:

For enterprise sales…

• Sales content audit and quick refresh of high-impact, immediately usable content that addresses a critical pain point in the sales cycle. This could be the sales deck, a competitive cheat sheet, an email sequence, etc…

• A new customer reference and/or a mini case study: get a quote and a video/sound bite regarding 1-2 pain points that the solution addressed to add a new logo added to the web page and sales deck.

• A dedicated ABM push either refining and prioritizing an ongoing effort, or identify a few high priority accounts and launching a targeted marketing play.

For product-led or a high velocity inbound engine…

• Optimize high traffic landing pages with testing around primary CTAs and content offers (blogs, solution pages, pricing, etc.).

• Review and fix sign up, demo request and/or free-trial forms by eliminating unnecessary form fields, using progressive profiling, and removing friction in the flow.

• Implement a targeted short term email nurture sequence for specific segment, cohort or vertical that is designed to increase conversion (MQL-SQL or Trial-Paid)

• Deep dive into 1-2 paid marketing channels, review performance and adjust spend to maximize high performing campaigns.

For AI adoption…and Paramita believes all marketing leaders should be at the forefront of driving AI within a company:

• Accelerating content creation: train and use custom GPTs for marketing channel content especially SEO/GEO, landing pages and lifecycle emails as well as sales enablement decks, battlecards, account research, and RFP assistance.

• Increasing conversion in the funnel: AI chat with faster qualification & demo scheduling.

• Removing friction in the pipeline: AI-assisted propensity scoring + lead routing to speed handoffs and raise SDR hit rate. Could even implement AI-SDR if you run high velocity inbound marketing.

Share these wins! Paramita recommends the new leader send out a weekly update to the leadership team. A brief, consistent, and outcomes focused update builds trust.

Looking Ahead

By the end of the first month, your Head of Marketing should start laying the groundwork for longer-term plays. It’s ok if these plans aren’t fully baked yet, but it’s a red flag if they aren’t bringing forward ideas and hypotheses for long term initiatives.

• What bets will drive sustainable pipeline growth?

• What brand or content initiatives are worth investing in?

• How should the team scale to meet company goals?

The key is to help your new leader build credibility and momentum now, so that when it’s time to make bigger asks (budget, headcount, strategy shifts), the rest of the org is already bought in.

The TL;DR on Paramita’s advice? Don’t try to do it all. Prioritize ruthlessly. Deliver early wins. Build trust.

Until next week!

DEAR SPLITTING FOCUS: Launching something new is exciting, but your concerns around juggling priorities and fear of overextending your team are real.

I sat down with Kathie Johnson, Stage 2 LP, and former CMO of Talkdesk, Sitecore and SVP of Salesforce (just to name a few) to unpack how experienced go-to-market leaders manage this kind of shift without throwing their teams off balance.

Read on for her advice:

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Start by Asking the Right Strategic Questions

Before you even think about putting a sales deck together, pause and evaluate:

• Does this change your ideal customer profile?

• Are you targeting a new vertical or segment?

• Will the personas you’re engaging be different?

• Is this an expansion motion or a completely new land?

If the answers point to a similar ICP, similar use case, and a path to expand existing customers, this launch shouldn’t derail your team. But if it’s a departure from your current focus, it’s important to treat it like a new motion.

Key Takeaway #1: Budget for the Distraction

Any and all new product launches will take time and attention. Kathie recommends setting aside a dedicated slice of your marketing resources, both budget and time, for testing.

“Ten percent of my marketing budget is always reserved for experimentation. That’s the pool I draw from when we want to go after something new.”

The percent may vary depending on your circumstances and the level of priority of this new launch, but the idea holds - that X% is your sandbox. Use it to:

• Pressure test messaging and positioning

• Validate ICP and segmentation

• Build out early enablement and value props

Let marketing take the lead on planning the launch. Put them in the leadership seat and build the launch team for feedback around them…

Key Takeaway #2: Create a “Tiger Team”

You can’t ask everyone to focus on everything. Instead, build a cross-functional squad or “tiger team” representing sales, marketing, and product. You want input from all teams who will be impacted, but the goal is to pick a few people to represent the broader team to limit the distraction.

Give this team:

• A clear charter (what you’re trying to validate)

• A time constraint (4–6 weeks is a good start)

• Specific deliverables (e.g., messaging doc, pitch deck, beta outreach)

When expectations are clear, team members can better manage new initiatives alongside their core responsibilities without feeling overwhelmed.

Key Takeaway #3: Bring Sales In After You’re Ready

Resist the urge to “future sell.” Sales teams are quota-driven and short-term focused by design. Bringing them in too early can hurt morale or distract from pipeline initiatives that’s already working.Instead:

• Loop in sales leadership early so they can give feedback, are aligned with the plan and ready to support the launch when the time comes

• Hold off on enablement until you’ve locked ICP, messaging, and use cases. Bring a fully baked GTM strategy to the launch.

• Revisit comp and quotas if this product is going to be part of the sales team number make sure the incentives are aligned to the company goals.

“People do what they’re measured on,” says Kathie. “If you want this to be real, make sure you’re aligning incentives accordingly.”

Key Takeaway #4: Build Credibility Through Your Customers

If you’re expanding your product footprint with the same customers and buyers, start there. This is the fastest way to learn and build momentum.

• Ask your Customer Advisory Board or a few key customers for input and fast feedback loops during development of both product and messaging.

• Find a design partner and over-deliver to earn a case study or reference.

Launching into new personas or industries? Follow Kathie’s example from Salesforce:

“We didn’t just show up to industry events. We put our customers on stage. We brought in experts who were already respected in that field.”

If you’re not already known in the space, surround yourself with people who are. This might mean hiring advisors or partnering with influencers to build trust. Critically, you have to be creative about how to build credibility and get in front of the right audience.

Key Takeaway #5: Don’t Confuse a Feature with a Product

Kathie’s final warning: be crisp on product strategy. Is this a feature enhancement for your core product? Or is this really a new product that requires a different go-to-market motion?

“You need a clear product naming structure so your team and your customers don’t get confused. Not every roadmap item deserves a ‘launch.’”

If you can’t explain the difference to your sales team, your customers won’t get it either.

Launching a new product doesn’t have to be a distraction if you’re deliberate. Start with a small team, use your customer base to validate before you go wide and build the right assets to arm your sales team.

Until next week!

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DEAR PIPELINE PAIN: Your team is already doing the hard work of getting prospects on the calendar - let’s count that as a win! But something is preventing those conversations from turning into qualified opportunities. Most likely this is going to come down to training and enablement on ICP, messaging and basic sales tactics.

I turned to two of our LPs, Justin Ryburn and Tito Bohrt, who have deep expertise helping companies improve their early-stage funnel conversion. Here’s how they suggest approaching the problem:

1: Collect Data Before Making Changes

Justin stresses the importance of starting with evidence before jumping into solutions: “First thing you need to do is get some data on why this is happening. If you have Gong, run the transcripts of first calls through an LLM and have it summarize what is going wrong. If not, have your reps provide structured feedback on where the disconnect was.”

This type of analysis helps determine where the issue lies.The most common culprits to check for:

• Is the meeting set with companies in your ICP?

• Is the right person on the phone? Confirm the buyer persona

• Is the messaging correct/resonating?

• Are the reps positioning the use cases well?

• When does the prospect disengage or realize the product isn’t a fit?

Without data, it’s just guesswork.

Pro Tip: Incentives drive behavior. Justin advises doing a review of comp plans in parallel. A common mistake is tying SDR or marketing compensation solely to # of meetings booked. “This celebrates that N number of meetings were booked while the reps are complaining they have a bunch of useless calls on their calendar.” Instead, we would recommend aligning demand gen functions with sales by tying comp to qualified pipeline and revenue contribution. More info on that here if you think comp could be contributing to this challenge!

Step 2: Define and Inspect Exit Criteria

Tito highlights that many companies struggle because of a lack of clarity around qualification. He explains, “I’ve seen the best companies convert 73% of outbound intro calls into pipeline and the worst ones around 5%. The problem often lies in stage names and exit criteria, inbound versus outbound discovery, and whether the conversation is post-project or pre-project.”

If your team doesn’t have clear stage definitions and exit criteria, reps may celebrate meetings that were never going to move forward. By tightening those definitions, you create discipline and consistency in the funnel.

Here’s an example of what a well designed sales process with clear exit criteria might look like to get you started:

Step 3: Diagnose with a Scorecard

Another approach Tito recommends is using an outbound scorecard to bring consistency to call evaluations. Scoring each conversation against criteria such as uncovering the desired state, illuminating a better future state, and driving alignment on next steps makes it clear where the funnel is breaking down.

This moves the conversation away from anecdotes and toward measurable diagnosis. If half your team consistently struggles to surface a future state, you know exactly where to focus coaching.

Step 4: Translate Findings into Training

Once you’ve identified the patterns, build targeted enablement. For example:

• If reps struggle to position use cases, run role-play sessions focused on storytelling.

• If messaging is too broad, refine your ICP and discovery questions.

• If buyers aren’t seeing urgency, coach reps on surfacing latent pain.

One final note: Tito warns that stage matters here. If you are under $1M in ARR and under 20 customers, there’s likely less meaningful data to work from and less need for exit criteria (that really matters as you onboard reps!). Instead, the focus should be on going deeper on what resonates with the market and learning to pitch the solution differently which means talk to customers. Tito advises “ask them to explain why they like the solution and what problem it solves for them as you want voice of customer to guide value-based messaging.”

The natural reaction will be to solve the challenge with volume and push for more meetings, but that’s not going to solve the down funnel challenge. Instead, create a system to understand what’s happening in those calls, tighten up definitions, and coach with intention.

Until next week!

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DEAR OUTBOUND OVERWHELMED: There’s a reason early outbound can feel like shouting into the void. You’re setting up systems, writing copy, sourcing leads, validating emails, and then trying to get all those parts to work in harmony. If it’s your first time building this muscle, hearing crickets is honestly expected.But the good news? Crickets don’t mean failure. They mean you’ve started. And now it’s time to iterate.

I spoke with Semir Jahic, Stage 2 LP and Co-Founder of Salesmotion, who recently built their own outbound engine from scratch. Their team hit the same early wall: “At the start our emails bounced, our copy was terrible, and we didn’t know who to go after.” But over time, they turned silence into signal.

Read on to hear how Semir built a successful motion by optimizing each part of that system, one step at a time.

Focus on Fit First

Before you write a single line of copy, lock in your target account list.

Semir and his team found traction by building lookalike lists: “We have a few case studies, we find 5-10 similar companies via Google, ChatGPT, or Ocean.io.” This grounds your list in companies that already map to your strengths and keeps your TAM tight enough to personalize without sounding robotic.

If your TAM is small, resist the urge to spray-and-pray. “Our lists are tight, just a few hundred people, so anyone reading it feels like it’s personalized based on industry/title/pain,” Semir said.

That balance between relevance and scale matters more than clever copy.

Invest in Deliverability Before Messaging

Even the best copy doesn’t matter if it never hits the inbox. “Only once you have valid emails and infrastructure that can deliver email to inboxes can you properly start to test messaging and plays,” Semir explained.

What does that look like?

• Use tools like FullEnrich to validate emails.

• Warm up your domains and mailboxes with providers like Smartlead, Salesforge or Lemlist.

• Keep email volumes low while testing to avoid deliverability issues.

A 1–3% positive reply rate might not sound high, but when that means real responses (even “not interested”), it’s a signal your emails are landing and that your infrastructure is working.

Experiment and Track Progress

Outbound is equal parts creativity and discipline. The best messaging play isn’t the one that sounds best, it’s the one that actually works. “This is quite hard being an early stage company where multiple pain points and features and value propositions can resonate with different buyers,” Semir noted. That’s why you need to test your emails scientifically, in small batches, with defined personas and hypotheses.

Steal This: Semir limits himself to a max of 10 emails per inbox per day and applies best practices for deliverability like using Spintax, meaning variation of text so emails don’t look the same and are less likely to get flagged as spam. It’s like mail merge to look human e.g. [Best|Regards|Kind Regards|Best Regards] spread across your email. One of his favorites? Try [AEs|reps|sellers|account execs|account executives]

“You’d think the play of ‘We went to the same university’ is completely outdated,” Semir shared. “Turns out, the reply rates are amazing, to date 20%+ and many positive ones in there.” A simple LinkedIn search filtered by persona and University led to Salesmotion finding 800 relevant alumni that they simply message starting with “Illinois Alum Here.”

The learning? Don’t believe LinkedIn or advice online, test it for yourself.

Add a Layer of Warmth

Not everything has to be cold. In fact, blending outbound with intent-based triggers from LinkedIn, news, hiring or other relevant activity can create a pipeline of “warm outbound” leads. Semir is an active poster on LinkedIn and shared that he checks every profile visit manually and adds ICPs into a follow-up campaign. Feels like a lot of work, but he explained that every sliver of intent can be used to engage and build pipeline.

The trick is to be human: ‘pitch-slapping’ (IFYKYK) on LinkedIn won’t work. But soft touches, thoughtful engagement, and content-driven outreach can move prospects into your funnel without burning your brand. One of the key sources of inspiration for Semir on this topic is Samantha McKenna from SamSales. Her “Show Me You Know Me” is the gold standard. While not always possible to go so deep, it’s what we should aspire to do in our outreach.

Who Owns It? You Do…for Now

In the early stages, outbound is a founder’s job. Simple as that.

“It’s where you figure out message-market-fit,” Semir emphasized. You’re not just writing emails, you’re learning what makes your market tick. As you grow, this can be owned by a jack-of-all-trades GTM hire or RevOps lead. But for today, embrace the role. The learning loops you build today will shape your future GTM motion.

Until next week!

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DEAR FIRST-TIME FUNDRAISER: Fundraising as a pre-seed founder is more than having a great idea for a product. You have to be a great storyteller, relationship builder, and show that you can execute. When it comes to building FOMO, it’s easy to get lost in the process and over-optimize. So, how do you generate real excitement and a competitive process?

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I recently joined a panel with Lily Lyman, GP at Underscore, and Ian Sigalow, Co-Founder and Managing Partner at Greycroft, on this very topic. We had a great conversation, and I wanted to share a few takeaways for founders preparing to raise:

Set your optimization priorities early.

Are you optimizing for valuation? Check size? Brand? Industry knowledge? GTM expertise? Customer intros? Partner chemistry? There is no right answer here, but you need to be honest with yourself and allocate your time appropriately.

Founders who don’t know their “must-haves” often get stuck over-optimizing the final round. If you know what you care about, you can focus your time and energy on the right firms and partners.

Lily shared a recent story of seeing a term sheet pulled after a founder pushed the decision deadline. Every point of interaction matters, and the VC looked at this moment as an example of the founder not holding up their end of the bargain. No deal is done until the money is wired.

Share your preferences, communicate them clearly, and be consistent.

Build the relationship over time.

The best kind of FOMO comes from visible, tangible progress. That means warming up multiple investor relationships over time so that when the time comes to raise, you can tighten your process to a 2–3 week window. These investors will already know you, have a view of your market/product, and be able to make a decision quickly.

• Take early calls to get feedback

• Make real asks of investors and see who follows through

• Share regular updates over time

When you’re ready to raise, be clear and specific about your timeline and priorities. But do not bluff. VCs talk. Bluffing term sheets or deadlines that don’t exist is the fastest way to have a deal fall apart.

Balance aggressive goals with realistic expectation settings.

VCs track founder interactions, and you will be held to and measured against the numbers you share. Avoid the temptation to stretch reality or toss out numbers that sound good but aren’t locked in.

I shared an example of a founder who repeatedly shared a plan to go from launch to $5M ARR in their first year. They ended the year at $3.7M but that caused some friction in the fundraise. Instead of being met with excitement when they said “we went 0 to $3.7M”, the investors were asking “why didn’t you hit $5M? What happened?”.

Founders often feel pressure to show detailed traction early. Instead of offering detailed metrics or future projections too early, try sharing the problem you’ve identified, your thesis, early signals, and what you’re learning. Let them get to know you and your vision first.

Don’t try to “win the room” with aggressive projections. Instead, focus on doing what you say you are going to do and delivering reliably and consistently.

Do your diligence!

You’re signing up for a long-term relationship and want to take the time to get to really know the investors on the other side of the table. The “nurturing period” is about mutual qualification. Not every interested VC is the right partner, and not every founder fits an investor’s strategy.

Ian shared, “If a founder doesn’t do reference calls on a VC, that’s a red flag,” and I couldn’t agree more. Before you accept a term sheet, call founders who’ve worked with your potential investor. Ask for intros to portfolio CEOs, work your network to get to off-book references, and talk to a mix of folks - not every investment is a success story and you want to hear how your prospective partner operates during hard times too.

Done well, fundraising is a structured process that favors preparation, authenticity, and consistency. And remember, the goal isn’t just to raise capital but to bring on a long-term partner who believes in the future you’re building.

Until next week!

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DEAR PLANNING TOGETHER: Q3 is wrapped, Q4 is underway (where did the summer go??) and we are squarely in 2026 planning season. The theme of this year’s planning season? Realism. Whether you’re gunning for a breakout growth year or or aiming for profitability, your 2026 plan needs to reflect reality using real historical data. And most importantly, the team that will execute on the plan needs to have a say in building it and be 100% aligned as you kick off the new year. Here’s how to make that happen.

1. Throw Out the One-Plan Mentality

Most founders start with a top-down number: “We need to hit $10M ARR before we can raise again” or “We need to 5x this year.” That number usually comes from the boardroom and trickles down with very little operational grounding. The number is handed to finance to build a model and…done.

Not quite. It’s often loaded with unrealistic assumptions: reps ramp in 30 days, conversion improves every month, CAC drops…magically.

What to do instead: Build three plans

• Base Case: Built off historical data + realistic hiring assumptions.

• Best Case: Your upside scenario that considers partnerships scaling, new products, revamped pricing, etc…

• Worst Case: Your downside scenario that accounts for rising churn, funding delays, turnover and/or sales misses.

Critically, each plan has a prescribed growth target and burn rate. They should operate in parallel throughout the year so you can see where you stand and how you are pacing at any given point in time. If you’re pacing to Best Case, unlock budget. If you’re under Base, cut spend.

2. Gather your data and build the Base Case

Stage 2 Capital has a planning model template that we use with our portfolio. If you’re not sure where to start, download this template, pull together the last 3-6 months of historical data and load it into this template along with your hiring plan → this is your Base Case!

Here’s a quick overview of the data you need to get started:

When you build from this data, you get a much tighter grip on what the team can actually deliver, and where you might want to place some strategic bets.

3. Bring the entire GTM leadership team together to pressure test the plan

With your VP layer in place, you now have the horsepower to pressure-test assumptions before they make it into the final model. We recommend involving the full GTM org. Bring Sales, Marketing, CS, and RevOps leadership together and get them in the same room to agree to the plan.

Scroll out to July, for example, and pressure test the assumptions together. Can marketing produce X leads 6 mos from now? Can the cost per lead hold constant at that volume?

What about sales? Is it realistic for a rep to close 1 more deal per month by mid year? Or grow ACV by 10%?

When you are evaluating, watch out for the common mistakes:

• Start with your actual historical data

• Don’t hire AEs ahead of demand

• Watch out for stacked assumptions

• Include realistic ramp time (be honest!).

4. Plan for What Can Go Wrong (and Right)

Once the Base Case is set, it’s time to go to extremes:

• Downside Planning: What happens if funding falls through? If two AEs leave? If your main channel underperforms? Map the trigger points and define the pre-agreed actions: spending freezes, hiring pauses, maybe even a RIF.

• Upside Planning: Where will you invest if things go well? This is the fun part. Maybe it’s hiring additional engineers to accelerate a product launch, or scaling a new GTM motion, or investing behind a partnership. Take the time to think about the investments you will make to grow faster now to ensure you are ready to respond quickly mid year.

5. Review progress quarterly with the board

A great planning process creates clarity and alignment from the exec team to the board. Once you’ve locked in on your 3 plans:

• Only one plan is shared with the company. Your team needs one target to rally around: one revenue goal, one burn number. Any variable comp or bonuses should be tied to attainment of this plan.

• Three scenarios reviewed at the board level quarterly. Best case, base case, and worst case should all live in your model, and the board should be looped in on all three. You’re proactively showing how the business will adapt under different conditions.

• Quarterly check-ins to stay aligned. Every quarter, review actuals vs. plan. Are you pacing ahead? Falling behind? These reviews make sure you’re not running on old assumptions or overspending without results.

• Decide actions upfront. Before the year starts, define what will trigger change. Example: “If we hit X revenue in Q2, we unlock Y hires.” Or, “If we miss A conversion rate for 2 quarters, we cut B from the budget.” This alignment on actions removes the emotion from tough decisions that can come midyear.

And with that…one more plug to go grab the template and get started.

Until next week!

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DEAR STRATEGY OVER SPEED: “AI is allowing us to go faster, but potentially in the wrong direction.”

Back for part two of our PMM conversation, Yael Burla, Stage 2 LP and Director of Product Marketing at Vimeo, nailed it with this quote. She captured what I’ve been feeling over the last few months, witnessing far too many random acts of marketing.

It’s never been faster or cheaper to go to market. With a few tools and AI agents, you can build a website, generate a campaign, and fire off emails before lunch. But you can’t automate the human thinking needed to create a clear GTM strategy. Otherwise,you’re probably just adding noise without a clear sense of distribution And in today’s world, distribution is everything.

The core work of understanding your customers, defining your ICP, and positioning your product is more essential than ever. That’s where strong product marketing comes in!

Before you launch… ask these five questions

According to Yael, there are five questions every founder or early team must answer before launching anything:

1. Who are you targeting? (Both buyers and users)

2. What are their pain points, and what’s their willingness to pay?

3. How do they solve the problem today? (Who are you competing with?)

4. Where do they go to research this category (i.e. key channels)?

5. How do they describe the value you bring?

This is your GTM strategy foundation. Without it, you might build the right product… but market it to the wrong people in the wrong way.

Speed + Strategy = Smart GTM

Yael shared a recent example she experienced at Vimeo. Her team launched an AI-powered translation feature that was monetized through AI credits. It took off with enterprise users, but didn’t quite land with their self-serve base.

Why? The team hadn’t correctly identified who the self-serve ICP was or how they’d use the feature before the launch. “Post launch, we interviewed three cohorts of customers: those who didn’t use the feature, those who used it but didn’t buy, and those who both used and purchased more credits. The customers who bought were in e-learning, with an urgent need to reach global audiences and monetize their own businesses.”

That insight led to two key adjustments:

• Updating where the feature was surfaced in the product, which drove a 91% uplift

• Refining when it appeared in the user’s workflow to match intent to use

But here’s the kicker: none of that learning would have been possible without the upfront GTM work to hypothesize who the ICP is, and a commitment to digging deep when early signals didn’t match expectations.

Hypothesize, test, and learn

Founders love to “run experiments”, but not enough teams are disciplined in what this means. Experiments without a hypothesis are just guesses without clear direction. The best PMMs use customer data (recorded calls, usage analytics, win/loss interviews) to form testable hypotheses. Then they run targeted campaigns, measure, and iterate. Yael called out “Triangulate data from every part of the business - customers, competitors, usage, product feedback. That’s how you know when something’s working… or needs to change.”

You don’t necessarily win by being first. You win by taking big bets and being right. And in today’s market, being right means:

• Knowing your exact customer

• Understanding their pain and willingness to pay

• Delivering the right message, in the right channel, at the right time

Until next week!