Buying AI for Customer Success? Start by Asking Where Your Team Spends Its Time
If your team is buried in low-value work, AI just does the wrong work faster. Here's how to find the real leverage before you buy.
DEAR STAGE 2: My team says they’re “drowning in meetings” and maxed out. We’re not adding any new headcount this year and the company directive is to use AI to create capacity. How do I figure out where the actual leverage is in CS and what tools to invest in? ~SEEKING EFFICIENCY GAINS
DEAR SEEKING EFFICIENCY GAINS: Whether you’re considering building or buying, your instinct is right: you have to figure out where time is going and what work can be replaced *before* investing in the tech stack.
I had a great chat with Shaun Porcar, Stage 2 LP, Advisor and multi-time Head of Customer Success on this exact topic. We agreed we’re seeing a lot of CEOs saying “use AI to create capacity,” then the CS leader starts demoing tools, pilots get started, and a few months later, there’s still no measurable change. Plus, all the overhead that comes with implementing and managing a new tool.
It feels like we’re not spending enough time on diagnosis and diving right into solutioning.
Vendors aren’t lying when they quote results like “30% time savings”. But 30% of what, exactly? If your team is spending most of their time on work that isn’t driving retention or expansion, you don’t have a capacity problem. You have a work allocation problem. And buying a tool to do the wrong work faster doesn’t fix that.
So the real challenge you run into in diagnosing this is that your team’s self-reported data is nearly useless.
Ask your CSMs where time goes, and they’ll all say the same thing: customer calls and activities related to meeting prep or next steps. That’s true, but it also tells you nothing. What kind of calls? At what stage of the customer journey? Are they proactive or reactive? Is the customer getting value from them or tolerating them? You need real data.
Run a time audit
The audit Shaun recommends is simpler than you’d think.
Start by connecting to your team’s Google Workspace or 365 calendars. Classify every meeting and logged activity as external or internal. Then try to map each external meeting and important activity to a stage or key inflection points in the customer journey: onboarding, adoption, renewal, expansion, escalations, stakeholder changes, etc...The goal is to understand where time is spent and what work is actually being done.
As Shaun puts it: “Where is time actually being spent? You can literally build something that will provide you with a dashboard. You’ll start to see where you’re bottlenecking around onboarding, renewals, or something vaguely classified as a check-in call. Something more is happening here that people are spending a lot of time in.”
Start lightweight and don’t let tools be the barrier. A spreadsheet works, or Cowork or Monocle if you want something automated. Shaun’s framing: “You don’t need a lot of fancy tools to do this. You just need something that’s going to help you break down and understand where people are spending time and what they are actually doing with that time.”
Once you see where time concentrates, ask one more question about that category of work. As Shaun frames it: “Is this something that you’re doing to be proactive, is it something that you’re doing to be reactive, or are you actually collaborating with that customer to action a specific task on their end? You can figure out what sort of value is being driven, if any, in that conversation.”
Proactive work is usually worth protecting. Reactive firefighting is almost always a signal of a process gap upstream (incomplete onboarding, unclear success criteria, a handoff that isn’t working). And customer collaboration calls are context-dependent. Sometimes high-leverage, sometimes a sign that self-serve is missing. Going further, sometimes the biggest opportunity isn’t automation at all. It’s eliminating or rethinking that part of the workflow altogether.
While the audit runs, talk to your customers
It’s easy to skip this part, but don’t! Shaun is direct about it: you need to spend real and meaningful time hearing from your customers. Shaun calls out a few specific topics to dive into: “Ask them about their experience with your company. What is the path they followed to see value? How are they thinking about ROI? The amount of time they’re spending with us, should they spend less? What are their preferred communication channels?”
The answer most CS leaders find when they ask customers directly: they actually want less of your time, not more. They want the right answer in the moment they need it, in whatever channel they’re already in.
White glove doesn’t mean a CSM on the phone 3 days from now. It means fast, accurate, in-context help (whether that’s a chat response, a triggered email, or something surfaced in the product).
Would you build it this way today?
One additional question worth asking: if we were designing this process today with AI available from day one, would we design it the same way?
For many companies, the answer isn’t finding ways to automate an existing workflow. It’s redesigning specific parts of the workflow entirely. An onboarding process, customer communication cadence, or escalation path that made sense a few years ago, or even a few quarters ago, may no longer be the highest-leverage way to create customer value.
That doesn’t mean every company should rip and replace existing processes and tools. Mature organizations often benefit from targeted AI improvements first, just as early-stage organizations should look for targeted opportunities to build agentic workflows with a human in the loop. The goal should be thoughtful workflow design, not simply bolting AI onto legacy operating models.
Now you can buy the tool
Once you know where time is bottlenecked and what kind of work is happening there, vendor evaluation becomes straightforward. You’re not buying “AI for CS.” You’re buying a specific solution to a specific problem, and you can hold the vendor accountable for the results in that slice of your workflow. Just as important, this gives you a clear business case and measurable ROI for the investment.
That’s the fastest path to actual leverage. Skipping it feels faster, but almost always lands you in the failed pilot graveyard.
Until next week!