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In this episode, Josh sits down with seven CS leaders at the Pulse Conference in Las Vegas for quick conversations about their biggest challenges and how AI is starting to move the needle. Different companies, different scales, same pattern: the ones making progress aren't waiting for a perfect strategy. They're looking at where time is actually going and doing something about it.
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Three Things We’re Taking Away:
AI’s first gift isn’t efficiency. It’s visibility. Angel Rogers at Rockwell Automation didn’t set out to fix meeting scheduling. Staircase showed her CSMs were spending 3,000 hours per quarter on it. She never would have guessed. The data surfaced the problem. The fix followed. That sequence, signal first, intervention second, is how every leader in this episode is approaching it.
Trust is the adoption barrier, not capability. Matt Krebsbach at Boomi found that his team’s first question about every AI insight was “can I trust this score?” Once they understood how the score was built and saw it working in pilots, they reported saving four hours a day. The technology wasn’t the blocker. The credibility of the output was.
Lagging indicators are no longer good enough. Margo Martin at Delltech doesn’t want to find out about a product defect because a customer calls to complain. She wants to know within 15 minutes that 20 customers submitted support cases so her team can get ahead of it. That shift, from reactive to proactive CS at speed, is what every leader in this episode is building toward.
🎯 The [Un]Churned Take: Two People Who Built the Last Era Debate What Comes Next
The [Un]Churned Take: What Seven CS Leaders Said at Pulse
At the Pulse Conference in Las Vegas, we sat down with seven customer success leaders across companies ranging from a 120-year-old industrial automation company to a platform serving 2,000 CSMs globally. The conversations were short, but the themes were consistent.
The Data Already Knows Where the Time Is Going
Angel Rogers leads a 300-person CS team at Rockwell Automation managing 100,000 contract renewals a year, none of which auto-renew. When Staircase surfaced that her CSMs were collectively spending 3,000 hours per quarter just scheduling meetings, her reaction wasn’t pride. It was a campaign to fix it. That’s the underrated value of AI intelligence tools: not the automation, but the audit. Knowing where time actually goes is the prerequisite to every other improvement.
Sean MacPherson at Fleetio named the same problem from a different angle. His team has the data. What they don’t have is a clean way to extract the story from it and present it at the right altitude for each stakeholder. A CSM needs granular account detail. A CEO needs three numbers. AI that can generate both from the same underlying data is the unlock he’s looking for.
The Trust Problem Is Real and Solvable
Matt Krebsbach at Boomi is running Gainsight, Staircase, and a third platform called Reef AI for scarcity-based churn regression modeling. His team was skeptical. When he walked them through how the insights were generated and piloted the tools in small groups, skepticism turned into adoption. Now they report saving four hours a day on repeatable tasks. The lesson: don’t deploy AI tools and expect trust to follow. Build the trust first, then watch the adoption accelerate.
Tiffany Taylor at Handshake is using Gainsight’s Impact Analyzer to close the feedback loop between on-site customer visits and action. What used to take six or seven days, a survey, a read, a one-on-one, a decision, is now near-immediate. Her goal: get customers to act on more things in less time. Not one recommendation per visit, but five, deployed at the right cadence.
The Long Tail Is the Unsolved Problem
Tony Pante runs a 2,000-CSM global organization at SAP that just deployed Gainsight from zero to full scale in a single phase. His team covers a range from one CSM to two enterprise customers all the way to one digital CSM covering 100. He’s using AI for multilingual content creation at 95% quality with local human review, and has an SAP agent called Joule coming to Gainsight within months. His underlying challenge is one every leader in the room shares: how do you cover more customers than you can possibly hire for?
Margo Martin at Deltek has a CCO’s version of the same problem. When one CSM covers 500 accounts on the small end, proactive relationship management isn’t just hard. It’s mathematically impossible without tools that surface the right signals at the right time. She wants Staircase at the relationship level so she can see the holistic picture across every product a customer owns, not just the one their assigned CSM manages.
Charlie Ferraro, an early Staircase adopter since 2023, named the next frontier: what does adoption even mean when the product is agentic? Traditional usage metrics, feature adoption, license utilization, were built for software that humans operate. When the agent does the work, the measurement model needs to change too.
Wrapping Up
Seven companies, seven different boulders. The ones moving fastest have one thing in common: they looked at where the time was actually going before they decided what to automate.
See you next week 🧠
Where to Find the Guests
Angel Rogers — Head of Customer Success, Rockwell Automation
Sean MacPherson — Fleetio
Tiffany Taylor — Handshake
Matt Krebsbach — Director, Technology & Strategy Operations, Boomi
Margo Martin — CCO, Deltek
Tony Pante — Global Head of Scale & Engagement Center, SAP
Charlie Ferrao — Director of Customer Success, EcoOnline
Referenced in This Episode
Staircase AI — Gainsight’s customer intelligence product, referenced by four of the seven guests for signal detection, engagement analysis, and sentiment-based prioritization. staircase.ai
Gainsight — The CS platform used by multiple guests in this episode, including SAP’s just-completed 2,000-CSM rollout and Handshake’s Impact Analyzer feature. gainsight.com
Fleetio — Fleet management platform Sean MacPherson’s team uses to manage vehicle lifecycle and maintenance for companies from 2 to 50,000 assets. fleetio.com
Handshake — Early talent platform Tiffany Taylor’s team uses to connect students with employers and career resources. joinhandshake.com
Boomi — Integration platform Matt Krebsbach’s team runs, using a three-platform AI stack including Reef AI for churn regression modeling. boomi.com
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