AI Strategy: Align or Adapt for Success?

A Note From our Head of Technical Services, Rishi Bhagwandeen

You Don't Know What You Don't Know

I've sat in more AI strategy conversations with Customer Success (CS) and Customer Experience (CX) leaders this year than I can count, and I keep noticing the same thing.

Most teams end up in one of two camps. Some chase every new AI capability that crosses their desk, adding one thing after another without much of a plan for how it all fits together. Others freeze up, waiting for the "right" moment or the "right" answer, while everyone around them keeps moving. Honestly, I've caught myself doing a version of both. Neither one is really a strategy. It's just reacting and calling it something else.

Here's where it gets genuinely tricky: the industry itself hasn't settled on one way to do this. Some AI approaches are built to run things for you, quietly acting on your behalf so your team can stay hands-off. Others hand you the pieces and expect you to build what fits. Neither is more advanced than the other. It really comes down to how your team works, the shape of your book of business, and what your CSMs actually want out of their day. There's no universal right answer, only the one that's right for you, and that's a hard thing to see clearly when you're the one living inside the decision every day.

That's the real issue, I think. When you're evaluating your own approach, you're grading your own homework. Nobody's standing next to you with an outside sense of what "good" looks like at this stage of things. And if someone on your team already pushed for a particular direction, they've got a reason to defend it now, which makes an honest gut-check hard to get from inside the building.

This is where bringing in someone from outside actually helps, and it's not because they carry stronger opinions about which approach to pick. It's that they've sat with a lot of teams working through this same decision, so they start to notice what tends to hold up and what quietly falls apart six months later. They can also ask the question that's genuinely awkward for someone internal to ask without it sounding like a jab at a colleague's work: is this actually working, or have we just gotten used to it?

The technology keeps getting better every quarter. That was never really the hard part. The hard part is knowing, with any real confidence, whether the way you're using it actually matches where your business needs to go.

So here's what I'd ask every CS and CX leader to sit with this week: if someone completely outside your world sat in on your last AI planning conversation, would they see an actual strategy, or a handful of reasonable-sounding decisions that have never been tested against each other?

Finding out now is a lot cheaper than realizing a year from now that nobody wants to be the one to say it isn't working.

Roles on the Radar

• Senior Director, Renewals and Retention at Blackbaud
• Customer Success Manager at EdSights
• Customer Success Manager at Client Giant
• Customer Success Intern at Vouched
• Manager, Customer Success Management at PayPal

Where Molecules Meet: Heading to Pavilion's GTM 2026? Let's Connect in NYC!

Our CEO, Sabina Pons, is heading to New York City for GTM2026, September 28-October 1 at The Glasshouse. The event will bring together 1,000 VP+ GTM operators for four days of conversations around growth, AI, revenue, and the future of go-to-market.

If you'll be there and are thinking about what's next for your CS or post-sale organization, Sabina would love to connect. Whether you're navigating AI, scaling your team, rethinking your customer journey, or looking for a fresh perspective on retention and growth, let's find time to talk.