CxX SuccessHour: How to Move from CS to CRO in the Age of AI
Ready to move from CS to CRO? Shawn Stiffler did exactly that, then went one step further into the CEO seat.
The CRO role is shifting. The hard-closer stereotype is fading. The leaders stepping into it now need to understand the whole customer journey, from first prospect conversation through renewal and growth. That is exactly the muscle Customer Success builds every day.
Shawn built his path through operations. He ran everything post-sales at his last company (support, onboarding, and CS among other functions), then took on a churn problem as a consultant at a scrappy AI startup. That consulting gig turned into a revenue leadership role. Today he runs the company as CEO.
Join Shawn Stiffler, CEO Caller ID Reputation, and Jan Young (StepUpXchange) for a tactical conversation on making the jump from one function to another in tech. You'll learn:
How Shawn identified the gaps between his CS experience and what a revenue leader needed to know
The specific steps he took to close those gaps
How he made the case for the transition, and how he'd advise you to make yours
Why AI-first companies need more leaders who have actually sat in the CS seat
Jan Young, co-host, has made her own moves across Product, Sales, Marketing, and CS, and will bring that perspective into the conversation too.
If you've ever wondered whether your CS background qualifies you for more, bring your questions to this one.
Guest Speaker:
Shawn Stiffler is CEO of Caller ID Reputation, an AI startup where he was originally brought on to solve a churn problem. He ended up rebuilding the business from the ground up, standing up onboarding and support functions that did not exist and eventually stepping into the CEO role. Shawn's background is in business operations, where he ran post-sales functions before building an enterprise sales motion from scratch at his last company. He believes the CRO of the future looks a lot more like a COO, and that curiosity about AI matters more than mastery of any one tool.
Host & Speaker:
Jan Young transforms CS leaders into business leaders in the age of AI. Founder of JanYoungCX and StepUpXchange, she also leads CxXchange, a global peer community. An award-winning leader and former VP for two exited startups, Jan has coached CS leaders and founders since 2016 to grow customer revenue and align go-to-market execution. With experience across Product, Marketing, Sales, and CS, her cross-disciplinary approach drives profitable, customer-led growth.
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