Opportunity Knocks for the Connected CS Leader ft. Andy Mowat (Whispered)

Customer Success (CS) leaders who know how to drive retention are about to become some of the most valuable hires at the newest wave of companies. That’s according to this week’s podcast host, who says the rise of AI will make experienced CS leaders even more essential.

Andy Mowat, founder and CEO of Whispered, joined host Josh Schachter for this week’s [Un]Churned episode, “208. 80% of VP Roles Are Never Posted. Here’s How to Find Them” They covered how the senior executive job market actually works, why most VP and C-level roles are never posted, and what it takes to navigate the hidden job market at the CCO level.

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Listen on YouTube, Spotify, Apple Podcasts, and Gainsight.com.

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🎯 The [Un]Churned Take: Your CS Skills Are a Secret Weapon in Today’s Job Market

AI companies have crossed the threshold from fledgling disruptors to mature, market-shaping organizations. In recent years, they moved quickly to gather customers, build their brands, and launch new features. This rush created high demand for CMOs, CROs, and engineering leaders, while CS leadership was less prioritized. Now, as these companies enter a new phase, the focus is shifting. In the first year, customers are onboarding. In the second, they decide if the product met their needs. By the third year, retention and churn start to look like a very real risk.

Data is beginning to highlight this trend as well. According to ChartMogul’s 2025 SaaS Retention Report, median gross revenue retention across AI-native companies sits at 40%—compared to 63% for traditional B2B SaaS.

Andy Mowat is watching that gap close and sees a reckoning ahead.

“A lot of these AI companies are in year two, and they’re about to face it.”

Throughout his career, Andy has led RevOps at four unicorn companies, advised companies and founders on GTM strategy and technology, and built his own companies. His latest venture, Whispered, is an executive career platform based on the insight that top senior roles are rarely posted publicly. With a career that’s intersected executive search and go-to-market, he has a unique perspective on where the job market is headed.

“I’m starting to see churn become a bigger and bigger issue with a lot of these high-flying companies.”

When that happens, the need for CS leadership will become urgent, quickly.

The C-Level Job Market Is Mostly Invisible

Posting senior roles publicly can come with a slew of issues for the businesses making these big moves. It signals leadership changes to competitors, overwhelms recruiters with too many unqualified applicants, and sometimes creates instability before a replacement is found.

“At the director level, 75 to 80% are posted, but you flip that to 20% posted at the VP level and at the C level virtually nothing is posted.”

Andy’s watched how the market operates differently outside of the job boards. Retained search firms don’t post jobs because their fees rely on managing the process. VC and PE talent partners connect companies with recruiters, and many opportunities come through warm introductions that only become job leads once they are already in motion.

“Do not apply through the front door. It just doesn’t work.”

CS leaders who rely on traditional job searches, like updating their LinkedIn profiles, applying to postings, and checking their inboxes, only reach a small part of the market. There are other strategies at play, and your experience in CS has equipped you to execute them whether you realize it or not.

The Skills You’ve Built Will Power Your Job Search

Andy lays out a set of must-have skills for thriving in the AI era. The good news? You’ve already been sharpening these abilities every day.

Tapping Into Relationships

You already know that lasting client relationships are built through trust and personal connections. In your job search, the same holds true. Instead of applying through the front door, connect with peers or recent hires inside your target company. Just like nurturing stakeholders within an account, these conversations can open doors that applications alone can’t.

Following the Funnel

As a CS leader, you’ve guided customers through the stages of renewal or expansion. The steps you use to navigate complex engagements work the same way as your job search.

“There’s the recruiter call, which is kind of a qualification step…Then there’s like the hiring manager call, which is effectively discovery. And so you have to approach that hiring manager. If you engage the hiring manager, they’re gonna make sure you get pulled through the process. So that’s like the critical stage of the funnel.”

Turning Targets Into Opportunities

You know how powerful a clear account list is when mapping expansion plans. The same principle applies to your job search. Targeting specific companies (Andy recommends 20-40) gives your network a concrete way to help you. When someone hears a company name, they’re much more likely to make a connection on your behalf.

Leveraging Peer Networks

Customer Success thrives on creating value through connection and collaboration. In your search, use the same approach. Reach out to people who have the job you want and ask them to pass along opportunities that aren’t a fit for them. It’s similar to gathering referrals. Low lift for them, high impact for you.

Searching or Not, Your Strategy Should Be Consistent

Not all CS leaders reading this are actively looking for a new job. Still, the hidden job market favors those who build relationships, keep a target list, and grow their network before they need anything.

When companies come looking, the first CS leaders they’ll call are the ones who never disappeared from view and have built genuine connections ahead of the curve.

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🎧 Listen for These Moments

If you're in an active search (or think you might be in the near future) the full episode goes behind-the-scenes of the executive search process. Three moments to listen for:

1. The Google group of 340 talent partners: how VC and PE talent partners communicate behind the scenes, and why moving too fast in that network can surface your search before you’re ready.

2. The comp conversation timing: when to bring up compensation in the process, and why roughly half of all posted comp numbers are negotiable even when they look fixed.

3. The “head of” signal: what to look for in senior job postings that indicates a company is open on title and level.

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🔎 Where to Find the Speakers

• Andy Mowat — LinkedIn: https://www.linkedin.com/in/amowat/

• Josh Schachter — LinkedIn: https://www.linkedin.com/in/jschachter/

📎 Referenced in This Episode

• Whispered — Andy’s executive career platform connecting senior leaders to unposted roles through a trusted peer network

• Gated — Andy’s previous company, which filtered cold email access through charitable giving

• Carta — equity management platform where Andy ran RevOps and used the target list strategy to land the role

• Zapier — referenced as an example of a target company Andy used to illustrate the specificity strategy with recruiters

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Wrapping Up

Every connection you nurture today is a door opening for tomorrow.

See you next week 🧠