CRO Stories: Scaling, Pivoting, and Leading Through Change with Bridget Winston

Bridget Winston has been a CRO across unified communications SaaS, a stock content marketplace, a membership platform for executive women, and now a vertical SaaS company serving med spas. Some people call that kind of range a liability. Bridget calls it the thing that lets her nail every role—especially in a world where the old playbooks don't work anymore.

In this episode of CRO Stories, Rachael Bueckert sits down with Bridget Winston, CRO of Patient Now, for a conversation that covers how she scaled Chief from 1.5k to 20k members and a $1.1 billion valuation, what broke along the way and the pivots that followed, why she purposely took a customer success role to become a better revenue leader, how she uses AI to impact revenue, and the change management discipline she runs at every company she joins.

[01:26] Intro to Bridget Winston and her path to Patient Now

[02:33] What Chief is and the B2C-to-B model

[03:39] Scaling Chief from 1,500 to 20,000 members—what broke along the way

[05:11] The Covid pivot: from in-person to national to back again

[06:23] Expanding to the UK and pulling back—hard lessons in product-market fit

[08:18] How AI data enrichment revealed a completely different ICP

[11:38] ICP is everything—the defining lesson of being a CRO

[13:06] Why most companies think they know their ICP but haven't gone deep enough

[15:22] The secret test: are you operating as a CRO or a glorified VP of Sales?

[16:13] Aligning comp across marketing, sales, and CS on a shared metric

[18:00] The ShoreTel story: when law firms kept churning and what changed

[20:22] Why Bridget purposely took a customer success role

[22:29] B2C vs. enterprise at Chief—competing for resources

[24:47] First team mentality and Five Dysfunctions of a Team

[27:32] Biggest lesson from Chief: you're never done with product-market fit

[28:31] Big problems don't always need big solutions—two-way doors

[30:08] The UK expansion failure and building the muscle to embrace failure

[31:15] "It's the people"—why that diagnosis is almost never right

[32:11] Shutterstock: 35% attrition, 10% quota attainment, and what was actually broken

[37:14] Why a Rev Ops partner is the most critical hire for a CRO

[38:28] What Bridget is bringing into Patient Now

[39:19] Evaluating three AI tools in the first two weeks

[40:14] The biggest hot take: B2B marketing is becoming consumer marketing

[42:38] Community-led growth and the CISO example

[46:50] Why Patient Now—the opportunity, the mission, and the team

[51:08] Goals at Patient Now: customer centricity as a leading indicator

[52:45] Universal CRO skills: range, financial acumen, and grit

[56:31] The story behind her leadership: change management as a discipline

[01:00:37] How AI has compressed CRO planning from five months to one

[01:03:28] Where to find Bridget

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