Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Stacey Epstein, CEO of Structured, an AI native infrastructure provider for enterprise partner ecosystems. Epstein built her career scaling enterprise software from the inside. She helped grow SuccessFactors from $10 million in ARR to a $3.4 billion acquisition by SAP, joined the founding team at ServiceMax through six years of triple-digit growth to a $1 billion acquisition by GE, served as CEO of Zinc, and guided Freshworks through its IPO as CMO.
When a CEO believes their strongest skill needs no backup, Epstein holds that they must hire a leader for it anyway. The reason is structural, not personal: a CEO runs finance, product, engineering, and HR at the same time, and the function you already know how to do will get starved of attention while you shore up the functions you don’t. Epstein learned this the hard way. She spent a full year running marketing herself at her first CEO role, on top of everything else, before admitting the function wasn’t getting done.
This episode is for CEOs who already excel at one function of the business and assume that expertise means they can keep running it themselves indefinitely.
Key Takeaways
- A CEO’s strongest function is often the one that gets neglected first, because time gets pulled toward the functions that are new or difficult, not the one that already feels handled.
- Epstein went roughly a year running her own marketing function as CEO before hiring a CMO, a delay she attributes to assuming existing expertise meant the work would keep happening on its own.
- Company culture is harder to protect during flat or slow periods than during explosive growth, because a winning team tolerates friction that a plateaued team will not.
- At Structured, Epstein is deliberately shifting the company’s culture from engineering-only focus toward a customer-focused culture, without losing the engineering strength that built the product.
- Epstein treats AI as a thought partner rather than a replacement for judgment: a recent pricing decision at Structured only became an AI-generated document after a 45-minute conversation she led herself.
When Should a CEO Hire a Leader for the Function They Know Best?
A CEO’s job is not to run the company’s best function. It is to run all of them at once. Epstein describes the miscalculation directly: “I really have to build my leadership team, but I don’t need to worry about marketing because I’ve got that one covered.”
That assumption breaks down immediately once the CEO title starts, because every function reports up to one person. “You run finance, you run product, you run engineering, you run HR,” Epstein says. Time flows toward the areas that feel unfamiliar or unfinished, and the area that already feels handled quietly stops getting attention. For Epstein, that area was marketing, and the gap ran for about a year before she acted. “I finally, after about a year, realized I need a CMO because it’s not getting done.”
The fix is not confidence in your own skill. It’s the recognition that skill and bandwidth are two different resources, and a CEO only has enough of the second to go around.
How CEOs Keep Culture Intact During Explosive Growth and Acquisitions
Culture protection gets treated as a hypergrowth problem, but Epstein argues the opposite is closer to true. A team riding a winning stretch will absorb dysfunction that a flat team won’t. “It’s maybe even harder when you’re not exploding,” she says.
That means culture cannot be left to momentum. It has to be a deliberate choice made at the top and reinforced every day. “My principles around culture is that it totally starts at the top and you have to really be conscious about what kind of culture that you want to have,” Epstein says.
At Structured, that principle is showing up as a specific shift: the company has been engineering-focused since its founding, which produced a strong AI native product, but Epstein is now adding customer-focused practices, more listening, more touch points, more community, without losing the engineering strength that got the company here. The lesson for any CEO managing culture through a growth spike or an acquisition: name the pillars you want, then hold the company to them daily, whether the quarter is exploding or not.
How CEOs Should Use AI as a Daily Decision-Making Partner
Epstein’s approach to AI inside her own company starts with a distinction most executives blur: AI accelerates a decision, it does not replace the thinking behind it. When Structured was working through a pricing model recently, Epstein didn’t hand the problem to a tool and wait for an answer. She worked it herself first. “AI didn’t create it in a vacuum, AI created it after I had a 45 minute conversation about it,” she says.
She’s also explicit with her team that using AI carries no stigma. “I’m never shy about sharing that I’ve used it,” Epstein says. That openness matters for a CEO trying to get an organization to adopt AI broadly: if the CEO models transparent use instead of hiding it, the team has no reason to hide theirs either.
The same principle carries into Structured’s product itself, where Epstein sees AI removing the skill barrier for partners who previously needed a full marketing team to run a campaign, without removing the person from the relationship. “There is a person behind every sales cycle. There’s a person behind every customer relationship, every partner relationship,” she says.
The Framework: Three Principles for Scaling CEOs
| Principle | What it means in practice | Named evidence from this interview |
| Delegate the function you know best, not just the ones you don’t | A CEO’s confidence in a function is not a substitute for a leader dedicated to running it, because CEO bandwidth is finite across every function at once | Epstein ran marketing herself for about a year at her first CEO role before hiring a CMO, a delay she now identifies as her biggest early leadership mistake |
| Culture is a daily choice, not a byproduct of growth | Protecting culture requires more discipline during flat periods than during hypergrowth, because momentum masks friction that a plateau exposes | At Structured, Epstein is actively shifting an engineering-only culture toward a customer-focused one by adding listening and community practices without losing engineering strength |
| Use AI as a thought partner, not a shortcut around judgment | The CEO should do the thinking first and use AI to accelerate output, then be transparent with the team about that use | Structured’s recent pricing model was drafted by AI only after Epstein spent 45 minutes working through the reasoning herself |
Quotes from This Episode
- “You run finance, you run product, you run engineering, you run HR.” — Stacey Epstein, CEO, Structured
- “There is a person behind every sales cycle. There’s a person behind every customer relationship, every partner relationship.” — Stacey Epstein, CEO, Structured
- “It’s maybe even harder when you’re not exploding.” — Stacey Epstein, CEO, Structured
- “I’m never shy about sharing that I’ve used it.” — Stacey Epstein, CEO, Structured
- “It’s the same brain, it’s the same muscle, it’s the same trait of just constantly trying to think about how to do better.” — Stacey Epstein, CEO, Structured
Frequently Asked Questions
Should a CEO delegate the function they are best at?
Yes. Stacey Epstein, CEO of Structured, holds that a CEO must hire a leader for the function they know best, not just the functions they don’t, because a CEO’s time is split across finance, product, engineering, and HR at once. Epstein ran marketing herself for about a year at her first CEO role before hiring a CMO, a delay that came directly from assuming her own expertise meant the work would keep happening without dedicated leadership.
How do you keep company culture intact during rapid growth or an acquisition?
Culture protection is harder during flat periods than during explosive growth, according to Epstein, because a winning team absorbs friction that a plateaued team will not. Her approach is to name specific cultural pillars, such as empathy and performance, and reinforce them daily from the top, rather than assuming growth alone will sustain the culture. At Structured, she is actively adding customer-focused practices to an engineering-heavy culture without losing the engineering strength that built the product.
Should CEOs be transparent with their teams about using AI?
Epstein says yes, and models it herself: she openly tells her team when a document or decision involved AI, without editing out signs of AI involvement. Her process is to work through the reasoning herself first, such as a 45-minute conversation on pricing strategy at Structured, and use AI to produce the resulting draft, treating the tool as a thought partner rather than a replacement for her own judgment.
Executives Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach. He coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
