Ali Wing, CEO of Oobli, treats a specific pattern as a warning sign rather than a compliment: the more often she was the only person who could answer a question inside her company, the more she worried about what that revealed. Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, spoke with Wing about the leadership lesson that shaped a decade running giggle and now shapes how she leads Oobli, the food technology company behind what she calls “happiness proteins,” fermentation-based sweet proteins that typically cut sugar in packaged food and beverages by about 75 percent without a noticeable taste change. When a CEO becomes the only person who can answer a critical question, Wing holds that the fix is not to answer faster. It is to build the team and framework that should have been answering it all along.
This episode is for CEOs who notice they are still the only person in the company who can answer certain critical questions, and want a framework for building teams that can answer those questions instead.
Key Takeaways
- Ali Wing holds that a CEO who remains the only person capable of answering a critical question has not built enough team or framework around that question, regardless of how capable the CEO is.
- Wing’s discipline, learned at Nike, is to choose deliberately what a company will not focus on, comparing a growth-stage company to a financially distressed company where the hardest daily problem is deciding what to leave undone.
- Wing scales herself personally by alternating between operating roles and board seats, including a public board seat at Casey’s, crediting the seat switching with giving her renewed perspective on her own operating decisions.
- Oobli’s fermentation process typically cuts sugar in packaged food and beverages by about 75 percent without a noticeable taste change, a result Wing says holds up in blind taste tests.
- Oobli runs its own internal enterprise AI tool, company-specific AI projects, and regular lunch-and-learn sessions to get AI into every function, from HR and finance to its core biotech R&D, revisiting its approach roughly every 90 days.
How CEOs Can Stop Being the Bottleneck as Their Company Scales
During her decade founding and leading giggle, Wing learned to treat her own indispensability as a problem to solve, not a strength to protect. The more consistently she was the one person who could answer a given question, the more she pushed herself to ask what that meant about the company: what wasn’t built, what framework was missing, what team hadn’t been given the authority to decide. Her standard is direct: a company is not built at real scale if one person has to answer every question.
That discipline plays out as an ongoing back-and-forth, not a one-time fix. In growth mode, a CEO often has to personally own a function the company cannot yet afford to hire for. Wing’s rule is to recognize the moment that changes: once the company can bring in the right person, the CEO has to actually let go of the function and shift into a different role, acting as editor, partner, or coach rather than the person doing the work. Knowing when you are the one directly accountable for a task versus when you are consulting on someone else’s work is, in Wing’s view, part of the core discipline of scaling a company past the founder’s own capacity.
How CEOs Should Decide What Not to Do as They Scale
Wing traces her sharpest scaling lesson back to her early career at Nike, where she learned that a real business exists to solve a specific problem for a specific audience, and that knowing what matters to that audience also means knowing what does not matter to them. She applies a specific comparison to growth-stage companies: they operate like a financially distressed company, in that the hardest daily decision is not choosing which good idea to pursue. It is choosing which good ideas to leave alone.
At Nike, Wing’s team stayed relentlessly focused on the single consumer need that mattered most and held a high bar for meeting it, a focus that only worked because the team consistently excluded other priorities by design. Wing carries the same practice forward today: define what’s most important, define how you’ll measure success against it, and track that measurement with discipline rather than letting the list of good ideas expand unchecked.
How CEOs Can Scale Themselves Through Board Seats and Outside Practices
Asked what CEOs most overlook when it comes to scaling themselves personally, Wing points to a practice she has kept for roughly a decade: serving simultaneously as an operator and as a board member. Moving between an operating seat and a governance seat forces a kind of awareness that staying in one seat does not produce, particularly around where a given tactic brings people along and where it leaves them behind.
The practice shows up concretely in her schedule. Even during an intensely busy stretch running Oobli, Wing still flies out for public board meetings, including a board seat at Casey’s, and describes coming back from those meetings refreshed and clearer about her own job at Oobli. Her broader advice extends beyond board seats specifically: CEOs benefit from building practices and rituals outside of work, the same way people build a habit around exercise, that create space to reflect and to observe and learn from other leaders.
How CEOs Can Build Company-Wide AI Adoption from the Inside Out
Wing compares the current moment in AI adoption to the early days of workplace computers: not using it is no longer a viable option for any employee, not just the CEO or the technical team. Her standard at Oobli is that every employee, across every function, should be actively rethinking how they get their work done using AI, even though she is candid that most current applications are still automation and incremental improvement rather than a full transformation.
Oobli backs that standard with specific internal infrastructure: an enterprise AI tool built for the company, company-specific projects running inside that tool, and regular lunch-and-learn sessions to keep the whole team learning together. The reach spans HR and finance as well as Oobli’s core biotech research and development, where food science work adjacent to gene editing is being enabled by tooling descended from the same technology wave that produced CRISPR. Wing is direct that the system is not settled: Oobli revisits and rebuilds its AI approach roughly every 90 days as the tools themselves keep changing.
What Scaling CEOs Can Take from Ali Wing’s Leadership
| Principle | What it means in practice | Named evidence from this interview |
| Being the only answer is a warning sign, not a strength | If you are the only person in the company who can answer a recurring question, treat it as a signal to build the missing team or framework, not proof of your own value | At giggle, Wing found that the more indispensable she became to answering questions, the more it revealed what she hadn’t built into the company |
| Choose what you will not do | In growth mode, the hardest decision is not picking the best idea, it is deciding what to deliberately leave undone or be bad at | Wing credits her time at Nike with teaching relentless focus on one consumer problem, treating growth-stage companies like financially distressed companies that cannot fund every priority |
| Switch seats to see your blind spots | Alternate between operating roles and board seats, or build outside practices and rituals, to get the perspective that day-to-day operating work does not provide | Wing serves as an operating CEO at Oobli and a public board member at companies including Casey’s, and describes returning from board meetings with renewed clarity on her own job |
| Make AI adoption a whole-company habit, not a department project | Push every function, not just developers or leadership, to rethink how they work with AI, and expect the approach to change on a short cycle | Oobli runs an internal enterprise AI tool, cross-functional projects, and regular lunch-and-learns spanning HR, finance, and biotech R&D, revisited roughly every 90 days |
Quotes from This Episode
- “It’s not something very big if one person has to answer all the questions.” — Ali Wing, CEO, Oobli
- “Great businesses solve problems.” — Ali Wing, CEO, Oobli
- “It’s what I can choose to be bad at.” — Ali Wing, CEO, Oobli
- “Changing seats really gives you that perspective.” — Ali Wing, CEO, Oobli
- “We use it all over the place internally.” — Ali Wing, CEO, Oobli
Frequently Asked Questions
How can a CEO stop being the bottleneck as their company scales?
Ali Wing holds that when a CEO is the only person who can answer a critical question, the fix is to build the team or framework that should be answering it, not to keep answering it personally. At giggle, she treated her own indispensability as a signal of what wasn’t yet built into the company, not as evidence of her own value.
How should a CEO decide what not to focus on as the company grows?
Wing compares a growth-stage company to a financially distressed company, where the hardest daily decision is not choosing the best idea but choosing which good ideas to deliberately leave undone. She credits this discipline to her early career at Nike, where her team stayed relentlessly focused on one consumer problem by consciously excluding other priorities.
How can a CEO use board seats to scale themselves personally?
Wing has spent roughly a decade serving simultaneously as an operator and a board member, including a public board seat at Casey’s, and credits the seat switching with giving her perspective her day-to-day operating role does not provide. She returns from board meetings, even during her busiest stretches running Oobli, with renewed clarity on her own job.
CEOs 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, there are two ways to go further: Apply for Executive Coaching | Apply to Be a Guest on The Scaling Executive Podcast
