If you've ever wondered whether you can restructure your own job description, here's a story worth bookmarking. Stuart Kelly built Zego from the ground up as its CTO in 2016. By the time the company had expanded from gig-economy driver insurance into full-stack coverage for fleets and corporations, he had handed off the executive mantle and carved out a new Staff Engineering role that lets him stay close to the code. The story, shared during a Tech Leaders Hub Fintech session, offers a practical lesson for anyone wrestling with the gap between their job title and their actual interests.
What makes this relevant to project managers and team leads isn't the insurance business—it's the signal it sends about how technical leadership roles can evolve when growth forces organizations to rethink structure.
The Growth Trap: When Scaling Pulls You Away From the Work
Here's what often happens in fast-growing tech companies. The founder-CTO starts as the person who builds everything. Then the team expands, and suddenly you're in meetings all day, managing managers, and fielding investor questions. That's exactly what Kelly experienced.
The irony? The work he originally loved—architecting systems and writing code—kept shrinking in his schedule. Many technical leaders hit a point where their job has evolved into something they didn't sign up for. The challenge is figuring out whether to push through or redirect.
What Kelly Did Differently
Instead of quitting or unhappily staying put, Kelly asked his organization to create a new role. The Staff Engineering position he secured lets him guide software development at a technical level without the executive overhead. This isn't a demotion—it's a deliberate restructuring that acknowledges where he adds the most value.
Zego's platform handles everything from three-minute policies to year-long coverage for thousands of vehicles. That kind of flexible policy management requires deep technical oversight. Kelly identified that need and positioned himself to fill it in a way that suited his strengths.
The move required several things: a strong relationship with the executive team, confidence to make an unconventional request, and skills that transfer across contexts. Which brings us to what Kelly recommends for others considering similar paths.
Skills That Travel Between Roles
Kelly emphasizes three capabilities for tech leaders navigating career transitions:
- Presentation skills** top his list. As a technical leader, you'll need to make cases to engineering teams, brief executives, and keep your own group updated. The ability to communicate clearly under these different contexts determines whether your ideas land.
- Conflict resolution** comes second. Teams grow contentious—it's inevitable. Mediators who can resolve disputes without creating new ones become indispensable as organizations scale.
- Interpersonal relationships** round out the foundation. Kelly credits his existing rapport with leadership for making his role-revision request feasible. Building those connections before you need them isn't optional.
Who Should Care
- Engineering managers considering promotion** who aren't sure whether executive track is right for them
- Individual contributors promoted into coordination roles** who miss technical problem-solving
- Startup founders serving dual technical-business roles** planning for when growth demands delegation
- HR and talent leaders** building career frameworks that accommodate non-linear progression
What This Means for You
Kelly's story suggests a third option exists beyond staying unhappily in a misaligned role or leaving entirely: negotiate a role that fits where you add the most value.
This requires proving your value in the new configuration. It means understanding what the business actually needs from technical leadership as it evolves. And it means having the soft skills to navigate those conversations persuasively.
Bottom Line
Kelly's pivot at Zego won't be the right move for every technical leader. Some thrive in executive roles as companies scale. But if you're quietly dreading your day-to-day while your organization expects you to keep climbing the management ladder, alternatives exist. The key is identifying where you add the most value—and having the relationships and skills to make your case.
Key takeaways
- Technical leadership paths can be renegotiated as organizational needs evolve; you don't have to choose between "executive track" and leaving
- Building strong relationships with leadership before you need a favor makes restructuring conversations far more feasible
- Presentation skills, conflict resolution, and interpersonal rapport are the transferable currency of any leadership transition
- Growth often forces role evolution; proactive planning gives you more options than reactive acceptance
Frequently asked questions
What is a Staff Engineering role and how does it differ from CTO?
A Staff Engineer maintains deep technical influence over a team's architecture and execution without taking on executive responsibilities like fundraising or board reporting. Unlike a CTO, who typically manages managers and corporate strategy, a Staff Engineer stays close to the code while still providing technical leadership.
Why would a company agree to create a new leadership role instead of hiring externally?
An internal candidate already understands the company's technical debt, culture, and systems. For organizations where insurance policy management requires nuanced platform knowledge, retaining institutional knowledge while satisfying a key contributor's career preferences can be worth the restructuring effort.
Does this story apply only to very small companies?
Not necessarily. While early-stage companies offer more flexibility, larger organizations also create individual contributor tracks for senior technical talent. The principle—negotiating a role that matches your strengths rather than accepting a mismatch—applies at any scale.
What should I do if I'm in a leadership role that no longer fits me?
Start by documenting where you add the most value and what the organization actually needs. Build stronger relationships with decision-makers. Then look for gaps in technical leadership that align with your preferences, and propose a restructure that serves both sides.
Are the skills Kelly recommends universally important for technical leaders?
Yes. Presentation, conflict resolution, and interpersonal skills matter whether you're staying in your current role or pivoting. They're the connective tissue that makes any technical leadership effective, regardless of company size or industry.