Wearing All the Hats: The Reality of Gaps in Startup Teams

Startups move fast. People jump between roles. And some days, it feels like everyone is wearing five hats at once. This blog shows what that actually looks like inside a small tech company.

Key Takeaways

  • Real value comes from connecting departments. Strategy only works when product, marketing, and operations move together.

  • Listening before acting matters. Spending the first weeks observing the business helped shape smarter decisions.

  • Flat teams move faster. When hierarchy is light, people speak up and better ideas surface.

Notable Quotes

  1. “Everybody is so busy just trying to make everything function that you often don’t have the time to think strategically.”

  2. “There was a gap to fill, so I just ended up filling it.”

  3. “Give that person who isn’t the exact right fit a chance because you might need a different perspective.”

Real-World Applications (with examples)

  1. Step into functional gaps without waiting for permission
    Example: Marketing loses its lead. A product manager with strong writing skills temporarily handles key campaigns so launches stay on track.

  2. Bring in people with unconventional backgrounds
    Example: A retail-focused UX designer joins a cybersecurity startup. Their fresh point of view leads to clearer onboarding and higher user adoption.

  3. Use quick learning as a core skill, not an afterthought
    Example: A newly hired generalist uses AI tools to learn a new system in a week. They end up owning a major piece of the workflow because they can move faster than expected.

Startups don’t run on perfect org charts. They run on people who learn fast, fill gaps, and help teams pull in the same direction. When roles shift and hats stack up, the ones who stay curious and adaptable make the biggest impact.

 
 

Time Stamps:

00:29 PTO and Work-Life Balance

01:53 Sabrina's Career Journey Begins

02:58 Transition to Strategy Consulting

04:15 Joining Remo Three

05:30 Challenges and Adaptations in a Startup

13:25 Evolving Role and Future Plans

26:38 Advice for Aspiring Chiefs of Staff

 

About The Author

Emily Sander is an ICF-certified leadership coach with more than 15 years of experience in the business world and the author of Hacking Executive Leadership. She’s been featured in several print publications, online articles, and podcasts, including CEO Today Magazine, Leading to Fulfillment, and Leadership Powered by Common Sense. 

Emily has a passion for helping business leaders reach their full potential. Go here to read her story from seasoned executive to knowledgeable coach. If you want to send Emily a quick message, then visit her contact page here.

Next
Next

The Secret to Great Teams: Understanding Core Human Drives (Learn, Acquire, Defend, Bond)