Podcast Guest: Culture as a Catalyst: Keys to Successful Business Operations, with Jen Hamilton

Jen Hamilton was a featured guest on an episode of The Scalability Code Podcast.

Host Matt Haney, Fractional COO and founder of Sinclair Ventures, talks with Jen about how fractional executives help owners get out of the weeds, hold their teams accountable, and rebuild businesses that don’t require heroics to run.

Every visionary hits a point where grit isn’t enough—and no amount of team “pep talks” will fix what’s actually broken. 

If you’re constantly hearing yourself say, “Why can’t my team just take initiative?” or “Why does everything still depend on me?”—you’re not alone. You're also not broken.

In this episode, Fractional COO and Founder, Jen Hamilton, offers a clear-eyed look at what those symptoms really mean—and how to stop building a business that runs on burnout.

1. When Accountability is Lacking, Look at the System—Not the People

One of the clearest signs you need a new operating approach? When your team isn’t doing what they promised—or you keep hearing yourself complain about it.

“If you're saying, ‘My people aren’t accountable’ or ‘They don’t take initiative,’ that’s the symptom. But it’s not the root problem.”
— Jen Hamilton

Instead of jumping to replace a team member, examine the clarity of their role, the tools they have, and whether their success metrics are actually measurable.

2. Great Hiring Is Built on Clarity—Not Perks

Jen debunks the idea that today’s workforce is just “too demanding.” People aren’t asking for ping pong tables and catered lunches every day. They want meaning, mastery, and flexibility.

“It doesn’t have to be expensive. A book club, real feedback, clarity around expectations—those things make you stand out.”
— Jen Hamilton

In interviews, talk more about how you lead and how you grow people—not just what the job is.

3. Red Scorecards Don’t Mean Failure—They Mean Feedback

If your scorecard shows red every week, it’s not necessarily a crisis. But it is an opportunity to reframe and recalibrate.

“Metrics are just feedback. They’re not grades. They’re not your worth as a human. They’re the dashboard of your business.”
— Jen Hamilton

Instead of punishing red, start with a question: “Is this metric giving us useful feedback, or do we need to adjust it?”

4. The Best Leaders Don’t Rely on Control—They Rely on Structure

If your team only performs when you’re watching, that’s not leadership—it’s dependency. Jen encourages owners to look in the mirror.

“If you can’t trust what’s happening when you’re not in the room, that’s not a structure issue—it’s a leadership one.”
— Jen Hamilton

Build scorecards and 90-day priorities that don’t require you to micromanage. Structure creates freedom.

5. Ideal Engagements Last a Year—Because Change Isn’t Instant

Jen shares her take on how long it really takes to implement a better operating rhythm—and why most Fractional COO engagements that succeed last 12 months or more.

“You’re not just hiring a fixer. You’re implementing a whole new operating approach. That takes a full cycle—and a bit more.”
— Jen Hamilton

Plan for a year. Use that time to redesign your org chart, hire and onboard better, and rebuild how decisions get made.

Let’s Make This Personal

Ask yourself:

• Are you frustrated that your team isn’t stepping up—or are they unclear on what “stepping up” even looks like?
• Do your metrics feel like judgment—or invitations to solve problems together?
• Are you still leading through control… or are you building a business that leads itself?

If you’re nodding, you may not need a new team—you may need a new system.

Next Steps

Here’s how to start moving from founder chaos to team clarity:

1. Audit Your Metrics: Are they measuring feedback—or silently shaming your team?
2. Clarify “What Good Looks Like” for every role—especially the ones you’re frustrated with.
3. Build Flexibility Into the Structure: Not perks, but real autonomy tied to accountability.
4. Use Scorecards as Dashboards: If everything’s red, don’t hide it—discuss it.
5. Bring in a Fractional COO for a Diagnostic: Even one conversation can surface what’s truly holding you back.

You don’t need more grit—you need more structure. When your business has an operating system that doesn’t depend on your heroic effort, everything changes. Your team steps up. Your revenue stabilizes. And you finally get your evenings back.

Ready to stop duct-taping problems?
Book an Education Session to see if it is time for a Fractional COO or if you need a different operations solution.