Resources for Business Owners & Leaders
Jane Gentry on operating models, decision rights, and what growth does to a mid-market company.
- Date
- October
- 2025
- Author
- Jane Gentry
You walk into a team meeting and something feels…off. The energy’s changed. The urgency is different. The spark—the shared sense of “how we do things here”—has faded. This isn’t just about headcount. It’s a sign your culture has lost its visibility.
- Date
- October
- 2025
- Author
- Jane Gentry
The data shows a trend every CEO scaling past $20M should pay attention to. Employees are doubling their use of new digital and automation tools, yet 95% of organizations report no measurable ROI.
- Date
- September
- 2025
- Author
- Jane Gentry
Your company’s growing fast. Revenue is up. Headcount has doubled. But decision-making? It’s crawling. Everyone’s waiting for answers. Meetings are multiplying. Execution is slowing. And you’re wondering:
- Date
- August
- 2025
- Author
- Jane Gentry
You’re growing fast. Revenue’s up. Headcount’s climbing. So why does everything feel harder—not easier? Sound familiar? You’re not broken. You’re just experiencing growing pains.
- Date
- March
- 2025
- Author
- Jane Gentry
If you’re a mid-market CEO in a season of growth, you’ve probably said some version of this recently:
- Date
- June
- 2024
- Author
- Jane Gentry
The days of producing a mediocre product/service and leveraging a powerful marketing engine to overcome deficiencies are over. Today’s buyer demands high quality and innovation. This has changed what strategy means to a business leader. Now, strategy is like building the plane while you are flying it. It requires continuous innovation, listening to the marketing and adjusting.
- Date
- June
- 2024
- Author
- Jane Gentry
As a CEO or leader, you are at the helm of steering your businesses through the choppy waters of competition, market changes, and internal challenges. How do you decide where to take the business or your offering? Here are four strategy frameworks that can empower you to chart your next steps.
- Date
- June
- 2024
- Author
- Jane Gentry
In a tough labor market, it can be tempting to keep an employee who is difficult or disruptive to the organization just to have a role filled. Too often though, leaders don’t realize the impact on productivity and engagement a toxic employee can have on the business’ culture. Unveil the hidden impact of toxicity on your business.
- Date
- June
- 2024
- Author
- ane Gentry
There comes a time in every leader’s journey when they must ask themselves a difficult question: “Is it time to fire myself?” The thought of stepping back as the CEO can be daunting. It’s not just about relinquishing control; it’s about acknowledging that the organization might benefit from a change in leadership.
- Date
- May
- 2024
- Author
- Jane Gentry
For many business owners, the idea of passing the torch to their children is not just a succession plan; it’s a legacy. It’s a way to ensure that the fruits of their lifelong labor continue to flourish within the family. However, before you decide to hand over your most valuable asset to your child, there are critical considerations to ensure that this transition benefits both the business and your family’s future.
About Jane Gentry
Jane helps CEOs redesign how their business actually runs—structure, roles, decision rights, and operating rhythm—while bringing their teams through the change with them. She knows the model doesn’t change just because the slide says it should; she works with leaders to reset expectations and ways of working in a way people can absorb, so the organization gets faster and sharper without losing the talent they can’t afford to lose.


