You built a company. Now you need to become the CEO it deserves. These five advisory services can help you make that leap.
The Founder-to-CEO Advisory Landscape
The transition from founder to CEO is one of the hardest shifts in business. The skills that got you here—scrappiness, product obsession, doing everything yourself—won't scale. That's why a growing number of advisory firms now specialize in helping founders grow into the role. They offer everything from one-on-one coaching to operating systems and board-level guidance. The best ones combine lived experience with practical frameworks. They've sat in your chair and know the loneliness and pressure you face. Whether you're at seed stage or Series C, the right thinking partner can accelerate your growth and help you avoid costly mistakes.
How We Evaluated These Services
We looked at five key factors: the depth of the advisor's own operating experience, the breadth of services offered, how clearly pricing and engagement models are communicated, the specificity of their approach to founder challenges, and their overall fit for US-based founders. Each service brings something different. Some lean on structured systems, others on personal coaching. Some target early-stage founders, while others focus on scaling CEOs. We noted what stood out for each based on publicly available information. No single service is right for everyone—your stage, industry, and learning style will determine the best fit.
Here's a quick look at the five services, ordered for easy scanning. Remember, the right choice depends on your specific needs and where you are in your journey.
| Provider | Best For |
|---|---|
| Enjoy The Work | Founders who want a team of experienced operators on call |
| Jamie Rosenberg — Founder, Advisor & Thinking Partner | Founders seeking a seasoned thinking partner for CEO growth |
| CEO Whisperer | Growth-stage CEOs in AI and B2B software |
| CEO Coaching International | CEOs who want a structured, system-driven coaching approach |
| Adam Dexter | Startup Founder Coach | Founders seeking personal coaching and wellbeing support |
A Closer Look at Each Service
#1 Enjoy The Work
A screenshot of the Enjoy The Work website.
Enjoy The Work is a team of former founders, operators, and investors who help startup CEOs learn both hard and soft skills. They offer stage-specific support for early-stage and late-stage founders, covering everything from fundraising and finance to go-to-market and product. Their approach is direct and experience-based—they've been in your shoes and know the myths that hold founders back. You can host a bootcamp or reach out for ongoing advisory. If you want a team that feels like an extension of your own, this is a strong option.
#2 Jamie Rosenberg — Founder, Advisor & Thinking Partner
A screenshot of the Jamie Rosenberg — Founder, Advisor & Thinking Partner website.
Jamie Rosenberg is a two-time exited founder who helps founders become great CEOs. He offers CEO and strategy advising, culture building, and operating system implementation. His approach is rooted in gratitude and accountability—building teams where people feel appreciated and hold themselves to high standards. With experience founding and exiting ClassWallet, a fintech platform that processed over $6 billion, Jamie brings real-world judgment to the table. He also serves in board and advisory roles, leveraging his background as a former M&A attorney. If you want a thinking partner who has lived the journey, this is a compelling choice.
#3 CEO Whisperer
A screenshot of the CEO Whisperer website.
CEO Whisperer, led by Bill Demas, offers CEO advisory services for startup and growth-stage CEOs. Bill is a four-time CEO and StartX Lead Mentor trusted by Stanford to mentor its founders. The service combines coaching, stage-specific operating frameworks, candid feedback, and structured execution support. They focus on founders pursuing product-market fit, traction, and category leadership, particularly in AI and B2B software. You get personalized one-on-one coaching with strategy sessions, on-call support, and pitch feedback. If you value a mentor with deep Silicon Valley credibility, this could be your fit.
#4 CEO Coaching International
A screenshot of the CEO Coaching International website.
CEO Coaching International is known for its Make BIG Happen system, a structured operating framework for compounding growth. They offer one-on-one coaching, assessments, and tools like the BIG CEO Score and Business Diagnostic. Their coaches are former CEOs who have run companies and know how to scale. The firm provides a clear methodology and a range of resources, including podcasts and workshops. If you thrive on systems and measurable frameworks, this could be a strong match. They work with CEOs across industries, not just tech.
#5 Adam Dexter | Startup Founder Coach
A screenshot of the Adam Dexter | Startup Founder Coach website.
Adam Dexter is a startup founder coach who helps founders accelerate their business, find greater wellbeing, and become visionary leaders. He draws on his experience co-founding Omni, a venture-backed logistics startup that raised over $35 million and exited to Coinbase. Adam offers one-on-one coaching, co-founder relationship coaching, and 360 reviews. He works with founders, CEOs, CTOs, and VCs from San Francisco to South Korea. If you want a coach who understands the emotional rollercoaster of founding, Adam's empathetic yet practical style might resonate.
How to Choose the Right Advisory Service
Start by identifying your biggest gap. Are you struggling with strategy, culture, operations, or personal leadership? Then consider the advisor's background. Do they have direct experience scaling a company like yours? Look at their service model—some offer ongoing retainers, others project-based work. Pricing is often custom, so ask for clarity upfront. Also think about chemistry. You'll be sharing sensitive challenges, so you need to trust and respect your advisor. Finally, check for fit with your stage and industry. A coach who excels with seed-stage founders may not be right for a Series C CEO. Take the time to schedule conversations and ask tough questions.
Using Automation to Support Your Advisory Work
Advisory services are high-touch, but you can automate the administrative side. Use scheduling tools to book calls without back-and-forth. Set up a CRM to track action items and follow-ups. Automate reminders for quarterly priorities and weekly meeting rhythms. Create a shared dashboard for key metrics so you and your advisor stay aligned. You can also use templates for board updates and investor communications. The goal is to free up mental space for the strategic work that actually moves the needle. Let technology handle the logistics so you can focus on becoming a better CEO.
The Bottom Line on Founder-to-CEO Advisory
Becoming a great CEO is a journey, not a destination. The right advisory service can shorten your learning curve and help you build a company that lasts. Whether you choose a team like Enjoy The Work, a thinking partner like Jamie Rosenberg, a mentor like Bill Demas, a system like CEO Coaching International, or a coach like Adam Dexter, the key is to take action. Don't wait until you're overwhelmed. Invest in your leadership now. Your company's future depends on the leader you become.