Advisory
Scaling to $50M+ requires a different playbook than the one that got you to your first $10M — and it's one of the hardest stretches in the journey.
I work with a small number of founders and startup CEOs each year who've already proven the business works. The hard part now isn't the idea, or the grind — it's things you haven't done before: making your first real senior hires, keeping culture intact as headcount grows, developing a revenue expansion strategy, building financial clarity into how you make decisions, and knowing when to push harder versus when to be patient with the business.
I work best with founders who are already winning — revenue is real, the team is growing, customers love the product — but you're running into completely new challenges. Not because you're doing anything wrong. Because the job has genuinely changed.
What Makes This Different
I'm not a mindset coach and I'm not a consultant who hands you a deck. I've been a CEO — I've made these decisions, built these teams, and felt the weight of these tradeoffs. I help founders make the call, hire the right person, fix the system, and move — with the strategic clarity and the honest conversation about what's actually in the way.
I've been a 2x CEO, VP at HubSpot (NYSE: HUBS), and spent 10+ years in the C-suite at The Motley Fool (a $400M+ revenue company). I was CEO/Advisor at The Hustle and was most recently CEO of Hampton.
What People Say
Jordan is my go to. I trust him implicitly. He helped me think through MAJOR changes in multiple businesses and then gave me exact templates and roadmaps to break through.
For the first time in 2 years, I can feel momentum. He's helped me make a mental shift from regression and fear to progression and ambition.
He brought a level of clarity and strategic direction that our leadership team didn't have before. The accountability framework he built for us completely changed how we run our business.
Jordan understands growth at a deep, structural level. He's one of the few people who can zoom out on strategy and zoom in on execution in the same conversation.
If you want someone real, who genuinely cares and gives it to you straight, Jordan's your guy. He's helped me stay focused and consistent toward my goals, but what I value most is how he challenges me. He doesn't just give me new ideas, he gets me to think differently.
Jordan is one of those rare advisors who actually gets it — he's been in the seat, made the hard calls, and doesn't sugarcoat anything. Every conversation moves the needle.
A few ways to work with me:
Single Session
A focused, high-impact conversation. One call, one problem, full clarity. No ongoing commitment.
Learn MoreOngoing Advisory
A real thinking partner — not just quick answers, but a trusted person in your corner for the long run. I work 1:1 with a small handful of CEOs each year on a biweekly basis.
Learn MoreFounder Handoff
For founders ready to step out of the CEO seat. I work alongside you and your executive search to find, vet, and transition a full-time CEO into the role — so the company doesn't skip a beat.
Learn MoreLeadership Sprint
Accelerated leadership training for your direct reports, which runs in parallel with the founder. I work side by side with your key hires on: communication levels, decision frameworks, escalation, and how to lead other leaders. You stop being the bottleneck because they've become better, faster.
Learn More