Let’s find out if this is the right moment to work together.
Most conversations start with The Bearing Diagnostic. If you've already taken it, or you already know what you're dealing with, book a call with John directly or email him at john@flagandfrontier.com.
Want to get the most from our conversation?
The Bearing Diagnostic will show you where belief is aligned and where it’s fractured. Taking this assessment ahead of time will help me know where to focus in our conversation together.
17 questions · Personalized findings · Clear next steps
Book a call with John.
A 30-minute call. No pitch unless you want one. Just a conversation about your situation and whether Flag & Frontier is the right fit.

Common Questions
Flag & Frontier works with a small number of companies at any given time. The right engagement is one where the stakes are real, the executive team is willing to do the thinking together, and the goal is durable alignment, not a deliverable to file away.If you're looking for a marketing agency, a brand refresh, or someone to validate a direction you've already decided on , this probably isn't the right fit. If you're looking for someone who will tell you what you need to hear, stay in the room, and have skin in the game, let's talk.
We could give you our own definition. Or just let one of our clients tell you:
"Before working with John, we were stalling on major decisions despite serious efforts to find our direction. John pushed back on our thinking and brought clarity, giving us the confidence we needed to finally move forward."
— Matt Kent, CEO, Q-PAC
I always work with the CEO, the CMO (or equivalent role), plus a select group of team members who are involved in making strategic decisions for the company. This typically means the heads of marketing, product, sales, finance, and other key roles.
It typically takes 6–10 weeks to get your team aligned on your category strategy and strategic narrative. Long-term advisory partnerships are available in 12-month terms.
Marketing agencies are great for execution work. But they aren't wired for the candid conversations and executive-level thinking that next chapter strategy requires. They're worried about deliverables; I'm worried about surfacing the truth. I often advise my clients' agencies on how to translate our vision into action.
When strategic work fails to land, it can happen for a few reasons.
The most common one we see is when someone internal attempts the work. When it gets derailed, it’s because building shared belief across departments rarely succeeds when the work is owned by one of them.
But strategy work can fail from the wrong engagement model with an external partner, too. Usually, a thoughtful strategy deck gets created and shared with much fanfare. But no one has skin in the game to bring it life.
Flag & Frontier was built around outcomes, not deliverables. We build belief across your entire executive team, not just within the department that hired us. And we stay with you on the journey long after the initial work is complete.
Clients typically spend between $60,000–$100,000+ on an initial engagement. My long-term advisory partnerships typically range between $10,000–$25,000 per month.
Three reasons to explore a partnership:
- Your competitive situation is shifting.
- Executives have conflicting views about the future.
- You know you have something special, but no one can see it.
You might also need help if: you just raised a VC/PE round and need to chart the next phase; you're preparing for an IPO; you recently went through a leadership transition; a competitor just leapfrogged you; your mojo feels off but you can't put your finger on why; or your team can't agree on the product roadmap.