Coming Soon in Strategic Leadership

The CRO role is, at its core, a leadership role — one that requires a different kind of judgment than what got you here.

You're no longer running a sales team. You're running a revenue organization that likely spans sales, marketing, customer success, and RevOps. You're managing a board. You're making bets on talent, structure, and strategy that compound over years, not quarters.

This pillar covers the people, career, and organizational challenges specific to the revenue leadership role — including the questions most aspiring CROs are quietly asking but rarely see answered directly.

Here's what I'm working on:

• What a CRO Actually Does — Day 1, 30 Days, 90 Days

  The reality of the first 90 days in the seat — what you're actually doing vs. what you thought you'd be doing. A diagnostic, not a honeymoon.

• The Path from VP of Sales to CRO

  What the jump requires — and the specific things most VP of Sales leaders are missing before they're truly ready.

• The Path from CMO (or VP of Marketing) to CRO

  A real path that gets almost no coverage in this conversation. What it takes, and where marketing leaders should invest to make themselves credible candidates.

• CRO Compensation: What the Role Actually Pays

  Base, variable, equity — the real numbers. How the comp structure works, and how to evaluate and negotiate a CRO offer with your eyes open.

• How to Evaluate a CRO Opportunity

  The diligence questions aspiring CROs never think to ask — about the board, the data, the team, and the true state of the pipeline before you arrive.

• When to Go Smaller to Go Bigger

  The case for taking a CRO title at a Series B vs. waiting for the VP role at a larger company. How to think about the trade-off.

• Red Flags When Evaluating a Company as a CRO Candidate

  The signs that a company will set a CRO up to fail — and how to spot them in the interview process before you accept the offer.

• What Boards Actually Want from a CRO

  The difference between what boards say they want and what they actually reward — told from the inside.

• Building the Revenue Leadership Team

  Who to hire first, how to structure the team, and when to promote vs. bring in outside talent.

• The CRO's Relationship with the CFO

  The most important internal relationship most CROs underinvest in — and how to build it before you need it.

• Managing the Board as a CRO

  What board dynamics actually look like from the CRO seat, and how to manage expectations without managing perceptions.

• Player-Coach or Pure Leader?

  When the CRO should carry a bag — and when that's a sign the company isn't actually ready for the role.

• When to Hire a VP of Sales Under You

  The inflection point where the CRO needs to rebuild the sales org rather than run it directly.

• Culture as a Revenue Strategy

  How the CRO's decisions about team culture show up directly in retention, performance, and pipeline.