Revenue Leadership

DRAFT for Kyler’s review. Not for publication.

Build the team, then build the leaders

Lessons from scaling commercial organizations quickly without losing the bar.

I have scaled commercial teams fast more than once. At Patmos I took the commercial organization from 3 to more than 40 people in about eight months, across sales, strategic growth and site acquisition, customer success and support, professional services, marketing, PR and revenue operations. Years earlier at AWS, I helped scale a new sales segment from 50 to more than 300 sellers as a bar raiser and hiring manager.

Speed is not the hard part. Keeping the bar while moving fast is.

Hire for the job eighteen months out

When a company is growing quickly, the role you are hiring for today will look different in a year and a half. I try to hire people who can do the current job well and grow into the next one. That means looking hard at how candidates learned in past roles, not just what they accomplished.

Single-threaded ownership

Every account should have one accountable owner. Specialists support on a dotted line, but the customer and the leadership team always know who owns the outcome. Shared ownership feels collaborative, but in practice it means no one owns the hard conversations.

Lead from the front at the moments that matter

I hire and coach the team, and then I step in personally on the moments that matter, from first enterprise closes to the largest terms. At Electric Era, I took a national warehouse retailer from an unqualified opportunity to a closed deal within my first two weeks by stepping in and coaching the team through the close. The point was not to be the hero. It was to show the team what the bar looked like, in a live deal, early.

Promotion is the real metric

Between 2021 and 2023, 39% of the 40-person AWS organization I led was promoted. I am prouder of that number than of most revenue numbers, because it compounds. Leaders who grow leaders create organizations that keep performing after you leave the room.

Practically, that means coaching on real work: annual planning, half-year business reviews, and deal strategy. It means giving people stretch scope before they feel fully ready, and backing them when they stumble.

New teams can outperform

One of my favorite results is a new AWS district of sellers with under one year of tenure that reached 119% attainment. New teams can outperform tenured ones when the operating model is clear, the territories are well designed, and leaders spend their time coaching rather than reporting.

What I bring as a fractional leader

Design the organization before you fill it

Fast hiring without a clear structure creates overlap and confusion. Before I open roles, I define the coverage model: which segments and accounts each team owns, where specialists sit, and how customer success, professional services and support connect to the sellers who signed the customer. At Patmos that meant building customer success and support teams in more than one location, with clear lines of ownership back to the account.

I also write the operating plan early. At AWS, I authored the operating plan and coverage model for a 35-seller organization that doubled partner-attached wins and grew daily run rate 50% against a 35% North America baseline. Good structure is a performance multiplier.

Coach on real work

Training programs matter, but most growth happens in live deals and real planning cycles. I coach junior account executives through their own opportunities, run annual planning and half-year business reviews as teaching moments, and make sure every manager spends meaningful time in the field with their team.

One example: I led a 7-person AWS account team on a strategic healthcare partner, growing revenue 6x in two years and winning competitive bids against the incumbent. The team grew as much as the account did, because every person owned a real piece of the outcome.

As a fractional CRO or CCO, my job is to build the system and the bench so the company does not need me forever. That means hiring plans, interview loops with a real bar, onboarding that gets sellers productive quickly, and a clear path to the permanent leader who will eventually own the function.

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