Advisory for founders, operators & CEOs

Turning the journey into repeatable lessons.

The next hire. The pricing change. The strategy that made sense six months ago. When you’re building a company, the decisions keep coming.

I advise a small number of founders, operators, and CEOs on the decisions that shape their companies. I bring the perspective of someone who built Riskalyze through 42 consecutive quarters of growth and is back at it today with Contio.

See if there’s a fit
Aaron Klein smiling at his desk in his study.
The conversation behind the decision

Bring the question you keep coming back to.

You’ve heard your team’s recommendations. You’ve looked at the numbers. You’re still turning it over on the drive home. That’s a useful place to start. We can get underneath the problem, challenge the assumptions, and work out what to do next.

Founders

What will make this business work?

Find the customer, product, pricing, and story that give the company a reason to win.

Operators

How do we turn the plan into progress?

Get the right people on the right priorities, with clear decisions and accountability that sticks.

CEOs

What does the company need from me now?

Work through the calls on strategy, talent, boards, and where your attention will make the greatest difference.

4,661days of learning
42consecutive quarters of growth
1founder still building
A few of the leaders I’ve worked with

The work, in their words.

Portrait of Robert Sofia.
“Working with Aaron has been a game changer. If you’re stuck, he is the perfect guide to help you see the path to take, and come out stronger on the other side.”
Robert Sofia · CEO, Snappy Kraken
Portrait of Phil McDaniels.
“Aaron helped me think through how to pivot my business to a new approach. It’s amazing how an outside perspective can help you find new paths to success.”
Phil McDaniels · CEO, Breakthrough
Portrait of Adam Ponder.
“Aaron helped our leadership team get aligned. The shift at Alta Trust is profound—clear priorities, real accountability, and momentum we can feel.”
Adam Ponder · CEO, Alta Trust
Portrait of Jason Barber.
“Over the past three years, partnering with Aaron ranks among my best decisions. Beyond his impact, I’m grateful to now call him a friend.”
Jason Barber · CEO, Holistic Planning and Uptick Partners
Two people in a thoughtful strategy conversation at a table with notes and coffee.
Where I can help

Let’s get into the business.

Strategy & focus

Make the hard choices about where to compete, how to win, and which good ideas to leave behind.

Product, pricing & growth

Get closer to what customers value, what they’ll pay for, and the story that makes it click.

Talent & leadership

Think through a pivotal hire, a struggling executive, or a team that needs a higher standard.

Execution & accountability

Translate the strategy into a few clear priorities, decisions people can own, and work that gets finished.

AI & the business

Find where AI can change what you deliver, how your team works, and what your customers can achieve.

Boards & big decisions

Prepare for the board conversation, pressure-test an investor decision, or get perspective on a turning point.

Sometimes the most valuable work is deciding what deserves your time. We’ll look at your calendar, your role, and the tradeoffs that come with building a company and having a life.

The relationship

A few relationships. Room to go deep.

I’m building a company, too. I keep my advisory work deliberately small so I can know the business, understand the people, and be useful when the next hard decision arrives.

See if there’s a fit
  • Two 90-minute advisory conversations each month, focused on what matters most in your business.

  • Video calls whenever possible, with phone calls when schedules require it.

  • Help by text between sessions when a crisis hits.

  • A flat monthly fee, paid in advance on the first. Cancel any time before the end of the month.

  • Strategy offsites and other focused engagements, subject to availability.