Aaron Klein
Founder / operator coaching + advisory

Turning the journey into repeatable lessons.

After building Riskalyze from a basement startup through 42 consecutive quarters of growth, I learned a lot of lessons—most of them the hard way. Now I bring that operating experience to a small number of leaders who are trying to get from here to there.

See if there’s a fit
Aaron Klein smiling at his desk in his study.
How I love to help

I help CEOs and leadership teams find their way through the jungle.

Sometimes the company is doing okay, but nobody can pinpoint what is driving success and what is a waste of time. Sometimes the team is rowing in a million different directions. To which I say: welcome to the jungle.

“I’m trying to figure out how to get us from here to there, and I can’t admit this to anyone, but I feel lost in a maze.”
“We’re doing okay…but honestly, I can’t pinpoint which things are driving our success and which are a waste of time.”
“I try to communicate to my team which way to go, but at times it feels like they are rowing in a million different directions.”
4,661days of learning
42straight quarters of growth
1hard-won operating perspective
A few of the people I’ve had the pleasure of serving

Outside perspective. A clearer path.

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

The operating questions that will not wait.

Product / market fit

Dig deep into customer feedback and product strategy until the path becomes repeatable.

Transformative AI

Find the places where AI can change the business and the team, not just speed up a task.

Pricing

Quantify what to charge and why, so value creation and value capture finally line up.

Messaging

Untangle the story so the market can understand what the product makes possible.

Path to Victory

Stress-test the strategy against valuation, addressable market, and input metrics.

Shared clarity

Create alignment around mission, vision, values, strategic initiatives, and objectives.

I’ve also helped leaders fix talent problems, hire amazing people into key roles, navigate board and investor issues, manage calendar and time allocation, and embrace work / life integration as high-performing leaders do.

The relationship

Direct, practical, and intentionally small.

See if there’s a fit

  • Two 90-minute coaching calls every month.

  • Video calls are highly preferred, telephone calls when schedule demands

  • Crisis help via text message in between

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

  • Subject to availability: optional projects or engagements like strategy offsites