The operator who hands founders their company back

I’m Jason Jackson, and I’ve spent two decades building and fixing the working parts of companies: the operating systems, the revenue processes, the teams, and the numbers.

I entered this career through a back door and fell in love with it.

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$Jason Jackson, fractional COO and operating partner behind Redwood Ridge Strategies$

This job began in a newsroom

Years of journalism taught me to ask the question the other reporters were avoiding, and to let people finish their answers. Product and operations came next, and I spent most of that time walking into messes and turning them into something that could grow. I started Redwood Ridge to do that work for the founders getting the least help.

Why she picked my team

I walked into the office early one morning, usually the first one in, and saw a light on in a small conference room. The best QA engineer on the team was sitting in there alone, crying. I knocked and asked what was wrong. She kept saying the same thing: “I missed it. I missed it.” A bug had shipped, and she’d found it. In a company where blame landed on QA first, she was sure she’d let the team down. Her life outside work was coming apart at the time, and this was where it surfaced.

The bug was small. I told her: “You didn't miss it. You caught it.”

At that company, QA engineers chose which product teams they worked with. For years after that morning, she picked mine first.

Growth-stage companies are full of people like her, and the founder often can't see it: when the operations land on you alone, there’s no time left to look.

The systems and the numbers matter, and so do the people carrying them.

Most of this work is systems: the cadence, the pipeline, the numbers. I build them around the people who’ll own them: how decisions land with the team, whether your managers can carry what you hand them, what holds a culture together when the headcount crosses 30.

Half the skill is seeing what a person can carry before they see it themselves. When I’m picking who to bet on, I want the one who watches a magician and needs to know how the trick was done.

One of the best bets I ever made was on an elementary school teacher with no technology background. It was his first paid job in tech, and I pushed for him because he needed to know how things worked. Today, he leads the flagship product at an enterprise software company.

The systems stick when they fit the people

Jason Jackson, operating partner, coaching a growth-stage founder in a working session

I work with growth-stage founders

Most of my work is with the people running companies between $1M and $10M in revenue who are on every sales call and trying to remember their last weekend without a laptop.

They’ve got something good, but the company can’t grow past them yet. My job is to change that.

In one engagement, a founder’s week went from 80 hours to 55 and revenue climbed 45% inside six months. In another, employee attrition dropped from 35% to 4%.

I set aside capacity for founders who often are overlooked

I make time for founders running on conviction and short cash. Often that’s women, immigrants, and people building something mission-driven. I do that work at the advisory level, free or close to it. If that’s you, say so when you book the call.

In their words

He effortlessly provides an empathetic ear while pinpointing the root cause of issues… Jason's insights, command, candor, and kindness, along with a touch of humor when needed, make him a respected leader.

— Michael Hirsch, Suzy, Inc.
His dedication to mentorship has nurtured promising individuals into leadership roles… Jason is a delight to work with. His positivity, even in the toughest of situations, has always been contagious.

— Marina Ilishaev, Boardstream AI
One of Jason's greatest strengths is in building up a rock-solid cross-functional team that is far greater than the sum of its parts. It's often said that one should look for people that use 'we' more often than 'I' in conversations. Jason embodies that trait in everything he does.

— Rebecca Nathenson, PandaDoc

Next Gear is my free 10-minute weekly read for more than 10,000 growth-stage founders and execs. I write down the hard lessons from operating to save you some of the pain I went through, so you can scale your company without breaking it. If you want a feel for how I work before you book anything, start there.