Meet the operator in the engine room
I’m Jason Jackson, and I’ve spent two decades down there. I build and fix the machinery underneath companies: the operating systems, the revenue processes, the teams, and the numbers.
I came to it sideways. I started as a writer and editor, then found I liked solving the problems more than writing about them.
The writing came first
Years of journalism taught me to ask the question nobody else in the room would ask, and to listen all the way to the end of the answer. Product and operations followed, at companies you've heard of and a couple you haven’t, most of it walking into messes and turning them into something that could grow. I started Redwood Ridge to do that work for the founders who need it most.
Most operators skip this part
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, and 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. The catch was the job. I told her so: “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.
I tell that story because most of the founders I work with have people like her carrying more than anyone’s acknowledging. They can’t see it, because they’re underwater in the operations only they seem able to do.
The systems matter. The numbers matter. 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 run them: how decisions land with the team, whether your managers can carry what you hand them, what holds a culture together when you cross 30 people.
Half the skill is seeing what a person can carry before they see it themselves. Show me someone who watches a magician and has 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 had to know how things worked. Today, he leads the flagship product at an enterprise software company.
The systems stick when they fit the people
I work with growth-stage founders
Most of my work is with growth-stage founders, the people running companies between $1M and $10M in revenue who are on every sales call, half-fixing every bug, and trying to remember their last real weekend. They’ve got something good, and the company can’t grow past them yet. My job is to build the systems and the people around them so it can. In past engagements, that’s meant one client’s week cut from 80 hours to 55, and employee attrition down from 35% to 4%.
I set aside work for founders who get overlooked
I make time for founders running on conviction and short cash. Often that’s women, immigrants, or someone building something mission-driven. That work happens at the advisory level, free or close to it. If that's you, say so when you book the call.
In their words
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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.
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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
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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
I write The Next Gear, a free 10-minute read that goes out to more than 10,000 growth-stage founders and execs every Wednesday. It’s the hard lessons from operating, written to save you some of the pain I went through. If you want a feel for how I work before you book anything, start there.
Check my work first
The next step is a conversation
This page was about me. The call is about your company and what I’d look at first. You leave with something useful even if we never work together.