About Jackson

Hi, I'm Jackson.

I like my problems the way I like my hiking trails: messy.

  • Based in: Portland, Oregon
  • Outside of work: Hiking, snowboarding, traveling
  • Professionally: I help growing companies untangle operational problems.
Jackson hiking in Sedona

Outside Work

I like going places I haven't been before.

For example, I spent two months working on farms across Italy. The food was incredible. Shoveling horse manure was less so.

I've hiked through the Pyrenees in Catalonia, somehow ended up partying with a country band in Cambridge, and taken a surfing trip through Mexico.

I tend to like trips where I don't quite know how everything is going to go. Give me somewhere new, a lot of walking, good food, and a few things going slightly wrong, and I'm pretty happy.

Jackson hiking the Pyrenees with friends
Hiking the Pyrenees in Catalonia
Jackson snowboarding near Portland
Snowboarding close to home
Jackson completing a muddy obstacle run
Occasionally choosing the muddy option

Where Next

The list keeps growing.

  • England: May 2027
  • Iceland: Fall 2027
  • Japan: Winter 2027
  • Mt. Hood: Snowboarding close to home
Jackson Riso at work

My Work

I help fast-growing startups create systems that enable humans to do human work.

Business Process Consultant & Automation Expert

I get machines to do machine work so people can spend more time doing the work that actually needs judgment, context, creativity, and care.

I began my career interpreting tech speak for marketers and marketing speak for engineers. That mix of business and technical thinking eventually led me to managing marketing and engineering teams inside fast-growing companies.

Over time, I found myself drawn less to any one function and more to the systems connecting all of them. I choose to build with simple-to-use automation tools like Airtable and Zapier when they are the fastest practical way to get clients where they want to go.

After working in almost every role inside fast-growing companies, I got very good at seeing the big picture of how a company operates and how all the little pieces need to fit together.

The same pattern shows up again and again:

  1. demand grows
  2. the team grows
  3. tools get added
  4. workarounds pile up
  5. processes become harder to trust
  6. the business starts to feel slower, messier, and more fragile than it should

That is the point where I tend to get involved.

Today, I help companies fix broken processes, connect systems, reduce manual work, and build operations the business can actually run on.

My Core Philosophies

The ideas I come back to on almost every project.

Your systems need to be simple

If you cannot explain your systems to a fifth grader, you do not fully understand them. The easiest way to do this is to keep things simple. Software developers have a version of this: "You have to be twice as smart to fix a bug as you were when you wrote the original code." The same is true when redesigning automated systems.

Growth comes with sacrifices

If we want to automate something, we cannot accept every possible variation coming down the pipeline. With focus and clarity, we can take one tiny step in a good direction. Potential hiccups matter, but they should not stop useful progress.

Trust the person on the ground

I like working directly with the person closest to the system: the person who struggles through the day because of the current process. They are usually hyper-aware of what is not working, which gives us invaluable insight.

Focus on the pain

Many people have big ideas for what they want to add, but it is more important to start by solving a real problem that already exists. If no one is in pain over it, it probably should not be first on the list.

Why Clients Hire Me

Clients usually need more than strategy and more than execution alone.

I understand messy problems quickly

Clients often come to me when they know something is off, but cannot yet explain exactly what is broken. I like turning that vague operational pain into something concrete and solvable.

I implement directly

I do not stop at identifying the issue. I make the changes, build the system, document what matters, and help the work move forward.

I care about team adoption

A better process is only useful if the people running it understand it and trust it. Training the team is not an afterthought for me. It is a core part of the work.

Proof

A few things clients have said.

Across clients, the feedback is usually consistent: I understand problems quickly, implement practical fixes, and help teams work better without adding unnecessary complexity.

Marcus Arcabascio

Marcus Arcabascio

COO, CoastFi

“From the first call, I knew Jackson was the most knowledgeable person I had talked to about business automation.”

Sam Wilcoxon

Sam Wilcoxon

CEO & Co-Founder, Storetasker

“Jackson’s secret power is his ability to automate nearly everything he touches.”

Start Here

If this sounds like the kind of support you need, let’s talk.

Start with a free 30-minute diagnostic. You walk me through what feels broken, messy, fragile, or harder than it should be, and I will help you get clearer on what is actually going on and what the best next move is.

Book a Free 30-Minute Diagnostic