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Hard problems. Small shop.

Your systems,
in good hands.

We're Jason and Tim. We look after your website and the tools behind your business, connect the ones that don't talk, and build what doesn't exist yet. We work with a small number of clients for the long haul, so we know your setup, and you know exactly who to ask.

Tell us about your setup How ongoing care works

Cleveland, OH · Wareham, MA

Why we're small

Small on purpose.

We want to do good work for people we enjoy working with, and stick around to take care of what we build. A handful of lasting relationships leaves us room to pay attention, solve problems properly, and make something interesting along the way.

  • We know your business. We remember why things were built the way they were.
  • You get both of us. Not a junior and a ticket queue.
  • No handoffs. The people who build it are the people who look after it.

You're probably a good fit if…

  • Your developer or agency moved on, and nobody really knows how your site or app works anymore.
  • You built something yourself, maybe with AI, and now the business depends on it.
  • Your business grew, and your tools didn't keep up. Too many logins, too much copying between systems.
  • You're a small team or nonprofit without an IT person, and you want experienced help with your website and business tools.
  • You've got an idea for a tool, but you assume it's too big or too expensive to build.
Ongoing care

Already running? We'll look after it.

Whether we built it or someone else did, most of the value is in what happens after launch. We keep watch, keep things updated, and keep a running memory of how your setup works, so small problems stay small.

What's covered
  • Monitoring for uptime and security
  • Updates for software, plugins and dependencies
  • Backups, checked so they actually restore
  • Small fixes and changes within an agreed monthly scope
  • A named person who knows your setup
  • A regular check-in on what's working and what's next
How bigger work fits

Anything bigger than routine care, like a new integration, a new tool, or a rebuild, gets its own scope and price up front. No surprise invoices.

Ask about ongoing care More about ongoing care
When you need more

And when you need something built, we build it.

Once we know how your business works, we can see what's missing. That's where the interesting work comes from.

Sound familiar? Data typed into three places that all disagree. A site held together by a plugin nobody remembers installing. IT points at the vendor, the vendor points at the contractor, and it's still broken.

01

Integrations & custom software

Connect the tools you have, and build the one that doesn't exist yet.

02

Operations & automation

Turn the process in someone's head into something that runs itself, with AI used where it actually helps.

03

Infrastructure & security

Hosting, monitoring and incident response, run by people who've done it at fleet scale.

"I'd love that, but it's probably too expensive."

We hear this a lot. More often than not, the thing you're imagining is smaller and faster to build than you'd guess. Ask us. If it's realistic, we'll tell you what it takes. If it isn't, we'll tell you that too.

Some of what we've built →

How it works

Three steps, no sales layer.

1. Tell us what's going on.

A real conversation with the people who'll do the work.

2. Straight scope, straight price.

What we'll do, what it costs, and what it won't do.

3. We build it and keep it running.

Then you stop thinking about it.

Our story

Roommates at Wentworth.
25 years later, back in the shack.

We met as roommates at Wentworth Institute of Technology in Boston, then went off in opposite directions. Jason spent the 2000s on the retail floor: home theater at Best Buy, a district's worth of installation technicians at Circuit City, two Cape Cod pharmacies for CVS. Tim started a one-man controls company in Las Vegas and grew it into DGS Energy, 45 people, sold in 2019.

Then we worked together again at DGS. There, the Woodshack was the nickname for the corner where the odd, interesting projects got built: door locks, HVAC, wifi and front desk systems that had never talked to each other, and the owners, operators, IT and construction crews who had to agree on them. Tim built the company around it. Jason ran its projects.

Now the Woodshack is where we do that work again. This time it's an actual shop.

"If we're wrong and this all falls apart, we can start it again in the woodshack out back."
Read the whole story → See the work →
Built in the shack

Products we run.

Tools we built because we needed them. We run them as products, and they're proof of how we build.

Walter Sentry Agentless security monitoring for WordPress sites. Audits, agency white-label and incident response. How Sentry watches → Walter Offloads WordPress media on a CDN, without ever deleting your only local copy on a guess. What already shipped → GeoDirect One QR code for every yard sign. Each scan opens the listing for the house the buyer is standing in front of. How it works →
How we work

Two people, a big shop's discipline.

Every project's history, every lesson and every change gets reviewed before it ships. We built our own system, Walter, to keep it all straight, so you get a big shop's discipline with a small shop's attention.

Meet Walter →

The physical stuff

And yes, the woodshop is real.

Jason runs Sawdust and Coffee out of Wareham: custom woodworking, 3D printing, signs and enclosures, for when the answer needs to be physical.

Sawdust and Coffee →

Notes

From the notes.

All notes →

Let's talk about your setup.

Something broken, something stuck, an idea you can't build yourself, or just a feeling there's a better way. A paragraph is plenty. We reply within one business day, the first call is free, and if we're not the right shop for it, we'll tell you who is.

Tell us about your setup

Or email hello@woodshack.net