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Hard problems. Small shop.

Software was supposed to save you time.

We're Jason and Tim. We look after your website and the systems behind your business, make your tools fit the way you work, and build what's missing.

Tell us about your setup How ongoing care works

Cleveland, OH · Wareham, MA

Sound familiar?

Your team is doing two jobs.

Your marketing person should be deciding what goes on the website, not fighting a page builder or figuring out why a plugin broke the contact form.

Your ops lead should be running jobs and moving product, not copying the same order into three systems and a calendar.

And everyone is juggling a dozen logins, working around tools that only do most of what you need.

Every hour spent on that is an hour not spent on the work you hired them for. It doesn't show up as an invoice, but you're paying for it.

We handle the technical side, so your team can get back to theirs. We don't replace anyone. We back them up.

Ongoing care

You use it. We look after it.

Whether we built it or someone else did, we keep watch, keep it updated, and keep a running memory of how your setup works. Small problems stay small, and nobody on your team has to babysit plugins.

What's covered
  • Monitoring for uptime and security
  • Updates for software, plugins and dependencies
  • Backups, tested 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

Priced per site or app, based on what it actually needs. No tiers to decode.

In practice: "Checkout's being weird" turned out to be a credit card skimmer that more than one security plugin had missed.

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

Tools that fit how you work.

You shouldn't have to change how your business runs to suit software that only does most of the job. Once we know how you work, we can see what's missing, and that's where the interesting work comes from.

01

Integrations & custom software

Connect the tools you have so data goes in once. 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 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. Sometimes the right answer is an off-the-shelf tool and a small bridge. 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 the work

Hard problems we've already solved.

Ongoing care

"Checkout's being weird"

One customer's complaint turned out to be a card skimmer more than one security plugin had missed. Custom software

One events system

Three sites, three old plugins, replaced by one. Staff enter a show once and it lands everywhere. Field service

Off the spreadsheets

A 49-state field-service company moved onto one system that ended up running the whole business. Hospitality

A big Las Vegas resort

3,005 rooms of door locks and thermostats in 12 working days, with the hotel open.

See all the work →

Why we're small

Small on purpose.

We work with a handful of clients for the long haul. That leaves room to learn how your business actually runs, solve problems properly, and stick around to look after what we build.

  • We know your setup. 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. Too many logins, too much copying between systems.
  • You're a small team or nonprofit without an IT person.
  • You have an idea for a tool, but assume it's too big or too expensive to build.
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. The first call is free.

2. Get a straight scope and price.

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

3. We build it and keep it running.

Then you and your team 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 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.

We worked together again at DGS. There, "the Woodshack" was the corner where the odd, interesting projects got built: door locks, HVAC, wifi and front-desk systems that had never talked to each other, plus 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 →

Products

Built in the shack.

Tools we built because we needed them, and now run as products.

Walter Sentry Agentless security monitoring for WordPress sites. 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 in front of you. How it works →

Two people, a big shop's discipline.

Every change gets reviewed before it ships, and every project's history is kept. We built our own system, Walter, to keep it all straight.

Meet Walter →

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 →

From the notes

All notes →

Let's talk about your setup.

Something broken, something stuck, a tool that almost does what you need, 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