Grow your business without
growing your workload.
We work with you and Winston - your dedicated AI partner - to build custom automations, workflows, and tools that save your business 5-10 hours a week. Your first automation is usually live within 48 hours.
Custom tools for real problems
We work with you to build exactly what your business needs. Then Winston keeps it running, evolving, and improving - you just guide the direction.
Paying for website hosting and maintenance? Winston can replicate your existing site and host it for free. Need changes? Just tell Winston what to change and it handles it instantly.
We set up your reminder and scheduling workflows together. Once running, Winston handles them automatically - you just decide how they behave.
We create your lead pipeline together. Winston captures, tracks, and follows up automatically - you review and close. Nothing falls through the cracks.
We build your content pipeline together. Tell Winston your goals and schedule - it generates, plans, and publishes. You review what goes out.
We map your manual processes together and build Winston-powered workflows to replace them. Your team guides Winston. Winston handles the execution.
Speak your notes - Winston transcribes, formats, and files them automatically. No more typing. No more backlog at the end of the day.
That's exactly what the discovery call is for. Tell us about your business and where you're losing time - we'll figure out what to build together first.
WHAT CUSTOMERS ARE SAYING
Working with Winston has been a game changer for our practice. Even in the early stages, Winston has been able to engage online leads, answer questions, guide prospective patients through our process, collect payment, and help get new patients scheduled. We've also built custom automations, landing pages, follow-up sequences, and reporting systems that allow us to better track patient flow, new patient acquisition, and overall clinic performance.
What impresses me most is how quickly Winston continues to learn our systems and improve. We're still in the early phases of implementation, but the potential is incredible, and I'm excited to see what we'll accomplish as we continue to expand Winston's capabilities.
Coaching is what I love, but the business side of running summer soccer camps was pulling me away from it. OkayWinston handles the things I don't have time to, so I can focus on the kids and the game - and run camps at a scale I genuinely didn't think was possible on my own.
Built for your industry
We focus on a few industries so we can go deep - not wide. We know the problems you face before you explain them.
Don't see your industry? Reach out anyway → If you run a small business and you're doing things manually that should be automated, we can almost certainly help.
Built for a specific kind of business owner
- You run an established business and your time is too valuable to spend on routine, repetitive activities
- You're doing things manually that you know should be automated - and it's costing you hours
- You need tools built for your specific workflow, not generic off-the-shelf software
- You want to grow without hiring more staff
- You're not technical and don't want to be - you just want it to work
- You need enterprise-scale infrastructure (5,000+ person organizations)
- You're not ready to invest a few hours of your time upfront to get back even more hours every week
Simple from day one
You guide Winston. Winston does the work. We set it all up together.
Tell us about your business, where you're losing time, and where you see opportunity. Free, no obligation, 15 minutes. We'll figure out exactly what to build together.
We configure Winston for your business in hands-on collaborative sessions. You guide the direction - Winston handles the execution. First automations are usually live within 48 hours!
Once up and running, you direct Winston the way you'd direct an A++ employee. New need? Tell Winston - it handles it. We're here for bigger builds and whenever you want to go further.
AI Business Audit
Not sure where to start? Before committing to anything, let's spend an hour mapping out exactly where AI can save you the most time and money. You'll walk away with a clear written plan - and if you move forward, the audit fee applies toward your Starter Package.
Straightforward. No surprises.
Start with a $299 AI Audit to map your opportunity. Then get set up with the Starter Package, and keep growing with monthly support.
We configure Winston for your business in collaborative hands-on sessions. You learn to guide Winston from day one - so you stay in control, always.
Your tools keep running, evolving, and improving as your business changes - without you thinking about it.
Built by someone who's been on both sides
I'm Ian McAllister. I spent over a decade building product and technology at Amazon, Airbnb, and Uber - where I saw firsthand how the right systems can make a business dramatically more efficient without adding headcount.
Then I co-founded a restaurant with my wife - and learned something the hard way: small businesses run on tribal knowledge, manual processes, and the owner's personal time. The tools that transformed the companies I worked at were simply out of reach.
I started OkayWinston to change that. To bring the same operational sophistication I've seen at world-class companies to small businesses - at a price that actually makes sense.
Let's figure out what your business needs
Fill out the form and we'll reach out within one business day. Choose how you'd like to get started - two options below.