Operations & AI for Commercial Contractors
Another tool your team won't use isn't the answer.
You know AI could help. You just have no idea what to build, no time to figure it out, and no proof it will pay off.
Here is what we do: we build AI into the way your business already runs, on your real jobs and numbers, then train your team to own it, so it actually gets used. We are operators, not a tech company, so we bring the use cases that pay off and skip the theory. We spark the aha moment, then your team starts finding and building the next ones without us in the room.
Strategy
The AI use cases actually worth your time, found in how your business already runs.
Systems
AI-powered solutions built on your real jobs and numbers.
Ownership
Your team keeps finding and building the next one without us.
Why AI Adoption Stalls
Contractors don't adopt AI because they don't know what to build, don't have time to learn, and can't trust the payoff.
The Blocker
They don’t know what to build
What We Do
We build it on your real work
The Blocker
They don’t have time to learn
What We Do
We train your team to run it
The Blocker
They can’t trust the payoff
What We Do
We guarantee the return
We build it on your real work, train your team to run it, and guarantee the return.
Where Growing Contractors Get Stuck
We work with commercial contractors and companies generating $3M to $50M in revenue. If your business is growing but still runs on manual work and gut feel, we bring practical AI to the workflows costing you the most.
Your Business Runs on You
Every decision, every client call, every fire drill runs through you. If you step away for a week, things slow down or fall apart. That is not a business that scales. We find the AI use cases that take the daily grind off your plate, so the business runs whether you are in the office or not.
Your Team is Busy but Nothing is Standardized
Estimators do things their way. Project managers track things differently. Information lives in texts, emails, spreadsheets, and people's heads. We build one AI-powered source of truth on your real data, so your team works from the same playbook without the busywork.
You Are Growing but the Cracks Are Showing
Revenue is up but margins are flat. You are hiring but output is not keeping pace. Quality issues are creeping in. Growth without a foundation creates more chaos, not less. We put practical AI to work on the workflows straining under growth, so it compounds instead of cracking.
Not a contractor? We are operators first. If yours is a business we understand and have run ourselves, we want to hear from you too.
Our Method
We are business operators who found what AI can actually do.
Not a vendor. Not a course. We are your operations partner, here to help through all of it.
We started ClearOak because owner after owner told us the same thing: they knew AI could deliver real ROI, they just had no idea where to start. So we bring the practical use cases, built on your real data, and skip the theory that wastes your time. The first one lands the aha moment. After that, your team is spotting and building the next ones on its own, without us in the room.
01
We Build
The asset, on your data, before we walk in.
We identify the workflow costing you the most, then build the asset on your actual data before Session 01 begins. The first time you sit down with us, the work you have been doing manually is running in front of you. The aha moment lands on day one, on real work, not a demo.
02
We Train
Your management and key operators, side by side.
Not the whole org. Not an IT rollout. The operators who already own outcomes, who can take an asset, make it their own, and pass it to the next person without us in the room.
03
We Apprentice
Until you can build the next one yourself.
We teach how the asset was built, how to operate it every week, and the methodology underneath. You leave with the asset on your machine, the muscle memory to run it weekly, and the framework to find and automate the next workflow on your own.
Recent engagement: a weekly 1h 45m controller task, down to 30 minutes. $8,125 in labor recovered per year, on a single workflow.
Take the Next Step
Let's see what this looks like for your business.
Thirty minutes. No pitch. By the end you will know exactly how we can help.
Or read the long version: Company overview · One-pager · Meet the people behind the method
How We Work
Every engagement starts with a conversation. Then we put AI to work.
We are a true tech partner, with the operations strategy, business acumen, and execution to move quickly. You do not need to know which track you need. Tell us what is slowing you down, and we will recommend the right one.
Step one, always free
Discovery call
A 30-minute conversation where we listen, then point to the workflow costing you the most. No pitch, no pressure. By the end you will know how we can help and which track fits.
Step two, before any build
Alignment and proposal
Before we build anything, we agree on exactly what we are going to build, the first workflow we will train on, and a clear training plan built around it. We start from a proven structure and tailor it to your team and that workflow. You get it all in a written proposal, so the scope, the work, and the outcome are settled before we start.
Once the proposal is set, the build takes one of two shapes
“One operator is carrying too much.”
One operator, one workflow, fully automated
We find the job eating one key operator’s week, build the AI asset on their real data, and apprentice them through it. Watch, build with, own. They leave running it solo every week, with the time back for the work only they can do.
- Pre-buildWe build the asset on your real data before session one
- Session 1You watch it run on your live work. The aha lands here
- Session 2You take the keyboard and run it yourself, with us beside you
- Session 3You own it solo, then we hand over the method
- 30 daysWe stay on call for questions, edits, and what is next
This sounds like you if...
A single key operator owns a critical workflow that is becoming a bottleneck, or one you want unstuck before it costs you a hire.
“Three people, three different ways.”
One shared system, the whole team trained on it
You have a team doing the same task three different ways. We build one shared AI asset and apprentice all three through it together. One source of truth, three trained owners, consistent output across the team.
- Pre-buildWe build one shared asset on your team’s real data
- Session 1The team watches it run on live work. The aha lands here
- Session 2Each operator runs it themselves, with us in the room
- Session 3The team owns it, then we hand over the method
- 30 daysWe stay on call as the team settles into the new rhythm
This sounds like you if...
You have a team doing the same work differently and you want consistency, speed, and one place where the business rules actually live.
Embedded and ongoing
The Tech Enablement Partnership
For operators who want a standing partner as AI keeps changing, not a one and done.
We stay on as your tech enablement partner. We help your team spot the next workflow worth building, apprentice them through it, and stay on call as new opportunities surface. Over time, less of us building for you and more of your team getting sharper at finding and building on its own.
What you walk away with
You do not leave with information. You leave with a working asset.
Every engagement ends with the asset already running on your data, the muscle memory to run it weekly, and the framework to find and automate the next workflow yourself. Tools change and models change. What we leave you does not.
Not sure which track fits?
That is exactly what the discovery call is for. Tell us what is slowing you down, we will tell you which track fits and whether it will pay for itself.
Start With a Conversation30 minutes. No obligation. No sales pitch.
Why Contractors Choose ClearOak
Solutions That Stick
We do not hand you a strategy deck and walk away. We build solutions designed around how your team actually works, not how we think they should work. That is why our implementations get adopted and stay adopted.
Results in Months, Not Years
We prioritize quick wins that deliver measurable impact within the first 60 to 90 days. You will see the value before the engagement is halfway through.
We Speak Contractor
We have worked inside service-based businesses. We understand the chaos of managing crews, chasing estimates, juggling client expectations, and running thin margins. We are not learning your industry on your dime.
You Only Pay for Value
We tie our work to measurable outcomes. If we cannot show you the return, we have not done our job. Simple as that.
Free Frameworks
Tools for thinking clearly about your business
We turn the way we think about operations and AI into short, practical frameworks you can use on your own. Start with this one: a one-page test for whether revenue or margin is actually holding you back.
Technology We Deploy
Operations come first. We start by understanding your business, your team, and your processes before we ever discuss technology. Once the strategy and operational infrastructure are in place, we connect the right tools to make it all work. Many of these technologies power what we build behind the scenes. Some are client-facing. All of them are selected because they are the best at what they do.
This is a sample of the platforms we work with. We lead with Anthropic's Claude as our core AI and stay technology-agnostic around it, so the rest of the stack is chosen to fit your operation. Our stack is always evolving because we stay on top of what is new and what actually works. And if your business already runs on something specific, we can connect into just about anything.
How Much Are Broken Operations Costing You?
Most contractors do not realize how much time and money they lose to inefficiency every week. Adjust the sliders below to see what better operations could mean for your business.
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Annual rework cost
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Total annual cost of broken operations
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Projected annual savings with ClearOak
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Estimated payback period
* Assumes an estimated engagement cost of $15,000. These figures reflect direct operational inefficiency only. Your actual results will vary based on business size, complexity, and implementation scope.
Who is Behind ClearOak
ClearOak & Co. was built on a simple belief: the best operational strategy means nothing if the people using it cannot or will not adopt it. We are business people first, operators who understand your business through and through, and our entire team is equipped to both train your people and build the solutions, because we have lived and run everything we talk about. This is not theory handed down from a deck. Behind us sits a deep bench of technical builders and partners for anything that needs to go further, and based in the heart of Silicon Valley we stay close to where AI is being built, so we can automate almost anything, strategically and practically.
The ClearOak Team
John Baker
Founder and Head Strategist
John leads every ClearOak engagement, orchestrating the strategy, operations, and execution that move a business from owner-dependent to scalable. His core belief is that technology for technology's sake is useless. The best strategy, the best software, the best process in the world fails if it does not work with the people who are actually using it. People are not rational. They are emotional, habitual, and resistant to change they do not understand. That is why every ClearOak engagement starts with understanding the team, not the tech stack, and why every solution is designed around how people actually work, not how they should work on paper.
LinkedIn
Phillip Weinstein
Advisor, Investment and Growth Strategy
Phillip brings deep experience in evaluating and growing small to medium-sized businesses from both the investor and operator perspective. His focus at ClearOak is the intersection of growth strategy, capital allocation, and the operational improvements that drive enterprise value, particularly for owners preparing for a capital event and investment firms building value in portfolio companies.
LinkedIn
Jeffrey Ferguson
Advisor, Finance and Investment Strategy
Jeffrey brings deep experience in finance, investment, and building scalable business infrastructure. His focus at ClearOak is financial strategy and investment readiness, helping ensure that a company's financial and operational foundation is structured to attract capital and support sustainable growth.
LinkedIn
Zafir Dharssi
Advisor, Product and Technology
Zafir brings deep experience in product management, technology implementation, and systems design at enterprise scale. His focus at ClearOak is helping ensure that technology decisions are grounded in how teams actually work, not just what looks best in a demo, so that new tools are adopted and deliver real operational value.
LinkedIn
David Lovejoy
Advisor, AI and Process Innovation
David brings deep experience in applied AI, business automation, and coaching business owners through strategic decisions. His focus at ClearOak is identifying where automation and AI-powered tools can replace manual work and create real operational leverage, and just as importantly, where they cannot.
LinkedInThe ClearOak Model
We believe in specialization. John leads strategy and client relationships, and the advisory team brings focused expertise across finance, technology, data, and growth. What ties it together: every one of us is equipped to both train your team and build the solutions, because we have lived and run the work we advise on, not just studied it. Behind the team sits a deep bench of technical builders and partners for anything that needs to go further, so we can automate almost anything, strategically and practically. You get senior-level, business-first thinking on every engagement, backed by real hands-on capability, without paying for a bloated team.
Academy CertifiedWe lead with Anthropic's Claude, and we are certified to build on it
Anthropic's Claude is our primary AI platform, because it sets the bar for AI that is safe, capable, and ready for real operations. John has completed Anthropic's certification track across the areas that matter most inside a working business: building with Claude, applying AI with sound judgment, and training a team to run it. The assistant in the corner of this site runs on Claude, a live example of what we deploy for clients.
Building with Claude
Hands-on with the same tools we put to work inside client operations.
Applied AI judgment
Knowing where AI creates real leverage, and, just as important, where it does not.
- AI Fluency: Frameworks and Foundations
- AI Capabilities and Limitations
Training and collaboration
Bringing a team along, which is exactly how our apprenticeship model works.
- AI Fluency for Educators
- Human-AI Collaboration (Co-Work)
Our Technology Partners
We partner with specialized technology firms to implement solutions that stick.
Lety
Provides multi-channel AI agents across voice, chat, WhatsApp, and SMS for customer service, scheduling, sales, and operations across industries.
Hooma
Designs AI-powered lead generation and automation systems that qualify prospects, book meetings, and eliminate manual outreach, helping service businesses build predictable pipeline.
Notion Providers
Builds custom digital operating systems in Notion, combining workflow automation and integrations to help teams centralize information and standardize how work gets done.
What Our Clients Say
“John consistently demonstrated a deep understanding of market dynamics and client needs. His ability to craft and execute innovative strategies was instrumental in us closing over $100 million in transactions, a testament to his effectiveness and expertise.”
Sam Greely
Managing Partner, HG Real Estate Partners, Inc.
“Working with John has been a game-changer for DealsX. His deep knowledge of small businesses and the M&A landscape is evident in every conversation. What truly sets him apart is his practical, no-fluff approach to enhancing operations. He has been an invaluable asset to our growth.”
Sam Singh
Partner, DealsX
“John is a wizard. His ability to quickly and strategically optimize and enhance workflows and processes is second to none. He is relentlessly creative, always learning, and every conversation with him leaves you smarter and better equipped.”
David Lovejoy
Founder & CEO, Horizon Search, Inc.
Common Questions
What ClearOak & Co. does, who we serve, and how an engagement works.
Prefer to just ask? Chat with our assistant in the corner. It can go deep on your situation and send details to your inbox, and it is a live example of the kind of AI we build for clients.
What does ClearOak & Co. do?
- ClearOak & Co. is an operations partner for commercial contractors and trades companies. We work on the operational side of the business: we diagnose how a contractor’s whole operation runs and help owners get clear on exactly where they stand, rebuild the highest-impact workflows as AI automations on the client’s real business data, then train and apprentice the client’s own team to run those workflows without us in the room. We stay with our clients through it all, and we are here to help first.
Who does ClearOak work with?
- We work with commercial contractors and trades companies generating $3M to $50M in annual revenue, including painters, general contractors, and HVAC, electrical, and plumbing businesses, along with private equity firms that own commercial-trades portfolio companies. The trades are our specialty, but we are operators first, so we also work with other businesses when the model is one we understand and have run ourselves. If that is you, we still want to hear from you.
Where is ClearOak & Co. based?
- ClearOak & Co. is based in San Francisco, California, in the heart of Silicon Valley where much of the AI revolution is being built. We are business operators first, and our whole team is equipped to both train and build, because we have lived and run the work we advise on, backed by a deep bench of technical builders and partners for anything that needs to go further. That combination lets us automate almost anything, strategically and practically. We work with commercial contractors across the United States, both remotely and on site.
How do I contact ClearOak or book a call?
- You can email founder John Baker directly at john@clearoakconsulting.com, call (415) 831-7892, connect on LinkedIn, or book a free discovery call through the scheduling link on the website. John personally leads every engagement.
How much does ClearOak cost?
- ClearOak prices around measurable outcomes rather than fixed packages. Every engagement is scoped to the specific problem, and we show the projected return before a client commits, so the investment is always set against the value it is expected to create. The clearest way to get a number for your situation is a short call, where John can walk through what an engagement would look like for your business.
What is ClearOak’s AI enablement and how does it work?
- AI enablement is a three-stage apprenticeship: see it work, build with us, take it over. Before the first session we build a working AI asset on your real data. Across three sessions your operator moves from watching it run, to taking the keyboard, to owning it solo, followed by 30 days of on-call support. The goal is a team that is fluent in AI on its own data, not a one-time software install.