We help commercial contractors run better operations.
So you can grow, get time back, or finally stop leaving money on the table.
ClearOak works alongside contractors and companies to fix what is broken, build what is missing, and get your team operating at the level your business demands. No fluff. No consulting speak. Just practical strategy and execution that sticks.
Where Growing Contractors Get Stuck
We work with commercial contractors and companies generating $3M to $30M in revenue. If your business is growing but your operations have not kept up, we are built for you.
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 help you build operations that run 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 bring structure without adding complexity, so your team works from the same playbook.
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 operational foundation creates more chaos, not less. We help you build the foundation so growth actually compounds.
How We Work
Every engagement starts with a conversation.
You do not need to know which service you need. Tell us what is going on. We will figure out the right path together.
Step one, always free
Discovery call
A 30-minute conversation where we listen to what is happening in your business. No pitch, no pressure. By the end, you will know exactly how we can help and what the right next step looks like.
From the discovery call, we recommend the right path
“I do not know where to start.”
Comprehensive diagnostic and roadmap
Problems are coming from every direction. You need someone to understand your business from the inside, cut through the noise, and build a plan that starts with quick wins and leads to lasting change.
- Week 1We align on your goals, in your words, not ours
- Week 2-3We assess your team, operations, and readiness for change
- Week 3-4We identify every problem and prioritize by impact
- Month 2You see the full roadmap before committing to the build
- Month 2-3Quick wins first, then the systems that create durable change
- OngoingWe measure results and adjust as your business evolves
This sounds like you if...
You are overwhelmed, problems are coming from multiple directions, and you need a partner to build a real plan before committing to a big investment.
“I know exactly what is broken.”
Focused problem, precise solution
You have identified the problem, your estimating process, your scheduling, your follow-up. You do not need a full assessment. You need someone to solve it in a way that actually sticks.
- Week 1We go straight at the problem you have identified
- Week 1-2We assess your team readiness around that specific issue
- Week 2-4We design the right solution, process, technology, or both
- Month 2+We implement it and stay until your team has adopted it
This sounds like you if...
You already know what is broken, you just need someone to fix it right, and make sure it sticks with your team.
What we deliver
Solutions designed around how your team actually works
Whether it is a centralized operating system, a streamlined quoting process, or an automated tool that follows up with past customers, every solution is built to fit the people using it. Not the other way around.
Where the relationship goes
Fractional Partnership
For businesses that want a strategic second brain on an ongoing basis.
You do not need a one-time project. You need a strategic partner and a boots-on-the-ground operator who keeps your business moving forward while you focus on what you do best. We stay embedded in your rhythm, bringing structure, accountability, and execution on an ongoing basis. The systems get adopted because we are there to make sure they do.
Not sure where you fit?
That is exactly what the discovery call is for. Tell us what is going on, we will tell you how we can help.
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.
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. 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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Weekly hours lost
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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 combine deep strategic thinking with practical, on-the-ground execution. And we bring in specialized partners to make sure every solution is built right.
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.
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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.
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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.
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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.
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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. The advisory team brings focused expertise across finance, technology, data, and growth strategy. Implementation is supported by a curated network of technology partners who are the best at what they do. This model means you get senior-level attention on every engagement without paying for a bloated team.
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.