Who we are
Our mission, and what we believe
ClearOak & Co. exists to bring the contracting industry up to speed on the technology reshaping every other sector.
We train owner operators and their management teams in the timeless frameworks and modern AI systems that strip out monotonous work, sharpen the operation, and free their best hours for what actually sets a business apart to its customers.
That is the mission. Here is where we believe it leads.
What we believe
A shift in productivity is underway on the scale of an industrial revolution, and it will reshape business as we know it. Technology is moving fast enough that most teams are chasing the newest tool, hoping it will do the work for them. It will not. The tools only pay off when the foundation is there, and the foundation is what almost everyone is skipping. That foundation is what we teach. It is why the same tool produces radically different results in different hands.
Budget spent, software blamed
Nothing holds the tools square. They lean, the spend trails off, and the team goes shopping for the next one.
The same tools, now they climb
Set the same tools on a real foundation and each one holds, builds on the last, and returns more than the team still chasing the next tool.
The four beliefs we work from
They stack. The first is the frame, and the other three sit inside it.
Foundation before tools
Chasing tools without the foundation is how companies burn budget and blame the software. Owners who understand the underlying principles get more out of every new tool than the teams still shopping for the next one.
Learn by building, not by theory
The best way to build the foundation is to start from a real, painful problem and build the solution to it. That pulls you out of the theoretical and into reality, which is the only place learning sticks.
Iteration builds the moat
Learning that repeats reinforces itself and builds a real operational advantage over time, not just a one-time fix. Every cycle sharpens the foundation and makes the next tool easier to adopt.
Teach to fish, not catch the fish
Ownership compounds. Every cycle of learning is an investment that pays forward, not a one-time transaction. It is why we train your team to own the work, not why we run it for you.
We draw this thinking out in more depth in Foundation before tools.
None of it works without the people who carry it. Beliefs are only worth as much as the team that lives them, and that team is who we are.
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.
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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, 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.