We’re Strategic Technology Advisors for Seasonal Businesses

At Chatham Oaks Growth Solutions (COGS)

At Chatham Oaks, we specialize in providing strategic technology advisory services tailored for mid-sized businesses, particularly those operating in seasonal markets like Cape Cod, coastal Maine, and New Hampshire.

We provide Fractional CTO services for mid-sized seasonal businesses helping them grow through smart automation, AI, SEO, and modern systems integration.

Helping a Group get to their summit | Strategic Tech Advisors | Tech Consultants at COGS

How We Help

We combine practical operations consulting with smart, integrated tech strategy. You won’t find buzzwords or bloated roadmaps here. Instead, we focus on tangible wins that drive momentum:

  • Fractional CTO & Strategic Ops // Executive-level guidance without the full-time cost. We map your workflows, identify friction points, and build scalable systems that support growth.

  • Tech Integration & Automation // We help make your tools work together. Whether it’s syncing QuickBooks with your CRM or automating seasonal hiring workflows, we reduce the manual work.

  • Standard Operating Procedures (SOPs) // Clear, documented processes so your business runs without you in the room and becomes more valuable in the process.

  • Exit & Succession Readiness // For brokers, investors, and founders preparing for sale, we make businesses “turn-key” and “buyer-ready” with clean systems and reduced owner dependency.

What’s a Fractional CTO?

A Fractional CTO (Chief Technology Officer) is a part-time, contract-based technology leader who provides strategic guidance and oversight without being a full-time employee.

Think of it as "CTO-as-a-service." You get tech leadership and implementation on a flexible basis.

Why a Fractional CTO?

Fractional CTOs are ideal for businesses that need strategic direction into topics such as SEO, AI, automation, and business software but aren’t ready (or don’t need) to hire a full-time CTO.

Empowered with modern technology, businesses are operating 3x more efficiently leading to higher profits and shorter work weeks.

Our Mission

Our mission is to help businesses optimize operations, integrate technology, and prepare for future transitions without compromising their unique character. We strive to save seasonal businesses millions of work-hours annually through streamlined tech solutions, driving sustainable local prosperity.

Helping others set up their gear | Strategic Tech Advisors | Fractional CTO | COGS

Who We Serve

Our clients typically fall into one of these categories:

  • Scaling Seasonal Operators // Hospitality, tourism, e-commerce, and local service businesses managing summer surges and winter slowdowns or vice versa.

  • Exit-Minded Owners & Brokers // Business owners looking to sell or transition and the advisors helping them do it.

  • Investors & PE Firms // Angels, search funds, and holding companies looking to improve margins and efficiency post-acquisition.

  • Local Marketing Teams // Marketing teams that need support on the technical aspects of marketing and software tools.

Most have 5–50 employees, a mess of disconnected software tools, and a desire to “do more with less” without hiring a full IT team.

The COGS Team

Chatham Oaks is a small team, hyper focused on local knowledge, technical expertise, and hands-on support.


  • Founder

    Hi, I’m Matt. In 2009, I became a Cape Cod “wash-ashore”. My appreciation for the Cape Cod lifestyle combined with interest in all things technology led to the foundation of Chatham Oaks.

    My time at Bentley University and a decade of advising small businesses in marketing and operations taught me how fulfilling running a business can be.

    When I’m not working with my clients, you’ll find me on the golf course or rock climbing.


  • Partner

    Hi, I’m Cole. Originally from Western Massachusetts, I made Cape Cod my home in 2022 after studying political science and law at Emmanuel College.

    Along the way, I discovered a passion for business building, artificial intelligence, and emerging technology.

    At Chatham Oaks, I bring these interests together to help local businesses grow through smart, modern solutions.

Chatham Oaks is built to keep up with modern technology while maintaining direct working relationships with our clients.

Our internal infrastructure of AI agents and complex automations allow our small team to address the needs of companies of any size or scale.

“If you have built castles in the air, your work need not be lost; that is where they should be. Now put the foundations under them.”
― Henry David Thoreau, Walden