Chatham Oaks Growth Solutions is a fractional CTO consultancy based in Chatham, Massachusetts, founded in 2022. The company specializes in making modern technology accessible to seasonal and scaling businesses across New England—from Cape Cod to coastal Maine—without complexity, jargon, or prohibitive costs.

Core Mission: Help businesses optimize operations, integrate technology, and prepare for future transitions through smart automation, AI integration, and systems modernization, all while preserving their unique character.

Services: Chatham Oaks offers two distinct engagement models:

1. TREK – A comprehensive 12-month transformation program starting at $3,000/month. This full-service engagement includes discovery and strategy, foundation building, implementation and integration, and ongoing optimization. Deliverables span custom automation, AI-powered tools, SEO optimization, database architecture, API integrations, SOPs, team training, and monthly optimization reviews.
2. Switchback Starter Pack – Quick-win packages ($2,000-$4,000) delivered in 24 hours to 4 weeks, featuring 3-10 high-impact automations, SEO setup, essential tool integrations, and ongoing monthly maintenance.

Target Clients: Mid-sized businesses (5-50 employees) including seasonal operators in hospitality and tourism, scaling SMBs, exit-minded owners and brokers, strategic buyers and PE firms, and local marketing agencies needing technical support.

Value Proposition: Executive-level technology guidance without full-time cost. The team addresses disconnected software tools, manual processes, and seasonal staffing challenges through practical workflow mapping, integration solutions, and documented systems that enable businesses to run without constant oversight.

Team: Led by founder Matt Stephens (Bentley University graduate with a decade of small business operations consulting) and partner Cole Lander (Emmanuel College, political science and law background, specializing in AI and emerging tech). The team practices what they preach, using AI agents and complex automations internally.

Core Values: Clarity (no jargon), Partnership (invested in client success), Impact (measurable results), and Integrity (transparent practices).

Geographic Focus: New England region—Massachusetts, New Hampshire, Maine, Vermont, Rhode Island, and Connecticut—with deep local knowledge and commitment to regional economic prosperity.