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Deidre Jacobson
Principal, Marketing Strategy

Deidre Jacobson is a visionary marketing executive with more than 20 years of experience leading brand transformation, demand generation, and go-to-market strategies across B2B and B2C markets. As co-founder of Maximum Reach Marketing, she endeavors to help organizations unlock growth through brand strategy, marketing innovation, and AI-driven insights.

Previously, Deidre served as Senior Vice President of Marketing at Aztec Software, where she built and scaled a centralized marketing function for a private equity-backed SaaS company, driving rapid growth, sales acceleration, and a unified brand architecture. She also served as Vice President of Corporate Marketing at Navient, leading enterprise-wide brand strategy, launching a new digital lending product, and shaping the company’s market positioning through integrated campaigns, M&A support, and digital transformation initiatives.

Her earlier leadership roles include Vice President of Marketing Communications Operations at Liberty Mutual Insurance, Vice President of Participant Strategy at New York Life Retirement Plan Services, and Senior Marketing Manager at Fidelity Investments.

Deidre holds a B.A. in Psychology with a minor in Statistics from Boston University, cum laude. She is recognized for her ability to combine data-driven insights with creative storytelling to deliver measurable impact, build high-performing teams, and transform brands into growth engines.

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Jeffrey D'Entremont
Principal, Technology Strategy

Jeffrey D'Entremont, co-founder of Peak Strategy, is a digital strategist and revenue operations expert who helps organizations achieve sustainable growth by aligning sales, marketing, and customer success through HubSpot, AI-powered automation, and streamlined operational frameworks.

Before co-founding Peak Strategy in 2023, Jeffrey spent over a decade leading digital platforms and RevOps operations for high-growth organizations. His work has included scaling operations, implementing HubSpot across multiple hubs (Sales, Marketing, Service, Content, Operations), and driving significant improvements in customer acquisition, retention, and revenue growth.

Jeffrey specializes in designing tailored sales and marketing strategies for startups, non-profits, and SMBs—taking into account each organization's unique goals, target audiences, technology stack, and competitive landscape. He's known for bridging the gap between strategy and execution: not only designing systems and frameworks, but rolling up his sleeves to implement, measure, and continuously optimize alongside his clients. His leadership philosophy centers on agility, collaboration, and customer-centricity—principles that guide Maximum Reach Marketing's approach to every engagement.

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