Mary Naylor.

Two-time successful founder, CEO, and board member with 30 years of go-to-market and growth leadership.

30+

Years operating

Core specialties

Industry experience

The operator behind the coach

Mary Naylor is a repeat founder, CEO, and board member working across customer loyalty, consumer services, concierge and lifestyle, hospitality, travel, financial services, and technology platforms. She brings 30 years of expertise in enterprise business development, go-to-market strategies, sales optimization, channel partnerships, team building, and fundraising.

Mary founded and led VIPdesk, a venture-backed loyalty solutions and concierge lifestyles firm, from inception to a strategic exit at 2x industry multiples to a $2B global industry leader. Post-merger she grew her division to $70M in revenue and directed the global rollout to call centers in 21 countries, supporting 3,000+ clients and 1,500 employees. As CEO of Aspire Lifestyles Americas, she closed a $280M deal with a Fortune 100 credit card brand, the largest in the industry.

Mary also founded Capitol Concierge (acquired), pioneering tenant amenity services for 100+ commercial office buildings. She is Mid-Atlantic Region Chair of C200, a 23-year YPO member, and the author of Customer Chemistry (McGraw-Hill). She holds a B.A. in Communications from UC Santa Barbara.

Specialties
GTM • Board Relations • Succession Planning • Leadership Development

Selected accomplishments

Led VIPdesk to a strategic exit at 2x industry multiples
Grew post-merger division to $70M revenue across 21 countries
Closed industry-record $280M Fortune 100 customer contract

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Working with Mary

Questions CEOs ask about Mary

Who is the ideal client for Mary Naylor?

Founder-CEOs of $10M–$150M growth-stage B2B, B2C, and B2B2C companies, typically post-revenue, scaling go-to-market, building out the leadership team, or preparing for the next funding round or strategic exit.

What is Mary's operating background?

Mary is a two-time successful founder and CEO. She built VIPdesk from inception to a strategic exit at 2x industry multiples, then grew the post-merger division to $70M in 21 countries. As CEO of Aspire Lifestyles Americas she closed the largest customer contract in the industry, a $280M Fortune 100 deal.

Does Mary coach on go-to-market and sales specifically?

Yes. Thirty years of GTM, sales optimization, channel partnerships, and pricing are her sweet spot. She also authored Customer Chemistry (McGraw-Hill) on building loyalty-driven growth motions.

Does Mary work with female founders specifically?

Mary coaches both male and female CEOs, but she is the Mid-Atlantic Region Chair of C200, the leading women's CEO organization, and is a frequent mentor for emerging female founder-CEOs scaling past the first revenue inflection.

Where is Mary based and how does she engage?

Mary is based in Washington, D.C., and works with CEOs across North America through 1:1 coaching, board observation, and strategic advisory engagements. She brings deep board experience across AI, Web3, consumer products, and home services companies.