Tiffany Sizemore

Tiffany Sizemore

Partner | Marketplaces, Consumer Tech, and SaaS

US Founding Partner | Sales & GTM Leadership

Tiffany leads our Sales & GTM Leadership practice across North America, placing Sales, Marketing, Customer Success, Operations, and other leaders who drive meaningful impact for fast-growing startups, scaleups, and VC- and PE-backed companies. With 17 years across Executive Search, in-house recruiting, and RPO, she brings a consultative approach rooted in trust and a deep understanding of what GTM leadership actually looks like at scale.

Specialties

Typical Roles

CEOCOOCMOVP of Sales & RevenueVP of Marketing & BrandOperations & People LeadershipCROHead of ProductCFOCCOCPOCTOGTM Leaders

Geographic Focus

United States · Europe · Global · Transatlantic

Key Search is trusted by teams
that rely on clarity

SF

Alexandra Bashir

Super (formerly Snaptravel)

Tiffany was exceptional to work with in that she was effective and personable. She found us a stellar candidate in record time and managed the recruiting process such that anyone put in front of the client was well vetted and credible. Moreover, she was very professional and lovely to work with. Tiffany took time to understand our organization, the role and team culture which really helped. This allowed her to make recommendations aligned with my own ideas and needs. On top of all this, she was pleasant and fun to work with. I'd partner with her again for talent needs of all levels.

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Articles by Tiffany Sizemore

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You should speak with Tiffany if…

  • 1You are a VC/PE-backed founder building out your foundational U.S. leadership team.
  • 2You need a partner who understands the nuances of the Chicago and broader U.S. tech venture ecosystems.
  • 3You are looking to professionalize your executive hiring process and employer branding.
  • 4You need a leader who can balance technical vetting with a deep understanding of team culture and mission.