Tiffany Sizemore
Partner | Marketplaces, Consumer Tech, and SaaS
GTM Leadership, United States & Canada
Tiffany is Key Search's founding US Partner. She focuses on the United States and Canadian markets, placing Sales, Marketing, Customer Success, Operations, and C-suite leaders at high-growth companies across Marketplaces, Consumer Tech, and SaaS.
Tiffany is a trusted bridge for European and international companies expanding into North America. She works directly with founders and boards entering the US and Canadian markets for the first time, helping them build the go-to-market leadership teams they need to succeed.
Her GTM expertise is hands-on and hard to replicate. With 17 years across Executive Search, in-house recruiting, and RPO, Tiffany has built deep networks in Sales, Marketing, Customer Success, and Operations leadership, giving her a granular understanding of what great GTM talent looks like at every stage of growth.
Beyond core GTM roles, Tiffany works extensively with Marketplace, Consumer Tech, and SaaS companies, placing the executive talent needed to scale across the US and Canada.
She partners with founders, CEOs, and boards placing CROs, CMOs, VPs of Sales, VPs of Customer Success, Heads of Marketing, and GTM executives at companies from Seed Stage through Series A, B, and C.
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Alexandra Bashir
Super
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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Podcast
Leaders Lounge
Articles by Tiffany Sizemore
Navigating the New Retail Frontier: Executive Leadership Trends in US & Canadian DTC and Retail Tech
The line between scrappy DTC upstarts and legacy giants has blurred to the point where it barely exists anymore. What separates the companies that win from the ones that stall is leadership — the right executives, at the right moment.
How Your Search Process Sends a Signal in the North American Market
Your search process is your first demo. Before a single candidate reads your pitch deck, they're evaluating your organisation through the speed of your responses, the clarity of your communication, and the preparation of your interviewers. Maren Marcelis and Tiffany Sizemore on what a well-run North American executive search looks like — and the failure modes that cost founders their best candidates.
Why Parents Often Make Exceptional Executive Recruiters
There's a pattern in executive search that doesn't show up on a CV. It's not a methodology. Not a network. Not a track record with a particular sector or function. It's something you tend to notice only after you've watched a lot of searches succeed - and fail. Many of the recruiters who consistently […]
2026 Executive Search Market Insights: EU + North America
Every January, people ask the same thing in slightly different ways. Is hiring back? Is it still dead? Are we going to be “cautious” for another year? And what does any of that actually mean if you are the one who needs to hire a C-level leader yesterday? So yes, this is our 2026 […]
Hiring Under Pressure: 5 Essentials for Building Effective C-Level Teams in Robotics, IoT & Manufacturing
When a company faces crisis or C-level transformation, every leadership decision counts. Hiring under pressure isn't about finding the most impressive résumé - it's about identifying the people who can stabilize, rebuild, and inspire confidence when the stakes are highest. In restructuring or turnaround situations, the C-level suite plays a decisive role. Whether it's […]
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.