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.
Trusted by
Specialties
Typical Roles
Geographic Focus
Key Search is trusted by teams
that rely on clarity
1 / 3
Articles by Tiffany Sizemore
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 […]
Discovering the optimal Executive Search firm to guarantee success for your business
Finding Your Perfect Executive Search Partner. Are you on the lookout for that perfect executive search firm? With a whopping 5,658 of them in the US as of 2022, I know the choice can be overwhelming. Whether it's a global giant or a cozy boutique firm you're after, I'm here to help you navigate […]
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.