
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.
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Articles by Tiffany Sizemore

The First U.S. Hire: What International Founders Need to Prepare Before Scaling Abroad
The first U.S. hire is one of the highest-leverage decisions an international founder will make. Maren Marcelis and Tiffany Sizemore share what the preparation, candidate profile, and onboarding actually look like for companies entering the North American market.

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.
