Tiffany Sizemore

Expertise, Languages and Region

C-Level hiring
Working directly with founders
Large enterprises, early-stage startups, and fast-growing organizations across all different industries
Language: English
Region: USA, Chicago
❤️ Passion: I help purpose-driven startups grow by placing leaders who align with their vision, culture, and mission. I go beyond résumés to find people with the values and potential to drive real impact—partnering closely with founders and VCs to make every hire count.

Tiffany is the U.S. Founding Partner at Key Search and one of the firm’s first hires in the United States. She brings 17 years of experience across Executive Search, in-house recruiting, and Recruitment Process Outsourcing (RPO), with a focus on placing Sales, Marketing, and Operations leaders for fast-growing, VC- and PE-backed companies.

Since joining Key Search in 2023, Tiffany has played a pivotal role in scaling the firm’s U.S. presence, working with top-tier investors like SpeedInvest and growth-stage companies such as Starship Technologies, Groupon, and Neptune Software. She has successfully led executive searches that support rapid scale, organizational transformation, and long-term strategic growth.

Tiffany is known for her innate ability to connect with executive leadership and deeply understand the unique needs of each business. She brings a thoughtful, consultative approach to every search—rooted in trust, business acumen, and a passion for aligning the right talent with the right opportunity. Her expertise spans the full talent acquisition lifecycle, and she excels at building strong, enduring relationships with both clients and candidates across global markets.

Prior to Key Search, Tiffany focused on leadership hiring at a Chicago-based tech recruiting firm focused on the venture ecosystem. She holds a Bachelor of Science degree from Southern Illinois University and is passionate about helping purpose-driven companies grow by placing the leaders who will help take them there.

Clients who trust Tiffany Sizemore

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Groupon-Logo
SpeedInvest
AI Industry and Market Disruption: Examine AI industry growth and market disruption trends shaping the future of business innovation.
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What our clients say about Tiffany Sizemore

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 (me) 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.
Alexandra Bashir
Super (formerly Snaptravel)
I had the privilege to work with Tiffany on multiple occasions. She is a professional and committed individual. She is gifted with extraordinary interpersonal skills. Most significantly is the quality of her loyalty and dedication. I have the greatest respect for Tiffany’s knowledge, character, and integrity.
Adam Gnall
BD Flight Operations
Tiffany was an absolute pleasure to work with during her tenure at R&A, she was responsive, cheerful and proactive in meeting the client’s expectations and managing change, along with making the candidate experience a positive one. In her short time with the firm, she was able to enhance the recruiting function through process improvement, as well as manage the implementation project of a new applicant tracking system, sourcing strategy, staffing compliance and employer branding through candidate marketing efforts. Tiffany is professional and personable, and I highly recommend her for any role with an organization looking to move to the next level of success.
Tessa Owen
VP People & Culture at Cypher Learning

Feature talks

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Our team has successfully helped build some of the US and Europe’s most innovative businesses.