People & Talent Leader.
Startup Advisor.

FinTech, MarTech/Video Software, AI

About Taylor Roa

Taylor Roa is a People & Talent leader known for building the foundations for talent-dense teams that fuel high-growth startups. With a track record of scaling world-class hiring functions from the ground up, Taylor focuses relentlessly on quality of hire, performance outcomes, and long-term organizational impact. He believes talent density is the ultimate growth lever—and designs systems to measure, increase, and sustain it.

Currently leading the People & Talent function at January, a Series B AI-powered fintech in New York, Taylor has architected scalable org design, compensation strategy, performance management, leveling frameworks, and DEI strategy across multiple startups. His approach blends analytical rigor with cultural intent to drive high-performing, high-trust teams.

Taylor also advises early-stage startups and speaks regularly on the future of work, strategic hiring, and building organizations where ambition and authenticity thrive.

Over a Decade of Experience

building and scaling talent and people operations with a passion for maximizing talent density.

January

Series B, Fintech

As Head of People & Talent, I built the foundations for People & Talent function built to maximize talent density through scale.

Flywire

Series C to D, Fintech

(Now public: FLYW)

As the second Talent hire & Global DEI lead I scaled the talent team to 6, growing global headcount from 300 to 420 and I designed and launched the first global DEI initiative across 14 offices and 7 different cultures.

Axion Ray

Series A, AI

As Head of People & Talent, I built the company's first hiring function doubling headcount and laying the foundations for people operations.

The Sourcery

Bay Area Staffing Startup

As a top Technical Recruiter on the team, I partnered with clients to fill niche senior requirements in computer vision, machine learning, internet of things, drones and more.

Wistia

Profitable, Video/Martech

As Director of Talent & Culture I built and scaled the company's talent function doubling headcount. I also lead engagement, culture, DEI and workplace teams.