About
Jenn Tomassi spent nearly two decades building revenue engines in New York City — as a quota-carrying revenue leader who scaled a healthcare vertical from $25M to $150M ARR and launched a product line from zero to $30M. She didn't inherit results. She built them.
Unlike most revenue leaders who inherit functional responsibility, Jenn has held direct leadership accountability across every GTM function — from the ground up.
As SVP of Global Revenue Operations, she led GTM operations and was accountable for commercial performance through the one of the most complex and consequential integrations in HR tech — a $2.2B strategic acquisition at a 35% premium — then ran GTM operations for the combined entity post-merger.
She recently returned to her home state of Rhode Island with her husband to raise their daughter and build something entirely her own: Gradient GTM — an operating and execution partner for seed-to-Series B founders who need to get GTM right before it gets expensive to get wrong.
Speaking Topics
What Founders Get Wrong About Their First Revenue Hire
The costly GTM mistakes early-stage founders make — and the framework for getting it right before it costs you.
Inside One of the Most Complex M&A Integrations in HR Tech: What the Revenue Team Actually Lived Through
A rare operator-side account of a $2.2B acquisition in one of B2B's most complex industries — what broke, what held, and what no one tells you.
AI Is Eating the Sales Stack — What Survives
A practitioner's view on where AI creates real leverage in B2B GTM and where it just creates noise.
Why the Enterprise GTM Playbook Breaks at Series A/B
The operator's case for why what works at scale actively hurts early-stage companies — and what to do instead.
Betting on Yourself After a Major Exit
Leaving a $2.2B outcome to build something new — the operator's journey from enterprise to entrepreneurship.
By the Numbers
$2.2B
Strategic acquisition — One of the most complex and consequential M&A integrations in HR tech
35%
Premium above market at exit
6×
Revenue growth on healthcare vertical as quota-carrying revenue leader
$30M
New product line built from zero to revenue
20yr
B2B SaaS revenue leadership — New York City
