Jenn Tomassi

Founder & Chief Commercial Officer

Gradient GTM

Jan 2026 - Current (5 months)

Gradient GTM is a go-to-market operating and execution partner helping seed and Series A tech-founder-led companies build go-to-market foundations that scale and execute strategy, because tech founders deserve real access to GTM discipline and expertise, not just the companies three stages ahead of them. We partner with founders to provide senior hands on expertise to build your revenue engine with you - from GTM infrastructure, developing and executing your GTM strategy, pipeline development and revenue growth, and sequencing and hiring your early GTM roles, we are operators in the trenches with you every step of the way. Engagements are focused, customized and flexible — the kind of senior GTM perspective that moves the needle.

SVP, Head of Global Revenue Operations & Performance

First Advantage

Nov 2024 - Current (1 year 7 months)

Led global revenue function for newly combined $1.5B organization post-acquisition, with accountability for revenue strategy, growth execution, commercial planning, and GTM performance. Oversaw ~$20M budget and ~60-person organization spanning revenue planning, forecasting, sales effectiveness, enablement, strategic partnerships, and commercial operations. Partnered with CEO, CFO, and Board to establish unified commercial operating model and align GTM execution with margin and EBITDA objectives. Designed compensation strategy across six global variable plans to drive revenue quality, sales efficiency, and deal velocity. - Generated $400M in pipeline and closed $211M in revenue while accelerating deal velocity by 34% and increasing enterpri

Vice President, Chief of Staff to CEO and M&A GTM Integrations Executive

Sterling

Sep 2022 - Nov 2024 (2 years 3 months)

Served as strategic advisor to CEO with oversight of global commercial performance and P&L management across 10,000-employee public company operating in 240+ countries. Co-led quarterly earnings process with Head of Investor Relations, owning executive materials and performance analysis. Drove enterprise-wide commercial strategy, operating priorities, and capital allocation aligned to revenue growth and margin expansion. Executive sponsor for largest enterprise deals and strategic accounts, establishing repeatable commercial frameworks. Led GTM diligence and integration planning for multiple acquisitions, designing commercial integration strategy and leading execution across sales, customer success, and revenue operations. - Increased ave

Member

Chief

Jul 2021 - Aug 2022 (1 year 2 months)

Chief is a private network built to drive more women into positions of power and keep them there. Chief is the only organization specifically designed for senior women leaders to strengthen their leadership journey, cross-pollinate ideas across industries, and effect change from the top down.

V

Vice President, Revenue Leader, Healthcare Vertical

Sep 2019 - Sep 2022 (3 years 1 month)

Responsibility for $150M P&L driving revenue generation, expansion, retention, margin performance, and operating results. As Head of Customer Success, built and led 125-person global organization across Healthcare and Life Sciences vertical, including Client Success, Sales, Operations, and Marketing functions with four Directors and two AVPs. Served dual role as Interim Head of Sales from '19-'20, leading eight Enterprise and Mid-Market sellers with direct quota accountability and pipeline ownership. Led organization through Sterling’s transition from private to public company, ensuring commercial readiness, operational rigor, and regulatory compliance. - Grew new revenue by 25% YoY as Interim Head of Sales and exceeded quota by 10% throu

V

Vice President, Commercial Business, Healthcare

Sep 2019 - Sep 2022 (3 years 1 month)

Reporting to the General Manager, 𝗜 𝗼𝘄𝗻𝗲𝗱 𝗮 ~$𝟭𝟱𝟬𝗠 𝗣&𝗟 𝗮𝗻𝗱 𝗹𝗲𝗱 𝗮 𝗳𝘂𝗹𝗹𝘆 𝗶𝗻𝘁𝗲𝗴𝗿𝗮𝘁𝗲𝗱 𝘁𝗲𝗮𝗺 𝗼𝗳 +𝟭𝟱𝟬 𝗖𝗹𝗶𝗲𝗻𝘁 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 𝗮𝗻𝗱 𝗢𝗽𝗲𝗿𝗮𝘁𝗶𝗼𝗻𝘀, 𝗠𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴 𝗮𝗻𝗱 𝗦𝗮𝗹𝗲𝘀, driving significant wins and revenue growth, including 𝗶𝗻𝗰𝗿𝗲𝗮𝘀𝗶𝗻𝗴 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 𝗽𝗲𝗿 𝗰𝗹𝗶𝗲𝗻𝘁 𝗯𝘆 𝟭𝟮% 𝗮𝗻𝗱 𝗶𝗻𝗱𝘂𝘀𝘁𝗿𝘆-𝗹𝗲𝗮𝗱𝗶𝗻𝗴 𝗿𝗲𝘁𝗲𝗻𝘁𝗶𝗼𝗻 𝗼𝗳 𝟵𝟳%. Founded and 𝗼𝘄𝗻𝗲𝗱 𝗮 𝗚𝗧𝗠 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀, 𝗴𝗿𝗼𝘄𝗶𝗻𝗴 𝗮𝗻𝗱 𝘀𝗰𝗮𝗹𝗶𝗻𝗴 𝗶𝘁 𝘁𝗼 $𝟯𝟬𝗠. I successfully 𝘂𝗻𝗶𝗳𝗶𝗲𝗱 𝗮 𝗴𝗹𝗼𝗯𝗮𝗹 𝘁𝗲𝗮𝗺 𝗺𝗮𝗱𝗲 𝘂𝗽 𝗼𝗳 𝗱𝗶𝘃𝗲𝗿𝘀𝗲 𝗳𝘂𝗻𝗰𝘁𝗶𝗼𝗻𝘀, 𝗮𝗹𝗶𝗴𝗻𝗲𝗱 𝗶𝗻𝗰𝗲𝗻𝘁𝗶𝘃𝗲𝘀, 𝗮𝗻𝗱 𝗱𝗿𝗼𝘃𝗲 𝘀𝗶𝗴𝗻𝗶𝗳𝗶𝗰𝗮𝗻𝘁 𝗿𝗲𝘃𝗲𝗻𝘂𝗲 𝗴𝗿𝗼𝘄𝘁𝗵 𝘄

Director Client Success, Healthcare, Life Sciences and Financial Services

Sterling

Oct 2014 - Aug 2019 (4 years 11 months)

Led 19-person client-facing organization with eight direct reports across account management and operations. Directed organizational redesign and strategic planning to create Sterling’s first vertical alignment model for Healthcare industry. - Grew and scaled $25M book of business to $54M over four years through client expansion and strategic account growth - Improved client retention by 300 basis points through proactive account management and renewal optimization

S

Senior Account Manager, Healthcare and Financial Services

Jan 2014 - Sep 2014 (9 months)

Delivered 103% of quota with 100% retention on existing revenue. Led deployment of improved sales methodology, pipeline management, and CRM infrastructure. Built high-value enterprise relationships through strategic program expansion and renewal negotiation.

Sales & Account Management, Financial Services and Professional Services

Dow Jones

Nov 2009 - Jan 2014 (4 years 3 months)

Senior Account Manager, 2012–2014: Exceeded 100% of sales quota annually, reduced client churn by 5% and cultivated book of business rich with client references. Held responsibility for revenue growth of new and existing business and retention of enterprise clients within Financial Services and Professional Service industries. Held responsibility for maintaining and growing enterprise client business, drove higher adoption of SaaS solution, reduced customer churn and cultivated book of business rich with client references. Account Manager, 2010–2012: Held responsibility for revenue growth of new and existing business and retention of enterprise clients within Financial Services and Professional Service industries. Sales Executive, 2009–

Account Executive

Bratskeir Company

Jan 2006 - Dec 2009 (4 years)

Drove integrated marketing and corporate communications programs for consumer and B2B clients, managing media relations, special events, and brand-building initiatives.

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