Regional GM - Boston (Remote)

Role overview Lead enterprise sales across a regional market, winning major customers and building the sales approach in an early-stage environment. You’ll take technical AI and machine-learning capabilities to senior business and technology leaders, then develop customer relationships into long-term accounts. The role is remote and based in Boston, Massachusetts.

Responsibilities - Manage complex sales involving multiple decision-makers in regulated sectors such as financial services, healthcare, manufacturing, and retail. - Create a sales pipeline from the ground up and identify strategic enterprise prospects. - Explain technical AI and machine-learning offerings in terms of business value for executive buyers. - Develop multi-year account expansion plans and relationships across IT, product, and innovation teams. - Work with sales leadership and company founders to refine enterprise strategy and inform product direction.

Requirements - At least eight years of enterprise software sales experience, including consistent quota overachievement with Fortune 500 customers. - A record of closing deals worth $1 million or more in annual contract value in early-stage settings. - Experience selling complex technical solutions to CIO organizations. - Background in AI or machine learning platforms, digital transformation, enterprise data platforms, or management consulting. - Ability to work independently through ambiguity and build new sales efforts from scratch. - Experience selling into highly regulated industries with demanding compliance needs.

Nice to have - Experience in regulated sectors and success at an early-stage company.

Benefits and work setup - Remote role based in Boston. - Uncapped compensation with accelerators tied to sales performance. - Equity is offered. The role works directly with sales leadership and founders on go-to-market strategy. - Customer evaluations may include a tailored proof of concept delivered in days, with no data sharing or upfront charge.