Senior Enterprise Account Executive

Freshpaint helps healthcare organizations modernize their data infrastructure so they can run world-class analytics and marketing while staying fully privacy compliant. As an Enterprise AE, you’ll be responsible for driving new revenue, generating demand, navigating complex enterprise sales cycles, and representing Freshpaint’s value to senior executives across Marketing, Product, Compliance, and Legal.

Requirements

• 5+ years of closing experience in B2B SaaS, selling to enterprise & strategic level customers
• Strong outbound muscle: you consistently generate pipeline and teach others to do the same
• Experience running 60–90 day deal cycles with mid–six-figure ACVs (~$100k)
• Track record of meeting or exceeding quota (President’s Club, Rep of the Year, etc.)
• Excellent written and verbal communication skills, including the ability to present to executives
• Proven ability to run structured discovery, build compelling business cases, and influence buying committees
• Strong relationship-building skills with agency and consulting/SI partners
• Executive presence and comfort operating in high-stakes conversations
• Self-starter attitude with the ability to operate in a fast-paced, ever-changing startup environment
• Ability to travel up to 40% for events, customer meetings, and partner activities

Benefits

• Competitive pay + generous equity (10-year exercise window)
• Fully remote (U.S. only) with a $150/month coworking stipend
• Half-day Fridays, every Friday
• Unlimited PTO—with a required 2-week minimum
• Top-tier health, dental & vision (100% covered for you, 80% for dependents)
• 2 “Treat Yourself” days a year—$100 and a day off, just because
• Generous parental leave
• Epic offsites twice a year (past trips: Greece, Jackson Hole, Cabo, wine country + more)