[Remote] Senior Enterprise Account Executive

Note: The job is a remote job and is open to candidates in USA. Freshpaint is a privacy-first data platform that helps healthcare organizations use modern marketing and analytics tools without exposing protected health information. As a Senior Enterprise Account Executive, you will be responsible for driving new revenue and managing complex enterprise sales cycles while representing Freshpaint’s value to senior executives across various departments.

Responsibilities

• Own your revenue number
• Own leading and lagging indicators tied to pipeline generation, deal progression, and closed revenue
• Build and maintain a healthy pipeline through a mix of outbound, partner-sourced, and event-driven opportunities
• Run a tight sales process from first touch through close, with crisp forecasting and CRM hygiene
• Manage deal cycles of 60–120 days across multiple stakeholders, buying committees, and compliance/legal reviews
• Expand revenue via multi-threading, influencing executives, and reframing customer business cases
• Generate pipeline through high-quality outbound working alongside your SDR: sequences, social selling, signal-based outreach, and personalization
• Attend industry events, roundtables, and conferences, and turn those rooms into real opportunities
• Build strong relationships with digital agencies, who influence key buying decisions
• Develop partner go-to-market plays that help accelerate pipeline creation and deal momentum
• Build repeatable outbound motions that other AEs and SDRs can learn from
• Lead deep, consultative discovery that uncovers business problems, required capabilities, and success metrics
• Build account plans with whitespace mapping, multi-threading paths, and clear executive alignment strategies
• Drive deals forward with crisp next steps, mutual action plans, and alignment on decision criteria
• Work cross-functionally with Product, Sales Engineering, Marketing, and Partnerships to win complex deals
• Master competitive differentiation and objection handling across privacy, compliance, data, and activation
• Develop a deep understanding of Freshpaint’s value, capabilities, and architecture
• Become knowledgeable about healthcare data privacy, HIPAA, tracking changes, and the broader MarTech ecosystem
• Educate prospects on the changing regulatory environment and why modern data infrastructure is required to stay compliant
• Clearly communicate technical concepts to diverse audiences (marketers, PMs, engineers, data teams, and executives)
• Understand common Freshpaint use cases and how customers activate data while staying compliant
• Maintain rigorous CRM accuracy (HubSpot) across pipeline, forecasting, and next steps
• Run detailed qualification using MEDDIC/Command of the Message or similar frameworks
• Communicate deal status and risk clearly to sales leadership
• Track personal performance metrics and continuously improve your conversion rates, outbound effectiveness, and sales velocity
• Contribute to repeatable playbooks, messaging, and GTM learnings for the broader team
• Present to and influence CMOs, CPOs, General Counsels, VPs of Marketing, and VP-level executives
• Drive strong executive presence in meetings, events, and customer workshops
• Build long-term executive relationships that lead to both initial wins and future expansion
• Serve as a trusted advisor who deeply understands the customer's business, risks, and strategic priorities

Skills

• 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
• Experience selling into healthcare, regulated industries, or privacy/security personas
• Experience with Command of the Message
• Experience with MEDDIC or MEDDPICC
• Background in customer data, product analytics, MarTech, or data infrastructure

Benefits

• Offers Equity
• Offers Commission
• Competitive pay + generous equity (10-year exercise window)
• Fully remote (U.S. only) with a $150/month coworking stipend
• Half-day Fridays, every Friday
• 16 weeks fully paid parental leave (eligible after 6 months; commission-based roles receive 100% base salary during leave)
• 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
• Intentional & engaging company offsites 2x a year (past trips: Arizona, Jackson Hole, Cabo, Nashville, New Orleans & more) + a department offsite 1x per year

Company Overview