[Remote] Senior Enterprise Account Executive

Note: The job is a remote job and is open to candidates in USA. Freshpaint is a rapidly growing software company focused on helping healthcare organizations modernize their data infrastructure while ensuring privacy compliance. As a Senior Enterprise Account Executive, you will be responsible for driving new revenue, generating demand, and navigating complex enterprise sales cycles, while representing Freshpaint’s value to senior executives across various functions.

Responsibilities

• OWN YOUR REVENUE NUMBER
• 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
• DRIVE PIPELINE THROUGH OUTBOUND, EVENTS, AND PARTNERSHIPS
• 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
• RUN AN ELITE ENTERPRISE SALES PROCESS
• 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
• BECOME AN EXPERT IN DATA, COMPLIANCE, AND THE HEALTHCARE MARKETING LANDSCAPE
• 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
• OPERATE WITH EXCELLENCE
• 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
• REPRESENT FRESHPAINT AS A SENIOR, TRUSTED ADVISOR
• 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

• 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)

Company Overview