Job Overview
Location
Remote - CAN
Job Type
Full-time
Category
Sales
Date Posted
March 18, 2026
Full Job Description
đź“‹ Description
- • As a Senior Enterprise Account Executive at Freshpaint Inc., you will be a foundational builder in scaling the company’s go-to-market motion by driving new revenue and representing the value of its HIPAA-compliant data governance platform to senior executives in healthcare organizations. This role is critical to Freshpaint’s mission of enabling healthcare marketers to promote access to care while safeguarding patient privacy in a rapidly growing market where healthcare constitutes 20% of the US GDP.
- • You will own your revenue number by managing full-cycle enterprise sales, from pipeline generation to closed deals, navigating complex 60–120 day sales cycles involving multiple stakeholders including Marketing, Product, Compliance, and Legal teams, while maintaining rigorous CRM hygiene and forecasting accuracy in HubSpot.
- • Day to day, you will generate pipeline through high-quality outbound efforts in partnership with SDRs, leveraging sequences, social selling, signal-based outreach, and personalization; attend industry events and roundtables to convert conversations into opportunities; build relationships with digital agencies that influence buying decisions; and develop partner go-to-market plays to accelerate deal momentum.
- • You will run an elite enterprise sales process by leading consultative discovery to uncover business problems and success metrics, building account plans with whitespace mapping and multi-threading strategies, driving deals forward with mutual action plans, and collaborating cross-functionally with Product, Sales Engineering, Marketing, and Partnerships to win complex deals.
- • You will become an expert in data, compliance, and the healthcare marketing landscape by developing deep knowledge of Freshpaint’s platform architecture, healthcare data privacy regulations like HIPAA, tracking changes, and the broader MarTech ecosystem, enabling you to educate prospects on evolving compliance requirements and communicate technical concepts clearly to diverse audiences.
- • You will operate with excellence by maintaining precise CRM data, applying MEDDIC or similar frameworks for qualification, communicating deal status and risks to leadership, tracking personal performance metrics, and contributing to repeatable sales playbooks and GTM learnings for the team.
- • You will represent Freshpaint as a senior, trusted advisor by presenting to and influencing CMOs, CPOs, General Counsels, VPs of Marketing, and other VP-level executives, demonstrating strong executive presence in meetings and workshops, and building long-term relationships that drive both initial wins and future expansion opportunities.
- • Freshpaint is a fully remote (U.S.-only) company backed by Y-Combinator, Intel Capital, and notable angel investors, with a team composed of alumni from high-growth companies like Heap, Pendo, Iterable, Quantum Metric, and Retool; the company gathers twice yearly for offsites to strengthen culture despite its remote-first model.
- • In this role, you will have the opportunity to grow your expertise in enterprise sales within a high-impact, mission-driven startup solving a critical problem in healthcare data privacy, while enjoying significant autonomy, ownership, and the chance to shape the sales playbook as Freshpaint scales rapidly in response to updated HIPAA guidance that has made its platform a market requirement.
🎯 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)
Skills & Technologies
Senior
Remote
Degree Required
About Freshpaint Inc.
Freshpaint provides healthcare organizations with a HIPAA-compliant customer data platform that unifies patient and marketing data, replacing tracking pixels and third-party cookies with first-party, privacy-first collection. It routes cleaned, consented data to analytics, advertising, CRM and data warehouse destinations while automatically applying healthcare-specific governance, retention and security controls. The platform supports server-side and client-side integrations, consent orchestration, breach monitoring and audit trails to help hospitals, telehealth providers and digital health companies activate marketing campaigns and measure performance without risking PHI exposure or regulatory violations.
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