Senior Enterprise Account Executive

About Freshpaint: Healthcare is a $4+ trillion industry in the U.S. alone, and it’s undergoing a rapid digital transformation. Hospitals, digital health companies, and life sciences organizations rely on analytics and advertising tools to reach patients, measure performance, and grow. But those tools weren’t built for regulated healthcare data. That creates real compliance risk and forces teams to choose between growth and privacy. Freshpaint eliminates that trade-off. We’re a privacy-first data platform that helps healthcare organizations use modern marketing and analytics tools without exposing protected health information (PHI). Freshpaint sits between a company’s website or app and the third-party tools they use, automatically detecting and controlling sensitive data before it’s shared. In short: we let healthcare teams move fast, safely. Backed by Top Investors Freshpaint is backed by some of the most respected names in technology, including: Y Combinator (OpenAI, Stripe, Airbnb, Coinbase, DoorDash) Intel Capital (Broadcom, Astera Labs, VMware, RedHat, MongoDB) We’ve raised tens of millions of dollars in funding to build the privacy infrastructure layer for healthcare’s digital future. What you’ll be doing 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. This is a true builder role. You will be foundational to scaling Freshpaint’s go-to-market motion. Primary 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 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 Desired skills & experience 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 Nice to haves 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 Perks & Benefits We take care of our team—here’s a peek at what you get when you join: 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 And more! 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