Senior Enterprise Account Executive

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.

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.

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.

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.

• 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

• 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

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! Check out our careers page for the full list.