Head of Account Management

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.

Who we’re looking for

The ideal candidate has a proven track record of building and elevating high-performing Account Management teams, with particular strength in lifting up first-time managers and first-time leaders. They bring disciplined operational systems, strong forecasting accuracy, and a repeatable approach to driving net retention and customer outcomes.

What you’ll be doing

Our success is defined by the success of our customers.

This role oversees:

• Enterprise Account Managers (high-volume, scaled engagement model)

• Strategic Account Managers (high-touch, white-glove, deeply embedded accounts)

We are seeking a Head of Account Management to lead and scale our Enterprise and Strategic Account Management teams. This leader will own the health, retention, and expansion of our post-sale revenue base by driving best-in-class operational rigor, developing exceptional managers and leaders, and ensuring consistent customer value delivery across segments and then developing those into clear, repeatable playbooks for the team.

Primary responsibilities

1. Net Revenue Retention & Growth Strategy

• Own gross and net retention across the AM organization.

• Drive consistent upsell and expansion performance across both Enterprise and Strategic segments.

• Establish clear performance benchmarks for:

  • Net retention rate

  • Adoption metrics

  • Account health

  • Forecast accuracy

  • ARR per rep

• Partner cross-functionally with Sales, Product, Support, and CS Engineering to remove friction in expansion and renewal processes.

• Ensure renewal and expansion processes are predictable, disciplined, and measurable.

2. Segment Strategy & Engagement Models

• Enterprise Accounts (Scaled Model)

  • Ensure efficient management of larger account portfolios.

  • Optimize cadence, playbooks, automation, and KPI tracking.

  • Build repeatable frameworks for whitespace identification and product adoption.

• Strategic Accounts (White-Glove Model)

  • Standardize executive engagement strategies.

  • Ensure rigorous QBR frameworks and executive alignment.

  • Proven ability to hit commercial goals and develop clear commercial strategies.

  • Deepen value realization and measurable ROI storytelling.

  • Drive structured, proactive account planning and relationship mapping.

• Create clarity around what “good” looks like in each segment and ensure execution meets that bar consistently.

3. Develop Managers & Build Leadership Depth

• A critical priority of this role is developing people, especially:

  • First-time managers

  • First-time leaders

  • High-potential AMs transitioning into leadership roles

• You will:

  • Coach managers on:

    • Performance management

    • Forecasting discipline

    • Strategic account thinking

    • Executive communication

    • Driving accountability

  • Implement structured manager enablement programs to eventually develop top talent into leads as needed.

  • Create clear career paths within Account Management.

  • Raise the bar on talent density and performance expectations, and identify and implement training/certification and resourcing for the team - we want this team constantly learning and leveling up.

4. Operational Excellence – Best in Class

• You will:

  • Establish forecasting systems with high accuracy and transparency.

  • Ensure CRM hygiene and pipeline integrity.

  • Standardize:

    • Account planning frameworks

    • Value realization documentation

    • Adoption measurement

    • QBR structure

    • Health scoring

• Build dashboards and reporting that drive action, not just visibility.

• Run a disciplined operating cadence:

  • Weekly forecast calls

  • Performance reviews

  • Account line-by-line reviews

  • Quarterly business retrospectives

• Create scalable playbooks for renewal and expansion execution.

5. Customer Value & Executive Alignment

• Ensure every account has a clear value realization strategy.

• Raise the bar on ROI articulation and executive storytelling.

• Embed a culture of proactive risk identification.

• Strengthen executive sponsor engagement internally and externally.

• Serve as a key escalation point for complex strategic accounts.

6. Cross-Functional Leadership

• Act as the voice of the customer internally.

• Partner closely with:

  • Product (feedback loops, roadmap alignment)

  • Sales (handoffs, expansion alignment)

  • Marketing (case studies, advocacy)

  • Support & Engineering (issue resolution)

• Improve handoffs from implementation to ongoing account management.

• Reduce friction in the customer journey.

Desired skills & experience

Leadership & Management Experience

• Over 10+ years in enterprise SaaS, customer success, or account management.

• 5+ years leading managers and multi-layer teams.

• Proven experience developing first-time managers into high-performing leaders.

• Track record of scaling teams through growth stages.

Revenue Ownership

• Experience owning meaningful post-sale revenue targets.

• Strong history of improving net revenue retention and expansion metrics.

• Deep understanding of renewal forecasting and expansion modeling.

Operational Rigor

• Exceptional discipline in forecasting, CRM hygiene, and reporting.

• Process-oriented mindset with the ability to build scalable systems.

• Strong analytical orientation and comfort with adoption metrics and KPIs.

Strategic & Executive Presence

• Comfortable engaging with C-level stakeholders.

• Ability to coach teams on executive alignment and consultative value delivery.

• Strong ability to balance scaled efficiency with white-glove engagement models.

Talent Development Mindset

• Passionate about leadership development.

• Skilled at feedback, coaching, and accountability.

• Ability to raise performance standards while maintaining team engagement.

Nice to Haves

• Experience in healthcare technology or marketing technology.

• Experience in privacy, data, or compliance-driven environments.

• Background in building multi-segment AM organizations (Enterprise + Strategic).

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! Check out our careers page for the full list.