Head of Account Management, Freshpaint

• 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
• 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
• 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
• 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
• 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
• Passionate about leadership development
• Skilled at feedback, coaching, and accountability
• Ability to raise performance standards while maintaining team engagement

Desirable

• 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
• 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
• 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