[Hiring] Head of Implementation @Freshpaint

Role Description

Freshpaint’s success is defined by the success of our customers. As we scale our enterprise business, we are seeking a Head of Implementation to lead and evolve our implementation function. This is a director-level role responsible for building a world-class onboarding experience that accelerates time to value, ensures privacy-first excellence, and drives long-term customer outcomes. You will lead a team of Enterprise Implementation Engineers, define our implementation strategy, and partner cross-functionally across Customer Success, Sales, Product, Engineering, and Marketing to deliver operational excellence at scale. This leader will own the implementation lifecycle from signed contract to full adoption. They will ensure we deliver value efficiently, predictably, and with an exceptional customer experience. You will handle customer escalations effectively and unblock onboardings.

Qualifications

• 8+ years in customer-facing technical roles (Implementation, Solutions Engineering, Solutions Architecture, or Customer Success Engineering).
• 3+ years leading and scaling technical customer-facing teams.
• Experience operating at a director level in a high-growth SaaS environment.
• Proven track record of building processes from early-stage to scale-stage environments.
• Deep understanding of web technologies, analytics, and front-end development.
• Working proficiency with HTML, CSS, JavaScript, and tag management platforms (e.g., Google Tag Manager).
• Hands-on-keyboard experience implementing and troubleshooting complex platform configurations.
• Strong understanding of data pipelines, APIs, and marketing technology ecosystems.
• Working proficiency with analytics tools and data warehouses (Looker, Tableau, Snowflake, Redshift, etc.), with the ability to query and digest large data sets.
• Exceptional written and verbal communication skills.
• Comfortable engaging VP and C-level executives on both technical and business topics.
• Ability to translate complex technical concepts into clear business value.

Requirements

• Define and evolve Freshpaint’s implementation philosophy, operating model, and service tiers.
• Create a scalable onboarding framework that supports enterprise growth while maintaining high-quality delivery.
• Design segmentation strategies for enterprise, mid-market, and strategic accounts.
• Establish clear success metrics for onboarding, including:
  • Time to First Value (TTFV)
  • Time to Full Adoption
  • Implementation NPS
  • Feature activation rates
  • Onboarding-related expansion influence
• Lead, mentor, and grow a high-performing team of Enterprise Implementation Engineers.
• Set performance standards and define leading/lagging indicators for individual and team success.
• Hire and onboard new team members as the business scales.
• Develop career paths, coaching frameworks, and skills progression across technical and consultative capabilities.
• Foster a culture of operational excellence, customer empathy, and technical rigor.
• Build scalable onboarding processes, playbooks, templates, and internal documentation.
• Own forecasting and capacity planning for onboarding volume and complexity.
• Standardize project management practices and tooling (e.g., Monday).
• Develop dashboards to measure onboarding efficiency, adoption trends, and implementation quality.
• Continuously identify bottlenecks and drive improvements across systems and workflows.
• Act as executive sponsor for strategic or high-risk implementations.
• Partner with Sales during late-stage deals to validate technical feasibility and implementation strategy.
• Serve as a senior escalation point for complex customer challenges.
• Build trusted relationships with executive stakeholders (VP/C-level).
• Ensure full feature onboarding and activation across accounts.
• Collaborate with Account Management to drive expansion opportunities through technical enablement.
• Improve retention and expansion by ensuring strong technical foundations during onboarding.
• Develop implementation strategies that unlock upsell pathways.

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
• 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!