WorkHero is building the AI-powered back office for the skilled trades.
Tens of thousands of small HVAC businesses across the U.S. are overwhelmed by administrative work. WorkHero pairs experienced office managers with custom-built AI tools to reduce administrative burden and help owners grow thriving businesses.
Why it matters:
- We are helping local HVAC owners stay independent—growing their businesses and building meaningful wealth for themselves and their families.
- We are accelerating climate goals by expanding the capacity of small HVAC companies who are responsible for installing the millions of heat pumps our planet needs.
- We are proving that you can blend human expertise and AI to create exciting roles for our employees and exceptional results for customers.
WorkHero is an early-stage company with exciting traction and strong support from angel investors and Workshop Ventures. Our advisors include Chad Laurans (founder of SimpliSafe, the $1B+ home security company) and Gerald Chertavian (founder of Year Up, a $200M per year non-profit).
The Role:
We’re hiring a
Director of Customer Success to grow our team of office managers. This is a people-first leadership role, focused on hiring, developing, and managing a high-performing team. You’ll report directly to our Co-Founder and partner closely with our Founding Office Manager. WorkHero plans to more than double our service team headcount this year. The Director of Customer Success will play a central role in building the systems and capacity needed to scale this service operation. Your leadership will directly impact customer experience, employee growth, and overall company success.
What You'll Do:
- Grow, Onboard, and Lead the Team (Primary Focus)
- Hire, onboard, and train new office managers
- Conduct regular 1:1s, feedback sessions, and performance reviews
- Build clear career paths and support professional development
- Foster team cohesion and a strong culture of excellence
- Evolve the Service Model
- Define and standardize best practices across the service team
- Refine systems, processes, and templates for service scalability
- Create space for team input and continuous improvement
- Help maintain a personal, human touch while we grow
- Build Customer Success Model
- Allocate new customers across the team strategically
- Work with our Founding Office Manager to support office managers on escalations and troubleshooting around customer issues
- Help gather and act on customer feedback
- Maintain high levels of customer satisfaction and retention
- Collaborate Across the Business
- Partner with Sales to ensure smooth customer onboarding
- Contribute to cross-functional leadership conversations
- Partner with Product to align AI tools with team workflows
You're a Great Fit If You:
- Are a proven people leader who builds high-performing teams
- Love hiring, coaching and developing talent
- Take a systems-thinking approach to team and process design
- Balance quality, efficiency, and growth with a customer-first mindset
- Communicate clearly and build trust across functions
Nice-to-Haves:
- Experience leading Customer Success at a fast-growing company
- Background in service operations or process improvement
- Familiarity with AI-enabled tools and platforms
- Knowledge of the HVAC industry or skilled trades
Key Performance Metrics:
- Team growth, engagement, and retention
- Customer satisfaction and retention
- Office Manager efficiency (Contractor:Manager ratio)
- Internal promotions and leadership development
- Process implementation and adherence
Why Join Us:
- Lead and shape a growing team that’s core to our work and mission
- Work directly with co-founders to influence company direction
- Competitive salary, benefits, and meaningful equity
- Flexible, remote-first culture
- Shape what people leadership looks like in an AI-powered company
- Help redefine how small businesses thrive with expert support
We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.
Compensation Range: $110K - $140K
