United States onlyWorkHero 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.
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