Director of Customer Success

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.