Head of Member Services

Who We Are

Hassle Free Home Services was born out of a realization that home ownership came with its share of surprises – a never-ending to-do list, constant maintenance, and unexpected upgrades. Since 2003, we've assisted hundreds of homeowners with a simple motto: “one call solves it all.” Our monthly home maintenance and management services are designed to let homeowners reclaim their precious free time.

Join our passionate team in our shared mission to create lifelong relationships with our members, transforming home ownership into a truly hassle-free experience.

The Head of Member Services serves as the strategic leader responsible for operational excellence, technology enablement, and a seamless, high-quality member experience. This role ensures team efficiency and continuous improvement across all service channels, acting as the bridge between Member Services, AI-powered agents, and leadership to translate on-the-ground insights into strategic action. This is an onsite role in our Rockville, MD headquarters.

• Execute our vision for seamless member experience that delivers Four Seasons-like service across member communications, onboarding, and scheduling
• Partner with other department leaders to ensure member issues are handled thoughtfully, on-time and in-full
• Hire and train Member Service team members that fit with our culture and deliver to our expected service levels

• Continuously optimize AI-generated responses in email comms to ensure accuracy, clear next-step guidance, and strong member outcomes
  • Assist dev team in improving automated AI responses by contributing scenarios for the prompting and fine tuning of responses
• Partner with the technology team to define and refine Gorgias ticket assignment rules so member inquiries are routed to the right owner quickly, reducing handoffs and response time
• Audit customer communications (email, phone, texting, etc.) to ensure tone, accuracy, and consistency with brand standards

• Identify process issues and recommend improvements to streamline scheduling, onboarding, maintenance visit QA, and communication workflows
• Run point on high touch customer situations (escalations) that require triage and careful problem solving to maintain customer satisfaction
• Define clear triggers and pathways (escalation protocols) for when issues should move from frontline reps to leadership

• Enhance Quiq text messaging logic and communication flows to deliver accurate, relevant, and human-like responses to customer inquiries
• Identify and lead integration opportunities between Quiq and our CRM platform, Airtable (e.g. create repair tasks in our CRM from Quiq text messages, merge text message conversations into the Member Communication section in our CRM, etc.)
• Evaluate and improve the customer portal to improve usability, design, and overall member experience
• Develop and maintain internal documentation and “how-to” guides for team tools (Quiq, Airtable, Gorgias, Softr)

• Define and analyze KPIs for Member Services operations to measure onboarding efficiency, communication turnaround, and customer satisfaction, translating data into actionable insights
• Create dashboards/reporting for leadership visibility on the above performance metrics

• 3+ years of experience in customer operations, member services, or service delivery
  , preferably in high-expectation environments (e.g., membership, hospitality, logistics), with exposure to AI or automation
  .
• Exceptional written and verbal communication skills
  , with the ability to anticipate needs, reduce ambiguity, and enable fast, confident execution across teams.
• Strong systems and process mindset
  , with experience identifying root causes and improving workflows through rules, automation, tooling, and reporting.
• Demonstrated builder mentality
  , including experience documenting SOPs, refining processes, and scaling service operations in evolving or imperfect environments.
• High bar for white-glove customer experience
  , with comfort leading complex escalations and translating service failures into operational improvements.

• Competitive compensation, commensurate with experience
• High-ownership leadership role with real authority to shape systems, processes, and tooling across the company.
• PTO
• Health/Vision/Dental Insurance