Head of Customer Success and Operations

About the Opportunity

People Joy is at an inflection point. Our product works, our clients stay, and our customer support team is strong. As we scale, we are building the operational infrastructure that connects support, account management, and client success functions into a unified high‑performing system. This hire leads that build.

As Head of Account Management and Customer Success, you will own the end‑to‑end function, design systems, create playbooks, develop people, own metrics, and build the foundation that allows People Joy to scale with consistency and excellence.

Reports To: CEO

Manages: Account Manager, Operations Analyst, Customer Support Lead (4 CSRs)

Location: Remote‑flexible; must be available for Philadelphia whiteboard sessions

Type: Full‑time

Compensation: $120,000 - $150,000 base salary commensurate with experience, plus performance bonus tied to NRR, CSAT, and retention outcomes. Equity participation available.

Account Management & Revenue Retention

• Renewal forecasting and execution – own the calendar, conversations, and outcomes
• Expansion and upsell pipeline from existing accounts
• Q  cadence and renewal templates tied to client budget cycles
• Account Manager coaching, accountability, and commercial development
• Handoff protocols from sales to implementation to ongoing success

Customer Support & Frontline Experience

• Strategic direction and development of the Customer Support Lead
• CSAT performance, service quality standards, and continuous improvement
• Ticket resolution oversight and escalation thresholds
• Support‑to‑success handoff protocols – ensuring nothing falls between the cracks
• Frontline CSR performance visibility and accountability through the Support Lead

Operations & Infrastructure

• Operations Analyst direction, prioritization, and output quality
• Process documentation – SOPs, playbooks, and workflows built from scratch
• KPI dashboard: NRR, churn risk, CSAT, ticket aging, adoption rates
• Cross‑functional process inputs that give dev and product something real to build against

• 5+ years in Customer Success, Revenue Operations, or Service Delivery
• Proven process builder – SOPs, playbooks, and workflows created from zero
• Experience managing teams and developing team leads
• Comfortable owning hard renewal, retention, and CSAT metrics – not just activity
• Operated in B2B SaaS, benefits, financial wellness, or adjacent categories
• Experience in early‑stage or founder‑led environments where you built before you inherited
• Strong communicator – run difficult client conversations and team coaching in the same afternoon
• Data‑driven – build dashboards, you don't just read them
• Low ego, high ownership

• Sees an absence of process as an invitation, not an obstacle
• Develops people, not just manages their output
• Leans into difficult client conversations rather than routing them upward
• Measures your own success by outcomes and metrics, not effort and activity
• Has operated in environments where you had to build before you could scale

• NRR is trending up and you can explain why
• CSAT is maintained or improved despite organizational growth
• Your Account Manager is closing renewals and identifying expansion opportunities independently
• Your Customer Support Lead is running a tight, high‑performing frontline without constant escalation
• Every client‑facing process is documented, followed, and actively improved
• Renewal outcomes are fully owned – forecast, conversation, and close
• People Joy's clients and members feel the difference in response time, consistency, and care

People Joy is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.