Head of Customer Success and Operations

About Our Culture

Our culture is what makes PeopleJoy a great place to do meaningful work. We come from diverse backgrounds and experiences, but we're united by a shared drive to help others and improve lives.
• Put customers first and strive to exceed expectations
• Embrace change and adapt quickly
• Take accountability for our work and our outcomes
• Value trust, respect, and follow-through
• Focus on meaningful results, not just chasing numbers

Here, you'll find purpose, ownership, and a team that values progress over perfection.
Our Core Values

Do Right by Others - Have people's backs. Be someone others can rely on.

Improve Every Time - We don't do the same work the same way twice. We constantly streamline, simplify, and automate so each iteration is faster and better.

Be All-In - and Be Honest - We act in the best interest of PeopleJoy's mission and long-term success. We show up fully, take responsibility, and raise our hands early if something feels out of alignment.

Win Together - We prioritize team success over individual comfort, take feedback with humility, and step into whatever role helps the team win today.

Grit - We commit to long-term goals with resilience and discipline, pushing through obstacles even when progress feels slow.

About the Opportunity

This is not a manage-the-machine role. This is a build-the-machine role.

PeopleJoy is at an inflection point. Our product works. Our clients stay. Our customer support team is strong and our members feel it - CSAT scores reflect a frontline that genuinely cares. As we scale, we are building the operational infrastructure that connects our support, account management, and client success functions into a unified, high-performing system - and this hire leads that build.

As Head of Account Management and Customer Success, you will be the first person to own this function end-to-end. You are walking into a team with real capability and real heart - and the opportunity to build the operational system that takes them to the next level. You will design the systems, create the playbooks, develop your people, own the metrics, and build the foundation that allows PeopleJoy to scale with consistency and excellence.
Job Details

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.
What You Own
Account Management & Revenue Retention
• Renewal forecasting and execution - you own the calendar, the conversations, and the outcomes
• Expansion and upsell pipeline from existing accounts
• QBR 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

Who You Are

You have done this before - not at a company that handed you a playbook, but at one where you wrote it. You are equally comfortable in a spreadsheet, a client call, and a coaching conversation with a struggling direct report. You know how to manage a manager - giving a capable team lead the direction and development they need to keep their team performing while you focus on the strategic picture. You do not wait to be told what to build. You assess, prioritize, and execute.
• 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 - you can run a difficult client conversation and a team coaching session in the same afternoon
• Data-driven - you build dashboards, you don't just read them
• Low ego, high ownership

You'll Thrive Here If You Are Someone Who
• 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 their own success by outcomes and metrics, not effort and activity
• Has operated in environments where they had to build before they could scale

What Success Looks Like at 12 Months
• NRR is trending up and you can tell us exactly 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 escalating upward constantly
• Every client-facing process is documented, followed, and actively being improved
• Renewal outcomes are fully owned by you - forecast, conversation, and close
• PeopleJoy's clients and members feel the difference - in response time, consistency, and care

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