Head of Customer Success and Operations

🕒 April 29

🔔 Pennsylvania – Remote

🔔 Pennsylvania – Remote

💵 $120k - $150k / year

⏰ Full Time

🔴 Lead

🏆 Customer Success

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PeopleJoy

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2016

👥 HR Tech

☁️ SaaS

HR Tech • SaaS

PeopleJoy is a digital employee education and financial-wellness platform that helps employers offer, administer, and optimize student loan repayment, tuition assistance, Public Service Loan Forgiveness (PSLF) advisory, and related payment solutions. The company provides a SaaS-based benefits administration platform and white-glove service to streamline compliance, improve utilization of tax-advantaged programs, reduce HR administrative burden, and boost employee recruitment, retention, and engagement.

📋 Description

• 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. • 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. • 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 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.

🎯 Requirements

• 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

🏖️ Benefits

• Health insurance • Paid time off • Performance bonus tied to NRR, CSAT, and retention outcomes • Equity participation available