Stephen Schaffer

6x President’s Club · Senior Account Management Leader @ Rippling · Expansion, Retention, & Playbook-Building at Scale · PEO & SaaS

Los Angeles Metropolitan Area

About

Most SaaS teams treat retention and expansion as separate problems. I build the teams and the systems that solve both at once. Currently I am a Senior Manager of Account Management at Rippling with 8 years in SaaS revenue experience. I specialize in scaling high-performing AM orgs, driving net revenue retention (NRR), and developing the next generation of high performers and managers. At Rippling: · 101% retention rate in FY25 · 145% cross-sell attainment in FY25 · $30M+ ARR under management · 6× President's Club I don't just hit number. I build teams that exceed the number consistently. That means building repeatable playbooks, owning forecasting, promoting ICs into leadership, and holding teams accountable to both customer outcomes and revenue growth. Currently leading a team of 6-7 Account Managers across a $30M+ ARR PEO book at Rippling.

Experience

  • Rippling ()
    • Senior Manager, PEO Account Management
      Apr 2025 - Present · 1 yr 4 mos

      Achievements: -President's Club 2026 -President’s Club 2025 -President's Club 2024 -President's Club 2023 -President’s Club 2022

    • Manager, PEO Account Management
      Apr 2023 - Apr 2025 · 2 yrs 1 mo

    • Senior Account Manager
      Oct 2022 - Apr 2023 · 7 mos

  • Mavenlink ()
    • Customer Success Manager
      Feb 2019 - Jun 2021 · 2 yrs 5 mos

      Achievements: -President's Club 2019 -BDR of the Year 2019 -CSM Rookie of the Year 2020 -Sourced the largest deal in Mavenlink history

    • Enterprise Business Development Representative
      Aug 2018 - Feb 2019 · 7 mos

    • Business Development Representative
      Jul 2017 - Aug 2018 · 1 yr 2 mos