Senior Customer Success Manager

Workstream is a mission-driven company building the all-in-one HR, payroll, and hiring platform for managing the hourly workforce.

We are looking for a Senior Customer Success Manager who can combine analytical thinking with strong customer relationships. You will own the full customer lifecycle: from successful adoption and value realization through renewal and expansion opportunities.

Day in the Life

• Customer Success & Problem Solving (40%)
• Become an expert in Workstream and your customers' business
• Build deep understanding of how they manage hourly workforces, multi-location operations, and franchisee adoption
• Own a portfolio of enterprise customers and build trusted relationships with key stakeholders
• Use product usage data, customer activity, and financial signals to figure out what's working
• Leverage CSM tools to get visibility into account health, adoption, and risk
• Identify complex challenges and work with Product, Support, and Sales to solve them
• Run customer training, build content that helps them learn, and set them up to self-serve adoption where possible
• Keep accurate account records and notes

• Renewal & Retention (35%)
• Own renewal conversations and drive renewal outcomes for your portfolio
• Get ahead of at-risk accounts and develop recovery strategies
• Use customer data and CSM tools to surface renewal timing and risk signals
• Be the customer's voice internally, pushing for features, process changes, and decisions that protect retention

• Growth & Expansion Pipeline (15%)
• Surface expansion opportunities and generate CSQLs for Sales through discovery and account analysis
• Look at customer usage patterns and business fit to identify where Workstream can solve new problems
• Partner with Sales to brief them on expansion readiness
• Introduce customers to new features as it makes sense for their needs

• Feedback & Insights (10%)
• Share insights across your portfolio, identifying segments that stick around, drivers of churn, and healthy adoption
• Give the internal team feedback on product gaps, training breakdowns, and process improvements
• Use the renewal forecast to focus your energy and effort

Key Metrics You Will Be Measured On

• Renewal rate and NRR for your portfolio
• Customer retention and churn
• Customer engagement and health
• CSQLs generated for Sales
• Product adoption and usage

Who You Are

• 4–6 years in Customer Success, Account Management, or similar work where you've owned customer outcomes
• Analytical and strategic, able to read customer data and understand what it means
• Good at discovery, asking questions that matter, listening, and understanding customer goals
• Able to handle complexity and ambiguity, managing enterprise customers with nuance
• Clear communicator, explaining complicated concepts in simple terms
• Organized and detail-oriented, keeping accounts clean and tracking next steps

Nice To Have

• Experience with payroll, HR tech, QSR, or franchising
• Familiarity with CSM platforms like Gainsight, Totango, Churn Zero, or Intercom
• Background in renewals, contracts, or account management
• Experience managing multi-location or franchisee operations

What We Offer

• Mission-driven and value-based company dedicated to empowering deskless workers and local businesses
• Early employee opportunity at a Series B hyper-growth startup
• Competitive salary and equity
• Comprehensive health coverage
• In-office amenities and stocked kitchen
• 401K Plan
• Flexible PTO