Senior Customer Success Manager

Deputy is hiring a Senior Customer Success Manager to own a portfolio of high-value Mid-Market and Enterprise customers. The role drives implementation continuity, product adoption, retention, strategic account relationships, and qualified expansion opportunities.

Responsibilities:

• Implementation Shadow-Management: Actively shadow-manage accounts during the onboarding and implementation phase alongside Professional Services to ensure early stakeholder alignment, validate configuration against business goals, and step in swiftly to mitigate risk if milestones or timelines stall
• Go-Live Handoff: Lead a frictionless transition from implementation to steady-state operations, ensuring zero loss of institutional context and delivering immediate continuity for customer admins and executives
• Trusted Advisor: Build and nurture multi-threaded relationships across executive and operational leadership (HR, Operations, Payroll, and C-Suite)
• Mutual Success Planning: Co-create, maintain, and execute customer-specific Mutual Success Plans aligned with strategic business objectives, operational workflows, and quantifiable ROI
• Executive Business Reviews (EBRs / QBRs): Prepare and facilitate high-impact business reviews to showcase delivered value, present adoption metrics, share product roadmap updates, and realign on executive priorities
• Customer Advocacy & Proof Points: Cultivate referenceable customer relationships, partnering with Marketing to produce case studies, customer quotes, reference calls, and review platform engagement (e.g., G2)
• Drive Depth of Adoption: Monitor portfolio usage telemetry, guiding customers on best practices to deepen adoption of core and advanced modules (e.g., smart scheduling, award interpretation, timesheets, and payroll readiness)
• Tech Ecosystem Alignment: Comfortably navigate and advise on enterprise software ecosystems, troubleshooting and guiding standard workflows involving HRIS, payroll, and POS integrations (e.g., ADP, BambooHR, Gusto, Xero)
• Strategic Enablement: Conduct tailored consultative workshops and optimization sessions to help customers operationalize new product capabilities
• Internal Feedback Loop: Synthesize customer feedback, recurring friction points, and feature requests to champion customer needs with Product, Engineering, and Design
• Churn Prevention & Health Tracking: Continuously evaluate account health scores, platform telemetry (via Vitally/Salesforce), and support ticket trends to detect early indicators of risk or "silent churn."
• Escalation Management: Act as the senior point of escalation for complex account issues, mobilizing Support, Professional Services, and Product teams to resolve critical blockers
• Renewal Partnership: Partner proactively with Account Managers (AMs) 90–120 days ahead of renewals, sharing usage health, relationship sentiment, and delivered ROI to ensure predictable, on-time contract renewals
• Expansion Identification: Uncover organizational changes, new business units/locations, or unmet operational workflows suitable for add-on modules (e.g., Deputy HR, advanced compliance, payroll sync) or seat growth
• Pipeline Enablement: Scope and qualify expansion leads before passing them seamlessly to Account Managers to close commercial agreements
• Mentorship: Provide coaching, deal support, and onboarding guidance to Associate and Mid-level CSMs across the Customer Success organization
• Playbooks & Tooling: Contribute to internal CS best practices, standard operating procedures, EBR templates, and health check playbooks

Requirements:

• 5 to 8+ years of B2B SaaS Customer Success or Strategic Account Management experience, with at least 2+ years managing Mid-Market or Enterprise accounts
• Strong comfort understanding and navigating SaaS tech ecosystems, integration touchpoints (APIs, webhooks, SSO), and upstream/downstream data flows between operational tools and payroll/HR systems
• Proven track record of leading high-stakes meetings, workshops, and EBRs with senior leadership (COO, VP HR, Head of Payroll)
• Hands-on experience working with modern CS and CRM tech stacks (e.g., Salesforce, Vitally or Gainsight, Jira, Slack)
• Demonstrated ability to step into complex or stalled customer situations, diagnose root causes, and align internal cross-functional resources to drive swift resolution
• Direct background in Workforce Management (WFM), HR tech, payroll, or time-and-attendance platforms is strongly desired