Senior Customer Success Manager

Role Overview

As a Senior Customer Success Manager (Senior CSM) at Deputy, you are the trusted strategic partner and customer advocate for a dedicated portfolio of high-value Mid-Market and Enterprise customers (typically accounts with 250+ to 1,000+ RTE). You engage during implementation by shadow-managing alongside Professional Services—ensuring seamless alignment, intervening proactively if roadblocks arise, and taking formal ownership at Go-Live. Across the customer lifecycle, you drive adoption, mitigate churn risk, lead strategic EBRs, and partner closely with Account Management to identify and qualify expansion opportunities.

This role will be joining our CSM team on a 12 month fixed term contract.

Key Responsibilities

1. Implementation Partnership & Lifecycle Transition

• 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.

2. Strategic Account Ownership & Relationship Management

• 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).

3. Product Adoption, Enablement & Ecosystem Navigation

• 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.

4. Retention & Proactive Risk Mitigation

• 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.

5. Growth, Expansion & Commercial Partnership

• 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.

6. Team Leadership & Operational Excellence

• 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.

What You Bring (Qualifications)

• Experience: 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.

• Ecosystem Acumen: 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.

• Executive Presence: Proven track record of leading high-stakes meetings, workshops, and EBRs with senior leadership (COO, VP HR, Head of Payroll).

• Process & Tooling Fluency: Hands-on experience working with modern CS and CRM tech stacks (e.g., Salesforce, Vitally or Gainsight, Jira, Slack).

• Problem-Solving Rigor: Demonstrated ability to step into complex or stalled customer situations, diagnose root causes, and align internal cross-functional resources to drive swift resolution.

• Domain Knowledge: Direct background in Workforce Management (WFM), HR tech, payroll, or time-and-attendance platforms is strongly desired.

Key Performance Indicators (KPIs)

• Net Dollar Retention (NDR) & Gross Retention Rate (GRR): Achieve portfolio retention targets (standard benchmark: ≥110% NDR / ≥95% Gross Retention).

• Platform Utilization & Health: Maintain target health scores and active feature utilization across assigned accounts.

• Executive Engagement: Execution rate and quality score for scheduled BRs and active Mutual Success Plans maintained in Vitally.

• Customer Satisfaction: Achieve portfolio-level CSAT and stakeholder NPS targets (typically average stakeholder NPS 35+).

• Expansion Pipeline Generated: Total qualified expansion pipeline (leads and seats/ARR) handed over to Account Management.

Work Environment & Travel

• Work Model: Remote

• Travel Requirements: 10% to 15% travel required for on-site Executive Business Reviews, high-priority customer workshops, and occasional company offsites.