Senior Customer Success Manager

Deputy is a global SaaS workforce management company with hubs in Sydney, Melbourne, San Francisco and London, plus team members working remotely across the United States. Our platform serves over 1.5 million workers and 375,000 workplaces across 100+ countries. We are backed by top global investors and recently achieved Unicorn status. At Deputy, we’re improving the world of work, one shift at a time, for 80% of the world’s workforce: hourly workers. These are the dedicated employees who keep our world running – from baristas to nurses, cleaners to delivery drivers, florists to factory workers. Despite their vital role in society, most workplace technology has focused on those workers who sit behind a desk, but at Deputy, we transform the frontline. When businesses use Deputy, their workplaces thrive – the business is more profitable, compliant, and productive, while the workers are more engaged and happier at work. We're becoming an AI-native company, a commitment that means you'll be empowered (and expected) to use AI tools and thinking in your day-to-day work. You'll have the training, support, and freedom to use AI responsibly and creatively to spark ideas, solve problems faster, and unlock new ways of working. If you’re passionate about creating solutions that put people first and helping businesses and their teams thrive, join us at Deputy and make an impact where it matters most!

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.

Employee Perks - Enjoy a flexible work policy (with a work-from-home stipend to set you up for success at home!) - Own a piece of Deputy through our Employee Share Ownership Plan (ESOP) - Take paid parental leave to support you and your family - We’ll match your 401k contributions to help you save for the future - Access mental health support with Spring Health - Get comprehensive health benefits - Use our commuter reimbursement program - Take additional leave days — including 20 PTO days, study assistance, celebration days and volunteering - Join our global working groups; focused on collaboration, belonging and connection Deputy believes in equal opportunity and that inclusiveness and diversity promotes innovation. Our global team members are from a variety of cultures. And we welcome different perspective and skills.