Customer Success Manager

About the Role Title: Customer Success Manager- Activation & Retention

We are transforming the way Powerpay delivers value to new and existing customers. As part of this transformation, we are building a modern Customer Success Management function focused on improving customer health, product adoption, retention, and engagement across the Powerpay customer base. The Customer Success Manager will support a scalable, one-to-many customer success model for Powerpay customers, with a focus on identifying risk, driving adoption of key capabilities, improving customer outcomes, and reducing preventable churn. This role will support both early-life and existing customers by using data, lifecycle triggers, customer health signals, digital engagement motions, and customer feedback to help customers get greater value from Powerpay. This is a hands-on customer success role ideal for someone who understands payroll, enjoys solving customer problems at scale, and can work cross-functionally with Implementation, Support, Product, Sales, Retention, and other teams to improve customer experience and operational outcomes.

Key Responsibilities

1. Support Customer Health & Retention

• Monitor customer health signals across the Powerpay customer base, including payroll stability, case trends, product usage, engagement, adoption, and customer sentiment.

• Identify customers or customer segments showing signs of risk, disengagement, dissatisfaction, or reduced value realization.

• Execute proactive, targeted outreach where intervention is required to improve customer outcomes.

• Support retention by helping address preventable churn drivers before customers reach termination intent.

• Maintain accurate customer health, engagement, risk, and outcome information in Salesforce.

2. Drive Product Adoption & Value Realization

• Support adoption of key Powerpay capabilities, including priority features, workflows, and service offerings.

• Help customers mature in how they use Powerpay by identifying usage gaps and recommending scalable enablement or workflow improvements.

• Develop and maintain scaled success plans, segment-based value plans, and lifecycle playbooks that help customers progress from basic usage to stronger adoption and self-sufficiency.

• Partner with Product, Support, and Implementation teams to improve in-app guidance, digital education, and customer enablement.

• Use adoption data, case trends, and customer feedback to identify where customers are not realizing expected value.

3. Execute Scaled Customer Engagement Motions

• Create and support one-to-many customer engagement motions, including email campaigns, digital journeys, in-app guidance, webinars, templates, knowledge content, and targeted outreach.

• Use customer lifecycle stage, usage behavior, and risk indicators to determine when and how to engage customers.

• Ensure customers receive clear, timely, and relevant communications that help them use Powerpay effectively.

• Support customer education and community-oriented motions where appropriate, including webinars, feedback sessions, testimonials, or reference opportunities.

4. Support Early-Life Customer Stability

• Partner with Implementation teams during the early customer lifecycle to monitor customer stability, adoption, and readiness signals.

• Provide behind-the-scenes support to Implementation during hypercare, including risk identification, playbook recommendations, and customer health insights.

• Become customer-facing only when a customer moves into an at-risk state requiring Customer Success intervention.

• Support a smooth transition from Implementation-led hypercare to steady-state support once exit criteria are met.

5. Partner Cross-Functionally & Advocate for Customers

• Work closely with Implementation, Support, Product, Retention, Resolutions, Sales, and Support Operations to improve customer outcomes.

• Share recurring customer pain points, adoption barriers, process gaps, and product feedback back into the business.

• Partner with Support to identify case trends and opportunities to reduce preventable contacts.

• Share appropriate customer signals with Sales / Customer Base AEs, while ensuring CS does not own sales conversations, commercial negotiation, or expansion outreach.

• Help ensure customer communications across teams are coordinated and do not create confusion.

6. Contribute to Playbooks, Data & Continuous Improvement

• Help build and maintain scalable CS playbooks for customer health, adoption, at-risk intervention, existing customer engagement, and retention prevention.

• Support dashboards and reporting related to customer health, adoption, retention risk, case trends, campaign outcomes, and CS activity.

• Document CS interventions, customer signals, adoption barriers, and follow-up actions in Salesforce.

• Identify process waste, recurring friction points, and opportunities to simplify customer experiences.

• Contribute to broader Services transformation initiatives and the evolution of the Powerpay CS operating model. What Success Looks Like

• Improved visibility into customer health, adoption, and retention risk across the Powerpay customer base.

• Increased adoption of priority Powerpay features, workflows, and digital enablement resources.

• Earlier identification and intervention for customers showing signs of risk, dissatisfaction, or disengagement.

• Reduced preventable churn through proactive, data-informed customer engagement.

• Lower avoidable support demand through improved customer education, enablement, and in-app guidance.

• Stronger cross-functional coordination across Implementation, Support, Product, Sales, Retention, and Resolutions.

• More consistent Salesforce data, customer health tracking, and reporting to support decision-making.

• Clearer separation of responsibilities between Customer Success, Implementation, Support, Sales, and Retention.

Required Skills & Experience

• 3-5+ years' experience in customer success, customer support, implementation, operations, service delivery, or account management.

• Experience in SaaS, payroll, HR technology, or workflow software preferred.

• Strong Powerpay product knowledge or ability to quickly develop deep product understanding.

• Understanding of customer lifecycle management, adoption, retention, customer health, and value realization concepts.

• Experience supporting multiple customers, segments, campaigns, or workstreams in a high-volume environment.

• Ability to identify risk patterns using customer data, case trends, adoption metrics, lifecycle triggers, and customer feedback.

• Strong written and verbal communication skills, with the ability to simplify complex topics for customers.

• Comfort working with Salesforce, Pendo, dashboards, reporting tools, or similar systems.

• Strong cross-functional collaboration skills, including the ability to work effectively with Implementation, Support, Product, Sales, Retention, and Operations teams.

• Proven ability to take ownership, solve problems, and improve processes in an evolving environment.

Key Behaviours We're Looking For

• Proactive and outcome-focused.

• Comfortable working in a one-to-many customer success model. - Strong judgment on when to engage customers directly and when to coordinate internally.

• Customer-focused, while able to balance customer needs with scalable operations.

• Data-informed and curious about patterns, trends, and root causes.

• Strong customer advocate who can represent customer needs constructively back into the business.

• Collaborative, clear, and confident communicator.

• Able to work through ambiguity and help build new ways of working.

• Focused on prevention, adoption, retention, and long-term customer value - not just task completion.