Sr. Manager, Customer Success

As the Senior Manager, Client Success, you will lead our SMB and Mid-Market Customer Success organization, reporting directly to the Head of Customer Operations. You'll be responsible for leading a team of six Customer Success Managers overseeing approximately $5M in Annual Contract Value.

Your primary responsibility is maintaining and building a high-performing Customer Success team that delivers exceptional customer outcomes while driving retention, growth, and operational excellence. You'll coach and develop CSMs, establish scalable operating rhythms, and partner cross-functionally to continuously improve the customer experience.

This role requires equal parts people leadership, customer strategy, and operational execution. You'll serve as the primary escalation point for your segment while partnering closely with Sales, Implementation, Technical Account Management, Customer Experience, Product, Engineering, and Business Operations to ensure our customers realize maximum value from Benepass.

As Benepass continues to scale, this leader will play a critical role in evolving how Customer Success operates. We're looking for someone who is AI fluent and excited to rethink traditional Customer Success workflows by leveraging AI, automation, and scalable processes to deliver exceptional customer experiences while improving team efficiency and maintaining strong unit economics.

- Lead, coach, and develop a team of Customer Success Managers through regular 1:1s, performance management, and career development.

- Own team performance across customer retention, renewals, customer health, product adoption, and expansion pipeline generation.

- Partner with CSMs on strategic customer relationships, executive conversations, and complex customer escalations.

- Establish scalable operating rhythms for account reviews, renewal forecasting, health monitoring, and portfolio management.

- Champion the adoption of AI and automation across the Customer Success organization by identifying opportunities to eliminate manual work, improve customer experiences, and enable the team to scale without sacrificing service quality.

- Analyze customer and team performance data to identify trends, coaching opportunities, and process improvements.

- Partner with Sales to ensure successful customer transitions and identify expansion opportunities.

- Collaborate with Implementation, Technical Account Management, Customer Experience, Product, and Engineering to deliver an exceptional end-to-end customer experience.

- Build and improve playbooks, customer journeys, and operational processes that enable the team to scale efficiently.

- Serve as the voice of the SMB and Mid-Market customer internally by advocating for customer needs and communicating product feedback.

- Help recruit, onboard, and develop future Customer Success talent as the organization continues to grow.

- You love developing people and helping teams perform at their highest level.

- You balance empathy with accountability and enjoy coaching through both successes and challenges.

- You're highly organized and operationally minded, with a passion for building scalable processes.

- You're comfortable making data-driven decisions while maintaining a strong customer-first mindset.

- You enjoy experimenting with AI tools, automation, and new ways of working, and you know how to translate those innovations into practical improvements for both customers and internal teams.

- You thrive in fast-paced startup environments where priorities evolve quickly.

- You're an exceptional communicator who can build trust with customers, teammates, and executive stakeholders alike.

- 7+ years of experience in Customer Success, Account Management, or other customer-facing SaaS roles.

- 3+ years of experience managing Customer Success or Account Management teams.

- Proven track record of driving customer retention, renewals, and team performance.

- Experience coaching and developing high-performing customer-facing professionals.

- Strong analytical skills with experience using customer health metrics and performance data to drive decisions.

- Demonstrated ability to partner cross-functionally across Sales, Product, Engineering, Support, and Operations.

- Demonstrated experience leveraging AI, automation, or workflow tooling to improve team productivity, customer experience, or operational efficiency.

- Experience managing executive-level customer relationships and customer escalations.

- Experience working in SaaS, HR Tech, fintech, healthcare, or employee benefits is preferred.

- Experience leading SMB and Mid-Market Customer Success organizations.

- Experience building Customer Success operating models, health scoring, or scaled customer programs.