Sr. Manager, Customer Success

Swooped is a talent platform (not a staffing agency) representing this role.

About the Opportunity

The company is making benefits easy, believing people are the most important asset to any organization. Traditional one-size-fits-all benefits packages no longer meet the needs of today's hybrid and remote-first workforce. Through an easy-to-use and highly customizable fintech platform, People teams can implement, administer, and track benefits that meet employees where they are. Employers design their benefits and perks plan by setting a contribution amount and eligible spend categories, allowing every employee to define their own wellness and access what they need to be productive and fulfilled.

Mission

Helping companies reimagine how they take care of their people.

About the Investors

The organization is backed by leading investors and has raised approximately $75 million in equity capital to date.

About the Role

As the Senior Manager, Client Success, you will lead the SMB and Mid-Market Customer Success organization, reporting directly to the Head of Customer Operations. This role is responsible for leading a team of six Customer Success Managers overseeing approximately $5M in Annual Contract Value. You will maintain and build a high-performing Customer Success team that delivers exceptional customer outcomes while driving retention, growth, and operational excellence.

This role requires equal parts people leadership, customer strategy, and operational execution. You will 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 customers realize maximum value from the platform. As the company scales, you will play a critical role in evolving how Customer Success operates. The ideal candidate is AI fluent and excited to rethink traditional Customer Success workflows by leveraging AI, automation, and scalable processes.

Responsibilities

• 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.

Requirements

• 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.

Skills

• 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.

Bonus Skills

• Experience leading SMB and Mid-Market Customer Success organizations.
• Previous startup or high-growth company experience.
• Experience building Customer Success operating models, health scoring, or scaled customer programs.
• Direct experience in the employee benefits space.

Pay

$150,000 to $170,000 base salary + equity

Benefits

• 95% coverage of medical, dental, and vision
• Several team onsites a year
• Flexible PTO