Senior Manager - Customer Success

About Benepass

Benepass simplifies the administration of employee benefits, recognizing that people are a company's most valuable resource. In today's hybrid and remote-first workplaces, one-size-fits-all benefits are inadequate. Benepass's fintech platform allows companies to customize and manage benefits tailored to their workforce's diverse needs by setting contribution levels and spend categories, helping employees find their optimal wellness for peak productivity and satisfaction.

Our Mission and Backing

Our goal is to transform how organizations support their employees. Benepass is backed by prominent investors such as Centana Growth Partners, Portage Ventures, Threshold Ventures, Gradient Ventures, Workday Ventures, and Clocktower Technology Ventures, having raised around $75 million in equity funding.

Role Overview

The Senior Manager of Customer Success will lead the SMB and Mid-Market Customer Success team, directly reporting to the Head of Customer Operations. This role manages six Customer Success Managers responsible for approximately $5 million in annual contracts. The focus is on fostering a high-achieving team that drives retention, business expansion, and operational excellence through coaching, scalable processes, and cross-department collaboration.

Key Responsibilities

• Lead and mentor a customer success team through regular one-on-one meetings, performance assessments, and career development initiatives.
• Manage metrics such as customer retention, renewals, product engagement, health scores, and pipeline growth.
• Support CSMs with strategic client engagements, including executive-level discussions and complex escalations.
• Create efficient operating rhythms for account reviews, renewals forecasting, and portfolio oversight.
• Advocate for and implement AI and automation strategies to streamline workflows, improve customer satisfaction, and scale operations sustainably.
• Analyze performance data to uncover trends and opportunities for coaching and process enhancements.
• Collaborate with Sales to ensure smooth customer handoffs and identify opportunities for account expansion.
• Work closely with Implementation, Technical Account Management, Customer Experience, Product, and Engineering to deliver seamless customer journeys.
• Develop and refine playbooks, customer journeys, and scalable operational procedures.
• Represent SMB and Mid-Market customer perspectives internally, championing their needs and communicating product feedback.
• Contribute to recruiting, onboarding, and cultivating future Customer Success talent amidst company growth.

Preferred Candidate Profile

• Passionate about developing talent and maximizing team performance.
• Skilled at balancing empathy with accountability; capable of guiding others through ups and downs.
• Highly organized with a focus on scalable operational processes.
• Data-driven decision-maker who maintains a strong customer-centric approach.
• Innovative in adopting AI tools, automation, and novel workflows that enhance customer and team outcomes.
• Thrives in dynamic, fast-moving startup settings with rapidly evolving priorities.
• Exceptional communication skills to build trust with customers, colleagues, and executives.

Necessary Qualifications

• Minimum 7 years in Customer Success, Account Management, or related SaaS customer-facing roles.
• At least 3 years managing Customer Success or Account Management teams.
• Demonstrated success in driving customer retention, renewals, and strong team performance.
• Experience coaching high-performing customer-facing teams.
• Strong analytical capabilities using customer health and performance metrics for informed decision-making.
• Proven collaboration across Sales, Product, Engineering, Support, and Operations functions.
• Proficiency in leveraging AI, automation, or workflow tools to boost productivity, customer experience, or operational efficiency.
• Skilled in handling complex executive customer relationships and escalations.
• Background in SaaS, HR technology, fintech, healthcare, or employee benefits preferred.

Additional Advantages

• Experience leading SMB and Mid-Market Customer Success departments.
• Previous exposure to startup or high-growth company environments.
• Expertise in establishing Customer Success frameworks, health scoring, or scaled customer programs.
• Direct knowledge of the employee benefits industry.

Compensation and Benefits

Salary ranges from $150,000 to $170,000 annually, complemented by equity options. The precise starting pay depends on factors like market standards, interview outcomes, peer salaries, and candidate experience.

• Medical, dental, and vision coverage at 95%.
• One-time $250 work-from-home setup allowance.
• $500 annual budget for learning and development.
• $150 monthly reimbursement for cell phone and internet expenses.
• $100 monthly wellness stipend.
• $100 monthly commuting and co-working allowance.
• Multiple team onsite events yearly.
• Flexible paid time off policy.

Equal Employment Opportunity

Benepass is dedicated to fostering an inclusive workplace and building a diverse team representing the community we serve. We are an equal opportunity employer committed to fair hiring practices.