Associate Director, Customer Success

- Lead, coach, and develop a team of Customer Success Managers supporting the Commercial and SMB book of business, setting clear goals and holding the team accountable to outcomes.

- Own the health and retention of the Commercial & SMB portfolio, using account health signals to prioritize where the team spends its time each week.

- Run a recurring risk and renewal review cadence, ensuring every at-risk account has a clear, documented action plan and owner.

- Partner with Sales, Renewals, and Deal Desk to manage upcoming renewals and expansion opportunities across the segment.

- Translate customer feedback and escalation trends into clear recommendations for Product, Support, and other cross-functional partners.

- Standardize playbooks, onboarding, and account planning practices across the CSM team to improve consistency and support scale.

- Monitor and report on segment-level performance to CS leadership, flagging risk and opportunity trends early.

- Champion consistent, accurate use of CS systems and tools so account data stays current and actionable.

- Represent the voice of the customer in cross-functional planning and strategy discussions.

- Net/gross revenue retention targets met or exceeded for the Commercial & SMB book.

- Quarter-over-quarter reduction in at-risk account exposure within the segment.

- High renewal timeliness - the majority of renewals close on or before contract end date.

- Strong customer satisfaction (CSAT/NPS) scores across the segment.

- Healthy CSM team retention and consistent ramp time for new hires.

- 3+ years of experience in Customer Success, Account Management, or a related client-facing role, including 2+ years directly managing a Customer Success team.

- Experience owning a book of business with defined retention and renewal targets.

- Proven ability to build and scale repeatable Customer Success processes, such as playbooks, account health frameworks, and account planning.

- Strong analytical skills, with comfort working in Salesforce (or a similar CRM) and turning account data into action.

- Excellent written and verbal communication skills, including experience presenting to senior stakeholders.

- A proactive, ownership-driven approach to solving problems in ambiguous situations.

- Experience in the benefits, healthcare, or mental health space.

- Experience with Gainsight or a similar customer health/success platform.

The target base salary range for this position is $146,000 - $168,000 and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations.

We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay.