Senior Manager, Customer Success
- Compensation
- Not disclosed
- Location
- Chicago, IL
- Work setup
- Remote
- Seniority
- Senior
- Employment
- Not specified
- Experience
- 2+ years
- Category
- Customer success
- Posted
Skills
Must have
- Bachelor's degree in Business, Communications, Marketing, or related field (or equivalent experience).
- 5–7+ years of experience in customer success, account management, or client-facing roles, including 2+ years in a leadership, team-lead, or mentorship capacity (preferably in SaaS or technology-driven
- Proven track record managing a portfolio of enterprise or strategic accounts and driving measurable retention and expansion outcomes.
- Experience working with payroll systems, payroll integrations, or HRIS platforms (e.g., payroll providers, benefits administration, or related services) strongly preferred.
- Experience with professional services for finance and/or insurance a plus.
- You’re an A-Player. coachable, driven, and deeply mission-aligned. You thrive on ownership, competition, and personal growth. You embody First Gen’s core values:
- - Ironclad Integrity: You do the right thing, even when no one is watching.
- - 24-Carat Accountability: You own your outcomes and stay humble when corrected.
- - Catalyst: You’re a constant learner with curiosity, discipline, and resilience.
- - Wholehearted: You put relationships before deals and build authentic trust.
- You’re not just looking for another sales job you’re seeking a purposeful career where your work directly impacts business owners and their teams.
Full description
About the role
We’re looking for a high-performing Insurance Account Executive who thrives in a fast-paced, performance-driven environment. You’ll lead full-cycle B2B sales from prospecting warm leads and consultative selling to closing and onboarding new accounts, while helping shape the standards and culture of our rapidly expanding sales team.
Position Summary
The Senior Manager of Customer Success leads and develops a team of Customer Success Managers, owning the strategy, execution, and results for the Customer Success function's client portfolio. This person will lead a team of 3–4 CSMs and report to the Director of Customer Success. The Senior Manager ensures the team can confidently guide clients through these time-sensitive, high-stakes processes.
This role is a key strategic partner in shaping processes, driving retention and expansion, and scaling the CS organization as the company grows. The Senior Manager combines hands-on ownership of the company's most strategic accounts with people leadership, coaching a team of CSMs to help clients achieve maximum value from our products while reducing churn and increasing satisfaction. This is a high-visibility, high-growth opportunity for a leader ready to help build the future of the Customer Success organization, with a clear path to broader ownership of CS for the right individual.
Key Responsibilities
Team Leadership
- Lead, coach, and develop a team of 3–4 Customer Success Managers, providing performance feedback, career development, and day-to-day guidance.
- Support hiring, onboarding, and training as the CS team scales, helping build a high-performing organization.
Strategic Accounts & Client Outcomes
- Personally own and manage a portfolio of the company's most strategic accounts post-implementation, modeling best practices while driving retention, adoption, and long-term value.
- Serve as the point of escalation for complex or high-value client issues, partnering with support and product teams to drive timely resolution.
- Lead executive-level business reviews (QBRs) with key clients, delivering strategic insights and demonstrating ROI.
- Identify and drive opportunities for account growth, upselling, and cross-selling across the team's portfolio.
- Guide customers through onboarding, training, and implementation, and standardize scalable playbooks the team uses to ensure successful adoption — including payroll-related workflows, integrations, and time-sensitive processes, ensuring accuracy, compliance, and alignment with benefits administration.
Strategy, Process & Cross-Functional Partnership
- Own the Customer Success strategy for the client portfolio in partnership with the Director of Customer Success, including retention, expansion, and renewal targets.