Senior Manager, Customer Success in Chicago, Illinois at First Gen Financial

About First Gen Financial

We’re a fast-growing, purpose-driven B2B financial services company built on integrity, accountability, and continuous growth. We have developed our own proprietary insurance product for employers which is scaling rapidly. Our leadership team brings proven expertise from multiple sectors of finance, and every team member plays a direct role in expanding both our clients’ success and our company’s vision. We unlock capital to empower teams!

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.
• Monitor team and portfolio health metrics (usage, NPS, churn, expansion revenue) and build reporting that gives leadership visibility into performance.
• Partner cross-functionally with Sales, Product, and Support leadership to advocate for customer needs and influence the roadmap.
• Drive process improvement and automation initiatives for the CS function alongside the Director of Customer Success.
• Maintain accurate records and reporting standards for customer interactions across CRM & process management systems.

Education & Experience

• 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 environments).
• 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.

Skills & Competencies

• Proven people leadership skills, including coaching, performance management, and team development.
• Excellent communication, executive presence, and presentation skills, with experience engaging senior stakeholders.
• Strong strategic thinking, problem-solving, and conflict-resolution abilities.
• Ability to lead a team, manage a portfolio of accounts, prioritize effectively, and operate in a fast-paced, evolving environment.
• Proficiency with CRM platforms (e.g., Salesforce, HubSpot, or similar) and customer success tools, with comfort using data and reporting to drive decisions.
• A consultative, customer-first mindset with a focus on delivering measurable value at scale.

• Occasional travel may be required, including for client and team engagements.\
• Occasional evening or weekend availability may be required to support client training sessions, team needs, or critical payroll-related activities.

Who You Are

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.

• Fully remote role.
• Base compensation: $90,000 - 110,000 + 10% Bonus
• Comprehensive benefits package including health, dental, and vision insurance.
• Retirement plan options.
• Paid time off, holidays, and professional development opportunities.
• Compensation for this position is dependent on location, experience, and other requirements.

Equal Opportunity Statement

First Gen Industries LTD is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We prohibit discrimination and harassment of any kind based on race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by applicable laws.

Employment decisions at First Gen Industries LTD are based solely on business needs, job requirements, and individual qualifications.