Customer Success Leader

Goodwin Recruiting; Chicago (IL); Remote; USD 180,000 - 240,000; Full time

Job summary

A rapidly growing AI legal technology company is seeking a Customer Success Leader to build and scale its CS function. This is a hands-on leadership role reporting to executives and owning retention, renewals, expansion, and NRR while shaping processes, tooling, and metrics.

You will design the operating model, hire and mentor the CS team, establish health scoring and segmentation, and partner with Sales and Product to drive outcomes across SMB to enterprise customers.

Qualifications

• 6+ years of CS, AM, or related SaaS leadership experience.
• Experience building or scaling a CS function.
• Ownership of retention, renewals, expansion, and NRR.
• Experience developing health scoring, segmentation, renewal forecasting, playbooks, and CS processes.
• Strong executive presence and ability to earn trust with senior stakeholders.
• Ability to make sophisticated technology approachable for non-technical customers.

Responsibilities

• Own relationships with strategic customers and drive retention, adoption, and expansion.
• Take accountability for retention, renewals, expansion revenue, and NRR across the customer base.
• Hire, coach, and develop the Customer Success team as the company grows.
• Build the CS function from the ground up, including playbooks, workflows, customer-health frameworks, forecasting, reporting, and tooling.
• Establish customer segmentation and coverage models across SMB, mid-market, and enterprise accounts.
• Create scalable engagement strategies for firms of different sizes and sophistication.
• Partner closely with Sales on handoffs and expansion opportunities.
• Work with Product to ensure customer feedback informs roadmap priorities.
• Coordinate with service and discovery teams to ensure successful customer outcomes.
• Personally step into strategic accounts, escalations, and high-stakes customer situations.
• Provide leadership with visibility into customer health, retention risk, and CS performance.

Skills

Customer success leadership

Account management

SaaS leadership

Executive communication

Cross-functional collaboration

Job description

A rapidly growing AI legal technology company is seeking a Customer Success Leader to build and scale its Customer Success function.

This is a hands‑on leadership opportunity for someone who wants to create the operating model, not inherit one. Reporting directly to company leadership, you’ll own strategic customer relationships, retention, renewals, expansion, and NRR while building the processes, tooling, metrics, and team required to support continued growth.

The customer base ranges from solo attorneys to sophisticated litigation organizations. Many customers are working under intense deadlines and may not be highly technical, making the ability to establish trust, simplify complexity, and drive adoption especially important.

What You’ll Do:

• Own relationships with our most strategic customers and drive retention, adoption, and expansion.
• Take accountability for retention, renewals, expansion revenue, and NRR across the customer base.
• Hire, coach, and develop the Customer Success team as the company grows.
• Build the CS function from the ground up, including playbooks, workflows, customer‑health frameworks, forecasting, reporting, and tooling.
• Establish customer segmentation and coverage models across SMB, mid‑market, and enterprise accounts.
• Create scalable engagement strategies appropriate for firms of dramatically different sizes and levels of sophistication.
• Partner closely with Sales on handoffs and expansion opportunities.
• Work with Product to ensure customer feedback informs roadmap priorities.
• Coordinate with service and discovery teams to ensure successful customer outcomes.
• Personally step into strategic accounts, escalations, and high‑stakes customer situations.
• Provide leadership with clear visibility into customer health, retention risk, expansion opportunity, and CS performance.

What We’re Looking For:

• 6+ years of Customer Success, Account Management, or related SaaS client leadership experience.
• Experience managing, mentoring, or building Customer Success teams.
• Demonstrated success building or materially scaling a CS function, rather than only operating within an established organization.
• Ownership of commercial CS metrics such as retention, renewals, expansion, and NRR.
• Experience developing health scoring, segmentation, renewal forecasting, playbooks, and CS operating processes.
• Strong executive presence and ability to build trust with demanding senior stakeholders.
• Excellent communicator who can make sophisticated technology approachable for non‑technical customers.
• Comfortable operating hands‑on in an early‑stage, ambiguous environment.
• Strong cross‑functional partnership with Sales, Product, and executive leadership.
• Legal technology, law firm, litigation support, or eDiscovery experience is preferred but not required.
• Experience building CS within a Series A/B or similarly early‑stage SaaS company is highly desirable.

Why This Opportunity:

• Build the Customer Success organization rather than inherit a mature function.
• Join a rapidly growing AI company with meaningful existing customer traction.
• Work directly with company leadership and influence company strategy.
• Own both the strategic and operational sides of CS.
• Work with customers using the product on real, high‑impact legal matters.
• Fully remote U.S. role with travel as needed.