Head of Mid-Market Customer Success (Remote)

Foley; Michigan; Remote; USD 130,000 - 170,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

401(k) with company match

Paid time off and holidays

Job summary

Foley is seeking a Senior Manager, Mid-Market Customer Success to lead a growing team of ~8 CSMs serving 800+ mid-market customers representing $16MM in revenue. The role focuses on retention, expansion, and maximizing NRR/GRR in a largely remote environment.

You will recruit and develop talent, drive adoption strategies, and collaborate cross-functionally to deliver measurable business outcomes across Foley’s AI-ready SaaS platform for safety-sensitive industries.

Qualifications

• 3+ years of experience leading Customer Success teams (6–10+ CSMs).
• Experience building high-performing remote teams and driving growth.
• Comfortable handling pricing discussions during renewals and expansions.
• Experience cross-functionally with Product, Sales, and Marketing.
• Proven ability to build engagement and accountability in a remote environment.
• Experience leading teams through rapid growth and organizational changes.
• Comfortable joining and leading customer calls and coaching CSMs.
• Strong analytical skills: customer health scores, CS metrics, dashboards.
• Expertise with customer success platforms; hands-on automation/AI tools in CS workflows.
• Experience in a DOT compliance or fleet management environment is a plus.

Responsibilities

• Recruit, develop, and retain top CS talent while fostering a high-performance culture.
• Drive adoption, retention, and expansion strategies to meet NRR, GRR, and churn targets.
• Partner cross-functionally with Sales, Product, Marketing, and other teams to improve customer outcomes.
• Lead interdepartmental collaboration in a fully remote environment with clear communication.
• Provide leadership on special projects, operational improvements, and scaling initiatives.
• Lead team meetings, performance management, and coaching for accountability.
• Utilize Planhat to monitor customer health and guide data-driven decisions.
• Help build/refine Planhat workflows, including agentic workflows and proactive outreach as CS scales.

Skills

People management

Pricing conversations

Cross-functional collaboration

Remote team leadership

Analytical skills

Customer health metrics

Dashboards

Planhat

Tools

Planhat

Job description

Foley is seeking a Senior Manager, Mid-Market Customer Success to lead a growing team of ~8 CSMs serving 800+ mid-market customers representing $16MM in revenue. The role focuses on retention, expansion, and maximizing NRR/GRR in a largely remote environment.

You will recruit and develop talent, drive adoption strategies, and collaborate cross-functionally to deliver measurable business outcomes across Foley’s AI-ready SaaS platform for safety-sensitive industries.