Director, Customer Success

We are seeking a dynamic and experienced Director of Customer Success to lead our SMB, Mid-Market, and Enterprise Segments of the Customer Success team. This role will focus on driving customer retention, adoption, and expansion. The ideal candidate is passionate about customer experience, adept at managing an entire (SMB, MM, ENT) customer base, and experienced in optimizing team performance through data-driven insights and strategic initiatives.

Key Responsibilities:

• Lead and mentor a team of SMB, MM, and Enterprise Customer Success Managers (CSMs).
• Establish clear KPIs, target account health metrics, and growth objectives for your team.
• Accountable for driving Net Retention Rate (NRR), Gross Revenue Retention (GRR), reducing logo churn, and identifying expansion opportunities alongside the Sales/Account Executive team.
• Collaborate with Sales leaders, Product Managers, and Support leaders to ensure a seamless customer journey and provide a positive customer experience.
• Leverage data and analytics to track team performance, customer health, and engagement strategies.
• Develop and refine CSM playbooks for onboarding, account reviews, risk mitigation, and expansion tailored to multi-shop operators.
• Partner closely with Product and Engineering teams to voice the unique workflow needs of large automotive repair operations.

Prepare a 30, 60, 90-day plan outlining key milestones, strategies, and goals for onboarding and team development.

Qualifications & Experience:

• 10+ years in B2B SaaS Customer Success, with at least 5+ years in a people management role overseeing SMB, Mid-Market and Enterprise accounts.
• Proven ability to build, mentor, and scale high-performing teams.
• Excellent communication and relationship-building skills.
• Proven ability to leverage customer health scores, usage metrics, and retention data to proactively manage risk.
• Experience in automotive tech, field service management, POS, inventory management, or Vertical SaaS is strongly preferred.
• Exceptional verbal, written, and executive presentation skills.

In the United States the OTE is typically $180,000 to $215,000 + equity + benefits. The range provided is Shopmonkey’s reasonable estimate of the compensation for this role. The actual amount will be based on job-related and non-discriminatory factors such as location, experience, training, skills, and abilities. Consult with your Recruiter during the initial call to determine a more targeted range based on these job-related factors. In addition to this base compensation company stock options and benefits as outlined below are included.