Shopmonkey

Director, Customer Success - Hybrid/San Jose, CA area

Shopmonkey$180K — $215K *
Consumer Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years in B2B SaaS Customer Success, with at least 5+ years in a people management role overseeing customer segments.
  • Proven ability to build, mentor, and scale high-performing teams.
  • Excellent communication and relationship-building skills.
  • Ability to leverage customer health scores and retention data for proactive management.
  • Experience in automotive tech or Vertical SaaS preferred.
  • Exceptional verbal, written, and executive presentation skills.

Responsibilities

  • Lead and mentor a diverse team of Customer Success Managers across SMB, Mid-Market, and Enterprise segments.
  • Establish KPIs and growth objectives for the Customer Success team.
  • Drive metrics like Net Retention Rate and reduce logo churn through data insights.
  • Collaborate with cross-functional teams to enhance customer experience and journey.
  • Utilize analytics to track team performance and customer engagement strategies.
  • Develop CSM playbooks tailored for multi-shop operators.
  • Work closely with Product and Engineering to express customer needs effectively.

Benefits

  • Comprehensive medical, dental, vision, and life insurance starting the month after hire.
  • Short and long term disability coverage.
  • Access to an employee assistance program.
  • Reimbursement for personal wellness memberships.
  • Generous parental leave policies.
  • 401(k) plan available from the start.
  • 11 paid holidays and flexible time off arrangements.
  • Matching donations for approved charities and group volunteer opportunities.
Full Job Description
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. Please note this is a hybrid position, with 2-3 days/week on-site at our Morgan Hill, CA office for collaboration.
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.

Health & Wellness
  • Medical, dental, vision, and life insurance benefits available the 1st of the month following hire date
  • Short term and long term disability
  • Employee assistance program
  • Reimbursement for a personal health and wellness membership
  • Generous parental leave
  • 401(k) available upon hire
Time Off
  • 11 paid holidays
  • Flexible time off - take the time off you need!
Giving Back
  • Matching donations for approved charitable organizations
  • Group volunteer efforts

About Shopmonkey

Shopmonkey is a cloud-based shop management software designed for the automotive industry. The platform provides tools for managing appointments, estimates, invoices, and payments, as well as inventory and customer management. Shopmonkey's clients include independent auto repair shops and franchises.
Learn more about Shopmonkey
Size
100 employees
Industry
Net Income
-$5 million
Founded
2016
5 Year Trend
+150%
Revenue
$10 million

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