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.

Why Shopmonkey?

Shopmonkey has become an amazing environment where employees feel that they are valued as people, and not just worker bees. To ensure that our team thrives, we invest in the following perks (benefits below are mainly for U.S. based, full-time employees). Other benefits vary upon location outside of the United States, and employment status:

💪🏼 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

Check out our founder’s story, life page, or hear from real employees about what it’s like to work at Shopmonkey.

Join our team of hungry, humble, smart people who love what they do, and change the auto industry by helping every shop thrive.

About the Industry

The U.S. is the second largest passenger vehicle market with more than 260 million registered passenger vehicles, and the global car repair market is estimated to be worth more than $500B. Shopmonkey aims to change the status quo and enable auto shops to become more efficient and give their customers a more delightful experience.

About Shopmonkey

Shopmonkey is the leading auto-repair shop software company; it is a cloud-based solution that helps auto-repair shops consolidate tools, save time, and streamline their entire operation onto a simple, easy-to-use platform.

Headquartered in Silicon Valley and trusted by more than 3,500+ auto shops across the U.S. and Canada, Shopmonkey aims to change the status quo of the car repair market, estimated to be worth more than $500B.

In 2021 Shopmonkey raised a $75 million Series C, supported by top-tier Silicon Valley venture capital firms Bessemer Venture Partners, Index Ventures, Headline, I2BF, and ICONIQ Growth.

In 2022, Shopmonkey was named #4 on Forbes' annual ranking of America's Best Startup Employers list (and #1 in Business Products & Software Services). Shopmonkey was once again named as one of America's Best Startup Employers by Forbes in 2023, 2024, and 2026!

Shopmonkey is committed to building a diverse and inclusive team. We are looking for team members from all backgrounds that are committed to the Shopmonkey mission.

Shopmonkey provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

Shopmonkey is committed to the full inclusion of all qualified individuals. In keeping with our our commitment, Shopmonkey will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact our Talent Team at hiring@shopmonkey.io.

Please note: Shopmonkey will never request sensitive information such as your social security number, bank account information, or other non-publicly available information during the application and interview process. If an applicant is extended an offer of employment, such sensitive information will be requested at that time. Shopmonkey will never ask you to receive and ship packages or goods as part of the interview. Other practices to be on alert for:

Contact initiated via unsolicited text message or cold call. Shopmonkey does not follow up with candidates through instant messaging applications.
Our Talent Acquisition team only corresponds from email addresses with the domain ‘@Shopmonkey.io’. If a generic email ID ending with Gmail/Yahoo or other domain is used while receiving a job offer or interview call, there is a likelihood of a scammer.
While some of our jobs can be found on third party job sites, all of our current job opportunities and descriptions are posted on Shopmonkey’s Careers page, or our official LinkedIn Company Page

The U.S. Federal Trade Commission has published helpful articles to help individuals learn more about protecting themselves from recruiting scams and financial fraud. If you believe you were a victim of such a scam, you may contact your local law enforcement agencies. Shopmonkey is not responsible for any claims, liability, losses, damages, or expenses resulting from scammers or impersonators.

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

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