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Regional Director, Customer Success

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Fast Facts

Join HopSkipDrive as a Regional Director of Customer Success, where you'll lead a high-performing team to strengthen client relationships and improve retention strategies in a fully remote role.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Responsibilities: Lead and scale Customer Success teams, manage relationships with strategic enterprise clients, improve client retention, oversee onboarding processes, and collaborate across functions to enhance client experiences.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Skills: Leadership, strategic client management, retention strategies, data-driven decision making, onboarding and implementation oversight, cross-functional collaboration, process improvement, communication.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Qualifications: 5+ years in leadership roles within Customer Success or Account Management, extensive experience with enterprise clients, especially in educational or government sectors, strong analytical skills, proven success in client onboarding.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Location: This is a fully remote position available in AZ, CA, NV, OR, or WA.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Compensation: $135000 - $150000 / Annually



* This role will be fully remote in one of the following states AZ, CA, NV, OR, WA*

Who We Are: 

You’re passionate about developing strong relationships with clients and building and scaling a high performing distributed team. With the following skills, you’ll make a tangible and immediate impact:

  • Leadership Experience: Minimum of 5+ years experience building, scaling, and leading high-performing Customer Success or strategic Account Management teams, preferably in a B2B environment focused on complex clients.
  • Strategic Client Management: Extensive experience (e.g., 10+ years) managing relationships and driving successful outcomes for complex, strategic enterprise-level clients; experience specifically with school districts or government agencies is highly desirable.
  • Retention & Loyalty Expertise: Proven track record of developing and implementing successful regional or portfolio-wide strategies to proactively monitor client health, improve retention rates, and foster long-term loyalty.
  • Data-Driven Decision Making: Strong analytical skills and a data-driven mindset, with experience using key customer success metrics and client data to derive actionable insights, measure performance, and inform strategic planning.
  • Onboarding & Implementation Oversight: Demonstrated success in designing, overseeing, or significantly improving client onboarding and implementation programs, ensuring successful adoption of complex solutions or services.
  • Cross-Functional Collaboration: Proven ability to partner effectively with senior leaders across different functions (e.g., Sales, Operations, General Management) to align strategies, support growth initiatives, and ensure a cohesive client experience.
  • Process Improvement & Operational Rigor: Experience in identifying inefficiencies and driving continuous improvement within customer success workflows, processes, and tools to enhance team performance and client outcomes.
  • Communication & Advocacy: Excellent communication and influencing skills, with the ability to synthesize diverse client feedback, effectively advocate for customer needs internally, and contribute to product/service strategy.

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is 135,000-150,000 per year. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

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Average salary estimate

$142500 / YEARLY (est.)
min
max
$135000K
$150000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Regional Director, Customer Success, HopSkipDrive

Join HopSkipDrive as a Regional Director of Customer Success. In this fully remote position, you'll lead a passionate team dedicated to enhancing client relationships and improving retention strategies. Your role will involve scaling Customer Success teams and managing relationships with our strategic enterprise clients, particularly in educational and government sectors. You'll leverage your leadership skills to oversee onboarding processes, ensuring a seamless transition for clients into our offerings. Collaboration is key, and you'll work closely with various cross-functional teams to create a great overall experience for our clients. The ideal candidate will bring a wealth of experience, having spent over five years in leadership roles within Customer Success and Account Management. Your strong analytical skills will help you make data-driven decisions that boost client retention rates and drive long-term loyalty. Plus, your background in designing effective onboarding programs will ensure that our clients quickly find value in our solutions. If you're someone who thrives in a remote work environment and is passionate about enabling teams to excel, we can't wait for you to join us!

Frequently Asked Questions (FAQs) for Regional Director, Customer Success Role at HopSkipDrive
What are the main responsibilities of the Regional Director of Customer Success at HopSkipDrive?

As the Regional Director of Customer Success at HopSkipDrive, your primary responsibilities will include leading and scaling Customer Success teams, managing relationships with strategic enterprise clients, and enhancing client retention. You will oversee the onboarding processes and collaborate with other departments to improve client experiences, aligning strategies to foster loyalty and long-term partnerships.

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What qualifications do I need to apply for the Regional Director, Customer Success position at HopSkipDrive?

To apply for the Regional Director, Customer Success role at HopSkipDrive, you should have at least 5 years of leadership experience in Customer Success or Account Management, with proven success working with enterprise clients, ideally in educational or government sectors. Strong analytical skills and experience in designing onboarding programs are also crucial.

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How does HopSkipDrive define success for the Regional Director of Customer Success?

Success for the Regional Director of Customer Success at HopSkipDrive is measured by the ability to enhance client relationships and improve retention strategies. This includes achieving key metrics related to client health, loyalty, and satisfaction, as well as effectively onboarding new clients and ensuring they receive maximum value from our services.

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What skills are important for the Regional Director of Customer Success at HopSkipDrive?

Important skills for the Regional Director of Customer Success role at HopSkipDrive include strategic client management, data-driven decision-making, cross-functional collaboration, and excellent communication abilities. Leadership experience in a B2B environment focused on complex clients is also highly valuable.

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What kind of work environment can I expect in the Regional Director, Customer Success role at HopSkipDrive?

The Regional Director, Customer Success position at HopSkipDrive is fully remote, offering you the flexibility to work from home. You can expect a supportive and innovative work environment focused on developing strong relationships with clients and empowering your team to succeed, all while collaborating with colleagues across various functions.

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Common Interview Questions for Regional Director, Customer Success
Can you describe your experience in leading Customer Success teams?

In answering this question, share specific examples of how you've successfully built, scaled, or led Customer Success teams in the past. Focus on measurable outcomes, such as improved retention rates or enhanced client satisfaction. Highlight your leadership style and any strategies you employed to foster team collaboration.

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What strategies do you use to improve client retention?

Discuss actionable strategies that you've implemented in the past, such as regular check-ins with clients, utilizing customer success metrics to anticipate needs, and continuously improving onboarding processes. Providing examples of how these strategies led to increased retention rates will illustrate your expertise in this area.

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How do you handle difficult clients?

Explain your approach to resolving conflicts with clients by emphasizing your communication skills and ability to listen. Share a specific instance where you turned a negative situation into a positive outcome through your problem-solving tactics and commitment to client satisfaction.

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Can you give an example of a successful onboarding process you designed?

Provide an example that outlines the steps you took in the onboarding process, from understanding client needs to ensuring they were comfortable with all provided resources. Highlight any improvements you made based on feedback and how these changes affected client satisfaction or retention.

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How do you collaborate with other departments to enhance client experiences?

Detail your experience with cross-departmental collaboration, mentioning specific projects or strategies where you've successfully partnered with teams like Sales or Operations. Explain how collaboration improved client services and the overall experience, focusing on measurable outcomes.

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What metrics do you use to measure customer success?

Discuss your familiarity with key performance indicators (KPIs) used in customer success, such as Net Promoter Score (NPS), Customer Satisfaction Score (CSAT), and Customer Lifetime Value (CLV). Illustrate how you use these metrics to make informed decisions and improve client outcomes.

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Describe a time when you had to give difficult feedback to a team member.

Share a story about a time you provided constructive feedback. Emphasize your communication style focused on growth and improvement and how the conversation ultimately led to positive changes or results for the team member.

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What is your experience in working with enterprise clients?

Discuss your background with enterprise clients, mentioning specific challenges and successes you've faced in those relationships. Emphasize your understanding of the complexities involved in managing large accounts and how you've navigated them successfully.

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How do you stay updated on industry trends and customer success best practices?

Share any resources you use to stay informed about industry trends, such as webinars, publications, or professional networks. Mention how this information has influenced your strategies and practices in client success.

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What do you believe sets a great Customer Success team apart from a mediocre one?

Explain the characteristics you believe are essential for a successful Customer Success team, such as strong communication, a proactive approach, continuous improvement, and data-driven methodologies. You may wish to share examples that illustrate how these traits manifest in a thriving team environment.

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BENEFITS & PERKS
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DATE POSTED
April 20, 2025

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