Director, Customer Success

About the role

The company provides a modern platform that helps leading brands and service providers manage home and field service operations efficiently, from job acceptance through completion. The Director of Customer Success will lead the Customer Success organization, strengthen strategic enterprise relationships, and drive customer retention, renewals, and expansion.

Responsibilities

• Lead, coach, motivate, and develop the Customer Success team, creating clear expectations and helping Customer Success Managers grow into more strategic, commercially minded customer leaders.
• Own the Customer Success strategy and operating model across the company’s product lines, ensuring customers receive a consistent, high-quality experience regardless of product.
• Provide executive-level oversight for the organization’s most strategic accounts across all product lines, partnering closely with Customer Success Managers to strengthen relationships, remove obstacles, and drive customer value.
• Own the renewal and expansion strategy across the customer base, with accountability for retention, renewal performance, expansion ARR, and overall account growth.
• Personally lead or support complex enterprise renewals and expansions, including negotiation, pricing, value positioning, stakeholder alignment, contract strategy, and close.
• Coach Customer Success Managers on commercial strategy, executive engagement, account planning, negotiation, value selling, and identifying expansion opportunities.
• Build strong relationships with senior and executive customer stakeholders and help Customer Success Managers expand the depth and breadth of relationships within their accounts.
• Run strategic account plans, renewal and expansion forecasts, customer health practices, and operating cadences that improve visibility, accountability, and predictability.
• Leverage AI and automation to improve customer insights, renewal forecasting, risk identification, expansion discovery, and team productivity, while helping the organization rethink how Customer Success work gets done.
• Serve as a senior escalation point for critical customer situations, helping the team navigate complex challenges while maintaining a strong customer-first approach.
• Partner closely with Technical Success, Product, Engineering, and Sales leadership to remove customer obstacles, represent the voice of the customer, and create opportunities for retention and growth.
• Identify trends across the customer base and use those insights to influence customer strategy, product priorities, and broader business decisions.

Requirements

• 8+ years of experience in Enterprise Customer Success, Strategic Account Management, Account Management, or a similarly customer- and commercially focused SaaS environment, including meaningful people leadership experience.
• Proven experience leading and developing Customer Success Managers, including coaching teams toward stronger executive relationships, strategic account management, and commercial outcomes.
• Significant experience owning or leading enterprise renewals and expansions, with a demonstrated ability to personally negotiate and close complex renewal, upsell, and cross-sell opportunities.
• A strong commercial mindset—understanding that great Customer Success combines customer advocacy and value realization with retention, expansion, and disciplined commercial execution.
• Demonstrated ability to build trusted relationships with VP and C-level stakeholders across large ($250k+ ARR), complex enterprise organizations.
• Strong strategic account planning skills, including stakeholder mapping, whitespace analysis, renewal risk assessment, value realization, and growth planning.
• Experience using AI-powered tools to improve customer insights, team productivity, account strategy, forecasting, and decision-making, with genuine interest in rethinking traditional Customer Success workflows through AI.
• Strong business acumen with the ability to quickly understand a customer’s operating model, industry, strategic priorities, and financial drivers.
• Comfortable working in a hands-on environment where leaders are expected to get directly involved in customers, deals, team development, and organizational change.
• Ability to thrive in an evolving environment and is energized by the opportunity to improve and transform rather than simply maintain existing processes.
• Experience in field service, field service management software, or technology supporting distributed service organizations is strongly preferred.
• Experience with Salesforce or within the Salesforce ecosystem is helpful, particularly experience with Salesforce-native products, but is not required.

Preferred Qualifications

• Executive communication and presence
• Enterprise negotiation and commercial strategy
• Renewal and expansion forecasting
• Strategic account planning & executive stakeholder management
• Value selling and ROI development
• Cross-functional leadership and influence
• Coaching and mentorship
• Presentation and facilitation
• Analytical and problem-solving skills
• Familiarity with Salesforce and Customer Success platforms
• Working knowledge of SaaS metrics, enterprise software, and customer lifecycle management

Timeline Milestones

• Within one month, you’ll
  • Attend New Hire Orientation and build relationships across Customer Success, Technical Success, Sales, Product, Finance, and Engineering.
  • Develop a strong understanding of the field service industry, the company’s customer base, and the business challenges its solutions address.
  • Build deep functional knowledge of the company’s products, customer use cases, and value proposition.
  • Review the existing customer portfolio, renewal calendar, expansion pipeline, account plans, and customer health metrics.
  • Meet with key internal stakeholders to understand current renewal and expansion processes, strengths, gaps, and opportunities.
  • Begin developing strategic growth plans for priority enterprise accounts.
• Within three months, you’ll
  • Take ownership of renewal and expansion outcomes across your assigned strategic customer portfolio.
  • Establish account strategies for priority customers, including executive relationships, renewal plans, risk mitigation strategies, and expansion opportunities.
  • Develop strong relationships with key customer decision-makers, influencers, and executive stakeholders.
  • Establish a clear, accurate renewal and expansion forecast and operating cadence.
  • Begin leading commercial discussions, renewal negotiations, and expansion opportunities.
• Within six months, you’ll
  • Be viewed internally and externally as a strategic leader for the organization’s most important customer relationships.
  • Consistently lead successful executive-level customer conversations focused on value realization, strategic priorities, and future growth.
  • Build a strong pipeline of qualified expansion opportunities across the enterprise customer base.
  • Lead complex renewal and expansion negotiations with senior customer stakeholders.
  • Coach and support Customer Success Managers in strengthening their commercial and strategic account management capabilities.
• Within twelve months, you’ll
  • Consistently achieve or exceed the company’s renewal, retention, and expansion targets.
  • Demonstrate measurable growth across the most strategic enterprise accounts through additional use cases, products, business units, geographies, or service lines.
  • Maintain strong executive relationships across the customer portfolio and establish the company as a strategic partner to its customers.
  • Build a highly predictable renewal and expansion motion supported by strong forecasting, account planning, executive engagement, and value realization.
  • Become a trusted advisor to leadership on customer growth strategy, retention risk, market trends, and strategic opportunities.
  • Help establish a scalable model for how the company retains and grows enterprise customers as the business continues to expand.

Pay

The base salary range for this role is between $135,000 – $160,000 annually.

Location

The company fully accommodates remote work, as long as you have a permanent residence in the US and reside in one of the registered states. The organization also has an office available for use.

Benefits

• An amazing team focused on innovating and improving every day
• Room for growth and an emphasis on talent development, including a professional development reimbursement program
• A fun, casual team environment with co-workers who will make you feel like an important part of the team, engage you in developing new solutions to challenging problems, and help you leverage your strengths
• A generous medical, dental, and vision package with 90% covered by the company
• Paid parental leave
• 401(k) with company match
• Company-sponsored life insurance coverage, short-term disability, and long-term disability
• Additional perks including a wellness and adventure fund, as well as monthly personal Uber credits
• Flexible Paid Time Off (PTO), company holidays, and a flexible work schedule