Director, Customer Success

Accountabilities

• • Lead, coach, motivate, and develop the Customer Success team, establishing clear expectations and helping team members become more strategic and commercially effective customer leaders.
  • Define and own the Customer Success strategy and operating model across multiple product lines, ensuring a consistent and high-quality customer experience.
  • Provide executive-level oversight for the most strategic enterprise accounts, partnering with Customer Success Managers to strengthen relationships, resolve obstacles, and drive measurable customer value.
  • Own renewal and expansion strategy across the customer portfolio, with accountability for retention, renewal performance, expansion ARR, and overall account growth.
  • Personally lead or support complex enterprise renewals and expansion opportunities, including negotiations, pricing, value positioning, stakeholder alignment, contract strategy, and deal closure.
  • Coach Customer Success Managers on commercial strategy, executive engagement, strategic account planning, negotiation, value selling, and expansion discovery.
  • Build trusted relationships with VP and C-level customer stakeholders while helping account teams deepen and broaden executive relationships.
  • Establish and manage strategic account plans, renewal and expansion forecasts, customer health practices, and operating cadences that improve visibility, accountability, and predictability.
  • Leverage AI and automation to enhance customer insights, renewal forecasting, risk identification, expansion discovery, and team productivity.
  • Serve as a senior escalation point for critical customer situations, helping teams navigate complex challenges while maintaining a customer-first approach.
  • Partner with Technical Success, Product, Engineering, Sales, and other leadership teams to remove customer obstacles and represent the voice of the customer.
  • Identify customer trends and translate insights into recommendations that influence product priorities, customer strategy, and broader business decisions.
  • Develop scalable processes and operating models that improve retention and expansion as the enterprise customer base grows.
  • Establish a predictable commercial motion supported by strong forecasting, value realization, executive engagement, and disciplined account planning.
  • Drive measurable growth across strategic accounts through additional products, use cases, business units, geographies, or service lines.

  Requirements

  • 8+ years of experience in Enterprise Customer Success, Strategic Account Management, Account Management, or a similarly customer- and commercially focused SaaS environment.
  • Meaningful 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 proven ability to personally negotiate and close complex renewal, upsell, and cross-sell opportunities.
  • Strong commercial mindset with a demonstrated understanding of how customer advocacy and value realization connect to retention, expansion, and revenue performance.
  • Proven ability to build trusted relationships with VP and C-level stakeholders within large, complex enterprise organizations, particularly accounts with $250K+ ARR.
  • Strong strategic account planning capabilities, including stakeholder mapping, whitespace analysis, renewal risk assessment, value realization, and growth planning.
  • Experience using AI-powered tools to improve customer insights, productivity, account strategy, forecasting, and decision-making.
  • Genuine interest in using AI to rethink and improve traditional Customer Success workflows.
  • Strong business acumen and ability to quickly understand customer operating models, industries, strategic priorities, and financial drivers.
  • Comfortable working hands-on and directly contributing to customer relationships, commercial opportunities, team development, and organizational change.
  • Ability to thrive in evolving environments and actively improve or transform processes rather than simply maintain established playbooks.
  • Experience in field service, field service management software, or technology supporting distributed service organizations is strongly preferred.
  • Experience with Salesforce or the broader Salesforce ecosystem is helpful, particularly experience with Salesforce-native products.
  • Strong executive communication and presence, presentation, facilitation, negotiation, and stakeholder management skills.
  • Strong analytical, problem-solving, organizational, and forecasting abilities.
  • Working knowledge of SaaS metrics, enterprise software, Customer Success platforms, and customer lifecycle management.

  Benefits

  • Base salary range of $135,000–$160,000 USD annually.
  • Eligibility for an annual performance bonus.
  • Comprehensive medical, dental, and vision coverage, with approximately 90% of premiums covered.
  • Paid parental leave.
  • 401(k) retirement plan with company matching.
  • Company-sponsored life insurance.
  • Short-term and long-term disability coverage.
  • Flexible Paid Time Off (PTO).
  • 9 company holidays.
  • Flexible working schedule.
  • Fully remote work for eligible employees permanently residing in the United States and registered states.
  • Access to an office in Boston.
  • Professional development reimbursement program.
  • Wellness and adventure fund.
  • Monthly personal Uber credits.
  • Collaborative, casual, and supportive team environment.
  • Opportunities for leadership growth, talent development, and professional advancement.
  • Opportunity to influence Customer Success strategy and help scale an enterprise customer organization.
  • Opportunity to work with modern AI and automation tools to improve customer engagement, forecasting, and productivity.