Director, Customer Success

Dispatch · Boston, MA · 1 mo ago

RemoteRemoteOTHR$135k–$160k/yrFull-time

About the role

The Director of Customer Success at Dispatch is responsible for leading and developing the Customer Success organization. This role involves owning the Customer Success strategy and operating model, providing executive-level oversight for key accounts, and driving customer value through renewal and expansion efforts.

Responsibilities

Lead, coach, motivate, and develop the Customer Success team, creating clear expectations and helping CSMs grow into more strategic, commercially minded customer leaders.
Own the Customer Success strategy and operating model across Dispatch and Youreka, ensuring customers receive a consistent, high-quality experience regardless of product.
Provide executive-level oversight for Dispatch's most strategic accounts across all product lines, partnering closely with CSMs 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 CSMs 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 CSMs 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.

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

Skills