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HighlightTA

Director, Customer Success

HighlightTA

. Lead and develop the Account Management team .

Posted 11/11/2026full-timeRemote • Canada, United StatesLead💰 CA$184,714 - CA$225,762 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates significant leadership experience in enterprise SaaS Customer Success and Account Management, with a focus on driving customer retention, renewals, and expansion revenue. Proven ability to develop high-performing teams and navigate organizational change while enhancing customer outcomes through AI and automation.

Highest-signal resume keywords
Leadership Experience In Enterprise SaaSCustomer Retention And RenewalsManaging ManagersScaling Global TeamsCommercial Acumen

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Customer Success ManagementAccount ManagementOrganizational Change NavigationTeam DevelopmentRevenue Expansion Strategies
Soft Skills
Influencing Cross-Functional StakeholdersDecision-MakingCoaching And MentoringProblem-SolvingTeam Engagement
Tools & Technologies
GainsightCatalystSalesforceAI TechnologiesAutomation Tools
Industry Keywords
Enterprise CustomersHigh-Touch Customer ModelRetail TechnologyCustomer Coverage ModelsGlobal Customer Success Operations

About the role

Key responsibilities & impact
  • Lead and develop the Account Management team
  • Own customer retention, renewals, and expansion outcomes across enterprise customers
  • Monitor customer health, proactively address risks, and identify growth opportunities
  • Evolve team structures, customer coverage models, and operational processes with the VP, Customer Success
  • Lead organizational and operational changes to improve efficiency, team effectiveness, and customer experience
  • Champion AI, automation, and emerging technologies to streamline workflows and enhance customer outcomes
  • Partner with Sales, Product, RevOps, and other teams to represent customer needs and align priorities
  • Navigate complex challenges and drive solutions with autonomy and sound judgment
  • Support global Customer Success operations and consistent service across regions
  • Coach and develop Account Management leaders and team members
  • Identify professional growth and succession-planning opportunities
  • Lead through change while maintaining team engagement and focus on results

Requirements

What you’ll need
  • Significant leadership experience in enterprise SaaS Customer Success or Account Management, including managing managers
  • Proven success driving customer retention, renewals, and expansion revenue within a high-touch enterprise customer model
  • Experience leading and scaling global or multi-region teams
  • Experience navigating organizational change and evolving customer coverage models
  • Strong commercial acumen
  • Ability to develop high-performing teams, influence cross-functional stakeholders, and make independent decisions
  • Experience in a scaling SaaS organization, ideally within the $30M to $100M ARR range
  • Comfort collaborating across global time zones, particularly with teams and customers in North America and Europe
  • Experience working alongside customer support or technical support functions (nice-to-have)
  • Background in retail technology or familiarity with retail store operations (nice-to-have)
  • Familiarity with Gainsight, Catalyst, or Salesforce (nice-to-have)
  • Experience leveraging AI or automation to improve Customer Success operations (nice-to-have)
  • Ability to work East Coast hours to support overlap with European teams
  • Must be based in the US or Canada
  • Must be legally authorized to work in Canada or the United States
  • Up to 25% travel may be required

Benefits

Comp & perks
  • Remote-first culture and fully remote work
  • Stock options
  • Flexible time-off policy
  • Monthly coffee-shop stipend
  • Fully paid one-month sabbatical after five years
  • Medical, dental, and vision policies
  • Annual company off-sites
  • Paid day off each quarter for volunteering
  • Unlimited access to Udemy Business
  • Career development conversations with manager
  • 5 to 10% higher-cost-of-living salary multipliers, depending on location