Senior Director, Customer Retention & Growth

Posted 1 hour ago

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About the role

  • Leading SysAid’s AI-enabled customer retention and expansion strategy. Transforming post-sales operations for SysAid’s ITSM platform through automation, adoption, and predictive growth.

Responsibilities

  • Own SysAid’s net revenue retention (NRR) and lead the transformation of the post-sales organization into an AI-enabled, insight-driven growth engine
  • Drive churn reduction and expansion through upsell and cross-sell strategies
  • Build AI-enhanced forecasting models for churn risk and expansion propensity
  • Establish clear ownership across CSMs, AMs, and customer lifecycle stages
  • Drive AI-powered customer adoption and faster time-to-value across core ITSM capabilities, Spaces, and agentic AI capabilities
  • Partner with Product and Professional Services to embed AI into onboarding and deliver guided, automated adoption experiences
  • Operationalize AI-driven health scoring and next-best actions
  • Design a scalable, AI-driven expansion motion using automated signals, deal insights, business cases, and pricing recommendations
  • Equip teams with AI copilots for account planning, QBR preparation, and executive storytelling
  • Build AI agents for continuous customer-health monitoring, risk detection, and automated or human-led interventions
  • Identify systemic churn drivers and close the loop with Product
  • Define customer-facing AI use cases that automate IT workflows, improve service delivery, and increase platform ROI
  • Partner with Product to package AI use cases into value propositions and define agentic AI adoption practices
  • Deploy internal AI agents for QBR generation, call summaries, action tracking, ticket clustering, root-cause analysis, and renewal and expansion insights
  • Redesign post-sales workflows to minimize manual work and increase customer-facing time
  • Aggregate and analyze customer feedback to identify product and experience trends and create feedback loops into Product
  • Evolve team responsibilities for an AI-first organization and train teams to use AI-generated insights
  • Define AI-enhanced segmentation and coverage models, establish retention, expansion, adoption, and operational-efficiency KPIs, and hire and develop AI-augmented talent

Requirements

  • 10+ years in SaaS Customer Success, Account Management, or Growth
  • At least 5 years in manager roles
  • Proven ownership of retention and expansion targets
  • Experience leading AI/automation initiatives in customer-facing teams is a strong plus
  • Background in ITSM, enterprise SaaS, or workflow platforms preferred
  • Strong understanding of SaaS retention mechanics and NRR drivers
  • Strong understanding of customer lifecycle design
  • Strong understanding of AI/automation use cases in post-sales
  • Ability to translate AI capabilities into customer business value
  • Data-driven and systems thinker
  • Commercially oriented with a growth mindset
  • Comfortable leading through product and platform transitions
  • Balances strategic thinking with operational execution
  • Strong cross-functional influence across Product, Sales, and Engineering

Benefits

  • No benefits, perks, or compensation extras are specified in the posting

Job type

Full Time

Experience level

Senior

Salary

Not specified

Degree requirement

No Education Requirement

Tech skills

ITSM

Location requirements

RemoteCanada

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