Senior Director, Customer Retention & Growth

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take charge of SysAid’s net revenue retention (NRR) and spearhead the transformation of the post-sales organization into a growth engine fueled by AI and insights.

• Implement strategies for reducing churn and promoting expansion through upselling and cross-selling.

• Develop AI-enhanced forecasting models to assess churn risk and expansion potential.

• Create clear accountability among Customer Success Managers (CSMs), Account Managers (AMs), and throughout customer lifecycle stages.

• Propel AI-driven customer adoption and expedite time-to-value across key ITSM functionalities, Spaces, and agentic AI features.

• Collaborate with Product and Professional Services to integrate AI into onboarding processes and provide guided, automated adoption experiences.

• Operationalize health scoring driven by AI and recommend next-best actions.

• Design a scalable, AI-enhanced expansion strategy utilizing automated signals, deal insights, business cases, and pricing recommendations.

• Equip teams with AI copilots for account planning, preparation for Quarterly Business Reviews (QBRs), and executive storytelling.

• Create AI agents to monitor customer health continuously, detect risks, and facilitate automated or human-led interventions.

• Identify root causes of systemic churn and provide feedback to Product teams.

• Define customer-centric AI use cases to automate IT workflows, enhance service delivery, and maximize platform ROI.

• Collaborate with Product to package AI use cases into compelling value propositions and outline practices for agentic AI adoption.

• Implement internal AI agents for generating QBRs, summarizing calls, tracking actions, clustering tickets, conducting root-cause analyses, and providing insights for renewals and expansions.

• Revamp post-sales workflows to reduce manual tasks and increase time spent on customer-facing activities.

• Collect and analyze customer feedback to spot trends in products and experiences, establishing feedback loops with Product teams.

• Adapt team responsibilities for an AI-focused organization and train teams to leverage AI-generated insights.

• Define AI-enhanced segmentation and coverage models, establish KPIs for retention, expansion, adoption, and operational efficiency, and recruit and develop talent augmented by AI.

⛳️ Requirements

• Over 10 years of experience in SaaS Customer Success, Account Management, or Growth roles.

• A minimum of 5 years in managerial positions.

• Demonstrated ownership of retention and expansion objectives.

• Experience in leading AI/automation initiatives within customer-facing teams is highly advantageous.

• Background in ITSM, enterprise SaaS, or workflow platforms is preferred.

• Strong comprehension of SaaS retention mechanics and NRR drivers.

• Deep understanding of customer lifecycle design.

• Robust knowledge of AI/automation use cases in post-sales environments.

• Ability to translate AI capabilities into tangible business value for customers.

• Data-oriented and systems thinker.

• Commercially minded with a focus on growth.

• Comfortable navigating product and platform transitions.

• Balances strategic planning with operational execution.

• Strong ability to influence cross-functionally across Product, Sales, and Engineering departments.

🏝️ Benefits

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