Senior Director, Customer Success Operations & AI

TouchBistro is looking for a strategic, hands-on leader to own how Customer Success operates at scale. This is not a traditional CS Ops role. You’ll own the systems, data, and AI that power how we onboard, support, retain, and grow our customers and evolve it into a more intelligent, automated operating model, turning workflows into scalable systems and insight into action. Location: Toronto (Hybrid — 2 days/week in office) Your Impact Build a scalable CS operating system Design and evolve workflows across onboarding, billing ops, support, and retention Own and unify our CS tech stack (Salesforce, support tools, WFM, analytics) Improve how frontline teams operate — faster, simpler, more effective Turn data into decisions Own the Customer Success data ecosystem and reporting strategy Ensure clean, reliable data across systems Move reporting beyond dashboards into actionable insights that drive retention and performance Embed AI into how we work Lead the evolution of AI across Customer Success (agent assist, automation, self-service) Ensure AI is embedded into real workflows and driving measurable impact Shift operations from reactive to proactive Lead systems, strategy, and execution Lead CS systems, data, and AI initiatives Partner cross-functionally with Product and Engineering Define priorities and drive execution against the highest-impact opportunities What You Bring 10+ years in Customer Success Operations, RevOps, or Systems leadership Deep experience owning end-to-end CS technology ecosystems Strong Salesforce expertise (Service Cloud required; technical depth strongly preferred) Proven ability to design systems aligned to real operational workflows Experience working with data, analytics, and reporting ecosystems AI/automation in business operations (practical application > theory) Strong business acumen — understands how CS drives retention and revenue Ability to prioritize for impact and cut through complexity Comfortable in a hybrid work schedule. What Success Looks Like Systems are connected, scalable, and trusted by teams Data drives clear, confident decisions AI is embedded into daily workflows Customer Success operates proactively, not reactively

The Senior Director will build a scalable Customer Success operating system and design workflows across various functions. They will also lead the integration of AI into operations to enhance efficiency and effectiveness.

Candidates should have over 10 years of experience in Customer Success Operations or related fields, with strong expertise in Salesforce and data analytics. A proven ability to design systems aligned with operational workflows and a solid understanding of AI applications in business operations are essential.

Identified from the job description. Confirm important requirements above.

• Customer Success Operations
• RevOps
• Systems Leadership
• Salesforce
• Data Analytics
• Reporting
• AI
• Automation
• Business Acumen
• Workflow Design
• Operational Workflows
• Retention Strategies
• Proactive Operations
• Cross-Functional Collaboration
• Technical Depth
• Insight Generation

• Management & Leadership
• Customer Service & Support
• Data & Analytics
• Technology

Minimum experience

10+ years

Posting language

English

Working hours

40 hours per week

Office presence

2 days per week

Application method

Direct apply is available