Director, Customer Success and Operations Improvement

Softchoice • Toronto, ON

33d

About The Position

We are a software-focused IT solutions and services provider that equips organizations to be agile and innovative, and for their people to be engaged, connected, and creative at work. That means moving them to the cloud, helping them build the workplace of tomorrow, and enabling them to make smarter decisions about their technology. By doing these things we help them create success for their customers and their people. We stand proudly for our people and support their success through career development and advancement. We are recognized and respected for our culture of inclusion and belonging, continuously striving to do what’s good for our people and communities.

The Director, Customer Success & Operations Improvement owns the AI‑first operations improvement strategy and delivery across the customer journey. This role is accountable for improving operational quality, SLA performance, turnaround time, and team capacity by reimagining processes through intelligent automation and disciplined governance. Reporting to the SVP, Strategy Operations & CX, the Director is a player‑coach, leading a multidisciplinary team and stepping in directly on high‑impact, high‑ambiguity workstreams. They influence senior stakeholders across Customer Success, Operations, Technology, and Automation to prioritize outcomes, manage risk, and embed sustainable change into day‑to‑day operations. The Director also supports the SVP by driving organization‑wide enablement, team engagement, and executing on SVP‑sponsored priorities.

In this role, you will:

Strengthen the AI-first improvement model that shifts teams from manual, reactive processes to scalable, data and automation driven ways of working
Represent the function on foundational AI, automation, and integration initiatives, ensuring operational needs shape solution design

Lead cross‑functional governance and decision‑making on automation/AI priorities, including trade-offs, risk, and sequencing
Player‑coach: lead through others, and directly drive critical workstreams when timelines, risk, or complexity demand
Build team capability and embed continuous improvement discipline across customer-impacting workflows
Evolve SLA governance and performance management across key customer‑impacting processes to improve clarity, consistency, and outcomes
Support the SVP by running organization‑wide enablement and engagement execution, including recognition programs and SVP‑sponsored priorities

Requirements

• 10-12 years of experience in operations, customer success, or enterprise process improvement roles
• Proven experience leading process improvement and automation initiatives, ideally within complex, multi‑stakeholder environments
• Demonstrated experience leveraging AI, automation, or advanced analytics to improve operational outcomes (e.g., workflow automation, decision support, intelligent routing, quality monitoring)
• Strong understanding of AI‑enabled process design, including where AI adds value and where traditional integration or redesign is more appropriate
• Experience working with operational governance models (e.g., SLA, quality, performance frameworks)
• Strong grounding in process improvement and change management methodologies (e.g., Lean, Six Sigma, ADKAR)
• Analytical and systems‑thinking mindset; comfortable using data to assess feasibility, risk, and impact
• Ability to influence and build credibility with senior leaders across operations, technology, and customer‑facing teams
• Clear, concise communicator able to translate complexity into actionable insights and decisions
• Demonstrated people leadership experience, including coaching, prioritization, and performance management
• Proficiency with Microsoft tools (Excel, PowerPoint, Word, Visio) and strong comfort working alongside automation platforms, AI tools, and workflow technologies

Responsibilities

• Partner with Customer Success and Operations leaders to identify, prioritize, and design process improvements using an AI‑first mindset, assessing where AI, automation, or decision support can eliminate manual effort or reduce complexity, improving team scalability and operational outcomes
• Translate operational problems into clear automation and AI use cases, informed by volume, variability, risk, and impact
• Establish and operationalize standards for AI/automation delivery and lifecycle management, including documentation, monitoring, exception handling, controls, training, and performance measurement, to ensure solutions are adopted, governable, and sustained in day‑to‑day operations.
• Partner with automation and technology teams to ensure solutions are practical, scalable, and well governed
• Balance innovation with operational stability, ensuring AI‑enabled changes are introduced with appropriate risk management and change discipline
• Own the Operational Quality & Improvement program end-to-end, including KPI definition, performance dashboards, review cadences, and accountability mechanisms across customer-impacting operations
• Lead day-to-day SLA governance across key processes—maintaining clear definitions and metrics, and ensuring consistent application across teams
• Track and communicate realized benefits and performance outcomes (quality, SLA attainment, cycle time, productivity), ensuring visibility to leaders and stakeholders
• Partner with Customer Success and Operations leaders to address persistent performance gaps through targeted interventions (process redesign, enablement, automation, or decision support)
• Lead cross‑functional initiatives, ensuring clarity of roles, timelines, and success measures
• Communicate progress, risks, and outcomes clearly to leadership and stakeholders
• Drive change management and adoption efforts to ensure AI‑enabled improvements are trusted, understood, and sustained
• Prepare presentations and updates for senior leadership as required
• Lead, coach, and develop a high‑performing multidisciplinary team
• Set clear objectives, priorities, and expectations aligned to the mandate
• Foster a culture of accountability, experimentation, and continuous improvement, with responsible use of AI
• Establish and run the operating cadence for organization-wide enablement and engagement initiatives (planning, milestones, reporting, and follow through) to ensure consistent execution
• Execute recognition programs and engagement actions, partnering with leaders to drive adoption
• Manage SVP-sponsored initiatives and delegated programs end-to-end

Benefits

• Health and Wellbeing: Medical and Dental Care, Employee & Family Assistance Program
• Financial Benefits: RRSP/DPSP Retirement Savings Plan with Company Matching, Life and Disability Insurance
• Paid Time Off: Vacation and Sick Leave, Holidays, Parental Leave, Volunteer Days, Bereavement Leave
• Additional Perks: Employee Discount Program

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed