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From the employer's careers site First seen 3 Nov 2026

Senior Director, AI Roadmap and Strategy

Thomson Reuters Toronto, Toronto Hybrid senior full-time

Salary

$172,000 CAD - $222,000 CAD per year

Apply on Thomson Reuters

Description

We are looking for a Senior Director to own the AI roadmap and strategy for our go-to-market organization: Sales, Customer Success, Professional Services, and Partnerships.

You will partner with our segments and RevOps to decide where AI creates the most value across the customer lifecycle, and work with Engineering to deliver it through a deliberate mix of best-in-class SaaS platforms (such as Salesforce, Gong) and custom-built solutions where off-the-shelf products fall short.

Key Responsibilities

  • Define and own a multi-year AI vision and a quarterly roadmap spanning Sales, Customer Success, Professional Services, and Partnerships.
  • Identify, size, and prioritize AI use cases by revenue impact, productivity gain, cost to serve, and feasibility.
  • Establish clear principles for build vs. buy vs. configure, and make those calls transparently with business cases and total cost of ownership.
  • Align the GTM AI roadmap with company strategy, revenue targets, and the broader enterprise AI and data strategy.
  • Rationalize and govern overlapping tools and prevent AI sprawl across the GTM organization.
  • Run discovery, prototyping, pilots, and scale-up with clear success criteria and stage gates.

AI across the GTM functions

  • Sales: AI for prospecting and account research, lead and opportunity scoring, call and meeting intelligence, deal inspection and forecasting, proposal and RFP generation, pricing and quoting guidance, and rep coaching and ramp.
  • Customer Success: AI for health scoring and churn prediction, renewal and expansion signals, automated QBR and meeting prep, sentiment and call analysis, onboarding acceleration, and proactive risk alerts.
  • Professional Services: AI for scoping and estimation, project planning, knowledge retrieval, delivery acceleration, resource allocation, utilization, and margin improvement.
  • Partnerships: AI for partner identification and tiering, co-sell and pipeline insight, partner enablement, and ecosystem performance analytics.
  • Design cross-functional workflows that connect these motions, such as handoffs from sales to onboarding to delivery to renewal, so AI improves the whole customer lifecycle rather than isolated steps.

Adoption, change management, and value realization

  • Own adoption by partnering with Revenue Operations, enablement, and functional leaders on training, playbooks, and incentives so tools become part of daily work.
  • Define and report a KPI framework covering usage, productivity, pipeline and win rate, forecast accuracy, retention and expansion, services margin, and partner-sourced revenue.
  • Quantify ROI and report outcomes to executive leadership on a regular cadence.

Governance, data, and responsible AI

  • Work with Legal, Security, Privacy, and IT to set guardrails for AI use with customer and partner data, including access controls, data residency, model usage policies, and auditability.
  • Ensure AI outputs are trustworthy and that humans remain appropriately in the loop for high-stakes decisions.
  • Partner with Data and Analytics on data quality, definitions, and a shared source of truth.

Leadership and operating model

  • Build and lead a team of product managers and business analysts, and influence a broader matrixed group of Engineering, Data, and GTM Operations partners.
  • Establish intake, prioritization, and governance processes so GTM leaders (CRO, CCO, Services, Partnerships) jointly steer the roadmap.
  • Act as the executive-level voice on GTM AI, internally and externally, including with vendors, analysts, and peer companies.

Benefits

  • Hybrid Work Model: flexible hybrid working environment
  • Flexibility & Work-Life Balance: supportive workplace policies
  • Career Development and Growth: culture of continuous learning and skill development
  • Industry Competitive Benefits: comprehensive benefit plans
  • Culture: award-winning reputation for inclusion and belonging, flexibility, work-life balance
  • Social Impact: opportunities for community involvement and ESG initiatives

Skills

Required

Nice to have

  • Salesforce platform capabilities
  • data cloud or warehouse integrations
  • Gong or similar conversation intelligence tools
  • partner ecosystems
  • co-sell motions
  • channel programs
Apply on Thomson Reuters