Job 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.
You will work with internal stakeholders to define the problems worth solving, prioritize ruthlessly, and measure adoption and business impact. You will be the accountable leader for how AI shows up in the way we sell, onboard, deliver, retain, and grow with customers and partners.

Key Responsibilities
GTM AI strategy and roadmapDefine 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 functionsSales: 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 realizationOwn 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 AIWork 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 modelBuild 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.
Required Qualifications12+ years of experience in product management, GTM operations or strategy, sales or revenue technology, or related roles, with 5+ years leading teams.
Demonstrated success owning a technology roadmap that serves revenue-generating teams, ideally across more than one of Sales, Customer Success, Skilled Services, and Partnerships.
Deep working knowledge of the GTM technology stack, including Salesforce and conversation intelligence tools like Gong, and how data flows between systems.
Hands-on experience delivering AI/ML or generative AI solutions into production, including a practical understanding of LLMs, agents, retrieval, prompt and workflow design, evaluation, and cost management.
Strong build-vs-buy judgment, vendor management experience, and comfort building business cases.
Proven ability to drive change and adoption among frontline revenue teams and senior business leaders.
Excellent executive communication, with the ability to translate between technical teams and business stakeholders.
Analytical rigor and a bias toward measurable outcomes.
Preferred QualificationsPrior experience as a sales, customer success, or services practitioner

📌 Senior Director, GTM AI Product Leader (Toronto)
🏢 Thomson Reuters
📍 Toronto