Director of Customer Enablement
Citylitics · Toronto, Ontario, Canada · 2026-08-13
About this role
Citylitics delivers predictive intelligence on where, how, and why infrastructure investments will occur across North America.
Infrastructure includes the foundational systems that shape our quality of life: water, transportation, transit, roads and highways, broadband, and power. It represents a multi-trillion-dollar market and a 20+ year megatrend in North America.
Citylitics transforms millions of documents across more than 40,000 cities, utilities, and public agencies into real-time market signals and high-value sales intelligence. Leading infrastructure vendors, engineering firms, and construction companies use the platform to identify and pre-position for major infrastructure opportunities earlier, helping them build relationships, shape project priorities, and influence scope before projects move to formal procurement.
Citylitics combines a network of AI agents, fine-tuned models, a proprietary infrastructure signals graph, and daily human-in-the-loop quality assurance workflows to deliver highly nuanced and reliable sales intelligence. The platform integrates seamlessly with CRMs, ERPs, and data lakes, embedding actionable insights directly into sales workflows so teams can prioritize the right pursuits and build stronger pipelines.
Our mission is to improve how infrastructure investments get made so critical needs can be addressed earlier and communities benefit from stronger, more resilient infrastructure.
Join Citylitics to work in a meaningful industry that will matter for decades to come while helping grow a company at the forefront of applied AI. We operate with a Results-Driven Mentality and a commitment to Raise The Bar, in a collaborative environment where Teamwork Makes the Dream Work as we tackle big challenges and celebrate wins together.
Who Are We Looking For?
Citylitics is seeking a Director of Customer Enablement to own the customer journey from pre-sales through kickoff, onboarding, workflow integration, and sustained platform usage.
You will oversee pre-sales support, including customer trial configuration, use-case guidance, and a coordinated transition into implementation. You will lead implementation and enablement, improve time-to-value, and own WAU, platform adoption, and workflow integration targets. You will build scalable engagement models that make Citylitics easy for busy sales professionals to understand, adopt, and use consistently, helping customers achieve the outcomes they purchased the platform to deliver.
You are a hands-on operator with deep strengths in operational rigor, project management, and team leadership. You have built scalable onboarding, enablement, or professional services functions and know how to drive adoption through clear processes, strong accountability, and disciplined delivery. Experience as a Revenue Operations leader is highly preferred, given that Citylitics’ primary users are sales and GTM professionals.
As a CEO-reporting leader central to our revenue growth, this role requires an in-office presence 4 days a week.
Vacancy Status: This position is for a new and active vacancy that Citylitics is currently seeking to fill.
What Will You Accomplish?
Customer Implementation, Enablement, and Change Management
• Own the customer journey from pre-sales support and trial configuration through implementation, onboarding, workflow integration, and sustained adoption.
• Establish a structured sales-to-implementation handoff that captures customer goals, priority use cases, configuration requirements, success criteria, commitments, and risks.
• Own WAU, platform adoption, and workflow integration targets, using engagement data to identify barriers and drive targeted interventions.
• Design scalable engagement programs including data workshops, recurring training, office hours, workflow reviews, adoption campaigns, targeted communications, and customer-facing standard operating procedures that activate users, embed new workflows, and sustain adoption.
• Develop customer-facing talk tracks, standard responses, role-specific narratives, and customer-facing collateral that make Citylitics easy to understand, create consistency across the team, and give customers clear processes they can implement within their own sales organizations.
• Equip the Customer Enablement team to support sales, advise on customer use cases, configure effective trials, and prepare customers for successful implementation.
• Update workflows, cadences, collateral, engagement model, and talk tracks with each product release or platform enhancement
Scalable Service Delivery and Resource Management
• Build the processes, systems, operating cadence, and team structure required to deliver a consistent customer experience at scale.
• Define which activities should be delivered through high-touch services, pooled resources, one-to-many programs, automation, or self-service.
• Establish capacity planning, utilization, workload management, resource allocation, and service delivery standards.
• Partner with Sales and Finance to define the scope, pricing, packaging, and delivery requirements of implementation and enablement services.
Team Leadership
• Build, lead, and develop a high-performing team. Establish clear roles, operating metrics, performance expectations, and accountability across the function.
• Coach the team to combine strong customer relationships with disciplined project management, standard talk track adherence, and operational rigor.
• Create a culture of urgency, ownership, continuous improvement, and measurable customer impact.
• Remain close to customers and participate directly in complex implementations, executive conversations, and adoption challenges.
Requirements
Experience and Track Record
• 10+ years of experience across customer enablement, implementation, onboarding, professional services, revenue operations, customer success, or related functions.
• 5+ years of experience leading customer-facing teams in a B2B SaaS,…
Skills asked for
- data science
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