Director of Customer Enablement

Citylitics•Toronto, ON

1d•Hybrid

About The Position

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.

Requirements

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, data, technology, or services environment.
Demonstrated success building and scaling implementation, onboarding, enablement, or professional services functions.
Proven track record of driving sustained platform adoption across thousands of distributed customer teams and active users, while improving weekly active usage, workflow integration, and time-to-value.
Experience supporting sales processes through solution design, trial configuration, use-case development, and structured sales-to-implementation handoffs.
Experience developing polished and effective customer facing collateral
Experience leading Revenue Operations or building customer enablement programs for sales and GTM teams is highly preferred.
Deep understanding of how to move customers from implementation through activation, workflow integration, sustained adoption, and value realization.
Exceptional customer-facing communication and facilitation skills, with the ability to translate complex products, data, and workflows into simple, practical, and compelling collateral and narratives for busy sales professionals.
Experience designing scalable engagement models, including role-based onboarding, data workshops, recurring training, office hours, adoption campaigns, self-service resources, and customer-facing SOPs that standardize how new workflows are implemented.
Ability to diagnose adoption barriers and design interventions that change user behaviour, workflows, and operating habits.
Experience leading executive conversations, training customer teams, and partnering with executive sponsors, RevOps leaders, and sales leadership to translate strategic objectives into measurable adoption and change-management plans.
Ability to coach internal teams to communicate with customers confidently, clearly, and consistently.
Strong project and program management capabilities, including managing implementation plans, milestones, dependencies, risks, resources, and executive stakeholders.
Demonstrated ability to build repeatable operating processes, metrics, governance, and accountability across complex customer programs.
Experience with capacity planning, utilization, resource allocation, service delivery, and team productivity.
Experience developing or managing professional services scope, pricing, packaging, statements of work, or implementation offerings.
Operationally Rigorous: Establishes clear processes, milestones, ownership, and accountability.
Strong Project Leader: Anticipates risks, manages dependencies, and ensures commitments are delivered on time.
Builder and Scaler: Able to create the operating model, processes, systems, and team required for the next stage of growth.
Team Builder: Develops high-performing teams and creates a culture of ownership and continuous improvement.
Change Management Leader: Understands that sustained adoption requires new habits, workflows, management practices, and accountability—not simply product training.
Hands-On and Data-Driven: Remains close to customers and uses WAU, adoption, workflow integration, time-to-value, and service delivery data to prioritize action.

Nice To Haves

Experience building effective, agentic on-boarding experiences is highly desirable

Responsibilities

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.
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.
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.