VP of Customer Success

Citylitics•Toronto, ON

7h•Hybrid

About The Position

Citylitics is seeking a Vice President of Customer Success to lead the company toward aggressive revenue retention and expansion targets. You will own Gross Revenue Retention (GRR) and Net Revenue Retention (NRR) goals and build a predictable, repeatable Customer Success engine that accelerates customer time to value and drives durable renewals and account expansion. You will hire and develop top-performing post-sale teams, strengthen our enterprise and mid-market motions, and help establish Citylitics as the category leader in predictive sales intelligence for public infrastructure. You are a commercial, customer-centric leader who lives in the details, obsesses over customer value outcomes, and has scaled high-performing Customer Success organizations in fast-growth software companies that achieved market leadership. As a CEO-reporting, Board-facing leader central to our revenue growth, this role requires an in-office presence 4 days a week.

Requirements

20+ years of commercial leadership experience, including 10+ years at the VP/SVP level, with a proven history of building and scaling Customer Success organizations.
Documented history of overperformance against retention and expansion targets, demonstrating consistent achievement of GRR, NRR, and post-sale revenue goals.
Multi-Product Expansion Expertise: Proven success driving upsell, cross-sell, and pricing expansion by increasing platform adoption and account-wide penetration within multi-product businesses, resulting in industry-leading NRR.
Domain Alignment: Experience or exposure to public infrastructure, information services, GovTech, or data- and AI-driven intelligence platforms is a strong advantage.
Methodology & Rigor: Deep expertise in Customer Success and Professional Services operating models, combined with a mastery in designing delivery frameworks that accelerate customer time-to-value
Workflow & Operational Integration: Demonstrated experience embedding Customer Success programs into customers’ core workflows, operating rhythms, and decision-making processes to increase adoption, switching costs, and long-term retention.
Data-Driven Operator: Proven ability to build and scale CS tooling and analytics, proficiency with modern revenue stacks, and a commitment to data hygiene as a driver of strategy
Revenue Alignment: Demonstrated ability to align CS compensation, KPIs, and operating cadences to revenue outcomes, including renewals and account expansions.
GTM Integration: Strong track record partnering with Marketing, Sales, Product, & Data to build a cohesive, feedback-driven GTM engine.
Revenue-Oriented CS Leadership: A commercially minded leader who combines deep customer empathy with a relentless focus on owning customer value realization and converting it into account expansions.
Executive Presence: Confident, credible communicator with experience engaging directly with customer C-suite and Board-level stakeholders in high stakes, strategic discussions; prior advisory experience is highly desirable.
High-EQ, Hands-On Leader: A coach and motivator who builds high-performance teams, drives accountability, and is willing to roll up their sleeves including: joining customer calls, coaching reps, and resolving issues as they arise.
Integrated GTM Leadership: Demonstrated ability to partner effectively with Marketing, Sales, Product, and Data leadership to drive a unified GTM strategy

Nice To Haves

Prior advisory experience is highly desirable.

Responsibilities

Design and operationalize scalable playbooks & operating cadences anchored in customer value realization, across onboarding, implementation, adoption, renewal, and expansion.
Evolve the Customer Value Journey, guiding customers from adoption to ROI realization through Customer Success programs embedded in their day-to-day workflows and decision processes.
Establish disciplined renewal, churn-risk, and expansion forecasting anchored in clearly defined customer value realization milestones that inform renewal decisioning and expansion readiness.
Define account segmentation and success motions to balance low-touch efficiency with high-touch, executive-level engagement.
Develop and standardize executive-level customer talk tracks that translate value realization and ROI into clear renewal justification and expansion business cases across customer personas.
Build, hire, develop, and mentor a top-tier Customer Success organization across CSMs, Implementation Specialists, emerging roles, and leadership.
Establish a coaching culture with structured account reviews, skill development, and clear accountability for customer outcomes.
Create a performance culture defined by operational rigor, transparency, and consistent commercial execution.
Build and operationalize skills development frameworks and career ladders across Customer Success, Implementation, and emerging post-sale roles, driving clear progression, consistent capability development, and performance excellence.
Deliver industry-leading GRR and NRR performance by driving adoption, value realization, renewal execution, and multi-product expansion.
Own and evolve renewal, expansion, and risk mitigation talk tracks used across the CS organization to drive consistent execution.
Implement structured training programs to ramp new CSMs, Implementation Specialists, and emerging roles to expected performance standards within aggressive timelines.
Partner closely with Sales, Marketing, Product, and Data to ensure GTM cohesion, strong handoffs, shared messaging, and continuous feedback loops.