• Citylitics is seeking a VP of Sales to lead the company toward aggressive revenue growth targets. You will own net-new ARR goals and build the predictable, repeatable sales engine required to achieve them. You will hire and develop top-performing AEs and BDRs, strengthen our enterprise and mid-market motions, and help establish Citylitics as the category leader in predictive sales intelligence for public infrastructure
• As a CEO-reporting, Board-facing leader central to our success, this role requires an in-office presence 4 days a week at our Toronto Headquarters
• Establish disciplined forecasting, pipeline coverage models & inspection cadences that drive predictability
• Define account segmentation and ICP clarity to ensure the team is aligned with our market strategy
• Create and refine sales playbooks, talk tracks, sales deck templates, and qualification frameworks for multi-stakeholder, high-value deals
• Build, hire, develop, and mentor a top-tier sales organization across AEs, BDRs, and leadership
• Enforce a coaching culture grounded in competency development and structured deal reviews
• Establish a high-performance environment rooted in accountability, transparency, and operational rigor
• Deliver consistent net-new ARR growth and support expansion outcomes in partnership with Customer Success
• Enforce rigorous sales process oversight to ensure the team performs deep discovery, builds trusted prospect relationships, and delivers compelling sales presentations & proposals that drive signed contracts at a higher win rate
• Implement best-in-class training and onboarding programs to ramp new AEs and BDRs to full productivity within aggressive targets
• Guide deal strategy on multi-stakeholder enterprise opportunities to personally influence outcomes and improve team performance
• Align with Marketing, Customer Success and Product to ensure GTM cohesion and feedback loops

Benefits

• Flex Time, All the Time: We believed in flexible hours and work from home days before it became the norm. We encourage a flow that works best for you
• Benefits and Perks: Our benefits cover everything from your trip to the dentist to massage therapy. We offer online learning, the right hardware to succeed, and time to hang out via yoga, donut chats, Gather, and more!- You are a leader who lives in the details, obsesses over winning, and has scaled high-performing sales teams in fast-growth software companies that achieved market dominance
• Documented history of overperformance, demonstrating consistent quota attainment and the ability to lead teams to exceed net-new ARR targets
• Complex Selling Expertise: Proven ability to navigate and close complex, multi-stakeholder deals involving executives, technical buyers, and procurement
• 20+ years in enterprise sales leadership, including 10+ years at the VP/SVP level, with a proven history of scaling sales teams
• Domain Alignment: Experience or exposure in public infrastructure, GovTech, or data/AI-driven markets is a strong advantage
• Data-Driven Approach: Proficiency with modern revenue stacks (CRM, Sales Intel, Forecasting tools) and a commitment to data hygiene as a driver of strategy
• GTM Integration: Proven ability to partner with Marketing, Product, and Customer Success to build a cohesive, feedback-driven GTM engine
• Methodology & Rigor: Deep expertise in sales methodology (e.g., MEDDIC, Challenger, Sandler), combined with a mastery of forecasting discipline and pipeline governance
• Relentless Operator: A seasoned leader with a resourceful, “hunter” mentality who obsesses over winning
• High-EQ Leadership: A motivator and coach who can drive accountability while building a culture of high performance and skill development
• Integrated GTM Leadership: Demonstrated ability to partner effectively with Marketing, Product, and Customer Success leadership to drive a unified GTM strategy