Requirements

- 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
- 20+ years in enterprise sales leadership, including 10+ years at the VP/SVP level, with a proven history of scaling sales teams
- 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
- Domain Alignment: Experience or exposure in public infrastructure, GovTech, or data/AI-driven markets is a strong advantage
- Methodology & Rigor: Deep expertise in sales methodology (e.g., MEDDIC, Challenger, Sandler), combined with a mastery of forecasting discipline and pipeline governance
- 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
- Integrated GTM Leadership: Demonstrated ability to partner effectively with Marketing, Product, and Customer Success leadership to drive a unified GTM strategy
- High-EQ Leadership: A motivator and coach who can drive accountability while building a culture of high performance and skill development
- Relentless Operator: A seasoned leader with a resourceful, "hunter" mentality who obsesses over winning

What the job involves

- Citylitics is seeking a VP of Sales to lead the company toward aggressive revenue growth targets. You will own net-recent 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

📌 Vice President of Sales (Toronto)
🏢 Citylitics
📍 Toronto