VP of Sales

Citylitics • Toronto, ON

10h • Onsite

About The Position

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.

Requirements

• 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.
• Proven ability to navigate and close complex, multi-stakeholder deals involving executives, technical buyers, and procurement.
• Deep expertise in sales methodology (e.g., MEDDIC, Challenger, Sandler), combined with a mastery of forecasting discipline and pipeline governance.
• Proficiency with modern revenue stacks (CRM, Sales Intel, Forecasting tools) and a commitment to data hygiene as a driver of strategy.
• Proven ability to partner with Marketing, Product, and Customer Success to build a cohesive, feedback-driven GTM engine.
• Demonstrated ability to partner effectively with Marketing, Product, and Customer Success leadership to drive a unified GTM strategy
• A motivator and coach who can drive accountability while building a culture of high performance and skill development.
• A seasoned leader with a resourceful, "hunter" mentality who obsesses over winning.

Nice To Haves

• Experience or exposure in public infrastructure, GovTech, or data/AI-driven markets is a strong advantage.

Responsibilities

• 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

• internal mentorship program
• in-role professional growth
• skill-based development & learning
• internal promotion opportunities

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed