VP of Sales

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.
Who Are We Looking For?

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.

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.

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.
Vacancy Status: This position is for an existing and active vacancy that Citylitics is currently seeking to fill.

What Will You Accomplish?

Sales Strategy, Process, & Operations:

• 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.
  

Team Leadership & Culture:

• 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.
  

Sales Execution & Growth:

• 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.

Experience & Track Record:

• 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.
  

Operational Mastery:

• 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.
  

Leadership Profile:

• 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.

Why Citylitics?

• This is a rare opportunity to influence positive change within one of the biggest societal challenges of our generation: sustainable public infrastructure
• You get to support a disruptive solution with a compelling value proposition into an industry that is eager to hear from you and in a market with no direct competition.
• We live at the cross section of infrastructure, scaleup and data science/AI. There is no other team like us in Toronto.
• There is no corporate bureaucracy here. You will accomplish more here in a few months than what you would in a few years at a large, entrenched technology company.
• We believe that Data and AI will play an outsized role in our future, so we equip every team member with access to Generative AI tools and our full Data Universe to enhance their productivity and encourage innovation through experimentation.
• We are proud to offer every CityZen an internal mentorship program, in-role professional growth, skill-based development & learning, and internal promotion opportunities.
• We work hard, we play together, we win as a team! We are on a mission to solve infrastructure while savoring the moment and celebrating the little details along the way.

Citylitics is an equal opportunity employer. We are passionate about providing a safe workplace where everyone is accepted and has the opportunity to grow with us. We are committed to making diversity and inclusivity part of our culture!