VP of Sales

Citylitics•Milwaukee, WI

11d•Onsite

About The Position

Citylitics is seeking a VP of Sales to lead aggressive revenue growth, own net-new ARR goals, and build a predictable, repeatable sales engine. The role will hire and develop Account Executives and Business Development Representatives, strengthen enterprise and mid-market sales motions, and help establish Citylitics as a category leader in predictive sales intelligence for public infrastructure. This CEO-reporting, Board-facing leader is expected to work in person at the Milwaukee headquarters four days per week. The VP of Sales will lead commercial strategy, operating processes, team development, and execution across the customer lifecycle. The role is accountable for net-new ARR, renewals, expansion ARR, and Net Revenue Retention (NRR), and will guide complex new-logo, renewal, and expansion opportunities. The leader will partner with Marketing, Delivery, and Product to build a cohesive go-to-market approach and maintain commercial continuity. Citylitics delivers predictive intelligence about infrastructure investment opportunities across North America. Its platform turns documents from more than 40,000 cities, utilities, and public agencies into sales intelligence for infrastructure vendors, engineering firms, and construction companies. The company combines AI agents, fine-tuned models, a proprietary infrastructure signals graph, and human quality assurance. Its mission is to improve how infrastructure investments are made so communities can address critical needs earlier and benefit from stronger, more resilient infrastructure.

Requirements

20+ years in sales leadership, including 10+ years at the VP/SVP level.
Proven history of scaling and strengthening sales and account management teams.
Documented consistent quota attainment and ability to lead teams to exceed net-new ARR, expansion ARR, renewal, and NRR targets.
Experience directly leading both Account Executives and Account Managers, or a comparable commercial organization responsible for revenue across the full customer lifecycle.
Ability to navigate and close complex, multi-stakeholder new-logo, renewal, and expansion opportunities involving executives, technical buyers, and procurement.
Demonstrated ability to create compelling sales narratives, messaging frameworks, and talk tracks that differentiate solutions, create urgency, and connect customer pain points to measurable business outcomes.
Deep expertise in sales methodologies such as MEDDIC, Challenger, or Sandler, and mastery of forecasting discipline, pipeline governance, and structured deal inspection.
Experience establishing operating cadences and forecasting across net-new sales, renewals, expansion pipeline, and NRR.
Demonstrated ability to implement whitespace analysis, account growth planning, renewal management, and expansion pipeline reviews.
Proficiency with modern revenue technology, including CRM, sales intelligence, and forecasting tools, and commitment to data hygiene.
Proven ability to partner with Marketing, Product, and Delivery to build a cohesive, feedback-driven go-to-market engine and maintain commercial continuity.
Ability to coach and motivate teams, address capability gaps, and build a culture of high performance, accountability, and skill development.
Resourceful, results-oriented leadership with a hunter mentality and focus on winning new customers, retaining customers, and growing strategic accounts.

Nice To Haves

Experience selling solutions that require customers to adopt new technologies, workflows, processes, or organizational behaviours.
Experience selling into risk-averse or highly regulated industries.
Exposure to selling AI applications.
Experience or exposure in public infrastructure, GovTech, Construction Tech, or data- and AI-driven markets.

Responsibilities

Own net-new ARR goals and build a predictable, repeatable sales engine to achieve aggressive revenue targets.
Implement operating cadences and daily KPIs to track pipeline health, renewal risk, expansion opportunities, and revenue performance.
Build and refine scalable sales playbooks, qualification frameworks, account planning, and lifecycle processes to support commercial continuity and improve NRR.
Develop sales narratives, messaging, and talk tracks that sharpen differentiation, create urgency, and connect customer needs to measurable business outcomes.
Create template pitch decks, presentation guidelines, and coaching frameworks for audience-specific sales presentations.
Establish whitespace analysis, account growth planning, and expansion pipeline reviews to generate predictable expansion ARR.
Develop and lead a high-performing commercial organization across Account Executives and Account Managers, with accountability for net-new ARR, renewals, expansion ARR, and NRR.
Foster a coaching-driven culture through structured deal reviews, account planning, and performance management.
Identify capability gaps, mentor talent, and build a team able to win complex deals and grow strategic customer relationships.
Coach Account Executives and Account Managers to deliver effective pitch meetings for executive and technical audiences.
Deliver consistent net-new ARR growth and achieve renewal, expansion ARR, and NRR targets.
Oversee sales processes so Account Executives and Account Managers conduct deep discovery, build trusted relationships, and deliver persuasive presentations, proposals, renewal agreements, and expansion contracts.
Implement training, onboarding, and coaching programs to accelerate productivity and strengthen performance.
Guide deal and account strategy for complex, multi-stakeholder new-logo, renewal, and expansion opportunities.
Partner with Marketing, Delivery, and Product to align go-to-market activities, maintain commercial continuity, and create effective feedback loops across the customer lifecycle.
Use disciplined forecasting, pipeline governance, structured deal inspection, and data hygiene to drive strategy and accountability.