VP of Sales

Citylitics • Milwaukee, WI

10d • 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 position requires an in-office presence four days per week at the Milwaukee headquarters.

The VP of Sales will lead commercial strategy, operating cadence, forecasting, sales processes, and full-lifecycle revenue performance across new sales, renewals, and expansions. The leader will develop a high-performing organization, coach teams through complex opportunities, improve sales narratives and presentation quality, and work cross-functionally with Marketing, Product, and Delivery to create a cohesive go-to-market engine. Success includes achieving net-new ARR, renewal, expansion ARR, and Net Revenue Retention targets while building a culture of accountability, coaching, and operational rigor.

Requirements

• 20+ years of sales leadership experience, including 10+ years at the VP/SVP level.
• Proven history of scaling and strengthening sales and account management teams.
• Documented, consistent quota overperformance and ability to lead teams to exceed net-new ARR, expansion ARR, renewal, and Net Revenue Retention targets.
• Experience directly leading both Account Executives and Account Managers, or a comparable commercial organization responsible for full-lifecycle revenue.
• Ability to navigate and close complex, multi-stakeholder new-logo, renewal, and expansion opportunities involving executive buyers, technical buyers, and procurement.
• Demonstrated ability to create compelling sales narratives, messaging frameworks, and talk tracks that sharpen differentiation, create urgency, and connect customer pain points to measurable outcomes.
• Deep expertise in sales methodologies such as MEDDIC, Challenger, or Sandler, along with mastery of forecasting, pipeline governance, and structured deal inspection.
• Experience establishing operating cadences and forecasting across new sales, renewals, expansion pipeline, and Net Revenue Retention.
• 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.
• Ability to partner effectively with Marketing, Product, and Delivery leadership to drive an integrated go-to-market strategy.
• High-EQ leadership skills, including coaching, motivating teams, addressing capability gaps, and building accountability and skill development.
• Resourcefulness, a hunter mentality, and a strong focus on winning new customers, retaining existing 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 deliver consistent revenue growth, renewal performance, expansion ARR, and Net Revenue Retention results.
• Build and refine scalable sales playbooks, qualification frameworks, account planning, and lifecycle processes.
• Implement operating cadences and daily KPIs to monitor pipeline health, renewal risk, expansion opportunities, and revenue performance.
• Strengthen Citylitics’ sales narrative, messaging, and talk tracks to differentiate the offering and connect it to customer priorities and measurable outcomes.
• Create pitch-deck templates, presentation guidelines, and coaching frameworks for Account Executives and Account Managers.
• Establish whitespace analysis, account growth planning, and expansion pipeline reviews to support predictable expansion revenue.
• Lead and develop a commercial organization across Account Executives and Account Managers, with clear accountability for revenue outcomes.
• Foster a coaching-driven culture through structured deal reviews, account planning, and performance management.
• Identify capability gaps, mentor team members, and develop talent able to win complex deals and grow strategic customer relationships.
• Coach Account Executives and Account Managers to deliver effective presentations to executive and technical audiences.
• Enforce sales-process oversight across discovery, relationship-building, presentations, proposals, renewals, and expansion contracts.
• Implement training, onboarding, and coaching programs to accelerate productivity and strengthen ongoing performance.
• Guide deal and account strategy for complex, multi-stakeholder new-logo, renewal, and expansion opportunities.
• Partner with Marketing, Delivery, and Product to maintain go-to-market cohesion, commercial continuity, and customer-lifecycle feedback loops.

Benefits

• Access to Generative AI tools and Citylitics’ full Data Universe to support productivity and experimentation.
• Opportunity to contribute to positive change in sustainable public infrastructure.
• Opportunity to work in a collaborative, inclusive workplace with room to grow.

What This Job Offers

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