VP Sales Jobs in Milwaukee, WI

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 Milwaukee 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:

• Implement operating cadences and daily KPIs that track pipeline health, renewal risk, expansion opportunities, and overall revenue performance.
• Build and refine scalable sales playbooks, qualification frameworks, account planning, and lifecycle processes that ensure commercial continuity and increase Net Revenue Retention.
• Elevate Citylitics’ sales narrative, messaging, and talk tracks by creating compelling commercial narratives that sharpen differentiation, create urgency, and connect directly to customer priorities, pain points, and measurable business outcomes.
• Create template pitch decks, presentation guidelines, and coaching frameworks that enable Account Executives and Account Managers to develop compelling, audience-specific sales presentations.
• Establish rigorous whitespace analysis, account growth planning, and expansion pipeline reviews that create clear ownership and convert customer opportunities into predictable expansion ARR.

Team Leadership & Culture:

• Develop and lead a high-performing commercial organization across Account Executives and Account Managers with clear accountability for net-new ARR, renewal performance, expansion ARR, and NRR.
• Foster a coaching-driven culture with structured deal reviews, account planning, and performance management rooted in accountability, transparency, and operational rigor.
• Identify capability gaps, mentor talent, and build a team capable of winning complex deals and growing strategic customer relationships.
• Coach AEs and AMs to deliver engaging pitch meetings that resonate with executive and technical audiences, deepen customer engagement, and connect Citylitics’ value to each prospect’s priorities, pain points, and measurable business outcomes.

Sales Execution & Growth:

• Deliver consistent net-new ARR growth and achieve renewal, expansion ARR, and NRR targets.
• Enforce rigorous sales process oversight to ensure Account Executives and Account Managers perform deep discovery, build trusted prospect and customer relationships, and deliver compelling presentations, proposals, renewal agreements, and expansion contracts that improve win rates, renewal rates, and revenue growth.
• Implement best-in-class training, onboarding, and coaching programs that accelerate Account Executives and Account Managers to full productivity within aggressive timelines and strengthen ongoing performance.
• Guide deal and account strategy on complex, multi-stakeholder new-logo, renewal, and expansion opportunities to achieve aggressive growth targets.
• Align with Marketing, Delivery, and Product to ensure GTM cohesion, commercial continuity, and effective feedback loops across the customer lifecycle.

Experience & Track Record:

• 20+ years in sales leadership, including 10+ years at the VP/SVP level, with a proven history of scaling and strengthening sales and account management teams.
• Documented history of overperformance, demonstrating consistent quota attainment and the ability to lead teams to exceed net-new ARR, expansion ARR, renewal, and Net Revenue Retention targets.
• Proven experience directly leading both Account Executives and Account Managers, or a comparable commercial organization responsible for revenue across the full customer lifecycle.
• Complex Selling Expertise: Proven ability to navigate and close complex, multi-stakeholder new-logo, renewal, and expansion opportunities involving executives, technical buyers, and procurement.
• Commercial Narrative Expertise: Demonstrated ability to create compelling sales narratives, messaging frameworks, and talk tracks that sharpen differentiation, create urgency, and connect customer pain points to measurable business outcomes.
• Change Management Experience: Experience selling solutions that require customers to adopt new technologies, workflows, processes, or organizational behaviours is highly desirable.
• Relevant Market Experience: Experience selling into risk-averse or highly regulated industries, combined with exposure to selling AI applications, is highly desirable.
• Domain Alignment: Experience or exposure in public infrastructure, GovTech, Construction Tech, or data- and AI-driven markets is a strong advantage.

Operational Mastery:

• Methodology & Rigor: Deep expertise in sales methodologies such as MEDDIC, Challenger, or Sandler, combined with mastery of forecasting discipline, pipeline governance, and structured deal inspection.
• Full-Lifecycle Revenue Management: Experience establishing disciplined operating cadences and forecasting across net-new sales, renewals, expansion pipeline, and Net Revenue Retention.
• Account Growth Discipline: Demonstrated ability to implement whitespace analysis, account growth planning, renewal management, and expansion pipeline reviews that produce predictable revenue growth.
• Data-Driven Approach: Proficiency with modern revenue technology, including CRM, sales intelligence, and forecasting tools, and a commitment to data hygiene as a driver of strategy and accountability.
• GTM Integration: Proven ability to partner with Marketing, Product, and Delivery to build a cohesive, feedback-driven GTM engine and maintain commercial continuity across the customer lifecycle.

Leadership Profile:

• Integrated GTM Leadership: Demonstrated ability to partner effectively with Marketing, Product, and Delivery leadership to drive a unified GTM strategy.
• High-EQ Leadership: A motivator and coach who can strengthen an existing team, address capability gaps, and build a culture of high performance, accountability, and skill development.
• Relentless Operator: A seasoned, resourceful leader with a hunter mentality who obsesses over winning new customers, retaining existing customers, and growing strategic accounts.

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.
• 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 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!