Strategy Operations Proptech Jobs in Wisconsin (NOW HIRING)

About ClickPay

ClickPay, a RealPage company, is a leading payment processing platform purpose-built for residential real estate. We power billions of dollars in rent, HOA dues, and property-related payments annually, connecting property management companies, homeowner associations, and millions of residents through a unified billing and payments experience. As part of RealPage, the industry's premier property management software provider, ClickPay sits at the intersection of fintech and proptech—modernizing how the residential real estate industry moves money.

The Opportunity

We are seeking a VP of Product Management & Strategic Initiatives to lead ClickPay's product organization and drive the company's highest-impact strategic programs. This is a dual-mandate leadership role: you will build and lead a team of four Product Managers responsible for new product features across the full product lifecycle, while personally owning key strategic initiatives that span the business—from monetization and payment network economics to enterprise partnerships and regulatory readiness.

You will operate in a cross-functional matrix organization, partnering closely with Sales, Marketing, Implementations, and Support to ensure products are not only well-built, but well-launched, well-adopted, and well-supported. The right candidate combines deep payments and fintech domain expertise with strong people leadership and the executive presence to influence senior stakeholders across ClickPay and RealPage.

Product Leadership

• Lead, coach, and develop a team of four Product Managers, setting clear priorities, raising the bar on product craft, and building a high-performing product culture.
• Own the product roadmap for new features and capabilities, balancing customer needs, revenue impact, platform scalability, and compliance requirements.
• Drive the full product lifecycle—discovery, requirements definition, development partnership with Engineering, beta programs, launch, adoption, iteration, and end-of-life decisions.
• Define and execute go-to-market strategies in partnership with Marketing and Sales, including positioning, pricing, packaging, enablement, and launch readiness.
• Establish and track product KPIs (adoption, transaction volume, authorization rates, revenue per unit, NPS) and use data to inform prioritization and investment decisions.
• Transform the ways of working into adoption of AI based product management tools to change the velocity of product and engineering initiatives.
• Launch of new features such as PayPal, Venmo, Cash App and other alternative payments into the product that will drive 10% growth in incremental revenue.

Strategic Initiatives

• Lead the transformation of cross-functional strategic programs of company-wide importance—such as payment economics optimization (interchange, network tokenization, account updater), enterprise partnership enablement, wallet and alternative payment method expansion, and regulatory compliance readiness.
• Serve as the connective tissue across Sales, Marketing, Implementations, and Support in a matrix organization—aligning stakeholders, removing blockers, and driving initiatives from business case to measurable outcome.
• Prepare and present executive-level analyses, business cases, and operating review materials to ClickPay and RealPage leadership.
• Represent product and strategy in enterprise client and partner conversations, supporting complex commercial negotiations with product expertise.
• Monitor the competitive, regulatory, and payment network landscape (card brand rules, state-level fee legislation, NACHA requirements) and translate changes into product and business strategy.

What You'll Bring

• 15+ years of product management experience, including 5+ years leading and developing product managers.
• Required: Deep domain expertise in payments and fintech—card processing, ACH, interchange economics, digital wallets, tokenization, payment gateways, and/or billing platforms.
• Proven track record of taking products from concept through launch and scale, including hands-on ownership of go-to-market execution.
• Demonstrated success leading strategic initiatives in a matrixed environment, influencing without direct authority across sales, marketing, operations, and support functions.
• Strong analytical and financial acumen—comfortable building unit economics models, sizing opportunities, and defending investment cases with data.
• Executive-level communication skills: crisp writing, confident presentation, and the ability to distill complexity for senior audiences.
• Bachelor's degree required; MBA or equivalent advanced degree preferred.

Nice to Have

• Experience in proptech, property management software, or residential real estate payments.
• Familiarity with payment network programs and compliance frameworks (Visa/Mastercard interchange programs, PCI DSS, state surcharge and fee regulations).
• Experience supporting enterprise partnership or M&A-driven client retention initiatives.

Why Join Us

You will own the product agenda for a category-leading payments platform at a pivotal moment of growth—with the resources and reach of RealPage behind you and the pace and ownership of a focused fintech business in front of you. This role offers direct exposure to executive leadership, meaningful P&L influence, and the opportunity to shape how an entire industry pays and gets paid.

RealPage is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

SALARY AND BENEFITS

• RealPage provides a competitive salary package along with a comprehensive benefit plan that includes:
• Health, dental, and vision insurance.
• Retirement savings plan with company match.
• Paid time off and holidays.
• Professional development opportunities.
• Performance-based bonus based on position.

Compensation may vary depending on your location, qualifications including job-related education, training, experience, licensure, and certification, that could result at a level outside of these ranges. Certain roles are eligible for additional rewards, including annual bonus, and sales incentives depending on the terms of the applicable plan and role as well as individual performance.

Equal Opportunity Employer: RealPage Company is an equal opportunity employer and committed to creating an inclusive environment for all employees.

USD $154,800.00 - USD $281,200.00 /Yr.