Short Term Rental Manager Jobs in Wisconsin (NOW HIRING)

As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to reinvent the rental housing ecosystem for the benefit of all. We successfully merge our passion for helping investors build wealth through real estate with cutting edge technology that transforms the way they do it.

As the leading end-to-end investment platform for single-family rental homes (SFR), our mission is to reinvent the rental housing ecosystem for the benefit of all. We successfully merge our passion for helping investors build wealth through real estate with cutting edge technology that transforms the way they do it.

With a talented team of 750+ Roofsters, our collaborative, can-do culture is what fuels our growth. In 2022, we closed on our Series E, raising $240 million, and have offices in the Bay Area and New York City. Our growth includes recent acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both Retail and Institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services.

The Senior Product Manager, Leasing is the dedicated product leader for Leasing on the Leasing & Resident Experience team. This is a hands-on, high-ownership position over a revenue-carrying surface for someone who thrives at the intersection of Product, Operations, and Growth. You will own the leasing roadmap end to end, deliver the products that help our teams lease more homes faster, and shape new leasing offerings for the landlords who manage on their own.

This role is built for an operator-minded product manager with a bias toward action, a focus on driving outcomes, strong written communication, and a genuine curiosity about how homes actually get leased. If you look at a leasing pipeline and your first instinct is to find the stage where prospects quietly stall, then fix the system so it stops happening, this is your job.

• Own the leasing product roadmap across our retail, institutional, and build-to-rent portfolios, balancing platform commitments against growth opportunities
• Lead initiatives from discovery through execution, partnering with Engineering and Design on scoping, rollout planning, and post-launch impact analysis
• Keep priorities, sizing, and sequencing legible so leadership, engineering, and operations are all reading from the same plan

• Build the visibility and workflow layer for the leasing funnel so handoffs, service levels, and automation status are clear and the team sees what needs attention without digging
• Partner with leasing operations to remove bottlenecks and help the team absorb more volume without proportionally adding headcount
• Understand how AI is working within the leasing funnel, from screening to scheduling to prospect communication, well enough to push automation where it helps and catch quality issues before customers do

• Shape and validate new leasing products and services for self-managing landlords, from customer discovery through pricing and business modeling
• Partner with Growth and go-to-market teams to take new offerings from thesis to launch

• Talk directly to the people who live in the funnel, including owners, prospects, leasing agents, and screeners, and synthesize what you hear into decisions the team can act on
• Build and maintain the feedback loops that keep operational signals flowing into product decisions in real time, not after the damage is done

• Serve as the product counterpart to Engineering and Design and the point of contact for cross-team dependencies across sales, operations, and account management
• Support prioritization decisions by balancing strategic goals and operational capacity

• Own leasing funnel metrics end to end, including conversion, speed to lease, service-level adherence, and vacancy
• Develop and track KPIs that surface risks and opportunities early, and identify root causes when results deviate from expectations

• 5 or more years of product management experience, including ownership of a revenue-carrying product surface at a software company
• Proptech, real estate, or marketplace background strongly preferred; leasing or property management context is a strong plus. You should know, or be hungry to learn, how a home actually gets leased
• Grit. You’ve shipped through ambiguity and constraint, and you can tell us how
• Strong roadmap and stakeholder management. You can hold deadline-bound platform work and growth bets in the same quarter and keep both moving
• Comfort in an operator-heavy business; your best discovery starts by shadowing the people doing the work today
• AI fluency. You use AI tools every day and have opinions about where agents belong in a workflow. You don’t need to write code, but you should have put AI into a product, not just into your own productivity
• Comfort working with data; you can define funnel metrics, read a dashboard, and root-cause a number that moved the wrong way
• Strong written communication. You can take a messy situation and write a clear one-pager about it
• Genuine curiosity about customers and comfort talking to them directly, whether that is an institutional owner, a self-managing landlord, or a prospect stuck in screening
• Bias toward action over perfect planning

This position is classified as a HYBRID work environment in Oakland, CA or NYC, New York.

This is a 2 day hybrid role in the Bay Area office, effective October 2026.

$214,000 - $225,000 annual base salary. The compensation range may be adjusted based on experience and location.

Our compensation reflects several US geographic markets. The base pay for this position represents the expected salary for this position. Ultimately, in determining your pay it will be based on several factors including location, job-related knowledge, skills, experience and other job related factors. Roofstock is a total compensation company; the base salary is only part of our total compensation package.

• Generous PTO Policy
• 13 Paid Holidays
• Volunteer Time Off
• Paid Parental Leave
• 401k Program
• Wellness and home office/cell phone subsidies
• Robust health, dental, vision insurance, and more

Authorization to work in the U.S. is a precondition of employment and we are unable to sponsor H1-B Visas at this time.

The company provides equal opportunity in all of our employment practices to all qualified employees and applicants without regard to race, color, religion, sex, gender, gender expression, gender identity, national origin, ancestry, citizenship, age, physical or mental disability, marital status, sexual orientation, military or veteran status, genetic information or any other category protected by federal, state and local laws. This policy applies to all aspects of the employment relationship, including recruitment, hiring, compensation, promotion, transfer, disciplinary action, layoff, return from layoff, training and social, and recreational programs. All such employment decisions will be made without unlawfully discriminating on any prohibited basis.

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