Director/VP of Product Management

New York | Technology | Full-time | Fully remote


The Director/VP of Product will serve as the head of the product organization, reporting to the SVP Technology and Product. Leveling and title commensurate with candidate experience relative to role qualifications. Company is distributed (Remote OK). At employees' option, offices available in Cleveland, OH and New York, NY.

Who We Are

Fund That Flip is an originator of market-leading loans for fix-and-flip, new construction, and rental properties. We also provide a platform for investors to earn passive income by investing in the real estate that we help finance.

Our technology team currently builds and maintains three primary systems: the loan origination and servicing software that powers our lending operation, the investing platform that helps us raise capital, and the payment service that processes millions of dollars in transactions every day.

At their core, the technology stacks are built on Ruby on Rails. Most of our code is in HTML and Stimulus (a Javascript framework), though we are experimenting with React for web and native apps. We also support fully-integrated third party services like SendGrid, HubSpot, HelloSign, and more.

Who You Are

An ideal member of our technology team is a person that is always learning and striving to improve their craft. As the head of product, you are the type to encourage this kind of behavior.

For this role, you are a seasoned product manager, someone who has been labeled a “High Potential” in a previous role, or both. You’ve previously managed a team of product managers and product owners, and have led teams through growth spurts within an entrepreneurial/startup environment; ideally, one that’s venture-backed. You take ownership of your team.

You’re familiar with the benefits of different technologies. At least one of your roles focused on scalable web application development with first-class data security and processing integrity. You understand when it’s appropriate to take on technical debt, when that debt should be addressed, and the conviction to manage those liabilities at the expense of greenfields and feature development within the broader business context.

You’re a strong communicator, both internally to the product team but also to your partners in the engineering organization, the operations organization, and across the wider company. You have represented the product organization at the highest level of the business, either as its leader or as a frequent delegate. You are a capable leader, both in-person and in distributed meetings.


  • Own the product team, including:
    • Operating day-to-day concerns
    • Planning long term strategy
    • Ensuring the team meets performance goals
    • Increasingly building team capacity through additional headcount and continual process improvements
  • With direct reports, create OKRs that align to organizational strategy
  • Ensure direct reports (and those within the management chain) have continuous  professional development
  • Cultivate a leadership culture and support growth 
  • Manage morale and team behaviors; maintain a psychologically safe and blameless environment
  • Establish and maintain product lifecycle: discovery, shaping, execution, and sunset, ensuring stakeholders have commensurate visibility and involvement, with adequate tooling to measure performance (i.e. Jira, et al)
  • Maintain a tight relationship with engineering leadership
  • Maintain point of view on market positioning against market trends
  • Define and maintain product roadmap with leadership input
  • Create and evangelize product vision

Basic Qualifications

  • 3+ years experience as a Director, Senior Director, VP (or equivalent) in a software product manager capacity, ideally on a web application 
  • Track record of managing teams that build software on-time and on-budget
  • An appreciation for Conway’s Law and its implications
  • Evidence of strong and clear communication
  • Proficiency in SQL; Data Literate

Preferred Qualifications

  • Degree in Computer Science, Information Systems, Business Administration, or equivalent experience/credentialing
  • 2+ years in a venture-backed startup
  • Experience managing greenfields projects as well as legacy products
  • Experience in fintech, financial services, payments, or similar
  • Experience working with QA/SDE-in-Test resources
  • Strong business analysis and data analytics
  • Strong financial acumen
  • Strong design taste, UI/UX