Sales Development Representative

Since 2014, Fund That Flip has challenged the status quo of slow, unreliable capital and gate-keeping into investment deals. We’ve grown into an end-to-end financial technology platform that helps entrepreneurs and investors generate wealth and make an impact in their own communities across the country. 

We are doubling down on an exceptional borrower experience. For the Sales Development Representative (SDR), that means providing clarity and enthusiasm for borrowers and creatively seeking new sales development opportunities for Fund That Flip.

This role is a great way to join a cross-functional, scaling, entrepreneurial team. With our fast-paced growth, you will be empowered to create your own career trajectory and upward momentum. We provide our SDRs with the knowledge, training, and resources to embrace each opportunity with stability and excitement.

What You’ll Do in a Typical Week 

Mondays on the SDR team are full of opportunity, and are usually a fast-paced, jam-packed day where there is money to be made. Potential borrowers who found our website and submitted their information over the weekend are anxiously awaiting your call. 

You will approach those qualifying calls with a plan, informed by a deep understanding of Fund That Flip’s solutions and underwriting practices. You will also drive & leverage your internal relationships with the account executives (AE) and territory managers (TM) that you frequently work with, ensuring you’re asking the right questions and keeping in touch with prospects. You’ll shadow members of the SDR, AE, and TM teams as they meet with the borrowers and build skill through their approach and feedback. 

As you make calls and send texts or emails, you’ll track activities in HubSpot CRM. You’ll be assigned and track the progress of inbound leads, but you’ll also have the opportunity to be creative and “hunt” for and generate your own leads. You’ll schedule follow up calls between these potential borrowers and the AE.

The team is well-supported through frequent team touchbases. The SDR team takes some time at the end of the day each Monday, Wednesday, and Friday to wrap the day and share challenges and accomplishments. Additionally, there’s a mid-week pulse meeting each Wednesday specifically for feedback from the front half of the week and focus areas for the latter half of the week. The entire sales team (VPs, Managers, AEs, TMs, and SDRs) meets on Friday for a Weekly Sales Health Meeting.

Your First 90 Days in the Role

Your training will begin with some Fund That Flip basics (who are we, what do we do, where does the SDR role sit relative to the org?) This is delivered in a combination of classroom style learning, shadowing SDRs & AEs, joining meetings with other parts of the business, and mock sales and discussion with the Manager, Sales Development. 

By 30 days, you’ll have a soft launch into the role and by 60 days you’ll likely be fully submerged in the role. You’ll accomplish this progression by asking great questions, keeping a big picture focus, and intentionally building a deep understanding of Fund That Flip’s unique value proposition.

Required Skills, Behaviors, & Experiences

  • A “Hunter” mentality who enjoys picking up the phone and proactively selling the benefits of the Company.
  • Active listening skills capable of identifying borrower needs. 
  • Strong oral and written communication skills.
  • Detail-oriented, analytical, and organized. 
  • Ability to critically think and manage diverse clients. 
  • Demonstrated patience and persistence. 
  • Understanding of value proposition and value-based sales techniques. 
  • Problem solving mindset.
  • Technology proficient and adopter of change.

Preferred Skills & Experiences

  • 2+ years’ business experience in a direct sales role. 
  • Prior service industry experience preferred including real estate, merchant services, financial services etc.
  • Bachelor’s degree in business preferred.


Who are we?

Fund That Flip is one of the fastest-growing real estate fintech companies in the U.S., with revenue and staff growth of almost 300% since 2018.

As of April 2022, we’ve originated more than $1.5 billion in funding with 99.6% of principal returned to investors, and more than 93% of our borrowers come back to fund their next deals! And we’re still challenging tradition with fast funding, unparalleled transparency, and personal service to help real estate entrepreneurs transform their neighborhoods and communities. 

Why work for us?

At Fund That Flip, we value transparency, hard work, and results. We support personal and professional growth with an entrepreneurial, tech-loving, creative, and solution-focused culture that rewards employees that push the bar higher for themselves and our company.

Our organization has team members working distributed, hybrid, or in-person at one of our offices in Cleveland, OH, or New York, NY. This role will be in-person in our Cleveland, OH office.

Glassdoor says Fund That Flip is a great place to work, and we’re proud to have earned some awards backing that up, including:

  • Inc. 5000 Fastest Growing Company 2019, 2020, 2021
  • Smart Culture Award 2018, 2022
  • Business Insider Fintech Startups to Watch 2020
  • GCP Best of Tech Awards Finalist 2021
  • Deloitte Technology Fast 500 2020
  • NorthCoast 99 Best Place to Work 2019

Plus, these awesome benefits:

  • Equity stock options for each and every team member
  • Medical, Dental, Vision, and Mental Health Benefit offerings including FSA or HSA enrollment eligibility on day 1
  • Flexible time off
  • Traditional and Roth 401(k)
  • Quarterly and yearly bonus potential based on company performance
  • Self-defined career growth in individual contributor and management pathways

At Fund That Flip, we start everything by understanding the needs of others. We’re all unique and in this together. We’re intentional about building relationships across teams and lifting one another up to help our customers improve communities and write their success stories. 

As you consider joining our team, know that we are committed to creating extraordinary experiences by offering an equal employment opportunity throughout your entire people journey without regard to age, race, color, disability, gender reassignment or identity or expression, genetic information, marital or civil partner status, pregnancy or maternity status, military or veteran status, nationality, ethnic or national origin, religion or belief, sexual orientation, or any legally protected class. 

We will provide accommodations during the entire people journey upon request. Information received relating to accommodation will be addressed confidentially.


Value Proposition
Sales Development
Financial Technology (FinTech)
Direct Selling
Financial Services
Listening Skills
Merchant Services
Service Industries
Written Communication
Selling Techniques