Vice President of Marketplace Sales

Real Estate | PropTech | Investor Marketplace

Location: Remote
Compensation: Competitive Base Salary + Performance-Based Sales Bonus

Build the Sales Engine Behind the Next Generation of Real Estate Investing

Easy Street Offers (ESO) is looking for an experienced, entrepreneurial sales leader to take ownership of sales and revenue growth across our real estate investor marketplace.

This is not a role for someone who wants to inherit a mature sales organization and simply manage the numbers.

We are looking for a player-coach who wants to build.

Someone who can lead from the front, engage directly with customers, close business, develop relationships, establish a repeatable sales process, and build a high-performing team around them as we scale.

ESO has built the technology, marketplace, partnerships, and infrastructure. We have tens of thousands of users and a growing pipeline of residential real estate opportunities entering our ecosystem. Our next phase is about turning that scale into transactions.

That's where you come in.

Who We Are

Easy Street Offers is a technology-driven real estate marketplace designed to connect real estate professionals and property opportunities with qualified investors.

Our platform brings together a diverse ecosystem of buyers, including individual investors, fix-and-flip operators, rental investors, professional investment groups, and institutional buyers.

Unlike traditional wholesalers, ESO does not operate as a principal or compete with its customers for deals. We are building the infrastructure that connects opportunities with the right capital and helps transactions move from opportunity to close.

Our marketplace combines technology, data, AI, valuation tools, financing solutions, and a growing network of industry partnerships to create a better way for real estate investors to discover, evaluate, finance, and acquire residential investment properties.

We believe the future of real estate investing is a true marketplace: the right property, matched with the right buyer, at the right time.

The Opportunity

As Vice President of Marketplace Sales, you will take ownership of the sales strategy and execution that drives transactions through the ESO marketplace.

Your mission is straightforward:

Build a world-class sales organization that converts marketplace opportunities into closed transactions.

You will work across ESO's growing buyer ecosystem, helping investors understand the opportunities available to them and ensuring that the right properties reach the right buyers.

Initially, this will be a highly hands-on role.

We expect you to pick up the phone.

We expect you to talk to investors.

We expect you to work deals.

We expect you to understand why buyers say yes, why they say no, and what prevents transactions from getting across the finish line.

You will use those insights to build the people, processes, playbooks, and technology needed to scale.

Over time, your role will evolve from player-coach to builder and leader of a growing marketplace sales organization.

What You'll Own

• Lead the sales strategy and day-to-day execution for the ESO investor marketplace.
• Drive buyer engagement, offers, contracts, and ultimately closed transactions.
• Build strong relationships with individual investors, professional operators, investment groups, and institutional buyers.
• Develop strategies to increase marketplace liquidity and improve the conversion of property opportunities into offers and transactions.
• Personally engage in high-value opportunities and strategic buyer relationships.
• Recruit, train, coach, and develop a high-performing sales team as transaction volume grows.
• Create a repeatable sales process that can scale across markets and buyer segments.
• Establish clear KPIs, accountability, forecasting, and performance expectations.
• Work closely with Buyer Success, Operations, Marketing, Product, and Executive Leadership.
• Help refine buyer segmentation, sales messaging, outreach strategies, and engagement campaigns.
• Provide real-world feedback to our product and technology teams based on what buyers need to make faster, more confident investment decisions.
• Identify friction in the marketplace and work cross-functionally to remove it.
• Develop a sales culture built around urgency, accountability, relationships, and results.

Who We're Looking For

The ideal candidate has significant experience selling within the residential real estate ecosystem and understands how real estate investors think.

You may have built your career in:

• Residential real estate investment sales
• Single-family rental or SFR
• Fix-and-flip
• Institutional acquisitions or dispositions
• Real estate brokerage
• PropTech
• Investor marketplaces
• Real estate SaaS or data
• Investment property sales
• Real estate lending or investor finance
• Title, settlement, or another transaction-driven real estate business

Your exact background matters less than your ability to understand the real estate transaction and build relationships that generate revenue.

You should be equally comfortable talking strategy with an institutional investor and picking up the phone to help an individual investor get comfortable making an offer.

You May Be a Great Fit If...

You are a builder, not just a manager.

You know how to create a sales process when the playbook isn't already written.

You are comfortable operating in a fast-moving entrepreneurial environment where the opportunity is significant and the organization is evolving quickly.

You believe great sales leaders should understand the business from the front lines.

You love coaching people, but you're still willing to jump into a deal yourself when needed.

You understand that marketplaces are different from traditional sales organizations. Success isn't just about generating leads. It's about creating engagement, liquidity, trust, and transactions.

Most importantly, you are excited by the opportunity to build something.

What Success Looks Like

In your first phase at ESO, you will deeply understand our buyers, marketplace, inventory, technology, and transaction flow.

From there, you will help us create a predictable sales engine that:

Opportunity → Buyer Engagement → Offer → Contract → Close

You will know where deals are getting stuck and why.

You will build the processes and accountability needed to improve conversion at every stage.

You will develop a sales organization capable of supporting ESO as we expand our buyer network, increase transaction volume, enter new markets, and introduce additional products and services to our investor ecosystem.

Ultimately, success in this role means creating a marketplace where great investment opportunities consistently find qualified buyers—and where ESO becomes an essential part of how real estate investors source and acquire properties.

Why ESO?

ESO is at an inflection point.

We have spent years building the marketplace, technology, infrastructure, relationships, and user base required to create something meaningful in residential real estate.

Now we are focused on scale.

For the right sales leader, this is an opportunity to join at the moment when the foundation has been built but the full potential of the business is still ahead.

You won't simply be joining a sales team.

You'll be helping build the sales organization that defines the next chapter of ESO.

If you have deep real estate sales experience, know how to build and lead high-performing teams, and want the opportunity to make a measurable impact on a growing PropTech marketplace, we'd like to meet you.

Total Rewards: Competitive executive base salary, uncapped transaction-based sales incentive opportunity, leadership overrides tied to team production, participation in ESO's company-wide profit-sharing program, and comprehensive employee benefits.