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Careers at Keyway
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Sales Executive

23 Oct 2025
Chicago, IL, USA

About the job

About Keyway

Keyway is building the AI infrastructure powering the future of real estate.
Our multi-agent platform automates high-impact workflows—from comp analysis and underwriting to document abstraction and investment scoring.

We’re trusted by leading investors like Starwood Capital and Two Sigma and backed by top-tier venture firms that have supported companies such as Stripe, Opendoor, Palantir, and Uber.


The Role

As a Sales Executive at Keyway, you’ll play a pivotal role in driving revenue growth and expanding our market footprint by strategically advancing our flagship AI platform. You’ll connect with investors, operators, and other real estate professionals to showcase how Keyway’s technology transforms deal-making—faster, smarter, and more efficient.


What You’ll Do

  • Sales Strategy Execution: Manage the full sales cycle—from identifying and qualifying prospects to negotiating and closing deals.
  • Client Engagement: Deliver exceptional client experiences by understanding prospect needs and presenting tailored solutions powered by Keyway.
  • Market Expertise: Leverage knowledge of real estate trends in your region to drive relevance and credibility in every conversation.
  • Performance & Metrics: Consistently achieve and exceed sales quotas through strong prospecting (50–80 cold calls/day), disciplined pipeline management, and closing skills.

Who You Are

  • Experienced Sales Professional: 3+ years in an inside sales environment in PropTech, SaaS.
  • Industry Insight: Familiar with the challenges real estate professionals face and skilled at positioning solutions that build trust and deliver measurable value.
  • Skilled Communicator: Exceptional written, verbal, and in-person communication skills, able to explain complex solutions with clarity.
  • Goal-Oriented: Proven track record of meeting and exceeding measurable sales goals under pressure.

Personal Qualities

  • Entrepreneurial mindset with a drive to refine strategies and deliver results.
  • High-energy, detail-oriented, and results-driven.
  • Analytical, data-informed, and adaptable to a fast-moving environment.
  • Low-ego team player with a can-do attitude and flexibility to prioritize what matters most.


Why Join Us

At Keyway, you’ll be part of a team reshaping the future of commercial real estate through AI innovation. You’ll have the chance to grow your career in a fast-paced startup environment, backed by world-class investors and industry leaders.

We are proud to be an equal opportunity workplace and believe diversity is core to our mission.

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