ZipRecruiter

Log In

1

Proptech Sales Jobs in Chicago, IL (NOW HIRING)

RET(Search)

Head of Sales (Chicago)

Chicago, IL · On-site

$180K/yr

Prior experience at Director level or higher in a sales leadership role, within a real estate company (brokerage, proptech, real estate marketplace, investment platform, title/mortgage, etc.). * 7+ ...

Job Mobz

SaaS Sales Recruiter (Remote)

Chicago, IL · On-site +1

Experience recruiting within SaaS, PropTech, FinTech, or other consultative sales environments. * Experience hiring candidates who manage relationship-driven or solution-based sales cycles. * Agency ...

Recruiter.com

SaaS Sales Recruiter (Remote)

Chicago, IL · Remote

Experience recruiting within SaaS, PropTech, FinTech, or other consultative sales environments. * Experience hiring candidates who manage relationship-driven or solution-based sales cycles. * Agency ...

SmartRent

National Sales Director (East)

Chicago, IL · Remote

$230K - $270K/yr

Recognized by Deloitte, HousingWire and the PropTech Breakthrough Awards, SmartRent is shaping the ... As a National Sales Director at SmartRent, you will be responsible for driving revenue growth ...

Kastle Systems

Account Director

Chicago, IL · Remote

Kastle Systems is immediately hiring sales professionals who: * Have a relentless passion to penetrate new markets with the best proptech solutions in commercial and residential real estate markets

The Scion Group

Product Manager

Chicago, IL · On-site

Gather and synthesize feedback from users across revenue management, sales, marketing, operations ... Experience in Revenue Management System (RMS), PropTech, or operational platforms * Bachelor ...

The Scion Group

Product Manager

Chicago, IL · On-site

Gather and synthesize feedback from users across revenue management, sales, marketing, operations ... Experience in Revenue Management System (RMS), PropTech, or operational platforms * Bachelor ...

The Scion Group

Product Manager

Chicago, IL · On-site

Gather and synthesize feedback from users across revenue management, sales, marketing, operations ... Experience in Revenue Management System (RMS), PropTech, or operational platforms * Bachelor ...

All JobsProptech Sales JobsProptech Sales Jobs in Chicago, IL

Proptech Sales information

See Chicago, IL salary details

$23.2K

$84.1K

$159.2K

How much do proptech sales jobs pay per year?

As of Sep 4, 2026, the average yearly pay for proptech sales in Chicago, IL is $84,077.00, according to ZipRecruiter salary data. Most workers in this role earn between $54,600.00 and $99,400.00 per year, depending on experience, location, and employer.

What is a proptech sales?

A Proptech Sales job involves selling technology solutions designed for the real estate industry. This can include software platforms, data analytics tools, property management solutions, or digital marketplaces. Sales professionals in this field identify potential clients, demonstrate product value, and negotiate deals to drive business growth. They often work with real estate firms, property managers, and investors to improve efficiency and profitability using technology. Strong communication, relationship-building, and industry knowledge are essential for success in this role.

What are the key skills and qualifications needed to thrive in proptech sales?

To thrive as a Proptech Sales professional, you need strong consultative sales abilities, knowledge of property technology solutions, and experience in real estate or technology sales. Familiarity with CRM platforms like Salesforce, property management systems, and digital marketing tools is often required, and industry certifications such as Certified Commercial Investment Member (CCIM) can be advantageous. Excellent communication, negotiation, and relationship-building skills help you navigate client needs and foster long-term partnerships. These competencies drive revenue growth and ensure you can effectively connect innovative proptech offerings with the evolving demands of real estate clients.

What are typical challenges faced in a proptech sales role, and how can I overcome them?

Proptech Sales professionals often encounter challenges such as educating traditional real estate stakeholders about new technologies, navigating long sales cycles, and differentiating their solutions in a competitive marketplace. Success in this role requires persistence, ongoing product knowledge, and the ability to tailor your sales approach to address each client's unique pain points. Working closely with product, marketing, and customer success teams can help you stay informed and provide comprehensive solutions to potential clients. Embracing a consultative and solution-oriented mindset will help you build trust and close deals effectively in this evolving industry.

What are the best Proptech sales companies to work for?

Proptech sales professionals often find opportunities at leading companies specializing in real estate technology, property management platforms, and smart building solutions. Top firms in this sector typically offer competitive compensation, training programs, and a focus on innovative solutions, making them attractive employers for sales roles. Researching company reputation, growth potential, and product offerings can help identify the best fit for a Proptech sales career.

What are the most commonly searched types of Proptech Sales jobs in Chicago, IL?

The most popular types of Proptech Sales jobs in Chicago, IL are:

What are popular job titles related to Proptech Sales jobs in Chicago, IL?

For Proptech Sales jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Proptech Sales jobs in Chicago, IL look for?

The top searched job categories for Proptech Sales jobs in Chicago, IL are:

Proptech Sales jobs near you
Infographic showing various Proptech Sales job openings in Chicago, IL as of August 2026, with employment types broken down into 94% Full Time, and 6% Contract. Highlights an 83% In-person, and 17% Remote job distribution, with an average salary of $84,077 per year, or $40.4 per hour.

Head of Sales (Chicago)

RET(Search)

Chicago, IL • On-site

$180K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 6 days ago

Key responsibilities

  • Lead, coach, and develop a team of sales professionals, setting standards for pipeline management, forecasting, and activity.

  • Personally source, build, and close enterprise-level partnerships and strategic accounts.

  • Build and run a repeatable sales playbook, establish CRM standards, and report on revenue targets and sales performance.

Job description

About BiggerPockets

BiggerPockets is the leading platform for real estate investors, helping over 3 million members build wealth through education, tools, and community.

About the Role

BiggerPockets is hiring a Head of Sales to lead and grow its sales team, spanning advertising/sponsorship sales and marketplace lead sales to real estate professionals. This is a player-coach role; you'll carry your own book of business while building the systems, process, and coaching that help the whole team perform at a higher level.

The ideal candidate has already sold and led sales teams specifically within real estate. The buying cycle, the players involved, and the trust-building required in real estate don't transfer cleanly from other industries.

Location:

At this time, only candidates local to the Salt Lake City or Chicago Metro markets are being considered.

What You’ll Do:
  • Lead, coach, and develop a team of sales professionals, setting clear standards for pipeline management, forecasting, and activity.
  • Personally source, build, and close enterprise-level partnerships and strategic accounts.
  • Build and run a repeatable sales playbook: outreach templates, qualification criteria, and stage definitions.
  • Establish CRM (HubSpot) standards for data hygiene, stage discipline, and reporting.
  • Own revenue targets for the sales org and report on attainment to leadership.
  • Partner cross-functionally with Marketing, Content, Product, and Finance on packaging, quota-setting, and forecasting accuracy.
  • Build a multi-year point of view on how the sales organization should scale.
What We’re Looking For:
  • Required: Prior experience at Director level or higher in a sales leadership role, within a real estate company (brokerage, proptech, real estate marketplace, investment platform, title/mortgage, etc.).
  • 7+ years in sales, with at least 2–3 years leading and coaching a sales team.
  • Proven “player-coach” track record of carrying and hitting a personal quota while managing others.
  • Demonstrated success building enterprise relationships from scratch.
  • Experience selling advertising, sponsorships, or event-based revenue is a strong plus.
  • Strong HubSpot fluency and comfort building reporting/forecasting structure within it.
  • Excellent coaching skills and ability to read pipeline data and diagnose why a reporting rep is missing quota.
  • Comfortable operating in a fast-moving, still-scaling environment.
  • Base Salary: Up to $180,000 (dependent on experience).
  • Target Commission: Up to $100,000, dependent on experience.
  • Health & Wellness: Comprehensive dental, vision, and health care coverage.
  • Retirement: 401(k) plan.
  • Time Off: Generous PTO package.
Note to Candidates:

Our client is an equal opportunity employer committed to building a diverse and inclusive team. AI tools may be used as part of the initial screening process to assist our recruitment team.

#J-18808-Ljbffr

Apply