$90K–$105K OTE • Uncapped commission • Full benefits + equity • Chicago field role

The opportunity

You'll spend your days inside beautiful Chicago homes, having genuine conversations with homeowners about a service that genuinely makes their lives better. No cold calls. No fighting for attention. Every prospect you meet is a warm, pre-qualified lead who's eager to hear how Honey Homes works.

Your job: show them what stress-free homeownership actually looks like, and help them say yes.

About Honey Homes

Honey Homes is a membership service for homeowners that takes care of the everyday to-do's, ongoing maintenance, and unexpected repairs that come with owning a home. Members are paired with a dedicated handyperson and use a simple app to coordinate. We're on a mission to replace the hassle of homeownership with the joy of comfortable living.

We're backed by Khosla Ventures, Era Ventures, Pear.vc, and the co-founders of DoorDash, Lyft, and Opendoor. Our team has built and scaled companies like Airbnb, Google, Opendoor, Yelp, Zillow, and Uber.

What you'll do

Every homeowner considering Honey Homes starts with a free in-home walk-thru, the most important step in our sales process. You'll run those visits.

In about 45 minutes, you'll walk the home with the prospective member, educate them on how the membership works, answer their questions, and capture their first 10+ tasks directly in our app. Your goal is to help them book their first handyman visit before you leave, and set that visit up to be a great one.

You'll do 5–6 walk-thru's a day, Monday through Friday, across the Chicago area. The playbook is proven and we've spent three years refining it, so you're stepping into something that works. Your job is to execute it brilliantly and make it your own.

Why this role is different

Warm leads only. Homeowners book the walk-thru themselves. You're not chasing anyone.
You're in their home. This is high-trust, in-person selling. If you've ever been frustrated by Zoom or phone sales, this will feel like a breath of fresh air.
Uncapped earnings. Top performers earn well above the OTE range and have a clear path into other roles at the company.
You sell something people actually want. Homeownership is stressful. We fix that. Every member you sign up genuinely benefits.
Real career upside. This isn't a dead-end SDR seat. Top performers move into senior roles as we grow.
Flexible engagement options. We're open to contract-to-hire and part-time arrangements for the right candidate.
Get in early in a growing market. Chicago is one of our newer markets, which means more opportunity to shape how we show up here and grow with it.

What we're looking for

You can sell. You have 4+ years of sales experience in high-performance environments, likely at a startup or in home services. You know how to read a room, handle objections in real time, and ask for the close.

You're a strong communicator. Excellent verbal and written skills. You're comfortable and confident in someone else's living room.

You build relationships fast. You're energized by people. You read them well, you're empathetic, and you make them feel heard.

You know your way around a home. You don't need to be a handyman, but you should understand the basics of plumbing, electrical, carpentry, and home systems. Maybe you're a homeowner yourself, or you grew up tinkering. Either way, you can talk credibly about what a membership covers.

You know Chicago. You're comfortable driving across the area, you know the neighborhoods, and traffic doesn't intimidate you.

You have a growth mindset. You'll follow a proven playbook, and you'll also push to make it better. Ambiguity doesn't faze you. Rapid change at a startup excites you.

You're relentless. Sales has up days and down days. You bounce back fast and keep moving.

You document everything. You sweat the details, track your progress, and keep your teammates in the loop.

You act like an owner. You do right by our members and your teammates, especially when it's hard.

What success looks like in 90 days

Walk-thru conversion rate is up. You prepare thoroughly for every visit and deliver consistently strong walk-thru's. A meaningfully higher percentage of prospective members sign up.
Your team is set up to win on every lead. Marketing and inside sales are your partners, and this role also carries a self-generated component: roughly 70% of leads are warm, and 30% are self-sourced.
Every first handyman visit is a great one. Your detailed notes, task lists, and internal handoffs make sure new members start their membership thrilled.

Compensation and benefits

On-target earnings: $90,000–$105,000 ($70 000 Base). Uncapped, with real upside for top performers.
Equity. Every employee is an owner at Honey Homes.
100% covered medical, dental, and vision for employees.
401(k), FSA, paid parental leave, and a flexible time-off policy.

A few things to know

This is a field role based in the Chicago area. You'll need a reliable vehicle, a valid driver's license, and a willingness to drive throughout the region.

If this sounds like your kind of role, we'd love to meet you.

#ZR

We are an equal opportunity employer and consider all qualified applicants equally without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability status. Women and under-represented minorities are encouraged to apply.

Walk-Thru Sales Representative