Head of Sales

Wonderly builds an AI-native operating system for home services businesses, replacing ServiceTitan, House Call Pro, RingCentral, Squarespace, Docusign, Square and others with a single system of record plus dozens of embedded AI agents.

The business model is unusual: the software and agents are free. Wonderly spends its own money on ads, sends contractors the leads, and takes a percentage of the revenue those leads produce. So the company only makes money when its customers close jobs.

Backed by Y Combinator and Sam Altman, with over $50M raised. The team previously built Motion to mid-eight-figure ARR, and pivoted fully into Wonderly in mid-May.

READ THIS BEFORE ANYTHING ELSE

Wonderly open the posting with an unusually blunt filter, and it is worth repeating in full because it disqualifies most applicants:

They are not looking for a tech salesperson. Not SaaS, not B2B, not enterprise.

They want someone who has personally sold remodels, additions, ADUs, kitchens, baths, hardscaping and decks. In a homeowner's living room, at the kitchen table, with the spouse present and three competing quotes on the counter.

If that is not your background, this is not your role.

WHO THEY WANT

You run sales at a home services company doing $10M+, or you were the top closer there and then built the team. You have done hundreds of in-home consultations and you know:

• What to say when someone says they are getting a few quotes
• How to handle the spouse who was not at the first meeting
• When someone is actually buying versus tire-kicking
• How to price without losing the room
• Why one rep closes 40 percent and another closes 15, and what the real difference is
• What financing does to close rate, and how to raise it

Wonderly say that last category is what they want most: the knowledge that is not written down anywhere.

THE ROLE, IN TWO PARTS

First, running the calling team. People who call customers' leads and book onsite appointments. You would run it, hire into it, and own quote follow-up, which is where deals die quietly.

Second, and the bigger one: making Wonderly's customers better at selling. Contractors on the platform close at wildly different rates on identical leads. You would build the playbook, the specifics of what happens in the first ninety seconds, how to handle the walkthrough, when to present the number, how to follow up. Then it becomes standard for every customer on the platform.

Their framing: if you have ever thought you could double a company's close rate if they would just do what you say, this is that job, across hundreds of companies at once.

WHAT THEY TELL YOU BEFORE YOU ACCEPT

This section is in the listing, and it is refreshingly direct rather than buried.

Expect around 60 hours a week, with weeks where it is more. Ambiguous problems, operational fires, decisions on incomplete information and constant context switching.

The playbook changes constantly. They note it is not unusual for it to say do A, B and C on Monday and be rewritten by Thursday. They changed revenue share terms across all leads essentially overnight because the numbers told them to.

They describe it as a sprint, probably a multi-year one, and say plainly that it will be hard.

They also describe the company's current position honestly: since April they have gone from "default dead" to a position where they believe they can win, and they operate like a scrappy five-person startup with the funding and expectations of a Series C company.

WHO YOU WOULD WORK WITH

The hiring manager introduces himself in the listing and sets expectations directly: he gives a lot of feedback, it will not be softened, and it is not personal. He expects to be pushed back on and says he changes his mind when the argument is good.

COMPENSATION AND LOCATION

• $100,000 to $400,000 total compensation, base plus equity
• Equity in Wonderly
• Remote across North America and Canada, with regular in-person time at hacker houses

HOW TO APPLY

The entire application is one question: tell them the one thing you do on an onsite that you think most people in your trade do not do.

That is genuinely the whole thing. No CV upload requirement, no screening questionnaire.

A HONEST NOTE FOR THIS BOARD

This is a demanding role with a stated 60-hour week and regular in-person requirements, so it sits at the intense end of what gets listed here. It is included because the pay band is wide and transparent, the equity is real, and the background it wants is genuinely uncommon in tech listings. If you have sold home improvement work in people's homes and want to apply that at software scale, there are very few postings like this one.