Head of Sales

About Wonderly

Wonderly is an end-to-end verticalized AI-native OS for home services businesses. We own the entire system of record, all business applications (we replace ServiceTitan, House Call Pro, RingCentral, Squarespace, Docusign, Square, and a dozen other applications), and dozens of AI agents ourselves embedded natively inside our business applications, with native data read & write access to our system of record. As a result, we can deploy dozens of production-ready AI Agents to our customers in under 30 minutes with no FDEs, no integrations, and no data cleaning work.

Wonderly has the most result-driven business model, because we’ve proven our system and AI Agents work. We are not trying to sell our customers a dream - we deliver real revenue and profit to our customers. All of our software and AI Agents are free - we charge a % of revenue we deliver for our customers. Each of our 10+ core AI Agents help improve their revenue by 5-20%. This is the ultimate outcome-based pricing, only possible when you own the entire end-to-end system and all the agents yourself.

Wonderly already has PMF and has gone from 0 → 1 (we are happy to share more over a call), with very clear moat and deep industry knowledge that took a team of 70 hardcore A-players 18 months of stealth to build. We believe Wonderly has the potential to be a $100B - $1T outcome. The market is massive: home service businesses across North America (a $2T market). We’ve raised over $50M from top-tier investors, have $20M a year in free cashflow from another product line (Motion) - all that $ gets pumped into Wonderly.

Read this first

We are not looking for a tech sales person. Not SaaS, not B2B, not enterprise.

We're looking for someone who has personally sold remodels, additions, ADUs, kitchens, baths, hardscaping, decks. In a homeowner's living room, across their kitchen table, with their spouse sitting there and three competing quotes on the counter.

If that's you, keep reading. If it isn't, this isn't the role.

Who you are

You run sales at a home services company doing $10M+. Or you were the top closer there and then built the team.

You've done hundreds of in-home consultations. You know:

• What to say when they say "we're getting a few quotes"

• How to handle the spouse who wasn't at the first meeting

• When someone's actually buying versus tire-kicking

• How to price without losing the room

• Why one of your guys closes 40% and another closes 15%, and what the actual difference is

• What financing does to close rate and how to bring it up

That last category is what we want most. The stuff that isn't written down anywhere.

Where we are right now

We're YC-backed and Sam Altman-backed. We built Motion and got it to mid-eight-figure ARR by end of last year. In mid-May we pivoted fully into Wonderly.

We generate leads for home services contractors. The software is free. We spend our own money on ads, send them the leads, and take a percentage of the revenue those leads produce.

So we only make money when our customers close jobs. Their close rate is our business.

Practically, we're operating like a scrappy 5-person startup with the funding and expectations of a Series C company. That gap is the job.

Since April we've gone from default dead, meaning we didn't have a winning formula, to "we can actually go win this thing." That's the honest version of where we sit.

The role

Two things.

1. Our calling team.

We have people who call our customers' leads and book their onsite appointments. You'd run it, hire into it, make it good. You'd also own quote follow-up, which is where deals die quietly.

2. Making our customers better at selling. The bigger one.

We have contractors closing at wildly different rates on identical leads. Some of that is territory. Most of it is that some are good in a living room and some aren't, and nobody has ever told them what good looks like.

You'd build the playbook. The specifics. What you do in the first ninety seconds, how you handle the walkthrough, when you present the number, how you follow up. Then it becomes non-negotiable for every customer on the platform.

If you've ever thought "I could double this company's close rate if they'd just do what I say," that's the job, except across hundreds of companies at once.

Why this is interesting

You've spent your career making one company good at selling. This is the same skill applied to hundreds of them, with real money and software behind it.

And you're building it from scratch. Nothing to inherit or defend. What you build is what we run.

Who you'd work with

Me, mostly. I'm Bishop, I run Customer Operations here.

To be straight about what that means: I give a lot of feedback and it's direct. It won't be softened and it isn't personal. If I'm spending time on your feedback it's because I think you can be much better.

I'd expect you to push back on me. I change my mind when the argument is good, and I've done it several times this month.

What I want out of this is someone who knows something I don't and can teach it to hundreds of companies at once. I've built the Call 1 playbook, the qualification criteria, the escalation process. I have no idea what happens in a living room after we book the appointment, and that's the part that decides whether any of this works.

You'd be the person who knows that.

What you should know before accepting

Expect ~60 hours a week, with weeks where it's more. Ambiguous problems, operational fires, decisions on incomplete information, constant context switching.

The playbook changes constantly. It's not unusual for it to say do A, B, C on Monday and get rewritten by Thursday. We changed our rev share terms across all leads essentially overnight because the numbers told us to. That's normal here.

It's a sprint, probably a multi-year one. It will be hard. We want to win.

Compensation

• $100,000–$400,000 TC (base + equity)

• Equity in Wonderly

• Remote (North America & Canada), with regular in-person at hacker houses

How to apply

Tell me the one thing you do on an onsite that you think most people in your trade don't do.

That's the whole application.

Wonderly is committed to creating a diverse and inclusive workplace where everyone is treated with respect and given equal opportunities. We do not discriminate based on gender identity, race, ancestry, disability, religion, sexual orientation, pregnancy status, veteran status, or any other characteristic protected by law. We welcome and encourage all qualified candidates to apply for our job openings.