Head of Sales

Wonderly

1d•$100,000 - $400,000•Remote

About The Position

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. 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. 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 involves two main areas: 1. Our calling team, where you'd run it, hire into it, and make it good, including owning quote follow-up. 2. Making our customers better at selling by building a playbook for in-home sales, covering everything from initial interactions to presenting numbers and follow-up, to be applied across hundreds of companies.

Requirements

Personally sold remodels, additions, ADUs, kitchens, baths, hardscaping, decks in a homeowner's living room.
Experience running sales at a home services company doing $10M+ or being a top closer who built the team.
Experience with hundreds of in-home consultations.
Understanding of how to handle objections like "we're getting a few quotes."
Ability to handle spouses who weren't at the first meeting.
Skill in discerning genuine buyers from tire-kickers.
Proficiency in pricing without losing the sale.
Understanding the reasons behind varying close rates among sales representatives.
Knowledge of how financing impacts close rates and how to discuss it.
Ability to push back and argue effectively on feedback.
Ability to teach sales strategies to hundreds of companies.

Nice To Haves

Experience building a playbook for in-home sales.
Experience with outcome-based pricing models.
Experience in a scrappy startup environment with high growth expectations.

Responsibilities

Run and build the calling team, including hiring and improving processes.
Own quote follow-up to ensure deals are closed.
Build a playbook for improving customer sales performance.
Develop specific sales strategies for in-home consultations, including initial interactions, walkthroughs, presenting numbers, and follow-up.
Apply sales expertise across hundreds of customer companies to improve their close rates.