Strong fit for home services sales professionals who have managed or executed contractor sales and can translate real-world sales dynamics into scalable systems.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Wonderly via Ashby
ABOUT WONDERLY
Wonderly gives Main Street businesses the AI agents, capital, and growth team they need to scale, and charges nothing for any of it. We only get paid one way: when they make real money. 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.
ABOUT THE HIRING MANAGER
Hey, I'm Bishop, Head of Operations at Wonderly.
I'm extreme, direct, and care a lot about getting to the truth. I started in FP&A, realized I wanted to be in the middle of building something instead of analyzing it from the outside, and ended up here.
I work best with people who are high-agency, low-ego, and can handle intensity without needing a perfect playbook.
THE ROLE
We’re hiring someone who understands contractor sales from the inside.
Not a generic operator. Not someone who has only read about sales. Someone who has actually seen how homeowners buy, how estimates get built, how onsites go sideways, how quotes get delayed, and why contractors lose jobs they should have won.
You’ll work across customer operations, homeowner sales, product, and contractor performance.
Your job is to help us figure out:
- Are we accepting the right contractors?
- Are we qualifying homeowners correctly?
- Are contractors walking into onsites with enough context?
- Why are quotes going out late or not at all?
- Why do some contractors close well and others close almost nothing?
- What should our CSMs inspect every week?
- What product/tooling should we build to help contractors quote faster and close more?
WHAT MAKES THIS ROLE DIFFERENT
Most sales roles ask you to sell.
This role asks you to take what you know about selling and turn it into a system.
We are not hiring you to be one good salesperson. We are hiring you to help hundreds of contractors close more of the leads we send them.
You’ll listen to homeowner calls, review contractor sales calls, inspect deals, shadow onsites, find where revenue is leaking, and turn that into scripts, workflows, playbooks, coaching, and product feedback.
If you want a clean sales role with a quota and a territory, this is not it.
If you want to help build the sales performance layer for thousands of service businesses, this is it.
BACKGROUNDS THAT TEND TO WORK
People from these backgrounds tend to thrive:
- Remodeling sales manager
- Remodeling sales rep
- Kitchen / bath / design-build sales
- In-home sales for high-ticket home improvement
- Roofing sales
- HVAC sales
- Plumbing sales
- Windows / doors / exterior sales
- Anyone who has run onsites, quoted jobs, handled objections, followed up, and closed homeowners
Backgrounds we care less about:
- Generic SaaS sales with no home services exposure
- Pure account management with no selling
- Big-company roles where you were far away from the actual customer
- Anything where you have never had to sit across from a homeowner and close a real job
What matters more than the resume:
- You understand homeowner psychology
- You know what a good onsite looks like
- You can tell when a contractor is legit vs full of it
- You can explain why a deal was won or lost
- You are direct, practical, and allergic to theory-only advice
- You can turn messy real-world sales behavior into a script, checklist, or process
- You are comfortable with ambiguity and fast changes
EXPECTATIONS
- 60–70 hour weeks during this growth phase
- Real ownership of a real problem within your first 2 weeks
- Performance is transparent — you'll see your numbers daily and so will everyone else
- The scope evolves constantly. If you want a stable job description, this isn't it.
- Regular travel to shadow contractors, homeowner appointments, and customer sales motions in the field
COMPENSATION
Base: $50,000-$90,000
OTE: $150,000-$200,000+
This is a performance-comp role. A meaningful portion of compensation will be tied to the revenue / closed work generated from the customers or book of business you help improve.
Equity in Wonderly may be included depending on experience and role fit.
Remote, with regular in-person work / field visits.
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.
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.
Source: Wonderly careers (Ashby)