VP of AI Engineering

About Wonderly

So you’ve been token maxxing and spending $4,000 a month on AI subscriptions. You’re vibe coding to the max, and sleeping barely 5 hours a day. You’ve embraced the polyphasic sleep cycle, so you can wake up in the middle of the night and press ‘Enter’ a couple times (I think that’s called harness engineering these days). And at the end of it, what exactly have you shipped? Have you made anyone’s life better?

If you are focused on technology purely for the sake of technology, then this is not the company for you. If you cannot tie your technology to real, obvious, business results, then this is not the company for you. In a world of slop factories, Wonderly had a radical idea: the purpose of software is to make someone’s life better. And in return, they pay you money.

Crazy, I know.

We are ruthlessly focused on helping small business owners in middle America put food on the table, send their children to college, and live the American Dream. And our customers love us for it.

Wonderly gives Main Street the AI agents, capital, and growth team they need to scale, and charges nothing for any of it. We only get paid when our customers make real money. No surprise fees or gotchas.

Most marketing agencies will charge you a monthly fee on top of the marketing dollars you’d have to spend, and at the end of all of that they can’t even guarantee revenue to you. Wonderly flips all that on its head. Running a small business is hard enough - you shouldn’t have to worry about whether your marketing dollars are cost effective or not on top of that.

We provide the entire system of record, all the annoying backoffice business applications (no more stitching together ServiceTitan, House Call Pro, RingCentral, Squarespace, Docusign, Square, and a dozen others and praying they work well together). 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.

We are the most outcome driven business model in the business 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 - as I said above, we only charge a percent of revenue we deliver for our customers. Each of our 10+ core AI Agents help improve their revenue by 5-20%.

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), and all that money gets pumped into Wonderly.

Who You Are

You are a technologist at heart.

• Your dream vacation is tinkering and building something new. Every couple months you have a new side project. If you do not tinker, you cannot have taste.

• You are someone who keeps up with technology for fun. If I pulled up your youtube feed, it would be littered with tech talks.

• You explore new ways of building purely for the craft.

• You’re able to work startup hours because work is fun. This is the type of career someone would have to pay you to not do.

You’re someone who’s guided engineering orgs before, and you know the importance of a steady hand. That doesn’t mean you’re afraid to make big calls when necessary.

You’re someone who’s thought deeply about engineering strategy. You have strong opinions about the SDLC, and how it changes in the age of AI.

Above all, you’re deeply practical. The world is a messy place. You work with the world how it is, not how it should be.

The Role

Wonderly is building the first enterprise grade dark software factory. We have 50 internal tools (and growing) built this way, and we are rapidly improving our own development methods based on feedback from this development process. We are extremely reluctant to use external vendors; with our internal tools factory, we have replaced ~50 vendors (and more will be replaced soon). We do this for three main reasons:

1. Margin

Software is entering a low-margin era. Most of our customers’ margins are only 30-40%, and as a result, we cannot pay frivolously for vendors that we could easily replicate in-house ourselves.

With AI, the cost of building – and yes, maintaining – these tools in-house has dramatically decreased. Every dollar that we can save is a dollar more we can invest on behalf of our customers.

1. Operational excellence

Stitching together well known tools can quickly bootstrap you to an MVP in terms of business and engineering processes, but as you scale, you’ll find yourself tied down to the lowest common denominator of what each of these tools allow you to do. As a result, you’ll naturally adopt sub-optimal processes, and this will drive down your operational excellence.

Every operational mistake costs our customers real money. We cannot afford for this to happen. As we rapidly scale, we must have maximum flexibility to choose the best process first, and build the tooling to enable that process after the fact.

1. Software revolution

As AI continues to eat software and its production lifecycle, we need to have a semi-production environment to push the boundaries. We need a place where we can experiment without risking customer outages. I say semi-production because everything can work in a toy sandbox environment. Our internal tools on the other hand have real customers, real traffic, and numerous edge cases. It is complex enough to give a real sense of whether this will work without immediately putting our end customers at risk.

Many of the architectural and AI coding decisions we took in production were first started in our internal tools test bed.

Your role is the ultimate culmination of both the tinkering in internal tools and the maturity of actual production. We need both to co-evolve with each other. We’re looking for someone who is bringing technical excellence (real money is on the line here!) first and foremost, but can also peer into the future for what’s coming and position Wonderly for the AI native era.

You are capable of holding two opposing view points simultaneously: AI is going to change everything, and yet, most of what it produces today continues to be slop.

And your answer to the above paradox is ultimately going to be your roadmap in this company.

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.