VP of AI Engineering

Wonderly

About The Position

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 when our customers make real money. We’re here helping real small businesses make a life, pay for their children’s college tuition, and live the American dream. No surprise fees or gotchas. 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. 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 - 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. "AGI" 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.

Requirements

Technologist at heart.
Enjoys tinkering and building new things; has new side projects every couple of months.
Keeps up with technology for fun.
Explores new ways of building purely for the craft.
Able to work startup hours because work is fun.
Experience guiding engineering organizations.
Experience with engineering strategy.
Strong opinions about the SDLC and how it changes in the age of AI.
Deeply practical.
Experience with enterprise-grade dark software factories.
Experience replacing ~50 vendors with internal tools.
Understanding of the decreasing cost of building and maintaining tools in-house with AI.
Understanding of how stitching together well-known tools can lead to sub-optimal processes and operational excellence issues.
Understanding of the need for maximum flexibility to choose the best process first and build tooling to enable it.
Understanding of the need for a semi-production environment to push the boundaries of AI and software production lifecycle without risking customer outages.
Experience with architectural and AI coding decisions that were first started in an internal tools test bed.
Ability to hold two opposing viewpoints simultaneously: AI is going to change everything, and yet, most of what it produces today continues to be slop.

Nice To Haves

Dream vacation is tinkering and building something new.
YouTube feed littered with tech talks.
Career someone would have to pay you to not do.

Responsibilities

Bring technical excellence first and foremost.
Peer into the future for what’s coming and position Wonderly for the AI native era.
Hold two opposing viewpoints simultaneously: AI is going to change everything, and yet, most of what it produces today continues to be slop.
Develop a roadmap for the company based on the paradox of AI's potential and current limitations.
Guide engineering organizations with a steady hand, but be unafraid to make big calls when necessary.
Develop and refine engineering strategy, with strong opinions about the SDLC and its evolution in the age of AI.
Work with the world as it is, not how it should be, demonstrating deep practicality.
Build and maintain internal tools, replacing external vendors.
Improve development methods based on feedback from the internal tools development process.
Experiment with AI and software production lifecycle in a semi-production environment without risking customer outages.
Co-evolve internal tools and actual production systems.

Benefits

AI agents
Capital
Growth team
All software and AI Agents are free
Percent of revenue delivered for customers
Potential to be a $100B - $1T outcome
Over $50M raised from top-tier investors
$20M a year in free cashflow from another product line (Motion)
Commitment to creating a diverse and inclusive workplace
Equal opportunities
No discrimination based on gender identity, race, ancestry, disability, religion, sexual orientation, pregnancy status, veteran status, or any other characteristic protected by law.