Wonderly

You would lead development of an internal software factory while shaping AI-native engineering strategy and balancing production systems with rapid internal-tool experimentation. | The role seeks a seasoned technologist with 10 or more years of experience, strong SDLC and engineering-strategy knowledge, and a record of connecting technical decisions to measurable business results. | About Wonderly Wonderly is a closed-loop, end-to-end system that self-improves on our customers’ revenue. We serve the home service industry ($1.3T), and can consistently double a new customer’s revenue within 90 days. We make all of our AI and software completely free - and 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. Pre-AI SaaS sold tools. AI companies claim they sell outcomes - task done, call answered, lead booked, ticket resolved - but calls or leads aren’t the outcomes that ultimately matter. Revenue is what ultimately matters, and today, none of the AI companies actually promise revenue. Wonderly changes that. Our 70-person team (mostly in PDE) spent over a year building in stealth; our thesis is that - if you actually want to control the end result (revenue) of a business and deploy AI fast/cheaply, you can’t just build the sexy part (agents), you must also build the unsexy parts and own everything end to end: the system of record layer and the application layer. We built from scratch every software a home service business needs - replacing ServiceTitan, Squarespace, Ringcentral, Jobber, Square, Hubspot, and a dozen others applications. And we built every agent necessary - AI marketing, AI receptionist, AI voice, AI sales outreach, AI sales coaching, AI follow-ups, AI 3D design, AI finance, AI quoting, AI collections, and more - all embedded inside our own system with native data access. As a result, we can deploy dozens of production-ready Agents to our customers in under 24 hours 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 actually work in driving the end result - revenue. We are not trying to sell our customers a dream - each of our 10+ core AI Agents help improve our customers’ 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 to build (we are at least 2 years ahead of anyone else in the space). We believe Wonderly has the potential to be a $100B - $1T outcome. The market is massive: home service businesses across North America (a $1.3T 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. Token maxxing 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 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. 2. 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. 3. 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. Compensation & Eligibility Base Salary: $337,500 Equity: $396,000 Bonus: $135,000 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.

Manage inside-sales team staffing, training, coaching, booking processes, and performance against revenue metrics. | Requires significant experience managing inside-sales or appointment-setting teams, coaching staff, and maintaining high performance in an intense, ambiguous environment. | About Wonderly Wonderly is a closed-loop, end-to-end system that self-improves on our customers’ revenue. We serve the home service industry ($1.3T), and can consistently double a new customer’s revenue within 90 days. We make all of our AI and software completely free - and 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. Pre-AI SaaS sold tools. AI companies claim they sell outcomes - task done, call answered, lead booked, ticket resolved - but calls or leads aren’t the outcomes that ultimately matter. Revenue is what ultimately matters, and today, none of the AI companies actually promise revenue. Wonderly changes that. Our 70-person team (mostly in PDE) spent over a year building in stealth; our thesis is that - if you actually want to control the end result (revenue) of a business and deploy AI fast/cheaply, you can’t just build the sexy part (agents), you must also build the unsexy parts and own everything end to end: the system of record layer and the application layer. We built from scratch every software a home service business needs - replacing ServiceTitan, Squarespace, Ringcentral, Jobber, Square, Hubspot, and a dozen others applications. And we built every agent necessary - AI marketing, AI receptionist, AI voice, AI sales outreach, AI sales coaching, AI follow-ups, AI 3D design, AI finance, AI quoting, AI collections, and more - all embedded inside our own system with native data access. As a result, we can deploy dozens of production-ready Agents to our customers in under 24 hours 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 actually work in driving the end result - revenue. We are not trying to sell our customers a dream - each of our 10+ core AI Agents help improve our customers’ 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 to build (we are at least 2 years ahead of anyone else in the space). We believe Wonderly has the potential to be a $100B - $1T outcome. The market is massive: home service businesses across North America (a $1.3T 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. 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 You’ll run the day-to-day of our inside sales team, the front line of how our contractors win jobs. Our team works the leads we generate for our contractor customers, qualifies them fast, and books onsite appointments on the contractor’s behalf. Every lead that goes cold is money our customers lose, and money we lose. Your job is to make sure the team behind those bookings is staffed, trained, and performing every day. That means: Managing the team: schedules, coverage, weekend rotation, attendance Hiring and onboarding new reps, and getting them productive fast Listening to calls and coaching reps on what to fix Tracking the numbers that matter (speed to lead, contact rate, booking rate, show rate) and acting when they slip Handling performance issues directly, including the hard conversations Keeping the process documented so the team doesn’t depend on any one person Flagging what’s broken in the process so we can fix it, not just work around it What Makes This Role Different Most ops manager roles inherit a team that’s already built and a playbook that’s already set. Here, the team is growing and the playbook is still being written. You’ll shape how the team is run, not just keep it running. If you see a better way to do coverage, coaching, or onboarding, you say it Monday and we’re testing it Wednesday. You’ll work directly with me and Victoria, who leads Sales Operations, and you’ll see exactly how your decisions affect our customers’ revenue. Backgrounds That Tend to Work People from these backgrounds tend to thrive: Running an inside sales or appointment-setting team Team lead or sales floor manager who coached reps every day Sales ops or support ops at a fast-growing company where you managed people, not just dashboards Home services or remodeling companies where you ran the team that booked in-home appointments Backgrounds we care less about: Managers who have never sold or booked on the phone themselves Ops or reporting roles with no people to manage Account management or customer success with no team of your own What matters more than the resume: You’ve managed a team and been responsible for its numbers You can listen to a call and know exactly what the rep should have done differently You can have a hard conversation, say what needs to be said, and move on You notice when something’s slipping before it shows up in the numbers You’re organized, and you keep the team organized without being told twice You’re comfortable with ambiguity and fast changes Expectations 60–70 hour weeks Coverage that matches when leads come in, including some weekends Real ownership of the team within your first 2 weeks You own the team’s numbers and we’ll review them together regularly The scope evolves constantly. As the team grows, so does the role. Compensation Total compensation: $130,000–$250,000 (base + equity) Remote (US & Canada) 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.

Manage inside sales staffing and performance, coach representatives, qualify leads, book appointments, track sales metrics, and improve team processes. | Requires experience managing a team and accountability for results, with a preference for inside sales, appointment setting, sales operations, or home services. | About Wonderly Wonderly is a closed-loop, end-to-end system that self-improves on our customers’ revenue. We serve the home service industry ($1.3T), and can consistently double a new customer’s revenue within 90 days. We make all of our AI and software completely free - and 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. Pre-AI SaaS sold tools. AI companies claim they sell outcomes - task done, call answered, lead booked, ticket resolved - but calls or leads aren’t the outcomes that ultimately matter. Revenue is what ultimately matters, and today, none of the AI companies actually promise revenue. Wonderly changes that. Our 70-person team (mostly in PDE) spent over a year building in stealth; our thesis is that - if you actually want to control the end result (revenue) of a business and deploy AI fast/cheaply, you can’t just build the sexy part (agents), you must also build the unsexy parts and own everything end to end: the system of record layer and the application layer. We built from scratch every software a home service business needs - replacing ServiceTitan, Squarespace, Ringcentral, Jobber, Square, Hubspot, and a dozen others applications. And we built every agent necessary - AI marketing, AI receptionist, AI voice, AI sales outreach, AI sales coaching, AI follow-ups, AI 3D design, AI finance, AI quoting, AI collections, and more - all embedded inside our own system with native data access. As a result, we can deploy dozens of production-ready Agents to our customers in under 24 hours 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 actually work in driving the end result - revenue. We are not trying to sell our customers a dream - each of our 10+ core AI Agents help improve our customers’ 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 to build (we are at least 2 years ahead of anyone else in the space). We believe Wonderly has the potential to be a $100B - $1T outcome. The market is massive: home service businesses across North America (a $1.3T 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. 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 You’ll run the day-to-day of our inside sales team, the front line of how our contractors win jobs. Our team works the leads we generate for our contractor customers, qualifies them fast, and books onsite appointments on the contractor’s behalf. Every lead that goes cold is money our customers lose, and money we lose. Your job is to make sure the team behind those bookings is staffed, trained, and performing every day. That means: Managing the team: schedules, coverage, weekend rotation, attendance Hiring and onboarding new reps, and getting them productive fast Listening to calls and coaching reps on what to fix Tracking the numbers that matter (speed to lead, contact rate, booking rate, show rate) and acting when they slip Handling performance issues directly, including the hard conversations Keeping the process documented so the team doesn’t depend on any one person Flagging what’s broken in the process so we can fix it, not just work around it What Makes This Role Different Most ops manager roles inherit a team that’s already built and a playbook that’s already set. Here, the team is growing and the playbook is still being written. You’ll shape how the team is run, not just keep it running. If you see a better way to do coverage, coaching, or onboarding, you say it Monday and we’re testing it Wednesday. You’ll work directly with me and Victoria, who leads Sales Operations, and you’ll see exactly how your decisions affect our customers’ revenue. Backgrounds That Tend to Work People from these backgrounds tend to thrive: Running an inside sales or appointment-setting team Team lead or sales floor manager who coached reps every day Sales ops or support ops at a fast-growing company where you managed people, not just dashboards Home services or remodeling companies where you ran the team that booked in-home appointments Backgrounds we care less about: Managers who have never sold or booked on the phone themselves Ops or reporting roles with no people to manage Account management or customer success with no team of your own What matters more than the resume: You’ve managed a team and been responsible for its numbers You can listen to a call and know exactly what the rep should have done differently You can have a hard conversation, say what needs to be said, and move on You notice when something’s slipping before it shows up in the numbers You’re organized, and you keep the team organized without being told twice You’re comfortable with ambiguity and fast changes Expectations 60–70 hour weeks Coverage that matches when leads come in, including some weekends Real ownership of the team within your first 2 weeks You own the team’s numbers and we’ll review them together regularly The scope evolves constantly. As the team grows, so does the role. Compensation Total compensation: $130,000–$250,000 (base + equity) Remote (US & Canada) 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.