Head of Operations

Wonderly · United States

About Wonderly Wonderly is building the first end-to-end AI business platform for service businesses. The roofers, contractors, med spas, and law firms that make up the majority of the economy are excellent at their craft and poor at running a business — and most of them should be generating 2–5x more revenue than they currently are. Today, solving this means hiring an agency, stitching together a dozen tools, and spending weeks on setup and maintenance. Even then, results are inconsistent and systems break constantly. Wonderly replaces all of it. Ads, website, lead intake, CRM, AI receptionist, follow-up, and project delivery — all in one platform, fully set up in minutes. Because we own every layer, nothing breaks at the seams. The integrations that fail in stitched-together systems simply don't exist inside Wonderly. What makes us different is that AI is native to the platform, not bolted on. Our agents don't just suggest — they actually run ads, build websites, answer calls, qualify leads, book meetings, follow up, and move deals through the pipeline. The goal is not incremental improvement. The goal is to take a business from a non-functional system to a high-performing one almost immediately. With backing from YC and Sam Altman, a $500M+ valuation, and hundreds of thousands of users, we're well positioned to lead. We're building for the majority of businesses in the economy. For them, AI doesn't need to be customizable — it needs to work. Wonderly is intense, fast, and not for everyone. If you want to work with top talent, push yourself harder than you thought possible, and help redefine how AI actually drives revenue for real businesses, you'll thrive here. About the Role We're hiring a Head of Operations to own the internal operating system behind Wonderly's sales, customer success, and AI deployment. There is only one goal for this role: operational excellence. This person will report directly to the Chief Product Officer and work in tandem with the Head of Customer Success. Head of Customer Success owns the team; Head of Operations owns the machine the team runs on. 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 embedded natively inside our business applications. All of our software and AI Agents are free and we charge a % of the revenue we deliver for our customers. Each of our 10+ core AI Agents helps improve our customers’ revenue by 5-20%. That business model has a consequence: we only make money when our customers make money. Which means the team that select customers & make them successful is the core of our company. It's not the sexy part, but being operationally world-class at it is the whole ballgame. This role is our version of that. Wonderly already has PMF and has gone from 0 → 1 (we are happy to share more over a call). 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, and have $20M a year in free cashflow from another product line (Motion) - all that $ gets pumped into Wonderly. The Role Wonderly has gone 0 → 1, we now need 1 → 100 Your job is to build the tooling, systems, and data brain that lets this team run a world-class operation. The customer lifecycle has three phases, and you own the operational machinery for all of them: 1) signing & onboarding a customer → 2) getting the customer to succeed → 3) collecting our revenue share that match our customers’ cashflows. You’ll manage a team of engineers, but you are also expected to vibecode stuff yourself - you must be a decent engineer for this role. What You'll Own

• Tooling for the full accept phase: qualification, sales script adherence, compliance guardrails, contracts, onboarding, deployment of software & AI
• Tooling for the nurture phase: CSM workflows, account health, lead hygiene, account performance visibility, AI copilots for CSMs
• Revenue share operations: revenue calculation, audits, collections
• The data brain: metrics, dashboards, and decision systems across the entire customer lifecycle
• The feedback loops back into the GTM engine
• Process design and capacity planning for this function as it scales

• Technical founders or early employees who built sales/CS operations from scratch
• Technical ops/product leaders at fast-moving marketplaces or vertical startups who built the internal tooling and deployment playbooks themselves
• Quantitative traders who 1) can manage a team of engineers and 2) deeply care about customers.

• Big-company ops roles where success meant managing vendors and approving process docs
• Pure CX leadership roles disconnected from tooling, data, and revenue

• You think clearly from first principles
• You are very resourceful and can become an expert in any topic fast
• You make decisions with incomplete information
• You can give shape and make sense of messy data
• You can write and you're fast with numbers in a business context
• You can work with engineers, and you understand what AI makes newly possible for internal operations
• You have strong taste (which is very important now in the age of AI)
• You have strong opinions, but held loosely

• Real ownership from day one
• Direct accountability for acceptance quality, lead outcomes, and revenue numbers
• Daily visibility into performance
• Deep collaboration with GTM and Product teams.
• Regular in-person work sessions and hacker houses
• A team that values speed, clarity, and ownership over process theater