Head of Operations

Wonderly is an end-to-end verticalized AI-native OS for home services businesses. We own the entire system of record, all business applications (replacing ServiceTitan, House Call Pro, RingCentral, Squarespace, Docusign, Square, and a dozen others), and dozens of AI agents embedded natively inside our applications with full data read & write access. This allows us to deploy production-ready AI Agents to customers in under 30 minutes with no FDEs, integrations, or data cleaning. Our business model is outcome-based: all software and AI Agents are free, and we charge a percentage of the revenue we deliver. Each of our 10+ core AI Agents improves customer revenue by 5-20%. Wonderly has achieved product-market fit, scaling from 0 to 1 with a clear moat, built by a team of 70 A-players over 18 months. We’ve raised over $50M from top-tier investors and generate $20M/year in free cash flow from another product line (Motion).

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. The sole goal of this role is operational excellence. You will report directly to the Chief Product Officer and collaborate closely with the Head of Customer Success. While the Head of Customer Success owns the team, you will own the machine the team runs on. Our business model ensures we only make money when our customers succeed, making operational excellence critical to our success.

Wonderly has gone from 0 to 1; now we need to scale from 1 to 100. Your job is to build the tooling, systems, and data infrastructure that enables this team to run a world-class operation. You will own the operational machinery across the entire customer lifecycle:

• Signing & onboarding a customer
• Ensuring customer success
• Collecting our revenue share aligned with customer cash flows

You’ll manage a team of engineers but are also expected to contribute hands-on—this role requires you to be a capable engineer. You won’t have a fixed lane; instead, you’ll identify the highest-leverage operational problems, solve them, build scalable solutions, and move to the next challenge. Some weeks, this might mean shipping an AI call-review system to score sales calls against scripts. Other weeks, it could involve diagnosing why account reviews take 40 minutes instead of 10 or designing data feeds to help the GTM team prioritize high-revenue leads.

You should be comfortable diving deep into the work: analyzing data, reviewing sales calls, writing product specs, and collaborating directly with engineers. While you don’t need to be the world’s best specialist in every area, you must be dangerous across all of them—able to diagnose problems, make decisions, manage specialists, and course-correct when standards aren’t met.

Responsibilities

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

Qualifications

We care less about your resume and more about these traits:

• You think clearly from first principles
• You are resourceful and can quickly become an expert in any topic
• You make decisions with incomplete information
• You can structure and make sense of messy data
• You can write well and are fast with numbers in a business context
• You can work effectively with engineers and understand how AI can transform internal operations
• You have strong taste (critical in the age of AI)
• You hold strong opinions loosely

Backgrounds that tend to work well include:

• 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 internal tooling and deployment playbooks
• Quantitative traders who can manage engineers and deeply care about customers

Expectations

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

This is not a role for someone who wants to "run operations" from a distance. You’ll be expected to build the system, run it, inspect the numbers, and adapt when reality demands it.

About Your Manager

You’d report directly to Luis, Wonderly’s CPO. He has built the initial versions of this role’s tooling (e.g., audit systems, CSM dashboards) but recognizes the need for a dedicated owner to scale it. The foundation is in place, the data exists, and the leverage is enormous. What’s missing is someone who wakes up every day focused on making 50 CSMs perform like 500 and helping the company scale from 1 to 100.

Luis promises: no slow decision-making, no context-free asks, and full recognition of the importance of internal tools and operations. In return, he asks for evidence over vibes, hands-on engagement with CSMs before redesigning workflows, and direct pushback when he’s wrong.

Pay

Compensation range: $400K - $650K