Head of Operations

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.

Our 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.

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

You won't have a fixed lane. Instead you'll find the highest-leverage operational problem, solve it, build to scale it, and move to the next one. Some weeks that means shipping an AI call-review system so every sales call gets scored against the script. Some weeks it means sitting with CSMs to figure out why account reviews take 40 minutes instead of 10. Some weeks it means designing the data feed that tells the GTM/BDR team which leads actually turn into revenue. You should be comfortable getting deep into the work, inspecting the data yourself, listening to sales calls, writing a product spec, working directly with engineers. You're a member of the leadership team but you are not above getting your hands dirty and always putting the customer first.

You do not need to be the world's best specialist in every one of these areas. But you do need to be dangerous in all of them. You should know enough to diagnose problems, make decisions, manage specialists (including engineers), and course correct when we’re not meeting our standards

Backgrounds That Tend to Work

People from these backgrounds tend to thrive:

• 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.

Backgrounds we care less about:

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

What matters more than the resume:

• 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

Expectations

This is a high-output and company-defining role.

You should expect:

• 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

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

About your manager

Hi, I'm Luis, Wonderly's CPO, and you'd be working directly with me. A confession: I've been building the first version of this role's tooling myself (e.g., the audit systems, the CSM dashboards) and I've taken it as far as one person with another full-time job can. The foundation is real, the data is there, and the leverage is enormous. What's missing is an owner who wakes up every day thinking about how to make 50 CSMs perform like 500 and who can help us take this company from 1 → 100

What I promise you: you'll never wait a week for a decision, you'll never be handed an ask without context, and you'll never have to convince me that internal tools and operations matter, I think they're the heart of the company. What I ask in return: bring me evidence, not vibes; go sit with the CSMs before you redesign their workflow; and push back on me hard when I'm wrong, because I will absolutely be wrong sometimes. If that sounds like a working relationship you want, I'd love to talk.

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.