VP of Product

The role

You run product at Olly Olly. Product, design, engineering, and production report to you: roughly 70 people across the US, Latin America, and the Philippines. You decide what we build and in what order, you build the team that builds it, and you sit on the leadership team that sets the direction of the company. The founder brings a lot of ideas and pushes hard. You are expected to push back harder when the evidence says so. The one thing not up for debate is the mission: small business owners make more money and spend less of their week running the business. Everything we build gets measured against that.

About Olly Olly

Olly Olly is a bootstrapped, profitable local marketing and SEO platform. Eight years in, 19,600 small business owners served, about $25M in ARR, 350 people, no outside money, no board. Our customers are small shops going up against big box competitors with bigger budgets and whole departments. We even the fight: their marketing and their front office run on their own, so the phone rings, the jobs get booked, and the owner gets back to the work they started the business to do.

Meet Hank

Hank runs a plumbing shop with four guys, reads everything on his phone in the truck between jobs, and pays us so he does not have to do marketing himself. He never gives feedback. He just stops using things. Every screen we ship has to answer yes to three questions:

• Will Hank use it?

• Does it pay him?

• Would he miss it if we turned it off?

If a feature fails one, it is the wrong model, not a polish problem. You hold the whole product to this test, and the people who build it too.

What you own

The product, from getting found to getting paid. SEO is the foundation and you own that strategy outright: how we rank a local business, what we deliver by hand, what we automate, and what it costs. You also own everything after the phone rings: lead capture, follow-up, booking, reviews, and the AI that runs Hank's front office. Websites, Google Business Profile, Local Services Ads, PPC, and reporting are not separate products. You make them one system Hank can rely on, and you keep us ahead of changes in Google and AI search.

The teams. Hiring, training, and deciding where people and money go across product, design, engineering, QA, and production. You set roles and accountability, grow managers, and decide which of the 70 seats stay, change, or get added, with a case for each. You replace process that does not fit Olly Olly with a process that does.

The plan and the build. Scope, sequence, dates, and the honest status of all of it. Intake to retro: specs, acceptance criteria, design handoff, build, QA, launch gates, and retros that change behavior. Nothing ships to a client with errors QA should have caught. You measure what shipped against what it was supposed to do, with the data we have today and the data you decide we need.

AI at the foundation. Our engineers use Claude Code every day. AI is how the work gets done here, not a tool on the side, and you are as fluent in prompts, agents, and AI coding workflows as in specs and roadmaps. You set that standard and prove it in output. In the product, you find where AI removes work for Hank and for our services team, you ship it, and you keep honesty rails on anything AI-generated a client will see.

Who you are

• A player/coach. You get your hands dirty when the work calls for it, and you build leaders who carry the work the rest of the time. Nothing is beneath you, and nobody on your team knows the work better than you do. You can write the spec, read the merge request, and run the retro, and your people know it.

• An operator. You do not wait for direction. You set the deadlines and you hit them.

• Someone who pushes back. When the CEO is wrong, you say so with evidence and keep saying so until one of you changes their mind. When a project needs to go the opposite direction, you make that call and own it.

• Never satisfied. The current product, process, and numbers are a starting point. You lead change; you do not wait for it.

• From this world. You have built for small businesses, ideally home services (Housecall Pro, ServiceTitan, Jobber, Thumbtack, Angi, Yelp, or a local marketing platform). You know how a contractor thinks about a lead, a phone call, a review, and a slow month.

• An underdog person. Giving a small shop an edge over the big box player is what gets you up in the morning. If it is not, this will feel like a grind.

Straight talk

• You are in charge of product and you have a seat in the company direction. The founder will be in the room for the big calls. Expect to argue, and expect her to change course when you bring the evidence. The mission does not move. Everything else is yours to shape.

• Our data instrumentation is early. You will make good calls with imperfect data and decide what we invest in to fix that. We will be clear about what we will and will not fund.

• Engineering output is the number one thing we need to move. The team is capable and the tooling is modern; the delivery system is not. You will be judged on shipped output.

• You will inherit a team and reshape it, without the safety of a playbook you wrote somewhere else.

• We are bootstrapped and well past the startup phase. We spend carefully and expect results before we add headcount.

Must-haves

• 8+ years in product, including several years owning both the roadmap and the ship date across product and engineering

• Built product for small businesses, with a strong preference for home services or local marketing, and shipped something that put money in an owner's pocket, with the number to show for it

• Deep local SEO knowledge: you can defend a ranking strategy to a skeptical founder and a skeptical SEO specialist

• Built teams of this size: hired, trained, grew managers, decided where people and money go, and led through a reorg or a team you did not pick

• Run multi-team project plans with real dates and kept them honest when things slipped

• Hands-on fluency with AI: prompting, Claude or similar, and AI coding workflows inside a real engineering org

• Based in or relocating to Austin, TX, with regular in-office time

Nice-to-haves

• A services-to-software transition

• Paid search or Local Services Ads

• Stood up product analytics from near zero

• Led teams across the US, Latin America, and the Philippines

Not a fit if you

• Want a purely strategic role

• Think this is an SEO or website job

• Build for the power user and assume Hank will figure it out

• Need to be the only voice in the room on product direction, or go quiet when you disagree

• Need mature data and process to be effective

• Have only built for enterprise, mid-market, or marketers

How we will interview you

We will not ask how you think about product. We will ask what you would do. Expect one of our real products (Local Services Ads, for example) and a request to walk us through exactly what you would change, in what order, with which people, and how you would know it worked. We will also show you how engineering runs today and ask what you would do in your first 90 days to triple shipped output without adding headcount.

Why this role

A real company with real clients, real revenue, and real problems that are yours to fix. No board, no runway clock, no pitch decks. We are the Cinderella story in a market full of funded players, and we like it that way. A founder who knows what she wants built and wants a partner who can get it built. And 19,600 small business owners who will feel it when you get this right.