Applied AI Lead

Why we are looking for you

We are scaling Owner's Applied AI organization. This is a fast-paced team that works on the most valuable opportunities we can find anywhere in the business. As an Applied AI Lead, you'll be responsible for finding those opportunities in the first place: looking across everything happening at Owner, understanding where AI can have the most impact, and sizing the potential before a single line of code gets written. Then you'll build, ship, and iterate on the solution until the impact shows up.

Some of these opportunities create efficiency by cutting out manual work that no longer needs to be manual. Others create better outcomes entirely: processes that now perform far beyond what they used to, and things we always wanted to do that only became practical with AI. You'll chase both, and you'll be the one deciding which come first.

This role is 100% remote and can be based anywhere in the United States or Canada.

💫 You should definitely apply if you…

• Care more about picking the right problem than about using the fanciest tool for it
• Love the hunt: scanning a business, finding what's broken or underpowered, and putting a number on the prize
• Get more energy from building and shipping than from analyzing and presenting
• Dive deep to understand root causes when solving problems, and become a subject matter expert along the way
• Aren't afraid to pick up new tools and skills, from Claude Code to custom ML pipelines, whatever the problem requires
• Want to see your work change the numbers, and feel unsatisfied until it does
• Thrive in ambiguity and don't need a playbook to figure out what to work on next

What we've built so far

• LLM-powered binary classifier for restaurant concept fit with Owner's product. Ran on over 300k establishments in the US.
• Hyperpersonalized outbound email engine, sending around 5k unique emails daily with a best-in-class reply rate.
• Automated pre-call research tool, eliminating the manual work that sales reps previously had to complete before every dial. Increased dial volume by almost double.
• Gradient Boosted Tree for predicting call pickup rate. Trained on dozens of features across tens of thousands of pieces of data, resulting in up to a ~2.3x increased pickup rate for top-identified leads. (ML experience is NOT required for this role; we used Claude Code to teach ourselves enough ML to build this.)
• Intelligent routing (iRouting) system incorporating our new pickup rate prediction score to optimize lead distribution on a daily basis.

The impact you will have

• You'll own the map of AI opportunity across the business: identifying problems and opportunities, dissecting and sizing them, and deciding what gets built next.
• The projects we work on are significant enough to alter the trajectory of the business. Recent builds have driven double-digit improvements to company-wide KPIs, and the backlog holds many more with similar potential.
• You'll carry each build from diagnosis through shipping, deployment, adoption, and iteration. A project is finished when the impact we set out for is visible, and you'll own that full arc.
• Many of the problems in our backlog are ambitious enough that they could be standalone products. We'll provide the tools and resources you need to execute them end to end.

Who you'll work with

• Reporting Structure: This role reports to Jonathan Shenkman.
• Team Collaboration: You'll work day to day with our Applied AI team and partner with key stakeholders across every team at Owner, including BizOps, RevOps, Sales, Marketing, Growth, Product, Finance, and Recruiting.
• Executive Visibility: Applied AI focuses exclusively on projects with the highest impact and ROI, which means regular exposure to senior and executive leadership.

What we're looking for

• A track record of finding the problems worth solving. You've looked at a messy business, figured out what actually matters, sized the prize, and picked the right thing to work on without anyone handing you a roadmap.
• Root-cause instincts. You dig until you actually understand the problem instead of its symptoms. You rabbithole, but you also know when you've gone too deep.
• Hands-on experience building with LLMs, integrating the models and APIs themselves: agents and assistants, structured output, evals, context engineering. You turn concepts into working code.
• 3+ years of experience in a 0-1 operations or startup role. We treat every build as a 0-1 problem to solve from scratch.
• You move fast, work scrappy, and thrive in the chaos of an early-stage startup environment, especially when things are ambiguous and timelines are tight.
• Comfortable taking ambiguity and turning it into a ruthlessly-prioritized roadmap. You don't need a playbook to figure out what to work on next, which matters more than ever given how easy it has become to build almost anything.
• You treat shipping as the midpoint. You watch how a build performs in the real world, gather feedback, and iterate until the impact you set out for actually arrives.
• Strong communicator who can break down complex concepts for teammates, both human and AI.
• Restaurant industry experience is a plus!