Head of AI (AI-Native Builder-Operator) - Ecommerce Holding Company

Our client is an Ecommerce holding company. They're self-funded, which means no outside capital, no VC timeline, and no portfolio they're propping up for a fund. They operate what they own, move quickly, and pay close attention to the things that make a brand work: the product, the creative, the funnel, the customer experience, and the unit economics.

Their current focus is their pet brand. It has strong traction across Amazon, TikTok Shop, and DTC, and serves hundreds of thousands of customers across North America. The rest of the portfolio is in health and wellness, all subscription-driven with meaningful recurring revenue. The business is profitable and on a clear path to a significant outcome in the next 24 to 36 months.

You would be joining a strong leadership team that has built and scaled brands at Goli Nutrition, Mars Men, Ryze Superfoods and The Farmer's Dog. The bar here is very high. They want a Head of AI who can match it and push it higher.

About the Role

We think the DTC brands that win the next decade will be the ones that rebuild how the company operates on top of AI, rather than the ones that add a few AI features around the edges.

We have already started. Much of the software in our stack, including the analytics dashboards, the ops tooling, the internal CRMs, the reporting layers, and the QA flows, is being replaced by purpose-built systems we ship ourselves, mostly on top of Claude. A sprawling stack of seat-based tools is becoming a small set of internal agents and apps tuned to exactly how we run.

We have also seen what this does on the customer-facing side. We rebuilt a quiz funnel on Claude, hosted on Shopify, and conversion rate went up 20 percent on a brand spending more than two million dollars a month. We want a lot more of that. The Head of AI owns this vision and ships against it across every department.

The role sits horizontally across the company, reports to the CEO, partners with every team lead, and is accountable for one thing: every department does its job faster, cheaper, and better because of systems this person builds. Marketing, growth, creative, CX, supply, finance, ops, people, product, and brand. All of it.

Responsibilities

• Embed and discover. The job starts with listening. You spend real time with every team lead, sit in on their meetings, watch them work, and map their workflows in depth. You find where things are slow, painful, redundant, or high-leverage. You decide what is worth building, what is worth buying, and what is worth retiring. Models and workflows change constantly, so you re-evaluate constantly.

• Build. You ship systems every week. You replace seats and SaaS subscriptions with internal tools tuned to how we actually work. You also build customer-facing conversion systems: quiz funnels, landing pages, and onsite experiences that move real metrics. You build the connective tissue across departments, so marketing data feeds supply, CX feedback feeds product, and finance feeds everyone. You own the model stack, the prompt library, the agent framework choices, the eval setup, and the cost ledger.

• Scale. You train teams to use what you build, so they become more capable rather than more dependent on you. You hire underneath you only when bandwidth is clearly the ceiling, not before. You set the standard for what AI-native operations mean here.

What success looks like

We hire against outcomes. Here is what success looks like by the end of your first year:

• Every department relies on something you built. Marketing, growth, creative, CX, supply, finance, ops, and product each have at least one system you shipped that they now use daily.
• The SaaS stack is measurably smaller. You have replaced a meaningful share of our seat-based software with internal systems, with a documented dollar figure saved.
• You have moved a hard business metric. At least one customer-facing system you built has improved conversion rate, CAC, or contribution margin, and you can show the numbers.
• Teams run what you build without you. The systems you shipped are owned and operated by the departments that use them, not dependent on you day to day.
• There is a roadmap, and it is real. You have delivered and are executing a twelve-month AI roadmap with KPIs and a SaaS-replacement target.

What we're hiring for

A builder-operator who treats the company like a product, and who is, above everything else, AI-native. This is the most important filter. We are not hiring someone to learn on us:

• You have built AI workflows and internal systems for other companies before, more than once, with results you can point to.
• You know the current frontier models cold, across Anthropic, OpenAI, Google, and the leading open-weight labs, and you have strong, defensible opinions about which to use for which job.
• You know the current build landscape: Claude Code, Cursor, MCP, agent frameworks, evals, structured outputs, tool use, computer use, RAG, and the leading automation and generation tools. You can defend your choices in 60 seconds.
• You stay genuinely current. You read AI news daily, you ship side projects, and you are several model releases ahead of the average operator.

Additional requirements

• Seven to twelve years of total experience, with the last two or more spent deeply hands-on with LLMs and agents in production.
• DTC fluency. You speak CAC, contribution margin, subscription cohorts, and MER without translation.
• A systems thinker who sees how marketing, CX, supply, and finance connect.
• A strong writer. You can align the CEO, the VP of Finance, and a junior creative with the same one-page document.

Preferred

• A public body of work on applied AI in commerce: GitHub, a Substack, conference talks, or podcasts.
• You have built and scaled, or built and sold, something of your own.
• Strong, defensible opinions on which model to use for a given task, on when to use a framework versus write it yourself, and on when to buy software versus build it.
• A pet owner. Not required, but it tends to show.

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Not for you if

• You are a researcher or academic whose proudest work is a paper.
• You are an AI strategist who lives in slide decks.
• You are a big-company product manager without shipping scars.
• You are an agency veteran without in-house operator experience.
• You have not built AI systems for real companies before.
• You want a stable, predictable scope. The scope of this role is the entire company.

How we work together

• Direct access to the CEO. You are in the room for every major commercial and operational decision.
• You ship weekly. Friday demo, where you show what shipped, what you retired, and what is next.
• Fully remote, async-first, and written. We run on Slack, Notion, and Loom, with one quarterly in-person offsite.
• Real budget for tools, compute, and contractors. We trust you to spend it.
• Your first 90 days: embed with every team, ship two or three internal systems, and deliver a written twelve-month AI roadmap with KPIs and a SaaS-replacement target.

How we hire

Our process is thorough by design. Expect in-depth interviews that walk through your career and your actual built work in detail, along with reference conversations. It is also fast. We don't let strong candidates sit.

Pay range and compensation package

• Base: $200K to $275K, depending on experience.
• Equity: an equity opportunity is part of the package. We walk through the structure at the offer stage.
• Bonus: 15 to 25 percent target, tied to systems shipped, KPI movement, and SaaS replaced.
• Full health, dental, and vision. A $3K annual learning budget. Unlimited PTO with a three-week floor. Equipment of your choice. Free product for life for your pets.