Engineering Leader

About Freehand

Most AI companies are building tools. We're building the worker.

Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians and supply chain professionals.

Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.

If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.

The Role & The Team

You will be Freehand's first engineering leader in the US. You will set the bar, the culture and the charter for every US engineer who joins after you, working as a close partner to our CTO and alongside our engineering team in India. There are two aspects to this role:

• You stand up US engineering — charter, hiring, operating rhythm — and act as the CTO's counterpart on the US side, while staying close enough to the work to make the hard technical calls.

• You own core product areas end to end, build and ship it yourself, and lead a small, high-caliber team around it.

Either way, this is not a management-only seat. You will own core, revenue-driving product that customers pay for, and you will build with AI every day.

What You'll Do

• Build Freehand's US engineering team from the ground up: hiring, culture and the quality bar

• Own core product areas that customers pay for, from requirements to production

• Ship agentic features to some of the world's largest enterprises

• Partner with the CTO on technical direction, architecture and the engineering charter

• Work directly with customers to understand their problems and turn them into product
  

Key Responsibilities

Product & Delivery Ownership

• Own core, revenue-driving product areas end to end: direction with product, delivery, customer escalations and business metrics

• Make fast technical and product decisions with incomplete information, and bring structure to ambiguity

• Measure success in revenue, users, cost and latency — with real numbers

Hands-on Engineering

• Stay close to the code and the system design; go deep on architecture and make the hard technical calls

• Take new products from 0 to 1, then scale them

AI-Native Engineering

• Run an AI-first engineering team that uses coding agents, eval loops and AI in review and testing every day

• Ship agentic features to real users, and hold a clear point of view on what works and what doesn't

Team & Org Building

• Hire and grow exceptional engineers (and, as the team scales, engineering managers)

• Set up the operating system: hiring loops, leveling, planning cadence, on-call, quality bar and delivery rhythm

• Work closely with our India engineering team as one org, with some overlap in IST hours
  

Required Skills & Experience

Core Product Ownership

• You have owned a company's core product, a paid product line, or a customer-facing platform that drives revenue — not internal tooling, developer productivity or infrastructure layers

• You can name the customers and quantify what your work moved: revenue, usage, cost or latency

Career Trajectory

• 8+ years in engineering, with title and scope rising steadily — ideally through promotions within the same company

• Currently a Director, Head of Engineering, Senior EM, or Staff-plus TLM, or a Principal at a top-tier company

• At least one stint at a startup or early-stage team

AI-Native

• You and your team use AI daily in how you build software

• You have shipped AI or agentic features to real users — not a thin AI layer on top of an existing product

Leadership & Building

• Director profile: has grown an engineering org from roughly 5 to 30+ people, including hiring managers, and set up its operating system

• Senior EM profile: has built multiple 0-to-1 products in startups, at least one in the last 3–4 years, and still codes and designs systems

• Strong product sense: you can explain the customer problem, why the product needed to exist, and the bets you made

• Thrives in ambiguity and works directly with customers
  

Bonus (Nice to Have)

• Has taken a product from 0 to 1 and then scaled that same product

• A network of strong engineers who have followed you before, or would join you

• Experience leading distributed teams across US and India time zones

• Background in enterprise SaaS, supply chain, procurement or financial systems
  

Working at Freehand

Series A, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles — the same philosophy we built our AI agents on:

Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding.

Decisions, not Recommendations. Freehand folks decide; they don't present options. You'll have real autonomy, and real accountability to match.

High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed.

Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover.

The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters.

This role is based in the San Francisco Bay Area and works closely with our team in India. We'll arrange fully paid trips to our HQ in Chennai to meet and build with the cross-functional teams.

Equal Opportunity

Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of them, apply anyway.