Engineering Leader (US)

Freehand•San Francisco, CA

About The Position

Freehand is hiring its first engineering leader in the US. The role will establish the US engineering team's charter, hiring practices, culture, quality bar, and operating rhythm, and serve as the CTO's counterpart in the US while partnering closely with the engineering team in India. The position combines organizational leadership with hands-on engineering: the leader will own core, revenue-driving product areas, make technical and product decisions, build and ship software, and lead a small, high-caliber team. The leader will own product areas end to end, from product direction and requirements through delivery, customer escalations, and business metrics. They will ship AI-agent features to enterprise customers, stay close to code and system design, and take products from inception through scale. They will build an AI-first engineering team that uses coding agents, evaluation loops, and AI in review and testing. The position works directly with customers and collaborates with the CTO on technical direction, architecture, and the engineering charter. The role is based in the San Francisco Bay Area and works closely with the team in India, including some overlap with IST hours. Freehand will arrange fully paid trips to its Chennai headquarters to meet and work with cross-functional teams. Freehand is a Series A company with approximately 100 people across the US and India.

Requirements

At least 8 years of engineering experience, with title and scope rising steadily; promotions within the same company are ideal.
Currently a Director, Head of Engineering, Senior Engineering Manager, Staff-plus technical leader, or Principal at a top-tier company.
At least one stint at a startup or early-stage team.
Have owned a company's core product, a paid product line, or a customer-facing platform that drives revenue; experience limited to internal tooling, developer productivity, or infrastructure layers does not meet this criterion.
Be able to name customers and quantify the impact of work on revenue, usage, cost, or latency.
Use AI daily to build software and have shipped AI or agentic features to real users.
For a Director profile: have grown an engineering organization from roughly 5 to 30 or more people, including hiring managers, and established its operating system.
For a Senior Engineering Manager profile: have built multiple 0-to-1 products at startups, including at least one within the last 3–4 years, and still code and design systems.
Have strong product sense and be able to explain the customer problem, why the product needed to exist, and the bets made.
Thrive in ambiguity and work directly with customers.

Nice To Haves

Have taken a product from 0 to 1 and then scaled that same product.
Have 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.

Responsibilities

Build Freehand's US engineering team from the ground up, including hiring, culture, and the quality bar.
Own core, revenue-driving product areas end to end, partnering with product on direction and managing delivery, customer escalations, and business metrics.
Make fast technical and product decisions amid incomplete information and ambiguity.
Measure product success using revenue, users, cost, and latency.
Stay close to code and system design, make difficult technical decisions, and take products from 0 to 1 and then scale them.
Run an AI-first engineering team that uses coding agents, evaluation loops, and AI in review and testing.
Ship agentic features to real users and develop a clear point of view on what works.
Hire and develop exceptional engineers and, as the team grows, engineering managers.
Establish the engineering operating system, including hiring loops, leveling, planning cadence, on-call, quality bar, and delivery rhythm.
Partner with the CTO on technical direction, architecture, and the engineering charter.
Work directly with customers to understand their problems and translate them into product.
Work as one organization with the engineering team in India, with some overlap in IST hours.