Engineering Leader (US)

Freehand•San Francisco, CA

2d•$300,000 - $350,000•Onsite

About The Position

Freehand is hiring its first US engineering leader to establish the US engineering team, set its culture and quality bar, and serve as the CTO’s counterpart in the US while working closely with the engineering team in India. The role combines organizational leadership with hands-on technical and product ownership; it is not a management-only position. The Engineering Leader will own core, revenue-driving product areas end to end, make technical and product decisions, build and ship products, and lead a small, high-caliber team. The role includes setting up hiring and operating practices, partnering with the CTO on technical direction and architecture, using AI-native engineering practices, and working directly with enterprise customers. The position is based in the San Francisco Bay Area and includes close collaboration with the India team, with some overlap in IST hours. Freehand will arrange fully paid trips to its Chennai headquarters.

Requirements

At least 8 years of engineering experience, with title and scope rising steadily; promotions within the same company are preferred.
Currently a Director, Head of Engineering, Senior Engineering Manager, Staff-plus Technical Lead Manager, or Principal at a top-tier company.
At least one stint at a startup or early-stage team.
Experience owning a company’s core product, a paid product line, or a customer-facing revenue-driving platform; internal tooling, developer productivity, and infrastructure layers do not meet this criterion.
Ability to name customers and quantify the impact of work on revenue, usage, cost, or latency.
Daily use of AI in software development by the candidate and their team.
Experience shipping AI or agentic features to real users, rather than adding a thin AI layer to an existing product.
For a Director profile: experience growing an engineering organization from roughly 5 to 30 or more people, including hiring managers, and establishing its operating system.
For a Senior Engineering Manager profile: experience building multiple 0-to-1 products at startups, including at least one in the last 3–4 years, while continuing to code and design systems.
Strong product sense, including the ability to explain the customer problem, why the product needed to exist, and the bets made.
Ability to thrive in ambiguity and work directly with customers.
Ability to work closely with the India engineering team, including some overlap in IST hours.

Nice To Haves

Experience taking a product from 0 to 1 and then scaling that same product.
A network of strong engineers who have followed the candidate before or would join them.
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 quality standards.
Own core, revenue-driving product areas end to end, including product direction, delivery, customer escalations, and business metrics.
Make timely 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 major architecture decisions, and take products from 0 to 1 and scale them.
Lead an AI-first engineering team using coding agents, evaluation loops, and AI in review and testing.
Ship agentic features to real users and develop a clear point of view about what works.
Partner with the CTO on technical direction, architecture, and the engineering charter.
Hire and develop exceptional engineers and, as the team scales, engineering managers.
Establish engineering operating practices, including hiring loops, leveling, planning cadence, on-call, quality standards, and delivery rhythm.
Work closely with the India engineering team as one organization, with some overlap in IST hours.
Work directly with customers to understand their problems and translate them into products.