First Engineering Leader – AI-Native Platform & Equity

Headways; San Mateo (CA); On-site; USD 180,000 - 280,000; Full time

Benefits offered by this job

Equity stake

Ownership

Job summary

Headways seeks an engineering leader to own the codebase and technical roadmap, writing code daily while guiding the engineering team. You will deploy on-site with customers, gather feedback, and translate it into platform changes that improve velocity.

You will champion security, data governance, and data integration as core product aspects while growing a small, high-trust team that builds AI-native software for enterprise customers.

Qualifications

• Designed and shipped complex enterprise software.
• Led or influenced a small team.
• Experience with on-site deployments and customer presence.

Responsibilities

• Own the codebase and technical roadmap; write code daily.
• Improve product velocity and prioritize scope vs speed.
• Deploy with customers on-site and gather feedback for next changes.
• Ensure security, governance, and data integration are central to the product.
• Build and manage the engineering team as it grows.
• Foster an environment where engineers and builders collaborate safely.

Skills

TypeScript

Full-stack

Kubernetes

Terraform

Data integration

Security and governance

Tools

Postgres

Prisma

SpiceDB

GCP

GitHub Actions

Job description

Headways seeks an engineering leader to own the codebase and technical roadmap, writing code daily while guiding the engineering team. You will deploy on-site with customers, gather feedback, and translate it into platform changes that improve velocity.

You will champion security, data governance, and data integration as core product aspects while growing a small, high-trust team that builds AI-native software for enterprise customers.