Senior Engineering Manager, Applied AI

About Headstart

Headstart focuses on empowering employees to think like founders, working within large enterprises with over $100M ARR. We deploy production AI solutions across diverse industries, tackling complex challenges without predefined answers. Operating as a bootstrapped and cash-positive company, we develop our own platform to deliver autonomous AI systems.

Role Overview

This role combines hands-on technical work, coaching, staffing leadership, and recruitment responsibilities. Initially, you'll join a client project to understand workflows and engineering challenges, eventually building and leading your own team while influencing company growth.

Key Responsibilities

• Lead and cultivate a high-performing engineering team by providing actionable, direct feedback and developing senior engineers into technical leads without adding unnecessary processes prematurely.
• Provide strong technical leadership by reviewing system architectures, agent designs, prompt development, and evaluation strategies. Handle challenging technical issues and unclear client requirements decisively.
• Identify recurring patterns from engagements and establish best practices, reusable implementations, and platform features to speed up future projects.
• Manage staffing by assigning appropriate roles for each engagement, planning transitions proactively, and identifying risks early.
• Lead end-to-end hiring processes for your team, including sourcing candidates and onboarding, setting clear standards for recruitment.
• Collaborate closely with product teams, client partners, and stakeholders to ensure successful engagement delivery.

Candidate Profile

• At least 4 years of experience managing software engineers, including seniors and staff, with proven skills in hiring and professional development.
• Over 8 years of software engineering experience, proficient enough to critically review designs and guide the team. Hands-on experience with Python is essential.
• Background in deploying software solutions in client-facing environments and establishing teams, practices, or recruitment systems from scratch.
• A keen interest in AI agents, evaluations, and multi-agent systems, understanding their reliability limits and when human intervention is necessary. Familiarity with AI coding tools is important.
• Preferred: Management experience within consulting, service-based, or forward-deployed engineering organizations.

Work Culture

• High-trust, empowered, low-ego environment encouraging open feedback and fast dissemination of insights.
• Internal use of proprietary tools (e.g., Friday coding agent, Statum knowledge system) to enhance productivity.
• AI-assisted coding approach with human accountability, ensuring every output is reviewed.
• Client partnerships involving direct engagement in critical decision-making.
• Exposure to a broad range of industries and challenges within a single year.
• Clear work-life boundaries with weekends off, transparent compensation, and a focus on results over hours worked.

Recruitment Process

• Initial 30-minute screening with a recruiting partner.
• Technical 30-minute coding exercise with an engineer.
• 45-minute behavioral and work history interview with the hiring manager.
• Two technical interviews totaling 2.5 hours covering coding and system design; use of AI tools is permitted.
• 75-minute live case study scenario evaluating staffing, feedback, technical leadership, and process implementation, requiring no preparation.

Compensation and Benefits

• Annual base salary of $300,000 USD with competitive equity packages.
• 401k retirement plan with a 4.5% employer match and fully covered medical, dental, and vision insurance premiums.
• Monthly wellness stipend, Citi Bike membership, and pre-tax commuter benefits.
• 12 weeks parental leave with an optional four-week phased return at 50% capacity.
• Office located in Soho with provided lunch and snacks.
• Hybrid work model in NYC; fully remote option available for locations in the US and Canada.