Senior Engineering Manager, Applied AI
- for any list of duties/requirements/benefits, and
for prose. We must remove boilerplate: cookie/navigation/legal/EEO etc. Not present. We must not repeat job title. We must not put Job ID/requisition numbers as headings. We need to output only HTML fragment. Let's parse content: About The Company: description of Headstart. Why join us: description of role responsibilities? Actually "Why join us" includes description of work: engineers work out what to build, build it, run it, etc. This is more about role. What You'll Own: bullet list of responsibilities: Your team, Technical leadership, Closing the loop, Staffing, Hiring, Partnerships. Your background: requirements: 4+ years managing engineers, 8+ years software engineering, hands-on Python, experience delivering software in real client environments, curious about agents, evals, multi-agent systems, fluent with AI coding tools, depth matters more than prior title, bonus: management experience in consulting/services/forward deployed engineering. How We Work: description of culture: high trust, high agency, low ego, etc. Could be part of About the role or maybe not needed as separate heading; but we could include under About the role as prose. What To Expect: interview process details. This is not responsibilities/requirements/benefits/pay/schedule. Could be omitted? The instruction: include a section ONLY when the posting has real, specific content for it — never emit a heading followed by filler/placeholder text. The allowed headings are limited; we could choose not to include a section for interview process if it doesn't map to allowed headings. But we must preserve ALL substantive information; we cannot drop info. However we could embed that info under a heading like "About the role" as prose? The instructions say we must use those headings for section headings. It doesn't say we cannot have other headings; but says "use
for section headings (e.g. About the role, Responsibilities, Requirements, Qualifications, Skills, Benefits, Pay, Schedule)." It implies we should use those headings for sections. It doesn't forbid other headings, but likely they expect only those. To preserve all substantive info, we could include interview process under "About the role" as prose, or maybe under "Responsibilities"? Not appropriate. Better to include under "About the role" as a paragraph describing expectations. What we offer: benefits list: Base salary $300k, equity, 401k with 4.5% employer match, fully covered medical/dental/vision, monthly wellness stipend, Citi Bike, pre-tax commuter benefits, 12 weeks parental leave with optional 4-week ramp-up at 50%, Loft office in Soho with lunch and snacks, Hybrid in NYC, fully remote in rest of US and Canada. Compensation Range: $300K (duplicate of base salary). We'll include Pay section with base salary and equity etc. Schedule: maybe hybrid/remote info. We need to avoid duplication. Let's structure:
About the role
... combine About The Company, Why join us, How We Work maybe.
Responsibilities
- ... each bullet from What You'll Own
Requirements
- ... background requirements
Qualifications
but we can combine with Requirements. The instruction says prefer a few substantive sections over many thin ones. So we could have Requirements covering both requirements and qualifications.Benefits
- ... benefits list
Pay
Base salary of $300,000 USD, plus competitive equity.
Schedule
Hybrid in NYC; fully remote for the rest of the US and Canada.
We need to ensure we don't include filler like "commensurate with experience". Not present. We need to preserve all substantive info: include details about company, mission, etc. Let's craft About the role paragraph: combine About The Company, Why join us, How We Work. About The Company: "Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems." Why join us: "Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room. This role is part player, part coach, part staffing lead, part hiring engine. You'll start on a client engagement to learn the work and where engineers get stuck. Then you'll build and lead a team and help shape the company as we grow." How We Work: "High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast. We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves. AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable. Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view. Breadth that compounds. You'll see more industries and problems in a year than most people see in a career. Weekends are yours. Pay is transparent, and we don't confuse long hours with good work." We can combine into a paragraph or multiple paragraphs. Usefor prose. Responsibilities bullets: from What You'll Own: - Your team. Hold a high bar and grow each engineer through direct, actionable feedback. - Develop senior engineers into tech leads. - Give clear priorities and expectations without adding process before we understand the problem. - Technical leadership. Review architecture, agent, prompt, and eval design. Step into the hardest technical and client situations, like production regressions and unclear requirements, and make the call. Raise trouble early, while it's cheap to fix. - Closing the loop. Spot patterns across engagements and turn them into standing practice, reference implementations, and platform capabilities. Check that the next engagement is faster because of it. - Staffing. Shape who works on which engagement, plan transitions ahead, and flag risks before they reach a client. - Hiring. Run hiring for your team, from sourcing to onboarding. You define the bar. - Partnerships. Work closely with product, client partners, and client stakeholders so each engagement lands. We need to keep each as
- . Requirements: from Your background: - 4+ years managing engineers, including senior and staff, with real experience hiring and developing them. - 8+ years in software engineering, deep enough to review designs and challenge the team's approach. - Hands-on with Python. - Experience delivering software in real client environments and taking something from zero to one, whether a team, a practice, or a hiring process. - Curious about agents, evals, and multi-agent systems, with a sense of where they're reliable and where a person needs to take the wheel. - Fluent with AI coding tools. - Depth matters more than prior title. - Bonus: Management experience in a consulting, services, or forward deployed engineering organization. We can list as
- .
Benefits: from What we offer:
- Base salary of $300,000 USD
- Competitive equity
- 401k with 4.5% employer match
- Fully covered medical, dental, and vision premiums
- Monthly wellness stipend
- Citi Bike
- Pre-tax commuter benefits
- 12 weeks parental leave, with an optional 4-week ramp-up at 50%
- Loft office in Soho with lunch and snacks
- Hybrid in NYC, and fully remote in the rest of the US and Canada
But note that hybrid/remote also goes to Schedule; we might avoid duplication. Could keep hybrid/remote in Benefits? But schedule section expects that. Let's keep hybrid/remote in Schedule, and not duplicate in Benefits. However the benefits list includes that; we could still include but risk duplication. The instruction: Preserve ALL substantive information; do NOT invent or summarize away detail. If we omit hybrid/remote from Benefits, we lose that detail unless we put it in Schedule. So we should put hybrid/remote in Schedule, and not duplicate in Benefits. But we need to ensure we still convey that info somewhere. So we will put hybrid/remote in Schedule.
Thus Benefits list excludes hybrid/remote.
Pay: Base salary and competitive equity. Could also mention compensation range $300K. We'll include base salary and equity.
Schedule: Hybrid in NYC; fully remote for the rest of the US and Canada.
Now ensure we don't include any filler like "commensurate with experience". Not present.
Now produce HTML:
About the role
Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems. Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room. This role is part player, part coach, part staffing lead, part hiring engine. You'll start on a client engagement to learn the work and where engineers get stuck. Then you'll build and lead a team and help shape the company as we grow. High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast. We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves. AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable. Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view. Breadth that compounds. You'll see more industries and problems in a year than most people see in a career. Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.
Responsibilities