Headstart careers
Headstart is hiring: 4 open roles as of October 21, 2026, all remote, 67% of them staff level. Posted pay runs $265k–$300k. The roles ask most for product strategy, observability and Python.
We use deterministic software and LLMs to create flexible, understandable systems designed for human oversight, not rigid automation.
Headstart is inApplied AIAI native companiesAI agentsArtificial intelligence
Open roles
4
Remote roles
100%
Hiring now · checked today
Headstart has 4 roles open right now.
landed applies to the ones that fit you on Headstart's own site, the hour they go live.
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Engineering Manager, Applied AI
Remote
Senior Engineering Manager, Applied AI
Remote
Staff Product Manager
Remote
4 open
Open roles at Headstart
Headstart
New York, NY
Engineering Manager, Applied AI
New York, NY
$285k–$285k
3w ago
Headstart
New York, NY
Senior Engineering Manager, Applied AI
New York, NY
$300k–$300k
3w ago
Headstart
New York, NY
Staff Product Manager
New York, NY
$265k–$265k
32w ago
Headstart
New York, NY
Staff Engineer, Applied AI
New York, NY
$265k–$265k
39w ago
100% remote
Headstart remote jobs
100% of Headstart’s open roles are remote. These are the remote roles open now, read from Headstart’s own careers page.
Headstart
New York, NY
Engineering Manager, Applied AI
New York, NY
$285k–$285k
3w ago
Headstart
New York, NY
Senior Engineering Manager, Applied AI
New York, NY
$300k–$300k
3w ago
Headstart
New York, NY
Staff Product Manager
New York, NY
$265k–$265k
32w ago
Headstart
New York, NY
Staff Engineer, Applied AI
New York, NY
$265k–$265k
39w ago
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Frequently asked
Is Headstart hiring right now?
Yes. Headstart has 4 open roles live on its own careers page today, and the list above refreshes daily.
Does Headstart hire remote?
About 100% of Headstart’s open roles are remote. The rest are based in its offices.
What does Headstart pay?
Across the Headstart postings that list pay, the middle of the range runs $265k–$300k.
How do I apply to Headstart?
Every role above links to Headstart’s own application. Or let landed apply for you: it fills the company’s form with your profile and writes the answers for each role.
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