Headstart benefits

Headstart builds AI-powered systems and custom applied-intelligence solutions for enterprise clients.

13 recorded benefits. Record edited: Wed Sep 09 2026 15:25:35 GMT+0000 (Coordinated Universal Time). Record edits are not policy checks. Confirm current terms and eligibility.

Recorded work model: Role-specific: hybrid in New York/Toronto; fully remote US/Canada may be considered for the right fit. Company-wide eligibility is not established by this label.

Health Insurance

Availability: listed

For eligible US employees in the cited full-time New York role, the posting says medical premiums are fully covered; plan design and other eligibility terms are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Dental Insurance

Availability: listed

For eligible US employees in the cited full-time New York role, the posting says dental premiums are fully covered; plan design and other eligibility terms are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Vision Insurance

Availability: listed

For eligible US employees in the cited full-time New York role, the posting says vision premiums are fully covered; plan design and other eligibility terms are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Wellness Stipend

Availability: listed

A monthly wellness stipend is listed for eligible US employees in the cited full-time role; amount and eligible expenses are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Parental Leave

Availability: listed

The current full-time New York role lists 12 weeks of parental leave plus an optional four-week ramp-up at a 50% schedule; pay level and other eligibility terms are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Remote Work

Availability: listed

The role is listed as hybrid in New York or Toronto, and the posting says fully remote candidates based in the US or Canada may be considered for the right fit.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Hybrid Work

Availability: listed

The current Senior Applied AI Engineer role is listed hybrid in NYC or Toronto; fully remote US/Canada applicants may be considered. No fixed office schedule is specified.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

401k

Availability: listed

For eligible US employees in the cited full-time New York role, the posting lists a 401(k) with an employer match; plan formula and vesting are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

401k Match

Availability: listed

An employer match is explicitly paired with the 401(k) in the cited full-time New York role; the match formula, cap and vesting are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Employee Equity

Availability: listed

Competitive equity compensation is included in the cited full-time role; grant type, amount, vesting and broader eligibility are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Free Lunch

Availability: listed

Free lunch every day in the NYC office is listed for eligible employees in the cited role; the posting mentions snacks separately but does not state that snacks are free.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Office Snacks

Availability: listed

The current Senior Applied AI Engineer posting says lunch and snacks are provided in the Soho NYC office; no allowance or broader location eligibility is stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.

Commuter Benefits

Availability: listed

The current posting lists Citi Bike and pre-tax commuter benefits for the cited role; subsidy amount and eligibility terms are not stated.

Policy checked: Not recorded. Countries: Unknown. Employee classes: Unknown. Roles: Unknown. Conditions: Not recorded.

  • Senior, Applied AI Engineer @ Headstart

    Benefits footer in a current full-time New York, US posting; it also lists Toronto and possible fully remote US/Canada consideration.. Accessed: 2026-09-09T15:16:53.300Z; published: 2026-09-08T00:00:00.000Z.