We're Hiring: Head of Content!
Kitchener, ON (Hybrid – 3 days in office)
Full-time | $65,000–$90,000
Who We Are
Gambit builds AI-powered personalities that people actually want to talk to—designed to adapt, remember, and deliver better outcomes.
Whether it’s addiction recovery, legal navigation, product discovery, or caregiver support, we design lifelike AI companions that spark real interaction—and turn that interaction into action.
We don’t build bots.
We don’t build “assistants.”
We build AI-powered personalities that connect, adapt, and deliver.
What You’ll Own
You’re not here to fill a role. You’re here to set the pace for how Gambit shows up in the world.
Who You Are
Skills
Bonus Points
We don’t care about job titles, awards, or where you went to school.
We care if you can create and if you can make people care.
So show us what you’ve made. And show us what’s next.
What to Submit (read carefully)
In addition to applying on LinkedIn (EasyApply), please email the following to AI@gambitco.io to be considered:
A one-pager answering:
Which brands or creators are already doing the future of content marketing—and why does it work?
Any relevant portfolio work (links or attachments)
Please use the subject line: Use the subject line: Head of Content – [Your Name]
Perks & Culture
3 days/week together at 137 Glasgow St., Kitchener (otherwise flexible)
Small, fast, irreverent—lots of trust, direct feedback, low management
You’ll have a front-row seat as we actually build the future of AI
Nothing is precious but the work. Mistakes > inertia. Outcomes > hours.
* The salary benchmark is based on the target salaries of market leaders in their relevant sectors. It is intended to serve as a guide to help Premium Members assess open positions and to help in salary negotiations. The salary benchmark is not provided directly by the company, which could be significantly higher or lower.