Chatdrill careers: we hire the next person, not a department.
Chatdrill careers move one role at a time. We are an early-stage, remote-first team building AI customer service software, so the work is broad, the decisions sit close to you, and plenty of it is not settled yet.
- Remote-first
- Ship weekly
- Paid exercises, never unpaid tests
Where we actually are with hiring
We open roles one at a time, when the work genuinely needs another pair of hands. The roles below are the areas we expect to open next — not live vacancies with a signed budget and a start date. We would rather say that plainly than run a job board full of postings that go nowhere. If one sounds like you, write now: a shortlist usually starts with the people who introduced themselves before the role opened.
A remote-first team with a short distance to the customer.
The good part and the hard part of an early team are the same thing: there is nobody between you and the work.
Remote-first, genuinely
No head office and no hub you are quietly expected to move to. A few overlapping hours, then your own.
Ownership, not tickets
You take an area, talk to the customers using it, decide what it needs and ship it.
Weekly shipping
Small changes released continuously. No launch theatre, no six-week freeze, no release train.
Time in the inbox
Everyone, engineering included, answers real customers. It is the cheapest research there is.
Written by default
Decisions are written down so they can be read in another time zone. Fewer meetings, more documents.
Straight answers about money
Salary range and equity are published in the job post. We never ask what you earn today.
Remote SaaS roles we expect to open next.
Illustrative, not live. Every card goes to the same place — a message to a person who reads it.
Salary range and equity are published in the job post when a role opens — never negotiated down from whatever you happen to earn today.
How we hire: five steps with no surprises in them.
We aim to go from first message to decision in under three weeks, and to tell you where you stand at every step.
You write to us
A short note about what you have built. Links beat CVs — a repository or a shipped product tells us more.
A conversation
Around 45 minutes with someone doing the work, not a screener reading from a scorecard.
A paid exercise
One small, real, timeboxed piece of work — roughly half a day, paid fairly. No unpaid take-homes.
Meet the rest
You talk to the people you would work with, and ask us the uncomfortable questions about runway and roadmap.
An offer in writing
Salary, equity and start date in the first message, with time to think. A no comes with a reason.
What we ask of you
Use the product before you write. Open the widget, ask the AI agent something hard, skim what we admit we have not built yet, and tell us what you would change. That single paragraph moves an application to the top of the pile.
Start with a message, not a form.
Tell us what you build and what you would want to own here.
We reply to every application, including the ones we say no to.