This one is closed
Live roles like this one
-
C
9h ago
Toptal Canada
- C 22h ago
- C 22h ago
- C 23h ago
See every "Chief AI Officer" role →
Get new “Chief AI Officer” roles by email
One email a day with what is new in "Chief AI Officer". Nothing new, no email.
We confirm the address first, and every mail carries an unsubscribe link. Alerts are ours, not a third party's.
Why this grade This listing scored 37/100, which is an F. It lost the most ground on freshness. See the breakdown
- Description depth 20 / 20 How much the posting actually says about the work, measured in characters of real text.
- Remote clarity 15 / 15 Whether "remote" means anywhere, or is quietly restricted to one country.
- Pay transparency 12 / 25 A published salary range, worth more than any other single factor because it is what a candidate cannot find out without applying.
- Corroboration 5 / 10 Whether more than one source carries this listing.
- Role specificity 0 / 10 Whether the listing is tagged well enough to tell what the role actually is.
- Freshness 0 / 15 How recently it was posted. Older postings are likelier to be filled or abandoned.
-15 Ghost-job penalty — Deducted for signals that this posting may not be a real, currently-open role — staleness, repeated relisting, or talent-pool language.
Every figure above is arithmetic over the posting itself — its salary field, its text, its age, its tags and how many sources carry it. How the grades work →
🧘 Beyond your base rate, we offer:
- Fully remote work environment – work from anywhere globally
- Unlimited time off
- Equity compensation
- Our own Global Safety Net, giving you worldwide health, income, and travel coverage
- Personal development and office budgets
- A new laptop when you need one
- Annual team gathering in amazing locations - our previous meetups were in Iceland, Vietnam and Argentina
🌎 About this Role
We believe AI is the biggest opportunity to amplify human potential that we've seen in decades. Your job is to embed AI throughout SafetyWing - across our operations, products, and ways of working.You'll have a blank canvas. You'll help define how AI is used across the company, identify the highest-leverage opportunities, build systems and workflows, train teams, and influence our product roadmap. You'll work closely with leaders across SafetyWing to rethink how work gets done and what an AI-native insurance company should look like.
Success in this role means that a year from now, people at SafetyWing can accomplish things that feel impossible today. AI should make every team smarter, more creative, more effective, and capable of delivering far more value to our members than a company of our size normally could.
👩💻Your responsibilities will include
- Define and execute SafetyWing's AI strategy so that every team, workflow, and product becomes meaningfully more capable with AI
- Build, test, and deploy AI-powered solutions across operations, claims, support, growth, product, design, and beyond
- Help shape SafetyWing's product roadmap so AI is embedded into what we build, not just how we work
- Help every team member become exceptionally effective with AI through training, coaching, experimentation, and hands-on support
- Reimagine how work gets done at SafetyWing from the top down. Not only removing busy work and creating new ways for people to operate, but thinking deeply about how an AI-native insurance company should run internally and how AI should be embedded throughout our products
- Measure the impact of AI across the company and continuously raise the bar for what our team can accomplish
🧪 We are looking for someone who
- Lives and breathes AI and is constantly experimenting with new models, tools, and workflows
- Has built AI-powered systems across a variety of use cases, especially in operations
- Has experience as a senior leader and knows how to influence, align, and drive change across an entire organization
- Can help both technical and non-technical teams adopt new ways of working
- Is comfortable switching between hands-on execution and long-term strategy
- Has a clear way to measure and demonstrate impact
😀 We like to work with people who
- Want to help build a global social safety net on the Internet.
- Think for themselves instead of copying others.
- Are willing to try new things, even with the risk of failure.
- Are intellectually curious and open to new ideas.
- Are creative and bold in the face of any problems.
- Have strong integrity and do the right thing.
Apply for this role Opens safetywing.pinpointhq.com — the employer's own page, as linked by the source that listed this role
Quick question · anonymous · one tap
Would you apply to this job?
Answer to see what other job seekers said.
Your turn · no account needed
Help the next applicant
You may know something about this listing that we cannot see from here. One tap. No account needed. Signed-in reports earn points once the evidence agrees with you.
I know what it pays
Sign in with Google to earn points for reports — 100 confirmed points buy a week of Early Access.
Where this listing came from
- 07 Jul 2026 Real Work From Anywhere first sighting
Seen on 1 board over 36 days.