Work at Chisel AI


We’re building something extraordinary.

And we want you to be a part of it.

The chance to create something entirely new comes along once or twice in a career – if you’re lucky. At Chisel AI, you’ll have a unique opportunity to solve complex problems, and build innovative solutions to address major challenges for a global industry. The ability for computers to read and extract information trapped in digital documents is set to change the way the world works. The skills, hands-on experience, and confidence you gain working for a fast-paced, high-growth start-up like Chisel AI will serve you well throughout your life and career.

If you’re a smart, driven, and adaptable self-starter who likes to dive in and make a difference, and who thrives in a super-collaborative, casual environment where there are no ordinary days, let’s talk!


Chisel AI is a Digital Disruptor to Watch in 2021

“These digital disruptors represent the very best of Canadian entrepreneurship and are truly paving the way in our increasingly digital economy.”

– Joe Canavan, CEO, NEXT Canada


Chisel AI Wins Gold at the 2019 Zurich Innovation World Championship

“We’re now working with [Chisel AI] to figure out how we can use artificial intelligence to improve the way we read, compare, accept and ingest documents in our [commercial insurance] world.”

– Saad Mered, CEO, Zurich Canada


Chisel AI is Well-Funded & Growing Fast

Chisel AI is backed by leading VC firms including Venrock and MTech Capital. We’re investing this capital in our people and growing our team.

MARG 400X400
Chisel AI is a powerful example of how technology can be leveraged to chisel away at the millions of documents sitting in data stores and data lakes to gain access to trapped business insights. The way in which Chisel AI is helping people work smart and enrich their lives is enticing to job seekers and highlights the vibrancy of our industry and abundant career paths.”
– Marguerite Tortorello, Managing Director, Insurance Careers Movement

Want to Know What We Do?

Take a quick tour of our solutions and sample the “secret sauce” that has made Chisel AI one of the fastest-growing AI companies in Toronto.

Our Story

Learn more about Chisel AI and get to know our leadership team. 

Our Team

We believe in giving our employees an environment that fosters learning, collaboration, creativity, and curiosity. We believe our employees should never stop asking questions.

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The problems we are solving for our customers using machine learning and AI aren’t easy. But big challenges create big opportunities. The team here at Chisel AI is doing something that has never been done before – and they’re doing it with imagination, creativity, and brilliance.”
– Colin Toal, CTO, Chisel AI

Our Culture by the Numbers

Chisel AI is committed to fostering an environment where every employee has the opportunity to realize their full potential. We’ve assembled a strong and diverse team and are proud of our progress in promoting diversity, equity, and inclusion. Work Visa sponsorship is available for new Canadians. 

female representation across our team
female representation on our senior leadership team
cultural diversity across our team

Our Core Values

At Chisel AI, we have five core values that guide everything we do. We don’t just have them on a poster. We live them every day. They even steer our recruiting process.

  • Strive for excellence, not perfection
  • Bring your A game to all that you do
  • Never settle for mediocrity
  • Quest for never-ending improvement
  • Strive to set the bar against world class standards
  • Be vulnerable and have the courage to share weaknesses
  • Assume positive intent, and give the benefit of the doubt
  • Actively create (psychological) safety in all conversations
  • Engage in crucial conversations when appropriate – no matter how difficult
  • Confront hurdles without drama
  • Admit mistakes and take responsibility
  • Happiness is when what you think, what you say, and what you do are in harmony
  • Merit is earned, not expected
  • Be direct, and challenge with respect
  • Play for the team, not for yourself
  • Teach what you know
  • Have your teammates back, and know they have yours
  • Seek opportunities to give, and request feedback
  • Help your teammates develop, grow and execute
  • Everything should be made as simple as possible, but not simpler
  • Challenge the status quo
  • Actively seek and explore new ideas
  • Live in the power of possibility
  • Don’t fear mistakes, learn from them
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We have created an environment where there is little fear of making mistakes. Mistakes mean we have taken a risk and learned something in the process. We applaud these lessons and celebrate together, no matter the outcome.”
– Peter Sam Raj, Manager, Product Development, Chisel AI

Benefits & Perks
(We’ve Got You Covered)

Flexible Hours & Location
Work at the office or from home. Canada-wide. The choice is yours. We stay connected using Zoom and Slack (our GIF game is strong).
Stock Option & Bonus Plan
Every full-time employee receives a stock option grant that starts vesting from Day 1. You won’t just work at Chisel AI, you’ll own it.
Hands-on Mentorship
Work closely with seasoned leaders who take time to mentor and offer valuable career support.
We Care about Your Wellbeing
100% company paid family health benefits from Day 1, with a flexible Health Spending Account.
Your Mental Health Matters
Unlimited professional mental health support and counselling is available to all full-time employees through our health benefits program.
Work-Life Balance is Key
4 weeks' vacation for all full-time employees. Additional “I Need Time” days to take care of everyday life stuff.
Your Choice of Equipment
We all have our thing. You can choose between a Mac or PC.
Just Hanging Out Together
Monthly townhalls (UberEATS lunch on us), coffee talks, Friday Happy Hour, holiday celebrations, and more (all virtual now to keep us safe).

Why People Like You
Love Working at Chisel AI

Section 12_RASHMI
Before joining Chisel AI, I worked in underwriting for several large insurance companies. It’s rewarding to have an opportunity to create and build something big for this industry. There is so much scope and potential to bring in new technology to digitally transform insurance, and that’s what excites me the most about working here."
– Rashmi Gupta, Customer Success Analyst, Chisel AI
Section 12_DAVE
Developers at any stage in their career can enter the world of AI, grow their skills and advance in every way when joining Chisel AI. It’s a safe space and provides opportunities for mentorship and cross-functional collaboration with experienced developers."
– Dave Mariano, Software Developer, Chisel AI
Section 12_ANA
I started working at Chisel AI part-time as a data labeller while completing my education. This was an amazing hands-on introduction to the company and the world of AI. Not only was the technology intriguing, but the team was very welcoming, so when a full-time opportunity came up to join the development team, I jumped at the chance."
– Anastasia Nesterenko, Software Developer, Chisel AI
Section 12_RADHA
Prior to Chisel AI, I worked for two leading insurance carriers, so I’m familiar with the pain points in the industry. I’m excited to be part of the team that is delivering powerful new capabilities to streamline core processes and make critical data more accessible. I wish I’d had a solution like Chisel AI when I was an underwriter."
– Radha Maharaj, Customer Success Analyst, Chisel AI
Section 12_GEORGE
Mentorship is a significant component of working at Chisel AI. Our senior leaders and experienced developers are accessible and generous with their time and share their perspectives to help drive our professional growth."
– George Hanna, Technical Product Manager, Chisel AI

Are You Awesome?

Check out our current open roles. Don’t see your dream job listed? Email us at and tell us why you want to work at Chisel AI.

Think Insurance is Boring?
Think Again.

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Without insurance, roads don’t get built, people’s lives don’t get put back together, businesses don’t get established – it’s so important. When I think about the millennial and post-millennial generations and their values, the insurance industry really represents an attractive career where you can make a difference in this world. So, I’m very excited about insurtech and what it’s done in attracting talent into our industry.”
– Bill Pieroni, CEO & President, ACORD

Productive AI Podcast with Colin Toal, CTO, Chisel AI

Chisel AI’s own Colin Toal shares how we are enabling insurance companies to accelerate the placement process, the business benefits of machine learning, and insights into his own career journey.


How Insurtech is Helping Insurers Attract Fresh Talent

“Insurance is one of the hottest tech places to be in. It’s a place where, as a young professional who is very tech-savvy, you have the opportunity to come, and invent, and create an industry that truly is reinventing itself.”

– Kirstin Marr, Head of Data Solutions, Insurity


The Power of the AI Learning Effect

Colin Toal, CTO, Chisel AI discusses the big challenges Chisel AI is solving for its commercial insurance clients through machine learning and applied AI.