Meet Our Team

Our Leadership Team

Jason McDermott

President and CEO

As President and CEO, Jason has overall responsibility for global strategy, organization, culture, and all aspects of operations at Chisel AI. Named to ACORD’s Top InsurTech Leaders of 2021 list, Jason is an insurance change agent and frequent speaker at industry conferences and events. He brings to the company a wealth of experience from his 30 years in the technology industry, helping early-stage companies scale by realizing their value through strategy, leadership, and innovation. Jason joined Chisel AI in 2018 as the company’s Chief Revenue Officer. Prior to Chisel AI, he served as Vice President of Sales at TECSYS Inc. Earlier in his career, Jason served as Vice President, Finance Solutions for NexJ Systems, and led the financial services delivery practice for insurance and finance industry leader Janna Systems, which was purchased for $1.4 billion in 2000. An avid skier, runner, swimmer, and cyclist, Jason actively competes in triathlons including ITU World Triathlon Grand Finals in Chicago and London. He holds a B. Math from the University of Waterloo.

Colin Toal

Chief Technology Officer

As CTO, Colin is responsible for the company’s product vision, roadmap, and long-term strategy. He is a seasoned software industry executive with over 20 years of experience building enterprise SaaS products and high-performing engineering teams at Amazon, IBM, Oracle, Siebel Systems, and most recently A proven technology and organizational leader, his role encompasses leading the company’s growing software engineering, data science, and product management teams with a focus on delivering exceptional results for customers. He is a recognized thought leader on the role of emerging technologies including machine learning and natural language processing in digitally transforming data-intensive industries like P&C insurance. Colin holds a BA in Computing and Communication from Wilfrid Laurier University. When he isn’t obsessing over how to make commercial insurance easier for carriers, brokers, and policyholders, he savors spending time with his superhero partner and their daughter.


Pearl Chiu

Vice President, Operations

As a strong advocate for people and cultures that foster great teams, Pearl oversees business operations, human resources, customer support, and finance. She is responsible for ensuring that Chisel AI’s systems and processes scale with our rapid growth, and all key resources are optimized. No stranger to scale-ups, before joining Chisel AI, Pearl was at OneEleven where she worked with a community of more than 50 emerging tech startups to help them grow and scale their teams. Pearl holds an Honors Bachelor of Science degree from the University of Toronto. When she’s not working, Pearl spends as much time as possible adoring her husband, their two wonderful daughters, and a new chocolate lab puppy named Shinny. Pearl also puts in a lot of hours in hockey rinks, as both daughters play hockey, and Dad is a coach for their teams.

Rupin Mago

Vice President, Sales

Rupin is passionate about solving customers’ challenges related to digital transformation. As a trusted advisor to customers and partners, Rupin’s core competencies include change management, enterprise solution selling, channel sales, and all things AI and insurance. A proven cross-functional leader, Rupin brings deep industry and technology domain experience to his role including AI, machine learning, file analytics, unstructured data, robotic process automation, big data, and information management. Before joining Chisel AI, Rupin was VP Sales, North America at omni:us, an insurtech focused on claims automation with AI, where he led the company’s go-to-market strategy for expansion into the North American insurance market. Prior to omni:us, he was VP, North American Sales at Adlib Software, a technology company focused on converting documents to PDF for enterprise clients in the insurance, banking, life sciences, and energy industries. Rupin’s interests outside work include spending time with his wife and three little humans, basketball, and travelling – he’s racked up 600,000 miles with Air Canada alone.


Hélène Barrette

Director, Customer Success

With more than 20 years’ experience in customer success roles helping financial services and insurance companies navigate their digital transformation journey, Hélène is a strong customer advocate, responsible for the satisfaction, loyalty, and advocacy of Chisel AI customers. Prior to joining Chisel AI, Hélène managed a portfolio of projects for TECSYS, and held the role of Vice President, Professional Services for NexJ Systems, where she led large, fully integrated CRM platform conversions. Hélène also held senior roles at Camilion Solutions (SAP), INEA (SAP) and Janna Systems (Siebel). Hélène holds an International MBA from the Schulich School of Business. A keen outdoor enthusiast, when Hélène is not visiting customers, she can often be found camping, hiking, and cycling.

Board of Directors

Chisel AI has some of the leading minds in artificial intelligence and insurtech as our trusted advisors.


Nick Beim 299 x 299
Nick Beim
Partner, Venrock
Brian McLoughlin 200 x 200
Brian McLoughlin
Partner and Co-Founder, MTech Capital
Ajay Agrawal
Professor at Rotman School of Management, University of Toronto, and founder of the Creative Destruction Lab
Jason McDermott 200 X 200
Jason McDermott
President & CEO,
Chisel AI