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Craig Hunter
Founder of Dwelling
Toronto, Ontario
Overview
Craig Hunter is the CEO of Dwelling, having previously served as the CEO of Bitmaker, which was acquired by General Assembly. He has a strong background in entrepreneurship and new business development, with a focus on sectors like E-commerce and FinTech, and has invested in companies like Superhuman and Clubhouse.
Highlights of Craig's career include his early involvement with Uber and his successful leadership at Bitmaker, which was acquired by General Assembly. He is currently driving growth and innovation as the CEO of Dwelling, focusing on sectors like Direct-to-Consumer and Real Estate/PropTech.
Work Experience
Partner
2025 - Current
Backing the best founders solving tangible problems that impact us all.
Founder & Managing Partner
2016
Operator invests in startups tackling real world problems. Our backers include founders and executives from Shopify, Uber, Stripe, Wealthsimple, Whatsapp, Rippling, and many more. We've invested in over 100 startups with a focus on fintech, deeptech, marketplaces, and teams tackling particularly antiquated industries. The unsexier the better. 🦕 The Portfolio: · Unit - the easiest way to embed financial services and banking into your business 🏦 ($1.2B valuation) · Boom - building the world's fastest commercial jet 🛫 ($700M+ raised) · Float - Canada’s best corporate card and all-in-one spend management software 💳 ($120M+ raised) · Relay Financial - banking built to streamline your business 🏦 ($70M+ raised) · Superhuman - the world's fastest email app 📧 ($115M+M raised) · Mast Reforestation - tech-powered, end-to-end reforestation company 🌳 ($40M raised) · Gradient - home heaters and air conditioners that are better for the environment 🌬️ ($25M raised) · Inspectify - The better way to do home inspections 🏡 ($23M raised) · CommerceBear - helping furniture manufacturers sell online 🛋 ($10M raised) · Aalo - nuclear reactors that fit in your garage, and can power anything 🔌 ($33M raised) · Daffy - a smarter way to give, the donor-advised fund for you 💛 ($17M raised) · Three Ships - 100% natural, affordable, and results-driven beauty products 🧴 (available in hundreds of Whole Foods + Target stores) · Sanzo - Asian-inspired sparkling water brand 🫧 ($16M raised) · And many, many more
Co-founder & CEO
2020 - 2024
We help you find the downpayment for your first home. 🏡 Get matched with up to $30,000 in down payment assistance from federal, state, and non-profit programs. Backed by Kleiner Perkins, Jack Dorsey, Night Capital, Garage Capital, Hustle Fund, and founders/execs from Ramp, Tinder, Shopify, Wealthfront, Not Boring, Meta, Wave, Skillshare, Morning Brew, Italic, and more.
Dwelling is a tech-powered real estate brokerage that finds buyers thousands to buy a home and makes the entire process incredibly simple.
Fellow - Scale
2021 - 2023
Fellow in the very first Scale cohort (ODS1).
Vice President, Growth
2017 - 2018
Notch (formerly ChefHero) aims to reinvent the food service industry. I invested in their pre-seed round (my first angel investment ever) and was recruited to grow the company from pre-seed to our Series A. Scaled Canada from one vertical to several and laid the groundwork for US expansion, starting in Chicago. The company has raised over $30M from Accomplice, Portage, Garage Capital, and more.
General Manager
2015 - 2017
Original General Manager of the business. Ritual's award-winning app now serves 10,000 restaurants in 50 cities in North America, Europe, Asia, and Australia. The company has raised over $180 million from investors like Greylock, Insight Venture Partners, Georgian, and many more.
CEO
2014 - 2016
Bitmaker was Canada's leading technology bootcamp. The company was acquired by General Assembly - the largest technology bootcamp in the world backed by Jeff Bezos, Yuri Milner, and Maveron. General Assembly was subsequently acquired by Adecco for $413mm in 2018. Our amazing graduates are still building at companies like Shopify, Facebook, Wealthsimple, and most top technology companies.
Marketing Manager & City Launch
2012 - 2014
Joined Uber as one of the first 50 employees globally with just a handful of cities. Wild ride. 🚀
Uber develops, markets, and operates a ride-sharing mobile application that allows consumers to submit a trip request.
Raised $30,212,450,000.00 from PayPal.
Account Executive
2011 - 2012
rTraction is a full-service digital agency serving clients across North America. I specialized in business development, sales, and project management, reporting directly to the founder & President.
Co-Chair
2010 - 2012
TEDxUWO was the official TEDx for the University of Western Ontario. Sold out event (several thousand applications to attend) with nearly 15,000 online viewers in over 80 countries around the world.
Education
Growth Series
2024 - 2024
QuantumShift
2015 - 2015
Investments
Latest Articles
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My last week at Ritual.
Talks about Entrepreneurship, Startups and Tech