About
Connor Wilson
I was told no one would take me seriously without a website, so here's my website.
🌱 I'm Connor, a Serial Founder with an 8-figure exit.
- I grew a marketing software startup to $3.4mil in annual recurring revenue without investors in 3 years, helping 15,000 small businesses grow in the process. We sold the business in an 8-figure exit in 2021.
- We also won the New Ventures BC Award, and made the Ready To Rocket list of the fastest growing companies in BC.
- I'm the Founder and CEO of Pilot (pilotplans.com), multiplayer consumer AI for travel: where groups plan, decide, & book trips together. He’s a 3x founder with a $30M bootstrapped SaaS exit and early travel unicorn experience. Now at Pilot we're centralizing everything needed to make trips happen in one place, and with it the intent and group data needed to power AI that incumbent OTAs covet but weren’t built for. CA$2.2M raised. As of this writing, more than 120,000 travelers come to Pilot to book and plan their trips. We've been featured in articles in the Washington Post, Techcrunch, WIRED, and the Vancouver Tech Journal.
- I was also listed on FoundersBeta's Top 30 under 30 list.
- I'm a C100 Fellow. In their words "selected from a pool of hundreds of nominees, [with] the potential to shape the future of the entire Canadian tech ecosystem."
📚 I also advise startups & entrepreneurs for fun
- I advised the CEO of 150-person fintech company with $90mil in revenue on their Mergers & Acquisitions strategy, previously leading their growth to help them get on the list of Canada’s Fastest-Growing Companies.
- I'm an alum and previous mentor for the NEXT Canada startup accelerator.
- I was a judge & mentor for the New Ventures BC Competition in 2025.
- I occassionally give free mentorship to entrepreneurial students and professionals from underrepresented groups. Learn more here.
- For everyone else (unless we work together), I offer paid mentorship here.
📈 And, I'm pretty good at digital marketing, growth hacking, product and people management.
- +13 years experience leading and growing startups
- UBC Sauder School of Business Education, Dean's Honour Roll, with a focus on software entrepreneurship and computer science.
- Mentored and educated by Harvard MBA professors, and top entrepreneurs
- Ran a micro-influencer event marketing agency in university that served top brands like Molson Canadian, Red Bull, and Jägermeister, with teams across 12 cities.
- Prior to being a Founder I was an early employee at Sonder, which went on to become a publicly traded unicorn (+$1bn in valuation) hospitality startup.
💖 Lastly, people seem to like working with me, which is cool, because I like working with them.
- As told by more than +33 positive reviews and testimonials (see below) from past clients, co-workers, teachers, mentors and managers.
- My investors for my current venture (Pilot), include past employees from my previous startup, investors through the various startup accelerators and incubators we were in, other angel investors, as well as a few funds, such as AngelList Quant Fund.
👋 The purpose of this website is to give prospective employees, investors, and mentees some context as to who I am, and how I can help.
I'm big on transparency, including making public everything from personality test results, management style, interests, and more.
You can read more about what working with me is like ➡️here.⬅️
My sole purpose in life is to help as many people as possible in as big of a way as possible and have as much fun doing so along the way.
Outside of work I've traveled to 31 countries (and 15 states & provinces), solo and with friends/partners. It's my favorite pastime. I also love being social with friends, soccer, skiing, boating, waterskiing, beach volleyball, reading, video games, hiking, working out, and flying.
NFX Signal
Connor is a true leader with the ability to put his vision into action. As an advisor to Next 36 portfolio companies, I was introduced to Connor by an internal connection in the program. Despite his background being more focused on the Growth/Marketing side, he has proven his ability to lead the company more holistically by also tackling: Operations, Product, Design and Engineering. I'm excited to see the company continue its growth heading into the new year!
December 31, 2021
Wellfound
Having worked with Connor for the past 7 months I can say with some certainly that he is the most hard-working individual I've ever met. He is dedicated, meticulous, intelligent, and he is always searching for a better way to do his work. He thinks well across the spectrum, from systems design to detailed implementation, drawing from a well of ideas dug deep through experience and education. His policies and methodology regarding hiring have brought great talent to the company, his engagement with our userbase has fostered genuine advocacy for the company, and his sales calls are works of art.
December 31, 2021
Wellfound
There are very few people who combine infectious enthusiasm, an analytical mindset, and a "get it done" attitude like Connor. He raises the bar for everyone he works with — and helps them exceed it. Work with Connor and you'll see tremendous growth within your company (and within yourself) every few months. A superb leader, adviser, and thinker.
December 31, 2021
Wellfound
His optimism was inspirational and his critical thinking was crucial to our operations and to my position as Human Resources Director. He made it his goal to make sure everyone had growth and learning opportunities within the company, and the company is much better off today because of that goal.
December 31, 2021
Wellfound
“Insanely talented” is the first thing that comes to my mind when I think of Connor... His enthusiasm, work-ethic and willingness to learn was contagious and always made me strive to do better and learn more. Above all, Connor is extremely personable. While he holds you accountable for your work, he also always provides you the freedom to try new things and be creative. I strongly recommend Connor for any position that needs a driven and passionate leader.
December 31, 2021
Wellfound
Connor is an extremely hardworking and knowledgeable individual. His organizational skills and dedication towards tasks are both inspiring and respectable. His knowledge and skill set regarding business development helped me personally by applying his teachings to my own company.
December 31, 2021
Wellfound
He was always investing his energy in building a sense of community in his team. I would definitely say that he has is skilled communicating ideas and getting people onboard projects.
December 31, 2021
Wellfound
Connor is one of the brightest and most motivated entrepreneurs I've met. He is dedicated and knows how to envision, plan and coordinate a project, end-to-end. I believe he can be a valuable asset to any company.
December 31, 2021
Wellfound
He is dedicated, highly ambitious, and always thinking of the future. This is a guy who regularly thinks in big ideas, and then will follow up on those big ideas by making a detailed plan on how to go about achieving them.
December 31, 2021
Wellfound
Working with Connor forced me to observe his unmatchable ambition and commitment to all he is involved in. Connor does not disappoint in tasks he commits to and is a great addition to any work environment.
December 31, 2021
Wellfound
Conner was a pleasure to work with and had outstanding customer service.
December 31, 2021
Wellfound
Connor was an absolute pleasure to work for! He is a natural born leader and has a knack for bringing out the best in his team. Connor thrives in dynamic work environments and takes a proactive, solution-oriented approach to problems. He is a constant source of motivation and provided me with an invaluable work experience!
December 31, 2021
Wellfound
I have met with Connor several times seeking his advice on various professional matters and each time I am overwhelmed by his motivation, broad knowledge and passion for all things business. A future leader for sure!
December 31, 2021
Wellfound
I've known Connor for a while now and if there's one thing I know for sure about him is that he hustles. He knows how to scale a business and would be an excellent addition to any team. I would definitely recommend him.
December 31, 2021
Wellfound
Connor is one of the most organized and dedicated entrepreneurs I know by far.
December 31, 2021
Wellfound
Connor is one of the hardest working, and brightest individuals I've met. What strikes me most about Connor is that he's innovative, extremely strategic, and an assertive leader.
December 31, 2021
Wellfound
He is always in the mode of looking for innovations and progressive ideas for the businesses that he takes care of. And nonetheless, he is also one of the most hardworking people I've ever known who would choose work over sleep.
December 31, 2021
Wellfound
Consistently thorough with his data management, there is never a reason why ideas didn't have a proper executable form to Connor. This approach to the business became contagious among his employees, whom he considered partners. Moreover, there was always something to learn from him, and he was always willing share his insights.
December 31, 2021
Wellfound
Connor was one of the first people I had the pleasure to work alongside after moving to Vancouver. He was always the man you would talk to if you needed anything answered because of his apparent leadership. Connor is an extremely dependable person. He is an opportunist that is constantly looking for ways to better himself and his employers. No matter the occasion Connor will will always thrive and i'm adamant he will be a great fit for any occupation he desires.
December 31, 2021
AngelList
I worked with Connor closely over a couple of years and in that time I have never met someone more dedicated to succeeding and creating a positive environment than him. Our work saw many ups and downs, yet he never strayed or swayed from his work ethic and objectives.
December 31, 2021
Manufacturing Process Engineer
Connor is a brilliant problem solver, even while under immense pressure in a very dynamic environment.
December 31, 2021
General Manager
Connor was a key contributor to the success of NiceJob helping take it from a startup to a successful SAAS business. He has a rare combination of skills: a deep understanding for marketing and product and how best to work with both to create a winning game. I’m confident he will succeed in his next adventure.
September 12, 2021
Full-Stack Developer, Architect and Technical Lead
Connor is a phenomenon; every encounter is a learning opportunity. He excels at establishing product-market fit and building realistic, data-driven growth strategies. At NiceJob, he has built a culture where everyone is equally focused on helping each other and building something incredible. Any company with a goal to rapidly grow their business will have much more success if partnered with Connor. I would not hestiate to work with him again.
September 1, 2021
Partnerships Coordinator at NiceJob Inc
When it comes to leadership and growth, Connor definitely earns my highest recommendation. From an operations standpoint, Connor is always about efficiency, growth and making data driven decisions. On a leadership level, he genuinely cares about his employees and imparts knowledge to them. His dedication, passion and employee empowerment are very contagious and anyone looking to have a driven leader would always want him on their team
August 30, 2021
Marketing Specialist, NiceJob Inc
It's difficult to write a full review on Connor because in my time working with him there wasn't anything he couldn't help with or collaborate on. What I appreciated most about him, though, was his ability to bring a team together. Connor has a knack for recruiting great people and makes them feel valued and capable from the get-go. He empowers people to make decisions but is always there for guidance or just a chat! Connor leads by example and his enthusiasm and dedication is contagious and motivating. I was lucky to work with Connor for even a short bit of time and have no doubt he'll bring the same attitude and work ethic to any company he starts or works with!
August 27, 2021
Product Manager at Paystone
Connor is an excellent entrepreneur and has a spreadsheet ready for any question! He is dedicated, intelligent, and easy to talk to. He is skilled in welcoming new team members as well as building community with the whole team.
August 27, 2021
Account Executive
Connor is a great leader and team player. He is always there to help solve a problem and come up with the best possible solutions while supporting the team. It was a pleasure working with him and a great learning experience!
August 27, 2021
Senior Product Manager (NiceJob) at Paystone
Connor's approach to his work is such that he always endeavours to (and succeeds in) being the expert in whatever he is working on. He is incredibly curious and thorough in his research, leaving you confident that whatever opinion he has on the matter at hand is very informed. What I also really respect about Connor is that he is not just a hard worker, but a smart worker. His output is truly admirable and the combination of work ethic with efficiency (plus a huge amount of drive) is what I believe has made Connor as successful as he has been to date, and makes him someone you always want on your team.
March 2, 2021
Digital Marketing Professional | SEO, Website Strategy, and Inbound Sales
Connor is an exceptionally motivated individual who impressed me as soon as I came aboard to the marketing team at NiceJob. Joining a startup company, I wasn't sure how comprehensive their operations & infrastructure setup were going to be but Connor had almost single-handedly strategized and implemented everything down to the smallest details. He's very analytical, goal-driven, and managerial. Connor distinguishes himself by his passion for always exploring new ideas and learning best practices to avoid stale revenue metrics—he zealously wears his growth mindset on his sleeve and entrepreneurs take notice.
March 1, 2021
Manager, Relationships at NiceJob of Paystone
I have had the privilege to work with Connor for the past two years, in which those two years he has been a great mentor to me. He is extremely approachable, and with a vast knowledge in Sales and Marketing, he always provides strategies that help my team grow. I appreciate how much dedication he has, and I am often impressed at how much time he dedicates to his professional growth, which results in growth to those around him.
March 1, 2021
Process Automation Expert
He has vision, he recognizes talent, he is always in sight of the bigger picture, and I would not bet against his success regardless of industry, competition, or setback.
October 25, 2020
Content Marketing Intern
Thank you so much for giving all of us useful tidbits of information about literally every business area ever! You are an amazing all rounder and an even more amazing leader!
October 9, 2020
Associate Product Manager
Your passion, drive, and work ethic is inspiring and I am so glad so have a mentor and friend like you!
October 9, 2020
Product Manager, HappyHour
This man is in fact a brilliant strategist and thinker, an excellent leader and a wonderful friend. Thanks for your friendship and mentorship Connor.
October 9, 2020
Marketing Intern
Thanks for being such a good mentor and taking a chance on me. I appreciate all the times you spend helping and guiding us in succeeding in our roles.
October 9, 2020
Software Engineering Intern
I remember the day you interviewed me, i was like .....OMG, he is too cool to be a boss.. 😁 I am really grateful to you as you gave me the chance in this hard time. You are super cool and i love how you treat your team as your buddies.. I am trying very very hard to make your vision come to life. You are a great Entrepreneur and one of most talented person i have met (digitally) in my life.. 😁 So great to work with you and there is so much to learn from you.
October 9, 2020
Product Chief @ Paystone & NiceJob
Connor is a very gifted analytical and strategic thinker. He has a voracious appetite for data, and has the unique ability to translate data into actionable opportunities. Connor is driven, loyal, and intelligent. A knockout combo. We're privileged to have him as our friend and on our team.
April 10, 2020
Data Engineer at Chelsea Football Club
Connor is a natural leader and working with him was a pleasure! He has a problem solving attitude and always gets the job done!
February 5, 2019
Customer Success Director at NiceJob
Working with Connor at NiceJob has been an absolute pleasure! It wasn't easy for me to step out of my old career and start again but he has been more than supportive, always eager to teach whenever I have a question. I am regularly impressed by his fount of knowledge and his ability to analyze problems. He has done an amazing job of building NiceJob from the ground up and am ecstatic to see where the future takes us :)
February 4, 2019
CPA Candidate with the Western School of Business
At such a young age he has achieved so much as an entrepreneur. Working with Connor made me quickly realize what a good leader he is. He holds you accountable for your responsibilities while giving you all the room to navigate in your own manner.
January 13, 2017
Sessional Lecturer, UBC Sauder School of Business
Even though this course was an elective for him, Connor stood out as THE top student in a class of 95 students - his achievement in an IT class is noteworthy considering that some of the students had previous background in computer science and business technology management - his A+ in the course is evidence to that fact. I had a few conversations with Connor outside the classroom; he showed me the 'blueprint' of some of his business ideas and asked for feedback. The thoroughness of his analysis, as well as the balance of ambition and realism in his plans made me believe that Connor would go very far! I recommend him without hesitation.
August 1, 2016
UX Designer at M&G plc
Something that quickly became apparent about Connor was his ability to communicate his vision for the company and get others on board with ideas, which undoubtedly has helped to create a committed team behind him. Connor’s work ethic is remarkable; never have I worked with anyone that displays the same level of dedication and concern while managing a team.
February 17, 2016
Frontend Developer at Thought Shop Creative Inc
Working under Connor was a great experience. Truly a force to be reckoned with.
April 2, 2015
Teacher at North Vancouver School District
During Connors grad year at Argyle he exhibited strength within all of his subject areas. He was an A student in the academic areas of English, Literature, Pre-Calculus, Calculus, Physics, History, Marketing, Accounting and Band. His excellence in academics was consistent throughout his secondary school career, which has landed him on the honour roll with distinction multiple times and the marketing award in grade 11. Connor was always one of the first students in class, prepared, focused, eager, ready to learn new material and manages his time effectively. He demonstrates strength within the subject areas of Marketing and Accounting while often relating the material to related business areas and real life situations. His ability to do so comes from his ability to manage his time efficiently. Connor's personal characteristics will undoubtedly bring him to success in his business career. I happily give Connor my recommendation.
November 11, 2014
