10/08/2020: QTMA is very fortunate to have had the opportunity to chat with Chris Grouchy (COMM’16), the co-founder of Convictional, a start-up that came out of Y-Combinator. Convictional is an e-commerce platform that helps suppliers sell to all of their business customers. This is realized through Convictional’s multi-channel B2B commerce platform.

What’s your background?

  • Worked many labour jobs throughout high school to pay for university (started a landscaping business)
  • Became involved in student leadership and was the youngest elected student trustee for his school board
  • Earned $118,000 in scholarships (including the TD scholarship) to study at Queen’s Commerce
  • Early experiences taught him resilience and that you have find opportunities for yourself

What’s the story behind Convictional? How did you come up with this idea?

  • Chris had previously worked at Cisco where he developed his love for enterprise software
  • Also worked at Shopify where he saw the huge opportunity in e-commerce
  • Noticed that a big problem that many suppliers faced was supplying to retailers, he did not see any pre-existing solutions in the market
  • Conducted TONS of customer research and realized that there was a large market willing to use this hypothetical service

Getting Convictional started with Y-Combinator

  • Y-Combinator (YC) is a seed startup accelerator that invests $125k into worthy startups
  • Chris (and his co-founder Roger) applied to the Y-Combinator program and were invited to California for an interview
  • They pitched Convictional to their panel of interviewers; Michael Seibel, Kevin Hale, and Kat Manalac
  • Super hard interview, their interviewers really grilled them with questions
  • Convictional was invited into the YC program; their interviewers saw Chris and Roger’s passion and commitment to their start-up
  • YC offers tough love: they give specific, direct advice on how you can grow your start-up
  • YC is not pessimistic or unfair, but they don’t sugarcoat their advice
  • TechCrunch selected Convictional as one of the top 10 startups that pitched to YC

Is it important to learn sales skills as a founder?

  • Sales is the backbone to the growth of a start-up
  • As a founder, it’s CRUCIAL to learn how to sell and how to position your product to potential customers
  • To hire a team and to grow the company, you also have to sell to investors to convince them to invest in your idea
  • If you don’t get your product out there and sell, you won’t grow your company, no matter how great your product may be
  • By getting your product to potential customers, you can get their feedback, modify your product accordingly, and achieve product market fit
  • Sales is not something you can learn overnight, it’s an ongoing learning process
  • Real world experience (ex. working as a sales intern) is the best way to grow your confidence in sales
Without sales, you will end up building something for nobody, [...] that’s the poison pill for start-ups

What is product market fit? Why is this important?

  • Product market fit: building something that people want
  • Ex. A product has product market fit if someone would be upset that you took that product away from them
  • Strong indicator of product market fit is when people are willing to pay for your product
  • Goal of any start-up is to achieve product market fit, this means that there is a large demand for the product
  • For customer research, Chris suggests i) building a list of potential customers, ii) cold-emailing them a personalized message, iii) scheduling a meeting to talk if they are interested, iv) during the meeting, ask questions and ask for feedback
  • By talking to potential customers in your target market, you can learn how to improve your product and achieve product market fit

Battling imposter syndrome

  • Super common for young entrepreneurs (including Chris) to have imposter syndrome
  • However, these feelings may affect your confidence and prevents you from achieving your full potential
  • It’s very challenging to put yourself out there and to take risks, but you’ll never know if you never try
[Imposter syndrome] is there to protect you from being eaten by the lion, but there’s no lions

Taking the leap from working at Shopify to starting your own company

  • Chris gave himself a clock; he would save 2 years worth of money, and spend the following 2 years starting his company
  • If he didn’t succeed within 2 years, he would rethink his plan
  • Important to have a solid plan and course of action before committing (while being practical about your financial situation)
  • Startups are often a really good place to get an outsized level of responsibility and to learn a lot very quickly. Some of the best people at larger companies are the ones who decide to make a leap and jump to start-ups anyways. This advice to go work at a start-up particularly applies to 1st and 2nd years; the outsized responsibility you take is a good mark on your resume for all types of jobs (exception to finance, where people just look for finance internships)

How do you prioritize your activities?

  • Each founder can only focus on 1-2 priorities at one time, any more and you’ll dilute your focus
  • Priorities of founders are centered around mitigating the risks that surround the company
  • Start planning from the annual level; what goals do you want to achieve this year?
  • Break up your annual-level plan into quarters, then into weeks
  • Chris uses Sundays to time-block his calendar for the following week

Any parting advice?

  • When entering the workforce, pick the position where you will the learn the most in the least amount of time
  • Additionally, when finding a job, pick someone you want to work with and learn from as your boss
  • When working on a start-up idea, don’t waste your time building a pitch deck or financial model, what you should be doing is talking to potential customers
  • BUILD YOUR NETWORK; many of Chris’s early employees came from his network


  • Paul Graham Essays (Schelp Blindness, Hiring is Obsolete)
  • Getting Things Done - David Allen
  • Influence: Science & Practice - Robert Cialdini
  • The Effective Executive - Peter Drucker