Interview with Craig Miller, Staircase Ventures Advisor, on his professional story and advice for startups

November 22, 2023

The Advisor Series – Featuring Craig Miller

Staircase Ventures has an outstanding team of advisors supporting our portfolio companies. In this blog series, we want to introduce you to each of our advisors, share their stories, and highlight some of their insights and advice they have on building startups. 

First up is Craig Miller. Craig is the former CMO and CPO of Shopify. During his tenure at Shopify between 2011 and 2020, Craig was the driving force behind the company’s growth from roughly 15,000 small businesses to over 1,000,000. Before Shopify, Craig had joined Kijiji Canada as its fourth employee and helped grow it to one of the most visited websites in the country.  Suffice it to say, Craig has endless wisdom to share with founders when it comes to marketing, product and growth.

Robbie Marks, Associate at Staircase Ventures, had the opportunity to sit down with Craig to discuss his journey at Kijiji and Shopify and what advice he has for startups today. The overall message was to keep it simple, fail fast, and always remember to use a feedback loop. 

Kijiji’s Early Days

Robbie: How did you end up landing your job at Kijiji?
Craig:They were looking for someone to be a developer and business analyst. At the time, I had no idea what that even meant, but I taught myself how to code when I was a kid and so I applied. My interview, which happened to be in a bar with 2/3s of the team, ended up being all about how Kijiji could get more traffic from Google and paid search. I got the job and instead of being a developer and business analyst, they asked if I could also help figure out marketing. So, I worked on SEO/SEM and took the site from infancy to being one of the top 10 sites in the country.
Robbie:I understand you have an engineering degree, when did you learn about Marketing and SEO/SEM?
Craig: To be honest, I’ve never read a marketing book, nor taken a class in marketing. When I was in university, I set up simple web pages with affiliate links to other companies and the next thing you know I was receiving cheques in the mail. I discovered I accidentally created a decent business doing this stuff. 

Shopify and the “P.S. that Changed Your Life”

Robbie: I’ve been told that you have a truly unique experience with how you ended up at Shopify. Can you tell us more about that?
Craig:Someone had reached out to me on LinkedIn asking some marketing questions and so I thought “Why not take the meeting?”. Turns out, it was a recruiter. Funnily enough, I thought they were talking about Spotify for the first half of the call. I eventually met with the leadership team in Ottawa and was inspired by what they were building. It was still early days, there were maybe 50 or 60 employees, and the company was just about to do its Series B.    Everything about the role sounded great, but they wanted me to move to Ottawa… I had no interest in moving to Ottawa because my family was in Toronto. So, I sent them an email saying “Sorry, it’s not for me, but here’s a bunch of things you should do anyways”, because if I took the job these would be things I would do on the first day.    A week later I got a call and they said “Hey, maybe we can make this Toronto thing work”, and the rest is history. 
Robbie:I love this story and I think it exemplifies Staircase Ventures’ value of a “give-first mentality”. Your intentions were simply to offer advice and give some suggestions to the team after declining their job offer. 
Craig: Yes, exactly – I was truly just trying to be helpful, even if there was nothing in it for me.

You can see Craig’s email to the Shopify team here.

Advice for Startups

Robbie:When you’re advising startups, what do you typically see as their biggest struggle?
Craig: For most of the startups that I work with, their biggest struggle is that they’ve built something and no one is using it.
Robbie:How then should founders think about getting more users?
Craig:They should start by thinking of their business as being incredibly simple. Think about “Who are your customers (or who do you want them to be)?”, “What is your product/how does it solve a need?”, and “How do you make money?”. Once you have a clear understanding of these three questions, you’ll then be able to start seeing growth.
Robbie:Why do you think this initial growth phase can be so challenging for founders?
Craig:People often like to work in “the known”. For founders, the known is what you want to build. On the other hand, the unknown is how you’re going to get people to use that product. Working in “the known” is much more comfortable, so founders often just focus on that. You should focus on the thing you’re most likely to fail at first: getting people to use your product.
Robbie:Why is it so important to build an initial base of customers?
Craig:When I joined both Kijiji and Shopify, the first thing I focused on was getting as many people as possible to use the product. This was critical for both companies. Once you have a sufficient number of people using the product then you can start to think about “Where does the product go next?”.
Robbie:What are some of the best ways to get people to use your product?
Craig:I think the concept of a feedback loop is the most important thing for founders. Do something. See if it works. If it works, do more of it. If it didn’t work, do something else. So few founders close that loop and properly measure it. Rather, they just do a lot of work, running around doing different things all at once.    Sometimes I’ll ask founders what’s making an impact and they say they don’t know. That’s scary to me. If they do know what’s making an impact, I often find it’s just a few things making the biggest impact. So, my advice to founders is to focus on those few things that are making the biggest impact.   For example, many companies I work with spend lots of money on online advertising, but they don’t know if the advertising is driving new customers or revenue growth (or whatever metric they should be tracking). My advice is to stop spending that money immediately, set up a proper feedback loop, and track what is making the biggest impact.
Robbie:Do you have a final piece of advice for entrepreneurs?
Craig:Speed should be your advantage. If you’re spending all your time thinking about what to build, you’re not building it. You have the freedom to fail. Because if you fail, it’s all okay, no one cares because you’re small. Learn from that failure and move on. Build your product and get people to use it! 
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