How We Landed One of Canada’s Most Sought After Engineering Leaders

When I saw this pop up on my LinkedIn newsfeed on July 1 earlier this year, I knew I had to reach out.

Ian Logan was an early Airbnb engineer (the 8th to be exact) who scaled with the company for over 6 years leading as a Director of Engineering. When he joined, the company had just moved out of the founders’ apartment. He helped automate customer support with engineering, built out the fraud engineering team and ultimately led all payments engineering. He also impressively managed double digit percentages of the engineering staff (ranging between 10–25% throughout his tenure ) at the high growth company. He helped to recruit hundreds of engineers at Airbnb. He is truly one of a kind.

We’ve all heard the saying: build an A-team and they will attract more A-team players. Ever since starting the company, we’ve had a relentless focus on not scaling too quickly and making sure we are extremely selective with who we hire. Many companies at our stage of funding often have a 50+ person headcount; we’ve kept and maintained ours at 20–25. We heavily guard our culture to ensure that as we scale, our culture scales with it.

Ian and I finally met on August 30th 2017. He came by our offices in Toronto. For someone as accomplished as him, he was extremely humble. I showed him what we were doing and he compared a lot of it to his early days at Airbnb. He even started to “sell” himself without knowing it. But we both quickly agreed that neither of us wanted to rush into anything. Like being asked to the prom, I wanted to make sure that we would be the right “date” for him. So I offered to introduce him to some of Toronto’s best tech companies so he can “date” around first.

Ian’s LinkedIn post sparked over 70 private and public responses, messages and emails — all before he even moved back to Toronto. Once he moved back, he met with 20 CEOs and founders and 7 local venture capital funds. He even met with one of the Dragons from Dragons Den. He was exploring a potential role as either a CTO or VP Engineering. I knew he was a hot commodity; so how did we end up winning him over?

“If you want to go quickly, go alone. If you want to go far, go together.”

Drop Culture, Values and Vision

I’m a big believer that people drive companies. There are a ton great companies in the country and a ton of really smart people. Along the way, I was sure that Ian was going to meet with the city’s top founders, CEOs, business executives and investors. At Drop, we built one of the fastest growing consumer tech companies in the country based on our company culture. We move fast and we move together. In investor pitches, I actually highlight that as one of our core competencies and areas of defensibility.

So a month after meeting Ian for the first time, I decided it was time to re-engage with him. So I sent him this note:

Our key selling points

Ian and I met again on October 3rd for the 2nd time. Over the next few weeks, we shared with him information about the company. We even invited him to meet with one of our potential investors. We gave him access to the guts of the company. Ian officially signed with us on November 18.

We debriefed afterwards on the whole process and what made Drop the “date” he wanted to take to the prom. It ultimately came down to four main things:

We sold the big vision

Candidates like Ian have all the choice in the world. After leaving Silicon Valley and moving back to Toronto, he was looking for the next “Airbnb” but in Canada. I’ve been told by many investors in the valley that often times, Canadian founders lack the big “vision”. Being a serial entrepreneur, we started Drop with a big bold vision — we wanted to build the first mainstream intelligent rewards program.

Google allowed marketers to target based on how people spend their thoughts; Facebook allowed marketers to target based on how people spend their time; Drop allows marketers to target based on how people spend their money”

We sold on both company and personal values

Despite conventional thinking, Ian didn’t move back to Canada because of Trump; he moved back because of family. Like a few other people on our team, he moved back looking for the same fast-paced, high growth culture that he experienced at Airbnb. When we spoke about the opportunity, we never really focused on the cliches like the “market opportunity” or “revenue projections”. We focused on our company values:

Drop’s company values — the raw, original PowerPoint smart-art version

Every person that we hire must exude these core values. During all the times we met, we both recognized the importance of these traits in our careers and also daily lives. We had a scrappy, entrepreneurial culture and this resonated with him. Not only that, we also promote work-life balance and being a new father, Ian saw this with some of our employees who have been balancing Drop and parenthood.

I am a big believer of bringing in potential candidates to experience the culture of the company prior to joining. We often bring in candidates on Thursdays when we have our team socials. That way, both parties can mutually gauge whether there is a culture and personality fit.

We treated him like a potential investor

Every hire should buy in to both the vision and underlying business. We pride ourselves in an extremely transparent culture. We are very open with our team on all aspects of the business: strategy, hiring, firing, and even cash run-way. Shortly after we met on October 3rd, we started sharing with Ian our company materials: investor pitch decks, sales decks, marketing decks, and even some of our board materials.

Every addition to an early stage company should look at the opportunity like an investor. One should only join a company only if they would invest their own personal money into it.

We didn’t hide anything and I truly believe that it is important to have full transparency around both the massive opportunities and on-going challenges. It’s often the challenges that get people most excited. Especially if they’re relevant to their past experiences.

Both Drop and Airbnb share similar opportunities and challenges

When hiring senior talent, especially at the stage that we’re at, they shouldn’t be brought in to “fix” things. They should be brought in to scale things. Just like Airbnb, Drop has a massive opportunity. Airbnb benefited by the increasing openness of consumers to share their homes; Drop is benefiting by the increasing openness of consumers to share their financial data.

However, every start-up has its challenges. Since the beginning of this year, we have 10x-ed all our major metrics (users, revenue, etc). This has brought us “scaling” challenges within areas like customer support, fraud and up-time. These are all issues that Airbnb also faced in the early days. And ultimately these are all issues that Ian was excited to help us solve. But this time with all the knowledge that’s been instilled onto him after seeing Airbnb grow from 8 engineers to now over 800.


What’s next?

We’re excited to welcome Ian Logan as VP Engineering to our team. (you can get a first-hand account of his side of the story here). Not only do we think he will add tremendous value to Drop, but we also know that we will bring a wealth of knowledge and experience to help scale the Toronto tech ecosystem. Like many others, I believe that Canada’s time is now. We started Drop in Canada because we believe that the country can and will be home to many more tech “unicorns” over the next few years; and we also believe that many of them will be consumer technology companies. We’ve even turned down the opportunity to work with some world-class investors because they wanted us to move down south.

If reading this has instilled a sense of excitement in you, please don’t hesitate to reach out to either of us! 2018 will be a very exciting year for us as we look to expand our engineering team by 2–3x and scale our product for our growing community of members. We won’t, however, be leaving our emails here on this post. As I’ve said earlier, hustle is an important attribute to thrive at Drop and we are confident that the candidates we’d like to hire will find their way to us, somehow.

Check out all the career openings at Drop: https://www.earnwithdrop.com/pages/careers

Drop HQ located in downtown Toronto
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