How I Landed at One of Canada’s Fastest Growing Startups

Ian Logan
9 min readJan 30, 2018

This past year, I moved on from Airbnb, one of the world’s most innovative companies, and more generally Silicon Valley. I now live in Canada and am the VP Engineering at Drop.

I’ll rewind history before sharing what led me to Drop. Originally from Canada, I graduated a decade ago from the University of Waterloo studying computer science. Immediately upon graduation, I moved to the US to pursue tech opportunities. My story up to this point isn’t unique given the well known Canadian brain drain: over the past couple decades, hundreds of thousands of engineers migrated south in search for tech jobs. I started in finance software engineering on Wall Street building trading algorithms and large scale investment banking applications (i.e. securities lending for BlackRock’s iShares ETFs).

Years into my career I was plateauing in learning and hungry for new challenges, so I decided to do something different and join a startup. In 2011, I joined Airbnb when it had 60 employees and less than 10 engineers. I started as their first payments engineer. Over 6 years, I built a multitude of systems and features to help them grow. I scaled with the company and grew as a leader. As we went from 8 engineers to over 800, I recruited and mentored hundreds of engineers, spearheaded new teams, and achieved Director level leading all of payments engineering. I had a reputation for running tight ships and leading large initiatives. I created a unique culture for payments within the company’s broader culture. The groups I led had high team engagement scores, healthy diversity profiles, modern system architectures, and consistently delivered strong impact for the business and community. I was happy and continuously challenged in my role. So, what changed and why did I move back to Canada?

Airbnb Payments team, circa 2016

One of the quotes I live by is from Gandhi: “Happiness is when what you think, what you say, and what you do are in harmony.” I made the easiest difficult decision of my life — to put family first. My son, Austin, was born in San Francisco but our broader family still lived in Toronto; where my wife, Charry, and I met and our hearts have always been. I grew up in a household and environment with plenty of family around. As parents, we wanted a similar experience for our son at an early and formative stage of his life. I’ve had a history of setting people up for success and I wanted to do the same for him. I announced my decision to move at the beginning of July which aligned pleasantly with the celebration of both countries: Independence Day and Canada Day.

Before moving back to Canada, one of my colleagues said: “Remember Ian, Canada is not the same as Silicon Valley.” Silicon Valley obviously is a place of significant tech innovation but these days isn’t the only one. I was inspired by the possibility of influencing the growing tech community in Canada. I saw the opportunity to cross-pollinate my own experience and knowledge in scaling companies. I wanted to make as big of a dent as possible in helping local innovation. I was now on a mission to contribute to Canada’s startup ecosystem by helping make globally focused companies that are locally headquartered a success. The challenge facing me was figuring out where to go and what to do.

I published a LinkedIn post which kicked off a series of new connections in Toronto. Derrick Fung, the CEO of Drop, happened to be one of those connections who wrote about his side of our story here. My LinkedIn post sparked over 70 private and public responses, messages and emails — all before I even moved back to Toronto. Once I moved back, I met with 20 CEOs and founders and 7 local venture capital funds. I even met with one of the Dragons from Dragons Den. I was exploring a potential role as either a CTO or VP Engineering. I knew there were a lot of opportunities; so why did I end up choosing Drop?

“It takes a village to grow and support an ecosystem.”

Choosing the Right Opportunity

A large part of the compass throughout my career has been to look for hard challenges. Also, I like to think that I’m developing an eye for identifying prospective successful businesses. I joined BlackRock, the world’s largest asset manager, only after being part of its acquisition of Barclays Global Investors. I joined Airbnb when it was a fledgling startup and watched it scale over 100X. Now that I’m in Canada (and in the country’s largest city, Toronto), I want to join its next rocket ship and be an early part of something that will grow the ecosystem.

Toronto has great potential to be a major hub for tech innovation especially in artificial intelligence which is its area of growing expertise. AI is important but I’m never a fan of using a solution in search of a problem. Added to this, I now bias towards consumer tech products because of my past experience and personal joy in delivering value to consumers. Toronto seemed to skew higher in B2B startups which helped narrow my search further. After countless hours of meetings with founders and investors, I found Drop best hit the sweet spot of having massive potential.

Drop’s mobile app

Drop’s key selling points

Derrick and I met several times to discuss current challenges and future opportunities. He’s an experienced entrepreneur with a track record of success. I found Derrick to be an inspiring leader who articulated a strong vision and lived by sound principles. After learning where Drop was headed, it was clear to me that my past experience aligned with their direction. I’m adept to working with millions of financial transactions and in the past led development of a closed-loop loyalty program with a new gift card.

Drop takes a huge leap forward by offering an open-loop program that is consumer led, works magically with cards in your wallet, curates brands intelligently, and delivers instant gratification. Above all else, I chose Drop for four main reasons:

They had a big vision

Drop’s vision is to make life more rewarding. They are building the first mainstream intelligent rewards program. For every employee at Drop, my impression was that work doesn’t get more rewarding than this. I saw the impact and technical challenge of leveraging people’s spending habits to influence behaviour.

The company is still early on its path to disrupting loyalty which is a $40 billion+ market ripe for innovation. They released initially in Canada and soft launched in the US late last year. Given its big vision and current iteration, the product can be more seamless and interactive but that’s where I plan to help. I see a wide runway and level of depth with the potential set of industries that Drop can partner with. Welcoming diverse brands is one clear opportunity. Another is capitalizing on various spend frequencies of wallets to maximize on ways members earn rewards. Drop will empower both members and brands to connect efficiently.

We share a common set of values

Coming from Airbnb, I deeply understood the significance of company values and aligning them with personal values. Being there during its formative stage of culture, I contributed to and exemplified many of its core values, such as: championing the mission and being a serial entrepreneur. Derrick shared with me Drop’s company values: passion, grit, humility, and hustle.

I was pleased to see a company that elevated the importance of an entrepreneurial spirit, egoless leadership, and lively “fire in the belly.” It was a clear sign of a group that focused on getting things done resourcefully while taking on different responsibilities to support each other. I appreciate how Derrick set an aligned cultural foundation for me to amplify and run with as a new role model.

Derrick & I at Drop’s favourite place to get caffeinated, Fahrenheit Coffee

They treated me like a potential investor

I was impressed with the speed and transparency that permeated throughout Drop. Each time I met with Derrick (and every other team member), he erred on the side of sharing more information than not and following up with all of my detailed questions. He connected me with existing investors to give access to different perspectives of the business and its people.

The details shared were not candy coated nor bloated with vanity metrics to lure me in. We held open discussions of existing company challenges that fell upon different time horizons. I was able to quickly identify areas where I would add value and areas of learning opportunity for myself. I’d be joining Drop at about a third the company size compared to when I joined Airbnb (and is my desired trajectory). My excitement gained momentum as I dove deeper into a company that was only 2.5 years old.

Both Drop and Airbnb share similar opportunities and challenges

After learning the ins and outs of Drop, my read was that I’d be coming in to make a strong team even stronger and applying my skills to really scale out the business. This is in contrast to fixing an environment that is broken or debugging a fragile system. Just like Airbnb, Drop has a massive opportunity. Airbnb benefited by the increasing openness of people to share their homes; Drop is benefiting by the increasing openness of people to share their financial data. With my extensive fintech experience, I plan to continue to secure Drop’s systems to protect critical member data while growing the platform to provide rewarding experiences. Fun fact: since Drop innovates on the spend history of millions of members, its scale of transactions already exceeds that of payments at Airbnb.

There are several areas for engineers, data scientists, designers, and product managers to innovate on at Drop. Some examples include: user acquisition (how do we effectively boost organic growth and unlock mass virality?), discovery and personalization (given a large supply of offers, how can we surface relevant connections between brands and member personas?), gamification (how do we productize making life more rewarding and fun?), transaction processing (how do we scale data infrastructure to stream and gain insight upon hundreds of millions of transactions each day?), and fraud (bad actors are constantly looking to defraud points, how can we be proactive and automate creative solutions?). It’s just the beginning with our community of over 1,000,000+ members as we aspire to grow 100X.

What’s next?

Broadly, I believe more top engineering talent should look to Canada for areas of opportunity and business growth. There has been a significant change in tech companies and innovation over the past years in Canada. I believe a bit more time and investment is required for more companies to reach scale and innovation to happen for it to be seen as a major hub of innovation. After meeting with several other companies in the area, I see a lot of exciting challenges and markets being addressed. I can’t wait for our family of companies to hit larger, global scale. Along the way, I’ll help make sure Drop contributes to the local tech community to support each other.

As VP Engineering at Drop, I plan to build and recruit a top tier, diverse technology team that embodies a culture of passion, grit, humility, and hustle. We’ll think strategically, move fast, design elegantly, and create delightful products. We’ll leverage data to drive growth and increase our competitive advantage. We plan to grow rapidly while unwaveringly maintaining our culture. If reading this has sparked a sense of inspiration in you, please don’t hesitate to reach out to Derrick or I! We’re looking for self-driven, curious, collaborative, and fun people to build products with. We can’t wait to meet you!

Interested in learning more? Check out more about Drop here:

Drop HQ located in downtown Toronto



Ian Logan

VP Engineering at Rose Rocket. Former VP Engineering at Drop & Director of Engineering at Airbnb. Proud father.