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The 20 Coffees Project: Kirsten Bailey

This post is the second in a series called The 20 Coffees Project. The goal of this project is to highlight the unique challenges and bright spots for leaders in the Vancouver business community (particularly startups).

This installation features Kirsten Bailey, Director of Online Education Products, New Product Growth at Hootsuite.

Kirsten and I met for coffee at Milano Coffee Roasters near the Hootsuite headquarters for an insightful interview about career progression, program growth, and how digital media and technology are changing the face of higher education.


Kirsten Bailey

EB: How would you describe the path that lead you to your current role?

KB: I graduated University with a degree in Art History and Classics. The first thing you wonder when you graduate with an Art History and Classics degree is what you’re going to do with that degree… The first natural step for me (maybe not entirely natural) was an opportunity to sell art on cruise ships. It was a great first job experience. It was essentially a franchise operation, 100% commission based, and it involved everything about running a business. From stocking inventory to balancing the books, selling, and educating folks on the value of the pieces. What I really learned in that experience was that university didn’t do a good job preparing me for a working career.

I think the majority of people who go to university expect it to either help them get a career, or help them get ahead in a job once they’re in it. That disconnect from my experience is probably what struck me the most, and has had the greatest impact on my career thus far.

I have a real fascination with education, and how we can get folks the skills that they need in order to be successful. That’s something that I’ve always been inherently interested in.

I’ve been fortunate to find myself first working at Invoke (where Hootsuite was born), and then evolving into a role heading up Hootsuite University when Hootsuite became its own company. I’ve been doing that for about 4 years now. The natural extension of that was a broadening of responsibilities that focuses on how can we deliver product training and social media education through online education. So now I head up our online education products at Hootsuite.

EB: How would you describe the balance between creativity and structure in your role?

KB: The way that I think about it is kind of like a horse and plough.

A lot of working with online education products is thinking about content; that’s a huge part of your product. You need to think about how to create an engaging experience that people will be truly engrossed with. What’s interesting about the last few years is there’s been a huge surge of people moving towards learning online. With the advancement of MOOCS, increased access to Internet, and better bandwidth, there’s been a huge consumerization of learning online. With that come a lot of higher expectations around quality of content. Specifically, the space is interesting because online education and “eLearning” as it’s more traditionally known is boring. It’s known for being super dry, super traditional, and in a way, death by its own structure. So the creative aspect is thinking through this unique problem.

We’re creating products for consumers with high expectations who are very technologically literate. The question is how can we make something enjoyable and also adhere to the important instructional design principles that give the content integrity? I would say that that’s the important interplay. We have a lot of fun working on it. We’ve tried a lot of different things and there have been lots of interesting challenges that have come up along the way.

In terms of the horse and plough, the horse is the creativity that keeps us moving forward; it gives us life, it gives us purpose, it gives us momentum, but the plough is what ensures that there’s structure and order around how we create our product.

EB: Internally, what are the three biggest accomplishments your team has had?

KB: My team is awesome. I think this depends of how you think about accomplishments, whether they’re team accomplishments, or individual accomplishments, but collectively I’m thrilled that we’ve been able to have more than 100,000 folks go through our program.

One the programs that I love the most that has grown out of Hootsuite University is our higher education program. Ryan really strongly believes in education, and this was a baby of his for a while. Now we’ve been able to grow it to around 20,000 students.

I guess another thing would be connecting with the people who have graduated from the program. They tell stories about their experience and about how it helped them bridge the mental divide between using social media personally and using it in a professional context.

We’re working in tandem with all the other educators out there, helping students get to the ‘aha’ moment of that one really important aspect.

One last thing would be hearing the stories about how Hootsuite and Hootsuite certification specifically has been helpful in differentiating students from other candidates who will apply for a job.

There’s actually been an independent study by academics who have studied not only the students who went through the program, but also the employers who they’ve ended up interviewing with. What they’ve found is a correlation between the credential and the signal that it sends the employer about proficiency and understanding of how to use social media in a professional context.

Really at the end of the day that’s what we’re trying to do, is help people feel empowered, comfortable, and confident in how they use social media.

EB: How do you deal with roadblocks in your work, or even failure?

KB: I think that there are two facets there – how you deal with it yourself, and how do you deal with it as the leader of a team.

Some people think this way naturally, but for most of us, it’s really important to practice a mental shift into thinking of roadblocks and failures as something that you actively want. Something that you need in order to be a strong and experienced professional.

There’s so much stigma attached to the notion of failure, but it’s like a stress test. It’s what helps you sharpen your capacity to really deal with the hard things. One of my favourite expressions is “the hottest fire makes the hardest steel”. First there’s the mental shift of thinking, “Yes, this is a good thing” and then, putting the roadblock in the context of your whole career.

If you look at this situation one year or ten years down the line, how big of a deal is this actually going to be? I think a lot of people are heads down, and thinking about what they’ve dedicated their days to. They’re passionate about their work and can be very emotional (which is understandable!), but you also need to take a step back in those tough moments and think “Ok, well, how big of a deal is this, in the grander context of things”. If you look at your career as a linear block of 40-50 years (if you really want to go that far!), how big of a deal is this problem?

It’s also about how far along in your career you are. You’re going to make a lot more of those mistakes early in your career path. It’s a learning curve.

Finally, you need to think about how much you can control; there’s no sense worrying about the things that you can’t control. If you just ask yourself “Hey, do I actually control this?” and the answer is no…then you need to scale back to the parts of the problem that you can control and be laser focussed on that. From a team perspective it would be similar; look at the problem in context, figure out how momentous it is, and decide what you can learn from it.

EB: How do you celebrate success?

KB: Vodka! (Laughs)

EB: Yeah, it seems like the immediate is always food and drink, all the way.

KB: Yeah, of course. It’s about something that you can do as a team. It’s also about taking moments of success and recognizing all the work that went into them. Not just celebrating the fact that it’s done, but really looking at everything that went into it and asking what does this represent? How does it connect to everything that came before it? That makes it helpful in the thick of things too. Knowing that the shit that you’re going through will contribute to something great down the line.

EB: Ok, last question, an Unbounce tradition: What is your favourite thing that doesn’t bounce?

KB: Cheques!!

And if that’s totally overplayed, then I would say dumplings. I actually ate 20 of them last night…



Erin Brown
Marketing Educator @ Unbounce