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Holly Knowlman

Marketing & Partnerships at The Working Group

Holly is TWG's marketing & partnerships lead, and the Editor of Stupid Magazine, a quarterly print publication about pop music. She organizes Startup Next in Toronto, the world’s #1 startup pre-accelerator, and curates a weekly newsletter for journalists and entrepreneurs. She digs brevity, verbosity, Kanye West and emoji's emergence as a shared global language, tweeting about all of those things and more @hollyknowlman.

Tell me more about what you do?

I lead marketing and partnerships at The Working Group. We’re a product agency, which means we design and engineer digital products for clients that are looking for support from a highly accomplished technical team to help them move faster. We work with big brands, startups and everything in between.

My role is a mix between spreading the word about the work that we do, and designing and delivering programs that help us to build strong relationships with our partners, contribute to the community and experiment with new ideas.

Right now, I’m working on a global event series with the Center for Investigative Reporting and Google called TechRaking. It’s all about bringing together journalists, designers and technologists to create solutions to challenges faced by newsrooms. The event series is also laying the groundwork for a bigger partnership between CIR and TWG. I also organize Startup Next, and recently wrapped up a program for indie arts organizations that taught them some of the techniques used by early-stage tech startups.

Outside of TWG, I’m in the early stages of launching a pop music print publication called Stupid Magazine and curate a weekly email newsletter for journalists and media entrepreneurs.

How did you get into communications and eventually into your role at The Working Group?

The first “thing” I ever produced was a photocopied music zine about bands in my home town. It lasted one issue, but putting that together and throwing the launch party got me hooked on the idea of making culture using words and events. I went to art school, although my degree was English Lit & Media Studies, where I started freelancing as a writer and helping friends promote their projects.

I also ran a weird pub trivia night with rounds like “name that snack” and “drum & bass or not drum & bass.” For the Christmas edition, we took photos of my two friends dressed as bad Santas in staged crime scenes, and the teams had to guess what law they were breaking.

My degree got me into online communications, and specifically how the Internet was changing and democratizing the news. After I graduated, I worked with a PR consultancy to build up their social media offering. The “community manager” was just becoming something companies were looking to hire, so that ended up being a way to explore something I was curious about and still pay my rent (I graduated during a recession in the UK… which is one of the reasons I moved to Canada.)

I moved to Toronto in 2011 and started working with the AGO as their first community manager whilst throwing parties and volunteering for a bunch of stuff on the side. Getting involved with events like NXNE, FITC and Startup Weekend helped me to meet lots of smart, interesting people and made me realize that the tech industry would be an amazing place for me to hone my skills.

It was through Startup Weekend that I met the team at The Working Group. At the time, they were just 20 people (there’s more than 50 of us now) and didn’t have anyone dedicated to marketing. TWG’s culture is very collaborative and partnership-driven, which ended up being a really good fit for my skill set and the kinds of things I was interested in getting better at.

I got super lucky. I get to interact with lots of different businesses solving lots of different types of problems, which is something I was actively looking for, and I get to work with really smart, nice, talented people every day. I’m proud to be representing such an excellent team.

I’m incredibly excited about the prospect of launching my own business, but I don’t think I could have found a better environment to be in whilst I’m learning how to make that happen.

What do you find most rewarding about your role? Most challenging?

I love creating situations that empower people to become better versions of themselves. Startup Next is a cool example of that. It’s a pretty intense program - five weeks of training and mentorship designed to help startups get ready to apply for accelerator programs or pitch investors. You get to see teams make so much progress and become so much better at communicating their vision. They become better entrepreneurs with stronger companies, and that’s a really, really cool thing to be a part of. Seeing the work that you do have a positive impact on other people’s lives is dope.

More selfishly, I’ve had some killer travel opportunities lately - Berlin, London and San Francisco already this year. Exploring other parts of the world is high on my priority list, so having that be part of my job is kind of mind blowing to me still.

Finding new challenges is what keeps me engaged and motivated, so generally I see them as a positive thing.

However… I’m curious about everything, so I have a tendency to try and do too much. I’ve flirted with burnout before and it’s zero fun. I had to learn where my limits were the hard way. The “learn how to say no” thing is such a brutally clichéd piece of advice, but it’s super important.

My confidence is generally pretty high but I definitely get those moments where I feel as if I have no idea what I’m doing or if I’m good at anything. Understanding where you can add the most value and having confidence in communicating that value is always tricky, especially if you’re still in the process of levelling up and figuring out what you’re best at and love doing the most.

How do you stay up to date with trends in your industry/field?

I’m a huge word nerd, so the vast majority of the information I consume is text: Blog posts, articles, Twitter etc. Also: Trying to convince people that are smarter and more experienced than me to hang out with me and tell me things.

What are your top five tools, applications or programs?

Jot: A chrome extension that turns new tabs into to-do lists
Miranda: Beautiful time zone converter for iPhone
Slack: For TWG team hangs
Headspace: We just kicked off a mindfulness program at TWG using Headspace. I’m a total convert.
Beats One: Apple’s new radio station, led by Zane Lowe (formerly of BBC Radio One) is my favourite thing right now. Especially Josh Homme’s Alligator Hour.

Best way to stay on top of email?

I love unroll.me for clearing out unwanted subscriptions. But I have 721 unread messages in my inbox right now so nobody should be taking my advice on this one.

I think the trick to staying on top of email is more about your relationship with your inbox, rather than it being about any one particular trick. Choosing to be deliberate about what you want to achieve in a day, rather than being reactive and letting emails rule your workflow, helps. Sort of.

What does your workspace look like?

Messy as hell. I like to think it’s because I’m some kind of crazy creative genius but actually I’m just disorganized.

Structure of your typical day, how do you divide your time?

My brain is a huge jerk first thing in the morning, so I wrote myself a ridiculously detailed, step-by-step to-do list to get me out the house. That way I know I’ve covered all the bases, like deodorant.

I work a 9-5ish depending on what’s going on that night. We just shipped a really cool piece of interactive long form content with TSN called Favela United, so I’ve been telling lots of people about that lately. I’m also preparing for Designer Adventure Club, a new event for designers and TEDxToronto, for which we’re the technology partner. I’ve also been spending a lot of time exploring how to grow marketing at TWG and thinking about my own professional development (we just kicked off the search for a new Director of Marketing, if anyone’s interested!)

If I’m not working an event, a post-work pint or coffee with an industry friend or two is pretty typical. Then I’m working on my own projects for the rest of the night. I try and stay in work mode during the week (although I’ll make an exception for shows I want to check out).

My weekends are gloriously self-indulgent and my time to chill with the important people in my life. Preferably outside, away from the computer.

What is the greatest piece of career advice/wisdom you've ever received?

Honour your feelings. This advice came to me from an Algonquin Medicine Man via a very good friend of mine. It’s about paying attention to your emotional reactions to different situations and being really honest about how things make you feel, with yourself and with others. I’m a big believer in the importance of communication, and it’s something I’m trying hard to get better at. This was one of those really simple, yet powerful, pieces of wisdom that made immediate sense and impacted how I carry myself and think about how I share my ideas with others.

Who would you like to see featured on Ways We Work?

Cindy Gallop, Alexis Madrigal, Willow Smith