5 Minutes with… Kira Montgomery
In September 2022, Kira Montgomery made the jump to Anomaly Toronto, leaving behind the roles of chief connections officer and partner at Juliet for a brand new challenge. Known these days as the agency’s first-ever head of comms strategy, she has spent the past few years evolving Anomaly’s strategy offerings, which has included building a talented team capable of redefining what it means to deliver strategies which inspire ultra-effective work.
Known for her triple threat of unrivaled comms planning know-how, entrepreneurial spirit, and strategic leadership experience, Kira is clear testament to the fact that comms strategy is far more than just being ‘the media person’ on the creative side. Whether she’s immersing herself in the audience’s day-to-day, looking for the contexts, or enabling creatives, IAT partners and clients to get excited about how an idea can show up, this impact can be felt both internally and externally, pushing each piece of work to higher heights in the process.
To learn more about this, her career, and just what it means to have good comms strategy, LBB’s Jordan Won Neufeldt sat down with Kira for a chat.
LBB> From the top, how did you get started in this business? Tell us about your story!
Kira> My first gig out of university was at a boutique consulting firm. At that point, I thought I’d eventually move into corporate environmental law. That was, until we partnered with McCann on a project. Thankfully, the 25-year-old me had the foresight to realise a career in advertising would be far more fun than the Bay Street grind!
LBB> With that in mind, how did you feel about advertising growing up? Was this career turn something that could have been predicted?
Kira> I often joke that I’ve been doing this job since the age of 10. As a kid, I ran what was arguably the most successful campaign of my career: the one that convinced my parents to get our family dog, Casey. When I think back, that definitely foreshadowed my future in comms. My parents still tell the story about how I targeted ads and messages all over the house – in the pantry, in the front hall, and even under the toilet seats. Media innovation at its best!
LBB> Notably, you’ve been at Anomaly for just over two years now! How has your experience been since joining?
Kira> The last two years have been some of the most rewarding and fulfilling of my career. When I joined Anomaly, strategy was evolving (the CSO had returned to New York City around 12 months earlier), and they’d never had a head of comms strategy in Toronto.
That’s all to say, I’m equally proud of the work that’s out in the world as the work that’s happened behind the scenes. Along with Mak Kattan, who I co-lead our strategy team with, a lot has gone on to bring together a group of people with ‘strategy’ in their titles, as well as build a team that’s highly-connected and collectively invested in redefining what it means to deliver strategies that inspire anomalous, ultra-effective work.
LBB> Of course, your joining created a lot of buzz, considering the fact that you’re an established talent in the industry with a great portfolio. What made Anomaly the right home for you? And what are you aiming to achieve with the agency?
Kira> Funny story, my journey to Anomaly was almost six years in the making. It’s a good reminder that chemistry and timing are two different things. It can be worth waiting until the two click. The reality is, Anomaly has always been a great home for comms strategists. What made it right this time around was the added leadership opportunity.
As for my North Stars as a leader: one is creating a culture that's defined by us, not our clients. The other biggy is creating work and a team vibe that – in order of priority – is envied within our walls, envied across Anomaly’s offices, and lastly, is envied in the industry. I fundamentally believe if you do the first well you’ll get to the last.
LBB> Building on this, in your opinion, what does developing a good comms strategy look like?
Kira> Comms strategy generally goes off the rails when people overly-fixate on creating a campaign instruction manual. Instead, the best comms strategies function more like an inspiration manual. They get creatives, IAT partners, and clients excited about where and how the idea can show up. Setting the tone and shape needs to come first. The tactics and detailed timing can follow.
With that in mind, for all the accolades we can receive in this industry, the one that really lights me up is when a campaign goes live and creatives from past agencies text me to say, ‘I can see the comms comms-ing’.
LBB> Within your career, you’ve had experience working both in and out of networks. In your experience, does comms structure change between the two? And how are you tailoring your approach to Anomaly?
Kira> My bigger observation would be, no matter the agency size or ownership structure, comms strategy usually starts as a team of one, or it becomes part of a generalist strategist’s job description. That means there are points where the waking hours of a human and the amount of work feel at odds.
At Anomaly, I’ve helped our team get through some growing pains by keeping two things in mind: first, that comms can take the shape of charts, and smarts. (‘Smarts’ being little kernels we drop into internals and conversation that inspire when, where, or how the idea shows up). If it makes it onto a slide, and then into the world, it’s a W.
The other is, comms is everyone’s job. Especially when you think of the above, it’s really about setting the pace and habit around prompting, asking, and innovating on these fronts. It’s amazing how that creates permission for others to do the same.
LBB> Interestingly, Anomaly operates under the belief that everything is media. Can you tell us more about what this means? Why is this ethos so important for the work you do, and how does it translate into meaningful output?
Kira> Love that you’re aware of this! I only learned it on my first day, but yes, it’s a core Anomaly principle. It also corrects a common misconception about the role of comms people. At first, people often think we’re ‘the media people’ on the creative side. In reality, we’re thinking ‘beyond media’, immersing ourselves in the audience’s day-to-day, and looking for the contexts (not just paid channels) where creativity can have its biggest impact.
A really simple example of this would be: as part of our Effie Gold-winning ‘Bud Friendship’ campaign, we asked, ‘what are the biggest damn Buds we can remove in the world?’. That led to removing the ‘Bud’ from ads, but also Budweiser Stage, Sportsnet’s Budweiser Studio, the Toronto Blue Jays’ outfield, and bar signs.
LBB> You’ve previously been described as combining ‘unrivalled comms planning know-how, entrepreneurial spirit, and strategic leadership experience’. How do you amalgamate these to enable effective results, and how would you personally describe your leadership?
Kira> Whoever said this is very kind! I’d say, knowing your craft is a must, but so is committing to always being a student of it. Part of the draw of Anomaly was the killer crew of comms people in our other offices. It’s like working with the Lebrons and Serenas of comms strategy. (Fun fact, we keep a global deck of all our favourite work!)
As for having an entrepreneurial spirit, it would be near impossible to do this role effectively without that. Especially in Canada, you’re often paving the way or stewarding the discipline.
Leadership, on the other hand, is something you grow into. I’ve had great mentors in my career who taught me the leadership ropes, and equally, I’ve been lucky to have some great champions who paved the way for my growth – especially in rooms that I wasn’t in earlier in my career.
That’s probably why my number one leadership philosophy is to be the wind under my teams’ wings. I’m always trying to support, elevate, and shine a spotlight on their talents. Across the agency, I mirror this by encouraging people to be each other’s biggest fans. I’m a huge believer in celebrating in public, critiquing in private.
LBB> Moving back to the subject of comms, often, it feels like those in adjacent roles end up being unsung heroes. Should the industry be shining a more diverse light, in your opinion?
Kira> I feel like I saw this one coming with my answer above! In short, abso-friggin-lutely! Everyone deserves their flowers, at all levels and in all roles. Nothing bad comes from bigging up and celebrating other people’s contributions. And I’m not saying with awards. Just use your words. This is a team sport after all.
LBB> Finally, work isn’t everything. What helps you destress after a long day at the office?
Kira> Getting on a plane and getting out of town. I never buy the wifi package on personal trips. Airplanes and movie theatres are two of my favourite places in the world because you’re forced to disconnect. Like I said, I’ve been doing this job since the age of 10 – more than flowers, what I crave most these days is a little rest!
