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Creative Ops

Toast’s Jon Reil on building and leading creative teams

April 19, 2023 · 4 min read

This is part of our 100 Creative Directors interview series. It has been edited for length and clarity. To return to the series homepage and browse other interviews, click here.

What type of creative director are you?

I’m the Senior Director of Brand and Creative at Toast. I arrived in this role via a long, windy road – from my early days working for a magazine, to advertising agencies and design firms, in-house agencies, and an array of startups - it’s been an interesting, surprising and fulfilling ride. My background is based in design / visual communication and acts as the foundation for building and leading teams that develop brand & creative for all channels: broadcast, digital, web, events, brand identity, and whatever else we can dream up.

At Toast, my team is responsible for all brand & creative touchpoints: from creative output to brand transformation to creative operations, and deeply understanding how our work affects business results, both internally and externally.

What is the most difficult part of shipping good creative? 

Balancing creative vision with practical constraints.

Creative work is often about pushing boundaries, taking risks, and coming up with ideas that capture attention. Then there’s the reality of: ‘What’s the deadline? What’s the budget? What are the technical limitations that can sometimes constrain us?’ You need to find that sweet spot. It takes time, energy, passion, and perseverance. 

Managing expectations and communication. 

Thankfully at Toast, we have a solid project management / creative operations team. Creative work often involves a variety of stakeholders each with specific opinions and priorities. Managing those expectations and communicating effectively is critical and our team is equipped to facilitate that. 

The creative process can be messy and unpredictable. 

There’s a lot of experimentation and iteration required to create something that's both creative and effective. That can be a challenge for our internal partners - people who may be more used to more linear predictable processes. So the key is getting people comfortable with the unpredictability of making something great. We have learned to embrace what we call the creative “swamp.”

How do you measure your team's success?

It begins with metrics: Sales, the funnel, brand tracking, and more. If our team’s work is driving those metrics in a positive direction, that's a strong indicator we’re doing work that works. We have an incredible SVP and extended leadership team that is passionate about this intersection. We lean on one another.

Brand excellence. At Toast, we have a brand excellence program where we measure the effectiveness / excellence of our brand. We do this via feedback from brand audits, our team, extended stakeholders, and most importantly, our customers.

And finally, team happiness is critical. Ensuring that our teams are happy and engaged makes a significant impact in how successful our work is. At Toast, culture and team come first.

What are the three things you couldn't do your job without?

  1. A growth mindset. How can you see things from a different perspective? Be open. Be action oriented. Learn as much as you can about anything that pushes you out of your comfort zone. Search for it.

  2. Communication skills. To make great work, you need to be able to explain ideas clearly and persuasively to the rest of the organization. Secondly, feedback to other creatives needs to be clear and constructive to help them take actionable efforts to improve their work. Clarity is key.

  3. Collaboration tools. Project management tools; design software. The norms and behaviors that come with Zoom, Slack and email in a collaborative space.

  4. An enablement / empowerment mindset via self-service. We need our internal partners at Toast to be able to create effective, on-brand work with velocity. We’re always asking how we can continue to unlock and empower the rest of the organization.

One unsolved mystery we run into is keeping things simple and in one place – it eludes us a bit. Everything’s connected to everything else - and there's a lot of creation happening outside our team. We’re adept at using collaboration tools and continually seeking to optimize for efficiency and scale, but we’re still searching for that one tool that rules them all. I’m confident we’ll find the answer to that.

What’s your best piece of advice for someone working in this space?

  1. On building teams: Hire people better / smarter than you and get out of their way. This one is from a former ECD - an incredible creative leader from my agency days - he held this mantra.

  2. On process: Allow autonomy. Focus less on the how; more on the results and final output.

  3. On creative output & timing: People won't remember if it's late, but they will remember if it’s bad.

  4. On brand campaigns: As creators, we often get sick of our work before our audiences do. With that in mind, I’ll end with a few words of wisdom from our CMO. Keep things in-market longer than you want to. Give it time to grow. Allow it to stick.

Spoiler: It works.

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