The Strategy Driving Leo Chicago’s Award Streak

In just 18 months, Samantha Cescau went from Leo Chicago’s head of strategy to chief strategy officer, landed Southwest Airlines, and, with her team, racked up over 15 effectiveness awards. But how? What’s the secret?

“I’d love to say we have a hack or a trick to winning these awards,” she begins when I ask what made the difference in winning both the Grand Effie and Jay Chiat Grand Prix in the same year. “Sadly, I have yet to discover any. In my experience… it takes two things.”

First off, “you need a brave client committed to doing brave work,” Samantha says, pointing to both The Field Museum and Visionworks, which welcomed category-disrupting ideas.

And, secondly, aside from writing awards entries early, “You need an agency-wide effectiveness culture,” she emphasises. “We trace ours back to our founder, Leo Burnett, who famously said, ‘What helps people, helps business.’ He recognised the fundamental relationship between serving the needs of people and the business success that falls out of that.”

A standout from the awarded work for Samantha is the insight that the agency’s Visionworks project hinged on. Their challenge was to convince ad-averse young people to book eye exams with the brand. Discovering that while they may skip ads, “subtitles have their undivided attention.”, proved a game changer, leading This led to the creation of the world’s first vision test administered via subtitles. “I love when insights fall straight out of people’s behaviour,” adds Samantha.

Her best piece of advice to strategists pursuing excellence today is to write the effectiveness case study before you even make the idea. “I’m not saying fill out a full Effie Awards entry; write the executive summary.” Samantha says the discipline of doing so will force strategists to ensure they are clear on what success looks like, and how they would measure it, “avoiding missing results when it’s time to turn that creative success into effectiveness success.”

She warns, though, against confusing “vanity metrics” like billions of impressions, encouraging strategists to rely on real business results like sales or market share growth instead.

When I ask about her progression, Samantha says she owes the rapid jump to CSO to “caffeine and the wisdom that strategy is a team sport”, and the latter to having found partners who valued the craft of strategy “immensely”. From their first meeting, it was clear they shared the same values, meaning the partnership had the capacity to turn into something special. “That is always a dream for a strategist,” Samantha tells me.

“Within the walls of Leo, we have and continue to expand upon a team of strategists with complementary superpowers that impress on day-to-day client business and new business pitches,” she continues. “From the strategist who uncovers new growth audiences to chase, to the strategist who lives and breathes social platforms, to the strategist who ‘Beautiful Mind’ architects how an idea lands with impact, I’m lucky to call on their respective superpowers every day.”

Right now, Samantha is excited about combining human intelligence with artificial intelligence – to do more, faster. Her team is already using AI to expand its research, ideation, and iteration capabilities. “That might look like deploying AI to scrape product reviews to identify overlooked brand stories,” she says, noting how much it beats strategists manually scrolling through lots of Amazon reviews or Reddit threads.

The team is also using synthetic audience research to help uncover new approaches and explore work. But, this doesn’t work in isolation. “We still need humans at the wheel to frame thinking (and prompts!), as well as to critically interrogate and shape the output.”

Front of mind for Samantha right now is one particular result from Leo’s proprietary report, ‘The 2025 HumanKind Study’, on the main issues and concerns impacting Americans today. Specifically, it focuses on something called the ‘Respect Gap’, referring to the lack of respect people feel, with over half of those surveyed saying they don’t feel they are thought of or cared about.

“This gut-punch stat has been top of my mind as I brief and shape work,” Samantha says. “How are we showing respect for people? Are we connecting with them as real people versus as an ID? Do we offer a value exchange for their attention (once we’ve commanded it)? And are we helping them make the most of their hard-earned dollars?”

With that in mind, she firmly believes brands that champion a deeper need for respect will lead the way, and that it’s high time for what she calls a ‘Respect Revolution’ – something marketers should be paying heed to before they think about winning awards.