Coaching as Culture Therapy: Lessons from Shopify and Mid-Day Squares
Last month at the EO One Canada conference in Montreal, I had the chance to hear from several inspiring startup and high-growth founders, including the team behind the fast-growing, authentic brand Mid-Day Squares and Canadian success story Shopify. What stood out wasn’t just their innovation or scale; it was their deep investment in leadership and coaching, and even therapists, to level up their personal and team performance.
Hearing Harley Finkelstein, President of Shopify, share how coaching and leadership development have been foundational to Shopify’s global scale was incredibly insightful. Equally powerful was the candid, passionate talk by Mid-Day Squares co-founders Jake Karls, Lezlie Karls, and Nick Saltarelli. Their openness about emotional resilience, therapy, coaching, and team dynamics as core pillars of their business left a lasting impression. They are a family business, and as we all know, families aren’t always playing nice together and are not easy to make work. But they have figured out that weekly team therapy and coaching help manage conflicts and issues that come between them.
It’s clear we’re seeing a shift. Coaching is no longer a luxury; it’s a strategic edge. Here’s what that new era of agile, open coaching looks like and why it matters now more than ever.
The New Wave of Business Coaching: Personal and Professional Growth for Scaling Founders & Teams
The era of once-a-quarter leadership offsite and surface-level executive coaching is over. In its place, a new model of business and leadership coaching is emerging, designed for the real, messy, high-velocity world of startup growth and scale. Today’s founders don’t just need guidance; they need real-time, high-impact support to grow themselves and their teams at the speed of their business.
At Ari Agency, we’ve worked with dozens of DTC, SaaS, B2B and B2C startups and scaleups navigating this exact challenge. One consistent theme? The founders and CEOs who build sustainable, high-performance teams aren’t going it alone. They’re turning to leadership coaches, therapists, mediators not as status symbols, but as strategic partners embedded in the business journey.
Coaching That Moves With the Business
What’s changed? Today’s top coaches don’t sit outside the business offering abstract advice. They’re part of the executive team, on-demand, and context-aware. Think of them less like therapists and more like elite coaches who understand how to scale leadership inside companies who are looking for hockey stick growth.
Take Mid-Day Squares, the Montreal-based chocolate startup shaking up the functional food category. Co-founder Jake Karls has spoken candidly about how emotional resilience and ongoing mindset coaching helped him show up better for his team and for himself as the brand scaled beyond just product into a movement. The company has built its entire leadership philosophy on transparency and vulnerability, concepts often nurtured through coaching work.
Or look at Shopify. Founder Tobi Lütke and President Harley Finkelstein invested heavily in internal coaching systems as the company scaled globally. Leadership wasn’t a checkbox; it was a discipline that took practice. Shopify developed programs to coach managers on decision-making, feedback, and self-awareness in a hyper-growth environment.
From Reactive to Proactive
Traditional coaching often waited until there was a problem like burnout, conflict, or turnover. Today, high-growth teams are bringing coaches in early, often alongside new executive hires, to help accelerate onboarding, improve team trust, and align leadership styles.
Methodologies like Conscious Leadership, The 15 Commitments of Conscious Leadership, and Radical Candor are frequently referenced. Many founders are also leaning into group coaching and cohort-based models, which create shared language and accountability across senior teams.
Coaching as Culture Insurance
Great hires are only part of the equation. What we’ve seen is that coaching amplifies the impact of those hires and protects the culture in high-stakes transitions. Especially when companies grow from 20 to 200 people or raise a major round, coaching helps translate founder vision into team-wide execution and clarity.
More than ever, coaching is not a fix; it’s a lever. It’s how ambitious companies turn managers into mentors, align co-founders before tensions escalate, and give high performers a roadmap to rise.
We believe the best executive hires thrive when they’re supported with the right tools. That often includes a coach in their corner. Because in the race to scale, it’s not just the business model that needs to grow; it’s the people building it.
