Steve Wheatcroft is the founder and former CEO of one of the largest landscape and snow & ice management companies in Canada. Over a 35-year career, Steve built the business from the ground up, sold it to private equity, and stayed on for four more years to help grow the company to over $100 million in annual revenue.
Steve has lived every stage of growth, from early operator-driven chaos to enterprise-level leadership and scale. His experience includes navigating rapid expansion, building executive teams, strengthening operational discipline, and preparing organizations for long-term sustainability.
Today, Steve works with landscape owners and leadership teams who are serious about building companies that last. His guidance is shaped by real-world experience, hard-earned lessons, and a deep respect for the people who do the work.
Judge me not by what I have said, but by what I have done.
Growth changes the game. At scale, discipline and leadership alignment matter more than ideas.
As companies grow, complexity increases. Decisions slow down. Accountability blurs. Meetings happen, but progress stalls. Without clear leadership discipline, growth becomes heavier instead of stronger.
Steve works with owners and leadership teams to clarify priorities, strengthen execution, and build the discipline required to operate at a higher level. His focus is helping companies move from reactive leadership to disciplined, aligned decision-making at scale.
Steve works best with owners and leadership teams who are committed to discipline, alignment, and building a business that lasts beyond them.
Start with a free business assessment from a LeanScaper Guide.
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Grow ($500K–$3M)
At this stage, growth is fast and structure is thin. Steve helps owners step out of reaction mode by clarifying direction and establishing leadership foundations that prevent chaos later.
Scaling ($3M–$10M)
Growth accelerates, but pressure increases. Steve helps owners and leadership teams tighten execution, clarify roles, and build discipline as complexity grows.
Enterprise ($10M–$30M)
Leadership alignment becomes critical. Steve works with executive teams to strengthen accountability, decision-making, and organizational focus.
Legacy ($30M+)
At this stage, the focus shifts to sustainability, succession, and long-term impact. Steve supports leadership teams preparing the business to endure beyond its founder.
Start with a free business assessment from a LeanScaper Guide.
Book a Discovery CallTo help business owners find clarity and confidence by sharing real experience, including the mistakes, so they can build stronger companies, better leaders, and lasting success.
Steve brings the same intensity and discipline to life that he does to business.
Outside of work, he remains active through hockey, hiking, fly fishing, and time outdoors, which he views as both a challenge and a form of reflection. Becoming a grandfather has added a new perspective on legacy and responsibility, reinforcing Steve’s belief that leadership is about what you leave behind.
Steve believes blue-collar leaders are often undervalued, despite carrying enormous responsibility. He is passionate about helping landscape owners and leaders earn the recognition, structure, and success their work deserves.
Getting great help from a LeanScaper Advisor is simple...
A LeanScaper Guide will meet with you to, discuss your needs and match you with the Advisor that can serve you best.
Your Advisor will clearly discuss the different options available to you and curate a service plan that you can both feel great about.
Together you can confidently overcome roadblocks and set your team up for success.
Start with a free business assessment from a LeanScaper Guide.
Book a Discovery Call