Systems Organized by Design is led by Dan Pestretto, a second-generation landscape professional who has worked in the industry from field labor to ownership to executive leadership.
With decades of hands-on experience running and leading landscape companies, Dan understands what happens when growth outpaces structure. His advisory work focuses on helping owner-led businesses move from reactive, personality-driven operations to documented, system-driven enterprises.
SOD specializes in installing real operational structure inside landscape businesses, aligning strategy, processes, leadership, and software so the company can grow without constant owner intervention.

Many landscape businesses grow through effort, not structure. The owner becomes the decision hub. Processes live in people’s heads. Growth creates stress instead of freedom.
SOD helps owners turn vision into documented systems, defined roles, and clear accountability. Dan works side by side with leadership teams to install operational frameworks, management rhythms, and technology platforms that support execution.
The result is a company that runs with clarity, produces consistent results, and no longer relies on the owner to hold everything together.
Process Architecture
Documenting how the business operates by linking every role, responsibility, and process to the organizational structure.
Executive Coaching
Guiding owners and key leaders to think systematically, communicate clearly, and lead through accountability and measurable outcomes.
Profit Clarity
Turning process and KPI data into actionable intelligence that exposes waste, strengthens margins, and stabilizes growth.
Software and Systems Enablement
Aligning tools and documentation platforms so systems are organized, usable, and tied to functional accountability.
AI Readiness Through Documented Systems
Preparing businesses for AI adoption by building systems that are documented, structured, measurable, and readable by AI platforms such as LeanScaper.
Start with a free business assessment from a LeanScaper Guide.
Talk to a Guide
Starter Stage (Up to $500K)
You need structure that makes execution repeatable. Dan helps establish foundational role clarity and documented workflows so growth does not depend on the owner holding everything together.
Growth Stage ($500K–$3M)
The business is moving, but consistency lags. Dan helps formalize processes, install accountability, and create simple KPI visibility so the team executes with less friction.
Scaling Stage ($3M–$10M)
Complexity increases fast. Dan helps companies break through plateaus with deeper process architecture, leadership clarity, and performance systems that stabilize growth and protect margin.
Start with a free business assessment from a LeanScaper Guide.
Talk to a GuideTo professionalize the landscape industry by transforming landscape businesses into systematic, profitable enterprises that create lasting value for owners, employees, and communities.
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Dan is wired for structure and clarity. He quickly sees how work actually flows through a landscape company and where accountability or process is breaking down.
Having grown up in the industry and built his career from the ground up, Dan understands both the operational grind and the leadership shift required to move from operator to system-driven owner. Outside of work, he spends time at his Vermont farm, hiking and staying close to the land that shaped his career.
He works best with growth-minded owners who are ready to document what matters, install accountability, and lead through structure instead of constant oversight.
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.
Talk to a Guide