Program
Skills, Talent & Development
Thought Leadership

Operator-to-CEO Winter 2027

A practical executive leadership program for Alberta trucking companies, designed to give owners tools and frameworks to scale beyond founder dependencies. Build leadership systems, strengthen decision-making, and grow your business through the Alberta Logistics Centre of Excellence in partnership with AMTA.
Date
Winter 2027
Duration
4 Sessions
Location
Calgary, AB
Format
In-Person
Registration
Invite-Only
Start Date
January 26, 2027
Duration
4 Sessions
Location
Calgary, AB
Format
In-Person
REGISTRATION Deadline
Ongoing

Program Overview

Operator-to-CEO is a practical executive leadership program for Alberta trucking company owners ready to scale beyond founder dependency. As trucking companies grow, owners often become the bottleneck for critical decisions, limiting the organization's ability to scale sustainably. This program addresses that challenge by equipping participants with the following:

  • Leadership systems
  • Decision frameworks
  • Management capabilities needed to transition from working in the business to leading the business.

Delivered in person in Calgary and Edmonton, the program consists of four highly interactive half-day workshops, with coaching included. The experience emphasizes practical application through facilitated working sessions, peer discussion, real business scenarios and implementation between workshops.

The commitment is approximately 20 hours per participant, including workshops and work between sessions. Tuition is fully sponsored by our funders.

Participants leave with:

  • Practical tools
  • Stronger leadership systems
  • Improved decision-making processes
  • A clear framework for building a business that can grow beyond founder dependency.

OPERATOR-TO-CEO

What You'll Learn

Throughout the program, you will develop the systems required to build a more scalable trucking business.

01

Workshop 1

Identifying the Owner Bottleneck

Discover where your business depends too heavily on you and identify the decisions preventing growth.

02

Workshop 2

Building Your Second-in-Command

Develop leadership capacity inside your company and define how responsibility will be shared.

03

Workshop 3

Making Optimal Business Decisions

Create decision rules that improve customer selection, lane profitability, pricing, and operational consistency.

04

Workshop 4

Becoming the CEO

Bring everything together into a practical roadmap for the next 90 days.

Target Audience & Fit

  • Alberta trucking companies operating approximately 10-40 power units
  • Owner-led and family-owned businesses
  • Companies preparing for growth
  • Owners who want to delegate with confidence
  • Emerging leaders preparing to become a second-in-command
Where possible, companies are encouraged to send both:
  • The Owner / President
  • An Operations Manager, Second-in-Command or emerging leader preparing for that role

Key Learning or Business Outcomes

Every participating company will complete the program with:

  • Owner Bottleneck Map
  • Second-in-Command Development Plan
  • Customer & Lane Decision Filter
  • Decision Rights Matrix
  • 90-Day CEO Transition Playbook
  • Practical management tools that can be implemented immediately
Operator-to-CEO workshop dates
Workshop Calgary Cohort Edmonton Cohort
1 December 17, 2026 February 10, 2027
2 January 14, 2027 March 3, 2027
3 February 11, 2027 March 31, 2027
4 March 4, 2027 April 28, 2027

Why This Program Matters Now

Growing a trucking company takes more than adding trucks. As operations expand, owners need leadership systems and a team that can share responsibility for decisions and day-to-day management. Helping more locally owned trucking companies make this transition strengthens their capacity to invest, innovate, create jobs and compete. Operator-to-CEO is designed to help Alberta operators take that next step.

Interested in Participating?

Use the calendar below to book a conversation with Pete Fenwick about the challenges you’re facing and how Operator-to-CEO might help. It’s an opportunity to explore your interest and ask questions, with no commitment to join.

Questions before booking? Contact pfenwick@mtroyal.ca

Having trouble viewing the calendar? Open the booking page

Program Lead

Peter Fenwick
Fenwick & Associates Inc.
Peter is an executive leadership advisor and program designer who has worked with executive teams from 100 established companies across sectors. As Program Lead for Operator to CEO, he combines that experience with direct input from Alberta trucking owners to build practical tools for stronger decisions, stronger leaders, and less owner-dependent companies.

Delivered in Partnership With