Trades Business Coach — Contractor Job at Entrepreneurial Capital, Chicago, IL

  • Entrepreneurial Capital
  • Chicago, IL

Job Description

Trades Business Coach — Contractor

Flexible, Part-Time Contractor Role | $100/hour equivalent

About Entrepreneurial Capital

Entrepreneurial Capital is a private investment firm focused on partnering with strong owner-operators and helping established small businesses grow. We also operate a 12-week Trades Accelerator designed to help HVAC, plumbing, and electrical business owners improve the financial and operational performance of their companies.

The Accelerator combines a structured curriculum, biweekly group workshops, and weekly 1:1 coaching focused on helping owners implement improvements inside their businesses.

About the Role

We’re looking for an experienced trades business owner, operator, or consultant to provide weekly 1:1 coaching to participants in our Trades Accelerator.

This is a flexible contractor role best suited for someone who has personally operated or advised HVAC, plumbing, or electrical businesses and enjoys helping other owners improve.

We provide the participants, curriculum, scheduling, meeting infrastructure, and overall program structure. Your role is to show up prepared, understand the participant’s situation, provide experienced guidance, challenge their thinking when needed, and help them leave each call with clear next steps.

How the Role Works
  • Conduct approximately 10–20 30-minute 1:1 coaching sessions per week
  • Sessions follow the topic currently being covered in the Accelerator curriculum
  • Review the participant’s situation, identify issues, provide guidance, and establish next steps
  • Answer participant questions based on your real-world operating experience
  • EC handles scheduling, logistics, curriculum, and meeting setup
  • Calls are held remotely through tools such as Google Meet or Zoom
  • Schedule can be arranged around your availability, but would need to be relatively open

Responsibilities
  • Lead 30-minute weekly 1:1 coaching sessions with business owners
  • Help participants apply the Accelerator curriculum to their specific business
  • Diagnose operational and financial issues based on your experience
  • Provide clear, practical recommendations and next steps
  • Share real-world examples from operating or advising trades companies
  • Discuss relevant processes, tools, workflows, people issues, pricing, financials, sales, and operations
  • Challenge participants when necessary and hold them accountable to implementation
  • Escalate issues to the EC team when appropriate

What We’re Looking For
  • Significant experience operating, owning, or consulting for an HVAC, plumbing, or electrical business
  • Strong understanding of the realities of running a trades company
  • Experience across areas such as operations, financial management, hiring, pricing, sales, marketing, service delivery, and growth
  • Strong communication and coaching ability
  • Genuine interest in mentoring and helping other business owners succeed
  • Reliable availability during the Monday–Friday workweek
  • Comfortable using basic technology such as Google Meet, Zoom, shared documents, and online scheduling tools
  • Able to give direct, practical advice rather than purely theoretical guidance

Ideal Fit

This role may be especially attractive if you:

  • Previously owned or operated a trades business and have since sold, retired, or stepped away from day-to-day operations
  • Currently consult, mentor, or train business owners
  • Enjoy teaching and sharing what you have learned
  • Want flexible, meaningful side work without taking on another full-time operating role
  • Have previously coached, mentored, trained, or developed other business leaders
  • Genuinely enjoy seeing other owners improve their businesses

Compensation
  • $50 per 30-minute coaching session
  • Equivalent to $100/hour
  • Approximately 10 sessions per week minimum
  • Opportunity to handle up to approximately 20 sessions per week as cohort capacity grows
  • Paid contractor arrangement
  • No sourcing, selling, or lead generation required

The role is intentionally focused on one thing:

To Apply:
  1. Take this personality survey to help us get to know how to communicate with you most effectively:  
  2. Send an email with your LinkedIn to cole.kirkpatrick@entrepreneurialcapital.com.
  3. If there is a potential fit, we will schedule a 30-minute intro call.



Use your real operating experience to help business owners make better decisions and build better companies.

Job Tags

Full time, Part time, For contractors, Remote work, Monday to Friday, Flexible hours

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