Trades Business Coach — Contractor
$100 per hourEntrepreneurial Capital
Flexible, Part-Time Contractor Role | $100/hour equivalent
About Entrepreneurial CapitalEntrepreneurial 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 RoleWe’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
- 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
- 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
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
- $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:- Take this personality survey to help us get to know how to communicate with you most effectively:
- Send an email with your LinkedIn to View email address on click.appcast.io.
- 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.
- ...a faith-based peer advisory organization that helps Christian business owners and executives grow spiritually, professionally, and personally... ...you grow, the more you earn. This is a 1099 independent contractor role There is a training and certification investment...For contractorsLocal area
- ...Trading Systems Engineer - Options Market Making Chicago Maven is a market-leading proprietary trading firm deploying its own... ...indicate by making the appropriate selection.As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act...For contractorsContract workFor subcontractorWork at office
- The Vice President, Trading and Product Risk Intelligence, will be a key member of the Intelligence... ...management and strategic advisor to business stakeholders, partnering across... ...requires affirmative action by covered prime contractors and subcontractors to employ and advance...For contractorsFull timeTemporary workFor subcontractorLocal areaImmediate startNight shift
- ...POSITION Community Trades & Apprenticeship Coordinator DEPARTMENT : Workforce Development... ...works with instructors, facilitators, contractors, employers, and workforce development staff... ...management, workforce development, business administration, renewable energy, or a related...For contractorsContract workApprenticeshipWork at officeFlexible hours
$150k - $250k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...and solutions in support of your business partners Stay up to date on product features... ...experience. (Disclaimer: interns and contractors are not eligible for benefits at CTC)...For contractorsWorldwide$175k - $225k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...model, subject to change based on business need. Our Benefits We strongly believe... ...experience. (Disclaimer: interns and contractors are not eligible for benefits at CTC)...For contractorsWorldwide$175k - $225k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...model, subject to change based on business need. Our Benefits We strongly believe... ...experience. (Disclaimer: interns and contractors are not eligible for benefits at CTC)...For contractorsWorldwide$175k - $225k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...model, subject to change based on business need. Our Benefits We strongly believe... ...experience. (Disclaimer: interns and contractors are not eligible for benefits at CTC)...For contractorsWorldwide$225k - $250k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...model, subject to change based on business need. Our Benefits We strongly believe... ...experience. (Disclaimer: interns and contractors are not eligible for benefits at CTC)...For contractorsWorldwide$225k - $250k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...model, subject to change based on business need. Our Benefits We strongly believe... ...experience. (Disclaimer: interns and contractors are not eligible for benefits at CTC)...For contractorsWorldwide$200k - $250k
...Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options... ...model, subject to change based on business need. Our Benefits We strongly believe... ...experience. Disclaimer: interns and contractors are not eligible for benefits at CTC...For contractorsWorldwide$190k - $220k
...of NinjaTrader! As an industry-leading trading platform and futures broker, we're on a... ...behind a rapidly growing segment of our business—enabling prop trading evaluation firms on... ...engineering team (backend, full-stack, and contractors), fostering a culture of technical...For contractorsWorldwide$90k - $100k
...Washington, D.C., is looking for a Trade Show Manager to join our... ...prospectus, general service contractor management, exhibitor management... .... people, financial) to meet business priorities; demonstrates... ...counterpoints. Provides guidance and coaches others on revenue, expense...For contractorsContract workWork at officeLocal areaImmediate startVisa sponsorshipWork visa$45k
...growing team. Someone ready to trade running their own book solo,... ...inside a larger agency, or coached clients solo, and you're ready... ...driving hard conversations with business owner ~ Proven ability to... ...sales team. About Contractor Dynamics We help roofing companies...For contractorsRemote work- ...Warehouse Operator-Grain - Lakeside Grain Trading LLC - Chicago, ILUnder the direction of... ...essential abilities including business knowledge, collaboration, communication,... ...Further, as a federal, state, and local contractor, we comply with government regulations and...For contractorsFull timePart timeLocal area
$100k - $175k
Project Manager - MechanicalPosition OverviewTop ENR mechanical contractor is seeking multiple Travel Project Managers to lead top of the... ...while coordinating with owners, design teams, contractors, and trades. The ideal candidate has strong Mechanical, HVAC and or Plumbing...For contractorsDaily paidContract workFor subcontractor- ...Confidential or proprietary information from any employer or university. Trade secrets or internal company or university data. Specific client... ...or other confidentialit obligations. Engagement type: Contractor assignment/freelancer, potentially full-time. Duration of...For contractorsFull timeContract workFreelanceRemote work
- ...organization that values quality, integrity, technical expertise, strong trade relationships, and long-term client partnerships. The... ...issues and keep work moving. Lead owner/architect/contractor (OAC), preconstruction, and subcontractor meetings. Serve...For contractorsFull timeContract workFor subcontractor
$130k - $150k
...estate development and ownership side of the business. Kiferbaum Development Group is an integrated Owner/Developer/General Contractor, and the Project Manager will work closely... ...level scopes of work to ensure complete trade coverage and minimize change order exposure...For contractorsFull timeContract workTemporary workFor subcontractor$185k - $235k
...client is a privately held design-build contractor specializing in heavy industrial... ...company leadership. Support estimating and business development with constructability, execution... ...involving multiple contractors, trades, vendors, and stakeholders. Strong knowledge...For contractorsFor subcontractor- ...About the Opportunity - Our client is an established General Contractor seeking an experienced Construction Superintendent with a proven... ...cold storage construction projects. Manage subcontractors, trade partners and site personnel throughout construction. Coordinate...For contractorsFull timeFor subcontractor
$30 - $40 per hour
...ENGAGEMENT TYPE: Freelance / independent contractor; 90-Day engagement with potential to... ...design production, brand guidelines, and trade/shopper marketing conventions, including... ...prioritizing based on program deadlines and business impact. Take on additional design...For contractorsHourly payContract workFreelanceWorldwideShift work$113k - $127k
...Managed Company and a recipient of the Better Business Bureau Torch Award for Ethics. Whether... ..., negotiating contracts, selecting trade partners, and ensuring timely subcontract... ...working for a commercial general contractor preferred Minimum of 5 years of construction...For contractorsFull timeContract workTemporary workWork experience placementFor subcontractorWork at officeLocal areaFlexible hours$79k - $92k
...currently seeking a full-time Solar Programs, Trade Ally Manager II located in Illinois to join... ...building strong partnerships with solar developers, contractors, Equity Eligible Contractors (EECs), Small and Emerging Businesses (SEBs), and other industry stakeholders. You'...For contractorsFull timeWork at officeRemote workRelocationNight shift$90k - $110k
...well-established Chicago-based real estate developer and general contractor is looking to add a Project Engineer / Assistant Project... ...maintaining strong relationships with owners, architects, engineers, and trade partners. Key Responsibilities Assist Project Managers...For contractorsContract workFor subcontractorWork at office$350k
...this one needs a proven leader to own it.An established General Contractor with 600+ employees is delivering one of the biggest data... ...working closely with the client, design consultants and major trade partners. You'll:Own the mechanical scope from preconstruction...For contractorsFor subcontractor$140k - $157k
...and a recipient of the Better Business Bureau Torch Award for Ethics... ..., and ensuring successful trade partner performance. Serve... ...responsibilities, providing coaching, and building high-performing... ...working for a commercial general contractor preferred ~9+ years of...For contractorsFull timeContract workTemporary workWork experience placementFor subcontractorWork at officeLocal areaFlexible hours$140k - $157k
...and a recipient of the Better Business Bureau Torch Award for Ethics... ..., and ensuring successful trade partner performance.Serve as... ...responsibilities, providing coaching, and building high-performing... ...working for a commercial general contractor preferred 9+ years of construction...For contractorsFull timeContract workTemporary workFor subcontractorWork at officeLocal area- ...Description Builders Concrete Services LLC is a structural concrete contractor serving commercial and industrial projects in the Hillside, IL... ...collaborate closely with general contractors, owners, and trade partners to complete projects safely, on time, and within budget...For contractorsFull timeFor subcontractor
- ...Our client is an established Chicago-area commercial general contractor specializing in construction management, design-build, and general... ...on plumbing, mechanical, electrical, and fire protection trades. Oversee installation of plumbing risers, vertical rough-ins...For contractorsFull timeFor subcontractor
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Trades Business Coach — Contractor. Be the first to apply!
- business coach Chicago, IL
- business mentor Chicago, IL
- executive coach Chicago, IL
- leadership coach Chicago, IL
- low voltage contractor Chicago, IL
- painting contractor Chicago, IL
- contractor program security officer Chicago, IL
- overseas security contractor Chicago, IL
- mail contractor Chicago, IL
- truck contractor Chicago, IL





