The Roofing Operating System Podcast: America’s Top-Rated Podcast for Roofing Software & Scalable Growth

#43 - How HeyPros is Disrupting Subcontractor Management for Roofers & Contractors

Jul 23, 2025

Dmitriy Ivanchuk, the founder and CEO of HeyPros, shares his journey from the trades to revolutionizing subcontractor management. He discusses how his platform simplifies chaos in the construction sector, making it easier for contractors to connect with skilled workers. Key topics include the importance of building strong relationships with subcontractors, effective communication, and automated processes for growth. Dmitriy also highlights the value of clear expectations and the future of technology in project management for roofing and contracting.

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ANECDOTE

Dmitriy's Origin in Trades

Dmitriy Ivanchuk started in construction by running a painting company from age 18, after years of painting with his father.
He noticed immigrants struggled to find subcontracting work, inspiring the core idea behind HeyPros.

INSIGHT

Misaligned Expectations Harm Subs

Poor subcontractor performance often stems from a misalignment of expectations rather than inherent bad behavior.
Proper communication and motivation can turn underperforming subs into top performers.

ADVICE

Set Clear Expectations and Reward

Vet subcontractors with consistent questions and set non-negotiable company expectations upfront.
Reward subs regularly with positive feedback to motivate and build trust.

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🚀 How HeyPros is Disrupting Subcontractor Management for Roofers & Contractors | The Roofing Operating System Podcast

Description:
Discover how HeyPros founder Dmitriy Ivanchuk transformed subcontractor chaos into streamlined growth. Learn how modern contractors scale using powerful, easy-to-use software tools. Perfect for roofers, painters, and project managers.

Podcast Episode:
In this high-impact episode of The Roofing Operating System Podcast, host Nick Peret interviews Dmitriy Ivanchuk, founder and CEO of HeyPros — one of the fastest-growing SaaS platforms for subcontractor management, automation, and growth.

Dmitriy shares his origin story in the trades, how HeyPros was born out of real operational pain, and what it takes to run a streamlined, subcontractor-friendly business today. If you're a contractor struggling with hiring, fulfillment, or scaling past the $1M mark, this episode is gold.

🕒 Episode Highlights + Timestamps:

00:00 Introduction to the Guest and Company
00:52 Founding Story and Initial Challenges
02:48 Subcontractor Management and SaaS Development
05:04 Scaling the Business and Future Plans
07:46 Best Practices for Working with Subcontractors
13:38 Creating Predictable Systems for Project Management
16:58 Identifying Non-Cooperative Workers
17:22 Simplifying Process Refinement and Tech Implementation
17:53 Introduction to HeyPros Software
18:55 Target Audience and Key Features of HeyPros
20:03 Challenges Faced by Growing Businesses
21:31 How HeyPros Supports Solopreneurs
23:05 Integration and Automation with HeyPros
28:35 Building a Self-Sufficient Business
31:31 The Importance of Mindset in Business
33:05 Conclusion and Final Thoughts

🚀 What You’ll Learn:

✅ Why most subcontractor issues come down to poor communication & lack of systems
✅ The biggest challenges scaling past $1M–$5M — and how HeyPros solves them
✅ How automating check-ins, compliance docs, work orders, and payments helps you reclaim time
✅ What makes HeyPros different from bloated “all-in-one” CRMs
✅ How mindset shapes your ability to build and lead with vision

🌐 Try HeyPros Free Today
🔗 https://heypros.com/

🧠 Bonus: Get a Free Roofing Growth Audit to scale your ops, sales & tech stack smarter.
🔗 https://mybetterboss.ai/

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💥 Built to Be Better. Let’s go. 💪

💥 That’s a wrap on another episode of The Roofing Operating System™—America’s top-rated podcast for roofing software and scalable growth.

If today’s insights sparked just one idea to scale smarter or grow faster, imagine what a full strategy could do for your business.

👉 Head to mybetterboss.ai to access free tools, book a discovery call, or explore systems trusted by top roofing companies nationwide.

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Until next time—build better, lead stronger, and scale like a boss.