In this episode of the Commercial Painting Podcast, host David Chism welcomes back Mike Green, VP of Sales at Ironhead Roofing and a commercial sales coach. If you missed Mike’s first appearance, catch up on Episode 43. Mike shares how he went from recruiter with no sales experience to out-generating three veteran reps in a single winter competition, and how that launched a career built on self-generated, non-referral commercial deals. He breaks down what a strong business development plan looks like for commercial painting contractors: a finite target list of 50 to 100 accounts, practiced messaging, and a defined outreach cadence.

Throughout the conversation, Mike and David explore why execution is where most sales plans fall apart. Mike explains that reps can have phenomenal scripts and detailed plans, but the real challenge is doing the activity every day. They discuss the role of sales managers and coaches in creating accountability, even for self-motivated high performers. They also cover what to look for when hiring salespeople, including a competitive spirit, comfort with hearing “no,” and a self-starter drive, whether the candidate comes from athletics, the military, or outside the trades.

CONNECT WITH OUR GUESTIronhead Roofing
mike@ironheadroofing.com

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Podcast website
Request a FREE 1-Hour Consultation with David Chism

EPISODE SPONSORS
The Wooster Brush Company
The Commercial Painting Industry Associate (CPIA)
DC Marketing Group

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In this episode, Aaron sits down with Chris Kiefer, founder of Boolean Automation and the PaintOS platform. Chris is an engineer by training who spent three years as marketing director at Webfoot Painting, where the company doubled from $10M to $20M in revenue. After other painting companies kept asking him to set up the systems he’d built, he started working as a “software integrator” for the industry. He helps owners cut through the noise of competing tools and build a tech stack around their business goals.

Aaron and Chris dig into what a good tech stack looks like, which tools to buy and which to build, why integration capability matters more than any single platform, and how to use AI without trusting it blindly. They also compare CRMs and project management tools, talk through software costs, and discuss why owners need to learn AI themselves rather than hand it off.

Key Takeaways

• Why a good tech stack starts with your vision for the business, not a software demo
• How to decide what to buy off the shelf (email, CRM, accounting) and what to build (estimating tools that capture your proprietary process)
• Why APIs, MCPs, and integration capability should be the first question you ask any software vendor
• The case for “the fewest tools possible, as many as necessary” over an all-in-one system
• A benchmark for technology spending (2-3% of gross revenue) and how to avoid being over-sold by software reps
• Why learning AI is today’s equivalent of learning to type, and how owners can build the skill

Connect with Our GuestChris on LinkedInEmail: chris@paintos.appWebsite: PaintOS

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Podcast website
Request a FREE 1-Hour Consultation with David Chism

Episode Sponsors
The Wooster Brush Company
The Commercial Painting Industry Associate (CPIA)
DC Marketing Group

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In this episode, Aaron sits down with Mike Barrett and Bill Curtindale, co-founders of Pro Paint Solutions in the Seattle metro area. Both Mike and Bill spent years as employees and eventually senior leaders at another commercial painting company before striking out on their own in March 2021. Now five years in, they share how they built a profitable, debt-free business, kept their 50/50 partnership strong, and set a plan to step back from day-to-day operations over the next five years.

This conversation is especially relevant for painting company owners worried about key employees leaving to start competing businesses, and for employees weighing whether to make the leap into ownership themselves.

Key Takeaways

• How Mike and Bill's decade-plus at a former employer shaped their approach to ownership
• Why it only took about three months to go from "we should consider this" to launch day
• The cultural commitments they made to avoid repeating their former employer's mistakes
• How they built a debt-free, self-funded company from year one
• What they track weekly to stay fiscally disciplined and catch problems early

• How a 50/50 partnership survives disagreements without a tiebreaker
• Their 10-year plan to grow to $15M in revenue and step back from daily operations

Connect with Our Guests

Bill on LinkedIn

Mike on LinkedIn

Website: Pro Paint Solutions

Connect with Us

⁠⁠⁠Podcast website⁠⁠⁠

Request a FREE 1-Hour Consultation with David Chism

Episode Sponsors

⁠The Wooster Brush Company⁠

⁠⁠⁠The Commercial Painting Industry Associate⁠⁠⁠ (CPIA)

DC Marketing Group

If you enjoyed this episode, be sure to like, share and subscribe!