Most excavation companies grow by grinding harder.
Jack Eso grew by tightening systems.
In this episode of the Skid Steer Nation Podcast, Ryan Deemer sits down with Jack Eso, owner of Rosebrooke Site Development in North Carolina. In just two months, Jack’s company landed over $4 million in commercial site work — without slashing margins or chasing the “going rate.”
This conversation breaks down what actually changed:
- Pricing with a 50% gross profit target on residential
- Tracking $300K–$350K revenue per employee before hiring
- Outsourcing estimating to free up leadership time
- Automating sales follow-up with CRM, email, voicemail drops, and video
- Building weekly meeting structure so crews don’t drift
If you’re running excavation, grading, utilities, concrete, or residential site work and want to scale without chaos — this episode is a blueprint for building a business that doesn’t depend on you being everywhere at once.
Links:
➡️ Visit Rosebrooke Site Development’swebsite – Follow his Jack Eso’s excavation journey.https://rosebrookelh.com/
➡️ Shop Attachments at Skid Steer Nation: https://www.skidsteernation.com – “Build your business with the right attachments.”
➡️ Marketing Help at Throttled Up: https://www.getthrottledup.com – “Marketing built for contractors.”
02:29 Starting as a weekend hustle while working DOT projects
03:06 Making more in a weekend than a full-time job → leap to full-time
03:52 “Education is expensive” – costly lessons in business
05:52 Saying yes to everything early → losing money & learning to specialize
06:50 Creating a filter for what jobs to accept (play to strengths)
07:30 Bringing concrete work in-house to control projects & margins
10:49 Scaling to 10+ employees & tracking revenue per employee
11:49 Investing in coaching & mentorship to accelerate growth
17:01 Scaling crews → communication breakdowns & need for systems
18:06 Using software (JobTread, Slack) to centralize communication
20:14 Building culture with core values, expectations & accountability
22:02 Defining “what done looks like” to avoid micromanagement
25:18 Outsourcing estimating to free up time & land bigger jobs
29:08 CRM + automation systems to follow up and increase conversions
31:10 Process-driven businesses = higher professionalism & trust
34:09 Weekly meetings + daily “tailgate talks” improve performance
39:29 Don’t sell yourself short → know your numbers & pricing
40:18 50% gross profit mindset for residential work
43:09 Managing money with separate accounts & financial discipline
47:31 Biggest mistake: underestimating how hard business really is
50:18 Goal: build a self-sustaining, sellable company by 2030
51:48 SOPs (“playbooks”) as the foundation for scaling
57:56 Using Loom/video to increase sales and improve communication
01:01:30 Final advice: do the right thing, even when it costs you
