I help contractors scale
- 01Attract
- 02Convert
- 03Operate
Cofounder of Sherpa with Matt Marshall, building the AI systems that help contracting companies attract more leads, convert them, and run the whole thing on less.
- 100+ Contractors scaled
- $231M+ In contractor revenue generated
- 95% Report a revenue increase in the first 30 days
The Sherpa System™
Jacob helped pioneer the Sherpa System, which helps contractors capture the numbers most never collect, then automate on top of them.
- 01 Trailhead
Attract
Tiers of efficiency. Max out the cheapest leads first, referrals, reviews, and organic search, then scale spend only once the lowest cost per acquisition is proven.
- 02 Base Camp
Convert
Speed to lead, then process. Every lead answered in seconds and followed up automatically, with one pipeline the whole team runs the same way and the right numbers tracked.
- 03 Peak
Operate
One system instead of thirty. Proposals, scheduling, dispatch, material orders, quoting, and invoicing connected in one place, so the business gets simpler as it grows.
Get a diagnosis
It's a 20 minute virtual workshop where you get personalized, actionable insights from Jacob, who helped scale Sherpa and its partner companies. No fluff, just a straight read on where your online presence, sales process, and operations actually stand.
- 01
One on one
Time with Jacob on your business specifically. Marketing, sales, and AI strategy.
- 02
The Sherpa scaling framework
How Sherpa thinks, operates, and scales a $250M a year partner portfolio, broken down step by step.
- 03
Three to five tactical next steps
Clear, actionable moves you can run this week to break past your current constraint.
What contractors say about Jacob
I'm having people say they found me on Google Gemini. No one ever heard of an AI lead two years ago. You guys have done an awesome job so far, we've got AI leads coming in!
I've had a ton of people approach me with this sort of thing in the past, and I never made the move. But after I talked to Jacob, I want to work with you guys as long as possible.
Our phone number would not ring, would not ring at all. We now have two people answering phones full time and an AI assistant catching overflow calls, and our phone won't stop ringing.
The AI stuff is really the future, that's why I wanted to go with it. Some things you're better off paying somebody that knows what they're doing. I make more money doing my job than I ever could doing it on my own!
It was just really overwhelming, the amount of leads that were coming in, five to thirty people a day filling out the forms. One job out of there was twenty-three grand, another was forty-one, another was sixty-something thousand. Having the automation is a game changer. If I'm on a roof, I don't have to worry that I missed a small window of opportunity. It definitely works.
When I pay a company, I expect them to do their job, and our last team just wasn't scaling us the way we needed. With you guys, it's great!
Nothing but very responsive and great to work with. I text, I reach out, you make time, even late at night. You can't beat that kind of hands-on. We're at 30 leads a week plus. You guys are innovative and you stay right on the edge of what's going on.
Jacob showed me why my site was not even being seen. And in the short time you guys took over, it's already starting to work, the calls are coming in, and I'm very happy about that. I trust you guys, because you really care about what you do!
Would I recommend working with Jacob? Oh, absolutely. Absolutely.
See where you rank against the contractors you compete with
The audit shows you where you stand on Google and AI search, where leads are leaking between the first call and the signed job, and the first three things to fix.
Get my 360° auditQuestions contractors ask
Who is Jacob Ragan?
Jacob Ragan is a cofounder of Sherpa and an AI systems consultant for contractors. He helps contracting and home-service companies across the United States implement AI by capturing the data most contractors never collect and using it to automate their marketing, sales, and operations. He cofounded Sherpa with Matt Marshall.
What is Sherpa?
Sherpa is the company Jacob Ragan cofounded with Matt Marshall. It builds AI marketing, sales, and operations systems for contractors, with a mission to help 1,000 contractors modernize their businesses in the next 18 months.
What does implementing AI in a contracting business actually look like?
It starts with data. Jacob instruments your business so leads, calls, quotes, and jobs are tracked, then layers in automation: instant response to new leads, an AI receptionist that books and follows up, and automated quoting, scheduling, and back-office workflows. Fewer missed leads and less admin, not AI for its own sake.
Why does Jacob start with the data?
Because you can't automate what you can't see. Most contractors have numbers scattered across tools and nobody really knows what's working. Capturing the data first turns every later decision, what to automate, where to spend, who to hire, into an informed one instead of a guess.
What can Sherpa automate across marketing, sales, and operations?
Marketing: lead tracking, speed-to-lead response, reviews, and reactivation. Sales: intake, follow-up, CRM pipelines, offers, and downsells. Operations: quoting, scheduling, dispatch, invoicing, and data entry. It all connects into one system where information flows automatically.
Do I have to replace the software I already use?
Usually not. Jacob builds around the tools you already run, your CRM, phones, and field software, and connects them so data flows between them. If something is genuinely holding you back he'll say so, but the goal is to make your current stack work like one system.
How fast do contractors see results?
The quickest wins are speed-to-lead, follow-up automation, and reactivation. Those usually show up within the first few weeks because they recover revenue from leads you already have. The deeper systems and data advantages compound from there.
What does it take to rank on ChatGPT and Google's AI Overviews?
First, treat it as worth doing: BrightLocal's 2026 Local Consumer Review Survey found 45% of consumers using AI to find local businesses, up from 6% in the 2025 survey. After that it's the same things that make you a credible answer to a person: a site that states plainly what you do and where, real reviews, business information that matches everywhere you're listed, and content answering the questions buyers actually ask. That last part carries more weight than it sounds like it should. The same survey found 88% of consumers still fact-check what an AI tells them, so the AI decides who makes the shortlist and your review profile still has to survive the second look. The contractors showing up in AI answers today mostly started before their competitors knew it mattered.
I don't have the team for this yet. Is it too early?
No. Systems are what let you hire well, not the reward for having hired. Most owners start while they're still doing too much themselves, because the automation takes work off their plate first. That's usually what frees up the time and the money to make the next hire a good one.