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4 contributions to Contractor Skoolkit
Question fo the day
Questions-- "do you guys ever go back and call leads from like a month ago or is that a waste of time" Answer -- Yes — and skipping this is one of the most common mistakes I see. If you've graduated to having a dialer, someone should always be mixing old data into the fresh stuff — people who weren't interested the first time and haven't DNC'd. Stay compliant, but those leads should absolutely get rehashed. Here's the reality: most teams don't call enough, period. They don't bang the phones, and they don't follow up consistently. And a lot of the time the lead was interested — it just wasn't the exact moment they were ready to sit down or buy. Stay consistent and you catch those people when the timing turns. You already paid for those leads. Every deal you pull out of old data drives your CAC down across every source you buy from. It's the cheapest revenue in your whole operation.
Question fo the day
0 likes • 2d
Hey @Jackson Doyle Absolutely. I’ve seen this on the outreach side too, a lead being “not interested” a month ago doesn’t necessarily mean they’ll feel the same way today. Sometimes the biggest missed opportunity isn’t the lead itself, but the lack of a consistent process for revisiting older conversations. If the timing, need, or offer has changed, those old leads can become some of the easiest conversations to restart.
You Don’t Have to Do It All 🏗️
Something I’ve noticed after working with business owners across different industries is that the ones who eventually build something sustainable usually have one thing in common: They genuinely care about what they’re building. They care about their customers. They care about their reputation. They care about their team. And they care about getting the business right. But caring about the business doesn’t mean you should be the person handling every follow-up, admin task, customer message, or operational detail. That’s where a lot of good businesses get stuck. The owner becomes the person everyone depends on, even when systems and automation are already in place. I’ve always believed the right support isn’t about finding someone to simply “do tasks.” It’s about finding someone who can take ownership of the work and treat the business with the same level of care. Whether you’re building an eCom brand, growing a service business, or using AI to scale your operations, that human execution layer still matters. Systems create leverage. The right people make that leverage actually work. 💯
0 likes • 5d
@Jackson Doyle Yeah, I’ve run into this quite a bit myself. It’s easy to get caught up in the AI and automation side, but I’ve found that if the underlying workflow isn’t solid, automation usually just helps you do a broken process faster. Curious what you’ve been seeing on your side, Jackson?
1 like • 4d
@Jackson Doyle Exactly. I think that manual phase is where you actually learn what needs to be automated in the first place. I’ve seen the same thing on the people and operation side. Sometimes the process works fine, but the owner or team is still spending too much time actually running it. That’s where I think the human and automation pieces can complement each other pretty well.
Hey everyone, Jem here 👋
I work around the people and operations side of service businesses, so I joined to learn more about how contractors are using AI and automation to improve the way they handle lead generation, follow-up, and day-to-day workflows. I’m especially interested in what actually works in the field versus what just looks good on paper. Looking forward to learning from everyone, exchanging ideas, and contributing where I can. 🙂
0 likes • 5d
@Jackson Doyle everything good, how about your side? 😄
0 likes • 4d
@Jackson Doyle Nothing in particular, but we are improving some bits and pieces to further add value on our services. How it look your side?
Reflection
Reflection: We just signed two clients we've been chasing for three years. Both are eight-figure home service companies. Both will likely be six-figure accounts every single month. And it took us three years of following up, sending free value, and staying in the conversation to get them signed. Three years. Not three touchpoints. Not a clever sequence. Three years of showing up. Here's what it actually took, and what I'd want you to take from it: 1. These relationships take a long time to nurture — longer than you want them to. The clients that are actually worth having don't sign off a cold pitch. They watch you. They wait to see if you're still there in six months. Most people quit way before the window even opens. 2. Part of it is your methodology — but a lot more of it is your skill. This is the piece people miss. The types of clients you need to land are people you have to level up to work with. Three years ago, we honestly weren't ready for these accounts. The follow-up wasn't just nurturing them — it was time we spent getting better. 3. You have to build the proof before you deserve the yes. We had to stack an enormous amount of proof through our current big buyers and smaller buyers in their industries — real case studies, real numbers — before these two would move. The persistence only works if you're compounding proof while you wait. The takeaway: when something isn't working yet, look at yourself before you blame the process. Part of what you're doing is a skill — and skills get better by iterating and staying in the reps. But only if you stick with it long enough for the compounding to show up. Three years of reach-outs. Two signatures. Six figures a month. That's the math of persistence. You need to pick a lane that has worked for other people — then put in the volume and iterate. Understand that part of it is the learning, part effort, and part skill. I say this as someone who switched to the "shiny object" and lost hundreds of thousands if not millions off of it. Don't be like me haha
Reflection
0 likes • 4d
This is a good reminder that persistence only works when you’re actually getting better while you stay in the game. Same with operations too, follow-up can easily become a process people try to automate before they’ve really figured out what good follow-up looks like. Three years of staying in the conversation and improving along the way is a pretty strong example of why the reps matter.
1-4 of 4
Jem Arcibal
2
12 points to level up
@jem-arcibal-2727
Executive Assistant & Operations Expert | Founder of ChoreChimps VA Agency | Helping Founders Run Leaner, Smarter Businesses

Active 1d ago
Joined Aug 27, 2026
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