42 minutes with Chiirp’s dealmaker Justin Judd

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AI is to the world now what the internet was back in the day… it’s not going anywhere, so in my opinion, the companies that don’t embrace and accept it are gonna miss out.

Justin Judd is the Head of Sales and Partnerships at Chiirp, a company that automates follow-ups for contractors and helps them close more deals.

Justin is a mental health-focused, traveling hustler who runs Chiirp’s sales team and works to ensure the success of their customers. Enjoy our conversation on Chiirp, AI, and more.

What is Chiirp?

Contractors are spending thousands to generate new leads, but there’s a gap between generating them and converting them. Follow-up is a huge part of this, and relying solely on a sales team for that is dangerous.

We’re a software product that blends the strength of a sales team with automation. Texts, emails, ringless voicemails — we help contractors with follow-ups. We integrate with contractors’ existing CRMs so they don’t have to change their workflows.

How would a contractor use it?

Estimate follow-ups are a big use case. Each contractor is already triggering events in their CRM — sending estimates — and Chiirp recognizes that, and automatically starts an estimate follow-up campaign, for example.

Big picture, why does that matter? 

The problem is contractors don’t follow up with leads. If you’re going to spend money on leads, you should make sure you’re getting the most out of them.

Jon Ryan, from one of our customers, Genz Ryan, said the best advice for companies looking to scale is to shift energy from generating new leads to taking advantage of customers you already paid for — so they pay for stuff over and over again.

But you can’t totally ignore new leads, right?

[Right], so here’s another use case: speed to lead. Salesforce did a study of over 2 million lead form submissions and found that if you respond to a lead within 1 minute, you’re 391% more likely to convert that lead.

Usually, a salesperson calls leads, and for the very best companies, that may be 5-10 minutes afterward. Chiirp does it within 30 seconds — a text, email, or ringless voicemail.

How do texting and email compare to each other as a marketing channel?

Text message has a 98% open rate with a ~15-50% response rate depending on the campaign. If you’re an email genius, you might be looking at a 17-28% open rate, and of those opens you might get a 5-10% response rate. Email marketing definitely has its place. But if you’re looking for conversion, there’s just no comparison. 95% of Americans prefer text as their main form of communication.

Where’s the industry heading, technologically, over the next five years?

AI. AI is to the world now what the internet was back in the day. A pain point we run into at Chiirp is when a lead comes in at midnight and there’s no person there to respond. So, we’re building bots to respond to lead forms how you want them to, for example.

People are scared of AI, but it’s not going anywhere, so in my opinion, the companies that don’t embrace and accept it are gonna miss out.

What’s your day-to-day like?

Right now I’m building out our sales team so I can focus on more high-level partnership stuff. I do sales training — but less about systems and processes, and more about building trust and getting rid of the “buyer/seller vibe.” I’ll do enterprise demos, put content together for existing partnerships, research new partnerships, and travel to a lot of events.

When you’re not working, what are you doing?

I read a lot of books (mental health, self-development), I play a lot of sports (softball, pickleball), I love to travel and experience new cultures, and I may or may not be slightly obsessed with food.

I focus a lot on my mental health. I’ve always been a very passionate person and it’s been a good and bad thing at different points in my life because I go hard in everything I do. So the older I get, the more I realize that I have to keep my mental health the first priority or the way I do things won’t be sustainable.

If you couldn’t do the type of work you’re doing now, what would you want to do?

[I’d] promote mental health through physical activity within the tech community. People tend to get burnt out in tech very easily. And if you want to get out of the mind, you have to move into the body.

So I want to create a place where people can get out of the office, compete against other tech companies in sports, and have some fun.

If you could have dinner with anyone in history, who would it be?

Napoleon Hill, who wrote the book Think and Grow Rich. The reason is because that book changed my life. I’ve read it more times than I can count.

I’m an absolute believer that what we focus on increases, and that everything is energy. I work on that stuff every day, so just to have the chance to sit down and pick his brain would be a really cool experience for me.