[SaaS Series] Unveiling Freight’s Hidden Secrets With Chadd Olesen of AVRL

Chadd Olesen is the CEO and Co-founder of AVRL, an Austin-based automation company specializing in logistics and supply chain technology. Since launching AVRL in 2017, he has led its transformation from a natural language processing startup into a freight tech powerhouse, now automating over 60 million shipments annually. Under Chadd’s leadership, AVRL has become one of the fastest-growing companies in the US, earning recognition on the Inc. 5000 list. He is known for his consultative approach to automation, empowering brokers and carriers to integrate technology without sacrificing human expertise.

Here’s a glimpse of what you’ll learn:

• [04:06] Chadd Olesen discusses how AVRL automates pricing for spot freight transactions
• [05:12] Why AVRL removed all content from its website and operates in stealth mode
• [06:45] The strategic decision to onboard only 18 companies annually
• [07:38] How Walmart introduced AVRL to JB Hunt, leading to its entry into freight
• [12:24] Chadd shares the origin of AVRL as a voice tech company and its pivot to logistics automation
• [15:26] Lessons from scaling engineering teams in Seattle, Toronto, and Latvia
• [22:47] Early niche explorations in automotive, CPG, and oil and gas
• [26:09] Startup mistakes including chasing big logos and overhiring
• [33:44] How customer relationships turned into mentorship and business growth opportunities

In this episode…

Breaking into a saturated and highly competitive industry like freight and logistics is no small feat — especially when innovation is rare and copycats abound. Startups in this space face challenges like differentiating their offering, managing growth without overexposure, and surviving tight margins. So, how do you build a technology-driven solution, scale it, and protect your edge in a legacy industry?

Chadd Olesen, a seasoned entrepreneur with a background in voice and automation technology, shares how he strategically navigated these hurdles by focusing on deep integrations, word-of-mouth growth, and selective client onboarding. He emphasizes the importance of starting with a clear problem — such as inefficient freight pricing — and solving it with adaptable, robust tech. He warns against the allure of big corporate logos, advocating instead for smaller, agile client relationships and value-based pricing. Through lessons learned the hard way, Chadd recommends hiring scrappy engineers over corporate veterans and using automation to minimize human error and maximize scalability.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Chadd Olesen, CEO of AVRL, about disrupting the freight industry through automation. Chadd discusses entering a legacy space without industry experience, how his team landed enterprise clients like Walmart and JB Hunt, and the strategic decision to operate in stealth. He also explores product-market fit, the funding process, and how his leadership evolved after becoming a parent.

Resources mentioned in this episode:

• Chadd Olesen on LinkedIn
• AVRL

Special Mention(s):

• Paul Transportation

Related episode(s):

• “Automation Solutions with Wade Foster Founder of Zapier” on the Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on the Inspired Insider Podcast
• “[SaaS Series] Tips To Thrive in the SaaS Space With Sujan Patel” on the Inspired Insider Podcast

Quotable Moments:

• “If you don’t do it, you die. That’s transactional freight into an automated process.”
• “I was attracted by big logos. It’s a trap for startup founders.”
• “We literally went in, internalized it, looked at how far we were in the process.”
• “Focus on base hit. Don’t focus on the grand slam right now. Protect equity.”
• “Founders aren’t shaped by wins. They’re shaped by failed things, issues, challenges — those define the journey.”

Action Steps:

1. Hire for hunger and trainability over pedigree: Recruiting motivated engineers with a willingness to learn often yields more adaptable and loyal team members.
2. Operate in stealth when entering competitive markets: Limiting public information reduces the risk of copycat competitors and protects proprietary strategies.
3. Use value-based pricing models: Tying your pricing to measurable value encourages fairness and reinforces your company’s impact.
4. Avoid chasing big brand logos too early: Large enterprises often bring complex legal, procurement, and payment challenges that can stall growth.
5. Automate customer success operations when possible: Leveraging technology to manage support and feedback increases efficiency and ensures scalability.

Episode Transcript

Intro: 00:00

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz: 00:22

Doctor Jeremy Weisz here, founder of Inspired Insider where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Chadd Olesen of AVRL. You can check him out at, although there’s not much on the site, and he’ll talk about why and we’ll pull it up at some point too, and I’ll go through it. Chadd, before I introduce you formally, I always like to point out other episodes of the podcast people should check out, since this is part of the top SaaS series.

Some other good interviews there. One of the co-founders, Zapier. That was a very interesting interview with Wade Foster, and he talked about, you know, just kind of the evolution, the journey a bit, which we’ll go through with Chadd too. I don’t know if I would compare this. You’re like the Zapier of logistics and freight, but you know some there along the lines.

And we’ll get into what Chadd does in his company. I also had one of the co-founders of Pipedrive on, I think, when I had him on. They were 10,000 customers. Now they’re at over 100,000. So they’ve grown quite a bit.

And the founder of Mailshake, who’s been kind of snatching up and buying smaller SaaS companies and rolling them into their portfolio, which that’s an interesting story of growth through acquisition. And I think they have over like 70,000 customers with Mailshake, which is a cold email campaign. So check that out and more on inspired Insider.com. This episode is brought to you by Rise25. At Rise25, we help businesses give to and connect to their dream relationships and partnerships.

We do that in two ways. One, we’re an easy button for a company to launch and run a podcast. We do the strategy, the accountability, and the full execution and production number two. We’re also an easy button for companies gifting, so we make gifting staying top of mind to your clients and partners prospects easy, seamless and affordable. All you have to do is give us the list of the people and we’ll do everything else.

And you know, from gift selection to the card to the brand, your branding on the box. You know, Chadd, we call ourselves kind of the magic elves that run in the background to make it stress-free so companies can build great relationships around their business. And for me, I found no better way over the past decade to build relationships through having the people I admire in my podcast and sharing with the world what they’re working on, and sending them sweet treats in the mail so you can go to rise25.com or email [email protected] I am super excited to introduce Chadd Olesen and his team.

You know, Chadd and his team launched AVRL in 2017 to connect disparate systems for Fortune 500 companies. And we’ll talk about they went through different niches along the way. Right. They didn’t just land on freight like the magical moment of product market fit and the right market. So we’ll talk a little about the journey.

And by 2000, you know, 2018, AVRL was working with most of the Fortune 10 and had secured two rounds of funding from extremely notable firms including SAP Social Capital, Fontinalis Partners and Morpheus VP. And today, leading three Pls in asset-based carriers. Leverage avails technology to automate and execute these disparate systems, and AVRL is currently 496 on the Inc. 5000, and one of the fastest-growing companies in Austin, Texas. And fun fact about Chadd is he grew up on a farm in a small town. I think this small town is maybe around 1,400 people, so if you can kind of visualize that, it’s probably for some people, Chadd, it’s that’s less than like their graduating class of their high school, but that’s the whole town.

So Chadd, thanks for joining me.

Chadd Olesen: 03:54

I appreciate you having me on.

Dr. Jeremy Weisz: 03:55

Let’s start off with AVRL and what you do. I’m going to share my screen and share the content-rich website of AVRL. All right. And you’ll talk about what you do?

Chadd Olesen: 04:06

So at AVRL, a lot of third-party logistics companies or freight brokers is what the industry calls them, or asset-based carriers. The trucking companies use our automation to automatically price their transactional freight. Most people in the world don’t understand that these asset-based carriers and brokers work on two types of contracts. One is an RFP, which is how many, how much volume you’ll move on an annualized basis. And then there’s another set of volume that trades on almost like a dark pool.

But it’s called spot freight. And we automate about 25 million transactions per month on the transactional spot side.

Dr. Jeremy Weisz: 04:49

So we’re looking at the site. People can see this, you know. This is it. I can’t click anywhere else. So if you’re listening to the audio, check out the video part.

And obviously, you probably put a lot of thought into this specific copy on this page because there’s only, you know, one, two, three, four, five lines on this whole page. So talk about the thought process behind this.

Chadd Olesen: 05:12

Yeah. So pre-2020 mid 2020 around Covid. We were operating outside of freight. The logistics industry. And we had a full website etc..

The moment that we moved into the freight technology space we had a website, we were talking about what we were doing and it was probably like two weeks later, another tech freight tech company said that they were doing the exact same thing. And as we started to look into that market, it’s really incestuous space. There’s not a lot of innovation. It’s a lot of copycat. And so we actually just removed all content from the greater internet for all practical purposes, and kind of went into almost like a stealth mode as we kind of consumed that market.

Today, we work with maybe almost 70% of the top 103 PLs and large asset-based carriers. And we’ve done it all via word of mouth. And it doesn’t mean that we won’t advertise at some point or market at some point. But right now it’s a lot easier to compete in the space when we’re not creating our own competition.

Dr. Jeremy Weisz: 06:18

Talk about so there’s a, you know, RL automation technology at 4.0 scale. Over the course of the year, we identify 18 companies to work with us to automate their processes. Talk about what you know, how you came up with this. I mean, it could be 17. It could be 19.

It could have been 21. What was the thought process behind this? I mean, this is the only line on the whole website.

Chadd Olesen: 06:45

It’s a little fear-mongering, to be honest, when you look at moving this bidding or this transactional freight into an automated process, if you don’t do it, you die. And when we were looking at how we control contract volume, how we can control contract price, etc., it was to limit the number of entries that we could consume. And our approach is a lot different than a lot of startups. A lot of startups will go after small, medium sized businesses and work their way up. When we came into the freight side, our first customer was JB Hunt, for all practical purposes on the railroad.

And what had happened was they just.

Dr. Jeremy Weisz: 07:25

Just for people’s, you know, vantage point. JB Hunt, they did 3.15 billion in the fourth quarter of 2020 for revenue. So that is a huge first client to get.

Chadd Olesen: 07:38

What had actually happened is we were working with Walmart and they had introduced me to JB Hunt and that was this really interesting like opportunity for us. We actually didn’t know anything about freight. We had actually gone in to pitch JB Hunt, this very unique use case that we thought that they would want spent a couple of days with them and they were like, actually, could you automate this other process for us? We went and learned it, deployed our technology to solve that challenge. And then we had another 3PL and asset-based carrier in Arkansas call us to do the exact same thing.

One of the things that a lot of people don’t know about the freight or logistics industry is it’s super incestual. Every company basically spurred out of, you know, 2 or 3 companies, and now there are, you know, 20,000 freight brokers and 500,000 asset-based carriers. But really, they launched out of these small groups.

Dr. Jeremy Weisz: 08:30

Talk about onboarding. You know, this is the first client you get in this industry. It’s a different industry from what you’re used to. How did you redefine and configure your onboarding based on this type of client.

Chadd Olesen: 08:42

So I had gotten really lucky. Part of the reason why SAP was interested in us originally is we had built a custom browser, and when you look at how SAP was created, it was a closed environment where they didn’t expose APIs so you couldn’t hook into it and extract data out of it. That also led to the opening and opportunity for Salesforce to come into that space. But part of our browser was to extract data out of and out of a legacy ERP system so that we could do ETL on it. When we went and looked at what JB Hunt wanted is they wanted to run automation on the web, but you couldn’t use robotic process automation because it’s a third-party system that you don’t own.

And so any page change or XPath change would break RPA. What we did was we started just inserting HTML into the site, and when we were looking at the process, we actually didn’t know how much opportunity there was. But it was probably like the fourth month in their head of data science was like, we were on a call like this, and he’s like, hey, we need a new contract. We were like, why? This doesn’t make sense?

And he was like, well, you’ve already made us $11 million. And I’m like, looking at my co-founder and like that tiny window in the corner and I’m like, don’t say anything right now. Like, just get off the call as fast as possible so that we could come in and look at like what we were pricing, etc..

Dr. Jeremy Weisz: 10:04

And when he was saying that and he’s like, let’s redo the contract, was saying, we want to pay you more.

Chadd Olesen: 10:08

Yeah. He was saying that they wanted like a longer term contract. We had done like an initial like, you know, six month, like proof of value. I don’t we’ve never done a contract we didn’t charge for. I think it’s like the biggest pitfall of any startup is doing anything for free.

But, you know, they wanted a longer contract. And what we wanted to do is do value-based pricing on it.

Dr. Jeremy Weisz: 10:29

Yeah. So how do you determine value-based pricing when they’re like, you just made us 11 million. You’re like, okay, you know, we’ll take two. I mean, I don’t know.

Chadd Olesen: 10:41

We’re like, you know, like shooting in the dark. We’re just like we literally went in, internalized it, looked at like how far we were in the process and where we were going to go. And we pitched based off of that. They accepted it, which meant we priced wrong. Right?

It’s like the worst thing to do. But it’s I mean.

Dr. Jeremy Weisz: 10:59

I mean, I guess, I guess part of it. But like you also, you know, they’re happy. You don’t want to get too much pushback. But we always think, oh, I could have done more if they just accepted it right off the bat. But yeah, you know, they’re happy, I guess.

Do you think, you know, from a company like that, are they typically sharing that type of stuff with you? Hey you saved us X amount or I.

Chadd Olesen: 11:21

Don’t know, I think the industry is really interesting because when you look at the freight brokerage side, these guys operate on like 2%, 4% more. And so there’s not this like this yield, this massive yield that comes out of like 11 million bucks right there, probably running it like a 10% margin on it. And so when you look at these large companies, pricing is really important. Like to maximize the contract value. We focus predominantly on yield.

And yield extraction has to be like I you know I make them more revenue. We want to work with them to turn that revenue into margin. Essentially.

Dr. Jeremy Weisz: 12:03

Talk about the you know, we talk about the onboarding a little bit. I mean, this is very highly technical. When you built the team originally, what did that look like. And then I’d love to talk about how the team evolved over time. But talk about the team and what you just, you thought you needed to build in the beginning.

Chadd Olesen: 12:24

Yeah. So most people don’t know this, but AVRL stands for Advanced Voice Research Labs. And my CTO had brought some technology out of Cornell that he had been working on. That essentially was natural language processing, but it measured sentence length and then looked for conjunctions and inflections inside a text. And that’s really hard to do because inflections do not live in text.

But if you measure the sentence length, you could start to predict where mis-transcriptions live inside of speech recognition and advanced voice research. Labs was created solely because BMW wanted us to build their in-car voice tech. And our original team was all based off of that as we started to look at, you know, scaling and companies like Soundhound in the market at the same time as us. We were like, well, we’re not going to be able to compete with like, you know, Siri had just acquired some tech or like Apple had just acquired some tech that turned into Siri and Soundhound was booming. This is all 2017 when there was like so much NLP hype.

We were like, let’s go after the business application space, which is why like SAP was like super, super interested in it and our team.

Dr. Jeremy Weisz: 13:43

How did you get in? Just to back up for one second. How did you even get into discussion with BMW?

Chadd Olesen: 13:50

Craziest like situation. Flew to Cal, like flew to San Francisco. We met with like Ford, BMW, Volkswagen, Mercedes-Benz all in one day. And we’re like, we’re going to pick one. We’ll go exclusive on that specific contract for in-car voice tech for a certain amount of time, and it was whoever signed it first took it, and BMW signed our contract.

No edits, which is wild.

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