May 2026: Stop figuring it out alone, Fixing LTL once and for all, and the shadow CFO

Work in Progress: May 2026

Over the past year or so I was in a constant state of dread and FOMO.  Every time I looked up, I was behind.  

LLMs were grossly better one day and regressing the next. SaaS was dead. Everyone was an automation expert. The economy was weird. Customers wanted more. Teams had less.  And my LI feed made it seem like everyone else had the playbook.

I did not have the playbook. 

Which was inconvenient because I make my living by anticipating. 

Then one day, not so long ago I woke up and realized: “Holy shit! no one else knows what is going on either. Like nobody!”

And weirdly, that helped a lot.

Because if no one has the playbook (since there isn't one) then the move isn’t to pretend we do. It’s to build it together. In the open. Brick by brick. 

All that and more from May:

1. Stop figuring it out alone

2. The Golden Era of software

3. How we fix LTL freight

4. The rise of the shadow CFO

1. Stop figuring it out alone

I’ve talked a lot about community as the next frontier for marketing. 

The real reason we’re starting our own is because I think a lot of people are tired of pretending they have the full picture. We’re trying to keep up with every new AI launch while making decisions with too little context and too many people acting like the answer is obvious. Which makes one feel anxious and alone - see opening paragraph.

So we’re starting something new at Junction.

A community for people who are done trying to figure it all out alone. 

The idea is simple: bring together people across distribution, transportation, operations, and tech who are seeing the change up close.

Not in a polished, “thought leadership” thing. a place where they can share what they’re learning.

We’re starting with Field Notes. A conversation series where I talk to people across distribution, transportation, and tech who are all trying to figure out how to meet the demands of the market in real time. The series will focus on folks in various stages of transformation.

We’re still getting it off the ground. It will probably be messier than I’d like. Most worthwhile things are.

We filmed the first episode last week. Big thank you to @Curtis Garrett for being our guinea pig and helping us get this thing off the ground. You can check out the episode here. 

If you’re open to contributing, come be part of it. No polished thought leadership required. In fact, preferred. Just shoot me a DM.

And if you want to follow along as we build it, we just launched our new LinkedIn page @withJunction - give it a follow. We’ll be sharing all of this and the useful stuff we’re learning as we go.

2. The Golden Era of software

Once upon a time, before some of you were born, or before you knew anything about anything, software was sold, customized, installed on a server, and then basically became yours.

You owned it. You maintained it. You customized it as needed.

Was it expensive? Yup.
Was it brutal to install? Also yup.
Did it take three years, a steering committee and consultants? Usually.

But when it worked, you ended up with something that actually fit your business. Not perfectly. Nothing ever does. But close enough that the software bent toward the business.

Then came SaaS.

And to be clear, SaaS was better in a lot of obvious ways. Faster to deploy. Lower cash outlay. Easier to maintain. Easier to update. Easier to try. Easier to cancel, at least in theory. But there was a trade.

You got speed, but you gave up fit. You had to squeeze your business into someone else’s product. And most of the time you were trying to figure that out after a few demos with a 24-year-old AE who had never stepped foot inside a business like yours, yet seemed very confident that their platform would “streamline your workflows.” So you rolled the dice. The cost looked low enough.

And then six months later, the thing was half-used, half-implemented, or sitting in the graveyard of “not quite the right fit” SaaS apps that exists inside basically every company.

Sometimes SaaS worked incredibly well. There are categories where the model is almost perfect. Payroll. CRM. Email. Accounting. Ticketing. Some parts of marketing. Some parts of finance. Things where the workflows are common enough that standardization creates real leverage.

But for messy, operational businesses? For companies where the workflow is the advantage? SaaS was often a pretty bad deal. Because the buyer was forced to adapt too much.

Salesforce is probably the best example. You could customize it, sure. But often that meant you got the worst of both worlds: "forever" SaaS pricing, plus consulting-heavy customization, plus internal admin complexity, plus a product that still never quite felt like it was built for how your company actually worked. Does anyone even really know why they need Salesforce anyway?

So yes, SaaS was a great model for SaaS companies. I’m less convinced it was a great model for many buyers. 

But now I think we may be entering something different. Maybe the golden era for the buyer.

Software is getting much faster to build. And because it’s faster to build, it’s becoming cheaper to shape around a specific customer, workflow, industry, or operating model.  For a start up, customization to a certain extent now scales.

People who are waist-deep in this, myself included, are seeing something like a 5x to 10x lift in speed. Maybe more in certain parts of the stack. Not without taste, judgment, architecture, and deep domain understanding.But enough that the old economics start to break.

The old logic was:

Custom software fits better, but it is too slow and too expensive.

SaaS is faster and cheaper (sort of), but you have to fit into it.

The new possibility is:

Custom-quality fit, with SaaS-like speed and maintenance. That is a big deal and it's a win-win.

The customer gets fit without taking on the full burden of ownership. The startup gets scale without forcing every customer into the same rigid product box.

But the hard part, (and this is where I think a lot of people are drifting) is that this does not mean “services are back” or “every customer gets whatever they want.” That would just recreate the old consulting mess with better tooling.  And to be clear, I am seeing a lot of both of these in the market.  

The real opportunity is that the product vendor can behave more like a software-enabled operating partner. The product that has a strong core, but can flex around the customer.

The vendor that does not just sell seats or modules, but takes responsibility for outcomes, workflows, automation, and continuous improvement. And the buyer does not have to choose between “buy the generic SaaS tool” and “spend millions building something custom.”

This, to me, is the new horizon.

3. How we fix LTL freight (once and for all)

I’ll save everyone from the deep dive into the root causes, history, tariff structures, broker politics, carrier incentives, and all the other details around how we got here. 

These are the high-level observations from someone (me) who has spent a lot of time in a lot of corners of this market, on the shipper, technology and carrier side.

1. First, freight class is mostly ridiculous.

The way we use NMFC codes today creates more confusion than value. It creates disputes, reclasses, mistrust, and a lot of wasted time. For most LTL freight, density-based logic is more honest. If something takes up space, weighs a certain amount, and has a certain handling profile, price it that way. It's just much better for everyone.

2. Second, carriers need to show real performance data.

Nobody cares that your “network OTIF” is 98%. Also, nobody believes it. Shippers want to know what will happen on the lanes they actually move. Not your global average. Not your best-case marketing number.

They want to know: if I give you this freight, from this origin to this destination, what should I expect? That is where service can become something real.

Which leads to the next point: carriers need to stop making price the only thing for sale.

Service matters. Coverage matters. Claims matter. Pickup consistency matters. Communication matters. Being ready to take on a customer without making the first 60 days a disaster matters.

But if you cannot prove those things with data up front, then all you are really selling is a rate and a promise.  Your ability as a carrier to earn more at scale lives and dies  right here in my opinion.

3. Shippers need to be more honest about RFPs.

Most LTL RFPs are a ritual. Everyone hates them. Everyone knows they are flawed. Everyone knows the lowest rate is often not the best answer. But everyone does them anyway because it checks a box and feels like progress.

If you are moving pure commodity freight, fine. Run the spreadsheet.

But if service matters, even somewhat, then buying LTL only on rate is a bad way to make a good decision. The cheapest carrier is not cheap if they create chaos.

4. On brokers: shippers do not always need them.

Sometimes they absolutely do. A good broker, 4PL, or managed transportation partner can create a ton of value. I have owned LTL brokerages. I have seen customers who would have been in real trouble without us.

But I have also seen customers who could have worked directly with carriers just fine.

The honest answer is: it depends.

If the broker is reducing complexity, improving outcomes, and giving the shipper leverage they would not otherwise have, great. If they are just sitting in the middle to collect 20 points because that is how the account was set up five years ago, hard pass.

5. Finally, carriers and shippers need to help each other to be easier to work with.

Both sides are hard to deal with. Carriers have their own rules, constraints, and exceptions. Shippers have their own bad data, internal politics, and unrealistic expectations. Then everyone acts shocked when the relationship is painful. 

This is where software should actually make the relationship smoother. But most software today is built for win lose outcomes, typically the shipper loads up on software to grind the carrier at every turn.  The carrier then buys software to defend.

I hate this dynamic.  I clearly see a play where carriers make more and shippers pay less. 

Clear expectations. Better data. Better carrier fit. Better onboarding. Better performance tracking. Less guessing. Less pretending.

That is what we are building at Junction. LTL does not need more noise. It needs better data pipelines.

4. The rise of the shadow CFO

A few months back at an offsite, this idea hit me: The absent owner.
It kind of means what it sounds like, but there is a bit more to it.

Say you are selling software to mid-market or SME distributors. You are talking about growth, more sales, better customer experience, better workflows, a business that runs better. And they all they want to know is what is the ROI, when do I get payback?

For a long time this annoyed me. I thought, why are they thinking so small? We are talking about growth and they are talking about expense reduction. Penny wise, pound foolish.

But then I asked… “who am I really selling to”?

Most people would say the CEO or the owner. But often the owner is not really there. The owner is a PE firm, a family office, the public market, a holding company, or an individual who owns the business but does not really spend time in the business, literally or figuratively.

So who is actually in charge? Often it is the CEO. But that CEO has a CPA.

So when you come in talking about growth, they hear cost and risk. And, they are not wrong to ask. They are playing the game on the field.

The owner sees the company through reports. These CEOs see the company through numbers. The team sees the company through pain. And the vendor usually sells to the pain. That is the disconnect.

Sales may know they are leaving revenue on the table. Customer service may know customers are frustrated. Ops may know the current process is broken. But the person approving the spend is often one level removed, staring at a spreadsheet, trying not to make a mistake.

So of course they want payback. You can get mad at that, or you can seel to it.

The lesson for me is you can still sell the bigger vision. You probably should. But you have to translate it into the language of the absent owner. Growth is great, but show the path. Better customer experience is great, but tie it to retention. Less manual work is great, but tie it to capacity (there is no such thing as half a head count reduction btw). Better workflows are great, but tie them to margin, speed, or risk reduction.

A better business is still the point. But in a lot of mid-market companies, ROI is the door you have to walk through first.

Justin

Helping B2B become Amazon-good