January 2026: I’m Trying Something New

Work in Progress: January 2026

I'm trying something new.

Each month, I share Investor notes, LinkedIn posts, and internal all hands. They’re all useful, but at times they can feel narrow, fragmented, and oddly performative.

This is an attempt to create a single place to share what building a company actually looks like. The decisions, experiments, and lessons as they’re happening, in a format that allows our team, customers, advisors, and anyone following along to join in. I’ll refine it as I go.

In this edition:

1. Why hybrid work beats fully remote (when the work allows for it)

2. What it means to automate 30% of operations and still need to hire

3. Two product unlocks that feel… different

1. Hybrid > remote work

Our culture committee (thank you Grace, Dani, and Alicia) threw a killer holiday party downtown Toronto.

The mood was merry, and watching our remote and in-office teams come together solidified for me (after years of oscillating on WFH) that hybrid models are superior to fully remote (where it’s feasible).

There's a particular confidence that comes from real builders who care about a shared mission coming together as friends, to share space, even just occasionally. You feel it immediately.

We spend so much time working our lives away. If you’re lucky, you get to do it with people you respect and genuinely enjoy. Why not make it as fun as possible? Creating moments where that’s possible isn’t a perk, it’s part of the job.

It's a privilege to serve and learn from this group.

2. What it means to automate 30% of operations and still need to hire

This is the funniest (not funniest) thing that happened all month.

We've been building AI automation for internal freight operations for a year. Our first EOY report showed 30% of our ops workflow is fully automated. Impressive, right? Huge cost savings, scale, all of it...

An hour after getting that report, I get a message from operations saying: we're overloaded and need to hire! 🙂

Turns out busy people find things to do. In fairness, we are moving more orders than ever but still this isn’t the infinite scale I imagined a year ago, what gives?

Two things can be true at the same time.

1. I'm bullish on AI. I see how it'll be "bigger than the internet" in sheer impact, despite the AI-washing creating divisive POVs and misrepresenting this incredible but still nascent technology on both sides.

2. I'm also confident humans aren't going away easily. When one job disappears, one or two more get created. This is how we've always adapted. To think otherwise is (in my opinion) immature and ignores historical norms.

The real question isn’t whether AI works or is impactful. It’s how it behaves inside messy, real-world businesses, where edge cases, volume, and people collide. That’s the work most of the hype skips.

If you’re interested in a well articulated, if not a bit nerdy, short article on how AI is actually progressing in the enterprise here it is.

3. Two unlocks that feel… different

a. Unlocking real-time, accurate LTL quotes (+inside ERPs)

We solved a hard problem: delivering real-time, accurate LTL quotes directly into the systems where deals are made- ERPs, inboxes, CRMs, portals.

This matters because:

• Sales stops guessing

• Ops stops patching problems downstream

• Finance stops dealing with the fallout of surprise freight costs

It’s one of those things that sounds obvious until you’ve tried to do it reliably.  It is actually a proper technical problem. And one we finally cracked.

Excited to get this in the hands of customers!

b. Percentage-of-PO pricing model

We also launched something I haven’t seen in LTL before: freight priced as a % of PO value.

Instead of “here’s your freight invoice,” we’re charging customers a contracted percentage of the PO value for their freight.

There’s something elegant about it. Customers get predictability, the business gets simplicity, and nobody has to play the usual invoice reconciliation games (except for us on the back end which is a bit of a nightmare but we’re working through it).

It’s not for everyone but for distribution companies whose “north star” KPI is freight cost as a percentage of PO, this is turning out to be a killer “set and forget” option.

That’s it for January.

If any of this resonated (or if you’ve seen similar patterns in your own work) I’d love to hear from you in the comments or in DMs. This is very much a work in progress.

Thanks for following along!

Justin