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SaaS Interviews with CEOs, Startups, Founders

From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman

SaaS Interviews with CEOs, Startups, Founders

Nathan Latka

Business, Entrepreneurship

4.6701 Ratings

🗓️ 26 February 2026

⏱️ 28 minutes

🧾️ Download transcript

Summary

How do you turn a failed public ecommerce company into a $5M ARR enterprise SaaS platform serving ~$2M+ contracts — while rebuilding with capital efficiency after bankruptcy and avoiding the growth-at-all-costs playbook?

In this episode, Nathan sits down with Jared Yaman, co-founder of Spresso and former founder of Boxed, the bulk ecommerce company that scaled to $187M in revenue before its IPO and eventual Chapter 11 restructuring. Today, Jared leads Spresso, the enterprise ecommerce software platform spun out of Boxed, now serving roughly 15 enterprise customers worldwide and growing ARR from $2.5M at spinout in 2023 to about $5M in 2025 through large ACV enterprise contracts.

What makes this story interesting is the transition from low-margin ecommerce operations to high-margin enterprise SaaS. Boxed generated hundreds of millions in revenue but operated on ~4–5% contribution margins. Spresso keeps the infrastructure, data, and enterprise relationships — but monetizes them through implementation fees and modular SaaS subscriptions, fundamentally changing the economics.

You'll learn:

- Why scaling revenue without contribution margin destroys optionality, even at $100M+ revenue
- How enterprise implementation fees subsidize onboarding costs and accelerate payback periods
- The pricing structure behind $2M+ enterprise contracts in ecommerce infrastructure
- Why founder-led sales and existing network relationships became the primary GTM channel post-spinout
- How to reposition operational technology into a standalone SaaS category buyers understand
- The debt strategy Spresso uses to keep leverage under 10% of ARR
- Lessons from raising $380M in venture capital and ending with low single-digit founder ownership
- How reducing deployment timelines from 4 months to 4 weeks unlocked enterprise expansion
- Why enterprise SaaS growth favors fewer customers with large ACVs over broad SMB distribution
- The strategic shift from retail unit economics to recurring software margins

Jared previously co-founded Boxed, raising roughly $380M before taking the company public, where founder ownership diluted to about 2.6%. After Boxed filed for Chapter 11 in April 2023, he helped spin out the software platform into Spresso with debt financing support, rebuilding the business around sustainable SaaS economics instead of venture-funded retail growth.

This episode is for founders navigating pivots, operators moving from services or commerce into SaaS, and investors studying capital efficiency in enterprise software. It's a masterclass in restructuring strategy, enterprise pricing, and rebuilding a company around durable margins instead of headline revenue.

Watch this episode on YouTube: https://youtu.be/vslJtgAtjuY 

Connect with Jared: https://www.spresso.ai/ 

Connect with Nathan: FounderPath.com

Transcript

Click on a timestamp to play from that location

0:00.0

My data shows December 2020 ending with about 187 million bucks or revenue. How much equity had you guys raised up to this date? Yeah, I think it was around 3.380. 380 million dollars. How much equity did you own when you guys went public? When we IPOed, I was down as a startup or as a founder to low single digit percent. It looks like you write about 0.000 percent. Surely he made more than 10, 20, 30 million bucks on this company, but it sounds like that was not the case. Is that accurate? Yeah, it was not the case. What was revenue of espresso when you spun it out? We sort of brought through, I'd say, around 2.5 million of ARR in early 2023. Are you comfortable sharing where you guys finished 2025 in terms of revenue? Yeah, it's about doubled. Then on April 2nd, 2023, you guys file for Chapter 11 bankruptcy there.

0:43.4

Hey folks, my guest today is Jared Gaiman.

0:45.7

He was previously the co-founder of Boxed.

0:47.8

He led the company's growth and innovation in the online wholesale retail space all the way through an IPO in 2021.

0:53.2

I think that was via SPAC. As its CEO, Spresso now today, deploys technology worldwide solving significant challenges in the e-com space. Jared, you ready to take us to the top? Yes, sir. Thanks for having me, Nathan. Thank you, the audience, for tuning in. You bet. We're going to mostly focus on Spresso today, but we can't do that without your background going back to 2013. Based off my

1:11.6

research, boxed was not a small company. I mean, when we look at year-ended 2018 total revenue, net revenue, we're looking at 140 million bucks. Well, I'm reading off the S-1. Is the S-1 inaccurate? No, no, no. That trust me. They're very accurate. Yeah, very accurate. That's the right answer, by the way. If your S1's inaccurate, you're in a whole lot of trouble.

1:28.8

Yeah, it's a S1, sCC.gov requirements or, you know, startup visionary, you know, a GMV calculations. But yes, sir, you are correct. I appreciate the research. This is ultimately about you. So look, my data shows December 2020 ending with about 187 million

1:45.1

bucks of revenue. What happened to Boxed? Okay. Yeah, well, let me explain a little bit more

1:49.2

about what Box did. So I came to New York. I can remember this off the top of my head, Friday,

1:54.9

September 12th of 2008 as a corporate lawyer. About 36 hours later, Lehman Brothers collapsed. So there went my, you know,

2:02.6

corporate lawyer trajectory and, you know, Wheeler, dealer in the M&A space, but stuck around in

2:07.5

law for a couple years. And around 2010, the rise, that was a very significant chapter of

2:13.2

startups, right? We're kind of exiting the social networking, you know, Facebook, you know, Twitter ascendance, right? And we were now fully into mobile apps and sort of in that like

2:22.3

max growth disruption, Airbnb, Uber, you know, 15 years ago, seems like it was 50 years ago

2:29.2

at the same time and also maybe not that long ago. But yeah, pivoted from law because I think

2:33.3

there was a great affinity, one with what was happening in venture capital and entrepreneurship, especially in New York where we're based, where you know, you had Silicon Valley and there were kind of Silicon Alley. It was small, tight-knit, like meetups were huge, like going to demo days. There's a lot of excitement. And, you know, our first foray was actually in gaming. So we did a small gaming startup that

2:52.8

essentially riffed on what Zinga or Facebook were doing with things like Farmville and CityVille.

2:57.7

We brought that to mobile. That got a good amount of attention. We sort of cut her teeth in

3:01.8

technology, you know, venture capital, entrepreneurship, data, data science, product user experience.

3:07.3

And we managed a gaming company for a couple of years. We exited that company and then, you know, a year, 15 months or so into that. We said, look, gaming is fun. What's kind of toy aisle of life? Like, let's go for the big swing. Like, let's go for the whole store. And that's to us what e-commerce was, right? So warehouses, fulfillment, pick, pack, and ship, last mile logistics. Like, you name it.

3:27.5

That's what's involved. whole store. And that's to us what e-commerce was. Right. So warehouses, fulfillment, pick, pack,

3:24.7

and ship, last mile logistics. Like, you name it. That's what's involved in e-commerce. And that's what boxed was. And we said, look, people are going to look for convenience. They're going to look for savings. Your time really matters. People are just going to want to look through guilt group, Amazon, right? E-commerce was there, but as far as buying consumables, that was very, very nascent.

...

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