Michael DeSimone

Michael DeSimone runs NewStore, a Boston software company at 60 South Street that sells unified-commerce software to global retail brands - the kind of product that quietly lives between the point-of-sale on the store floor, the mobile app on the phone in your pocket, and the warehouse in New Jersey holding the size 9 you want in blue. He took the job on April 16, 2024. He is not the founder. That is Stephan Schambach, who invented shop software in the 1990s, sold it, invented more of it, sold that too, and remains NewStore's Chairman.

DeSimone's job is roughly this: take a company that has raised about $185 million, that employs around 220 people, that ships genuinely useful software to retailers who sell shoes and coats and lipsticks, and turn all of that into a bigger, more profitable, more indispensable version of itself. This is a category of work with a very specific shape. He has done it three times already.

If you have what the customer wants, when they want it, you're the winner. — Michael DeSimone, on omnichannel retail

The Trilogy

Consider the résumé, which reads like a commerce-technology triptych. At Borderfree, an ecommerce platform that started life as a currency-conversion widget, DeSimone spent roughly eight years transforming the business into a cross-border ecommerce platform that Saks Fifth Avenue, J. Crew, Macy's and Williams-Sonoma used to sell things to customers in countries whose sales tax rules they did not want to think about. He took Borderfree public on NASDAQ in March 2014. Fifteen months later Pitney Bowes bought it.

At ShopKeep, a cloud-based iPad point-of-sale platform that put a cash register in a lunch bag, he joined as Chief Operating Officer in November 2015, became CEO, and in 2020 sold the company to Lightspeed Commerce for a reported $750 million. He stuck around at Lightspeed for two more years as Chief Business Officer, running M&A, and orchestrated five acquisitions in that seat, which is the sort of thing you can do when you have just been on the selling side and know what actually matters.

At SmartRecruiters, an enterprise HR platform, he arrived as CEO in April 2023, grew annual revenue by 22%, and improved profitability by 72% before decamping for NewStore twelve months later. The pattern, if you want a pattern: DeSimone shows up at commerce-adjacent software companies with real customers and real revenue, and he makes the numbers get bigger, and often he sells the company. He is a specialist at a specific kind of thing.

The Category Problem

NewStore sells something the industry calls unified commerce, which is a phrase that has been kicking around retail conferences long enough to have accumulated the barnacles of jargon. The clean version: the mobile app and the website and the physical store and the warehouse should all know about the same inventory, the same customer, and the same transaction. In practice this is genuinely hard, because most large retailers have inventory systems from the 1990s bolted to ecommerce platforms from the 2010s bolted to POS terminals whose manuals are lost, and the whole apparatus has to work while someone in a store in Munich is trying to sell a jacket to a tourist from Toronto.

DeSimone's read on where all of this is going, delivered in interviews since he took the job, is that retail is going to disaggregate. Customers will research online, decide where to buy, and then expect whoever they buy from to know them - to have the item, to route it correctly, to remember what they bought last time. This is a favorable environment for NewStore's product, which is why NewStore hired him. The company is now moving toward a la carte offerings, letting retailers adopt individual pieces of the platform rather than a monolithic buy, a strategy he sketched publicly in an August 2024 interview with Axios.

Make the decision. Recover fast. — The DeSimone method, roughly

Three Words, Repeated

In DeSimone's public writings on management he keeps returning to three words: transparency, clarity, collaboration. This is a small-vocabulary approach to running a company. He is skeptical of indecision. He believes decisions should be made quickly and, when they are wrong, unwound quickly. On his arrival at NewStore he told the company he intended to meet every one of its 220 or so employees personally within his first 60 days, which is an oddly specific promise for a CEO to make and, if kept, an oddly specific one to attempt.

He also says the employees he most wants to hire are curious, energetic and open. The list is notable for what it does not include - credentials, pedigree, background. He wants people who ask "what if," who are contagious to be around, and who are humble enough to change their mind. This is, in the abstract, what every CEO says. In DeSimone's case the through-line of his career - the willingness to sell a company he ran, the willingness to leave a job to take another one, the willingness to move from Borderfree's cross-border ecommerce to ShopKeep's iPad POS to SmartRecruiters' HR software - suggests he means it about openness.

Deals, Charted

The Currency Counter

Before all the software, there was cash - literal cash, in currencies. DeSimone spent the earlier chapter of his career at Travelex, Citibank, and Thomas Cook Financial Services, in senior roles across sales, operations and product development. These are companies whose business, in the pre-internet incarnation, involved humans behind glass windows counting bills from other countries and charging you a spread for the privilege. It is a useful early lens for someone who would go on to spend three decades building software that helps money move across borders and inventory move across zip codes. The tools change; the underlying problem - matching a supply somewhere to a demand somewhere else, at a price both sides accept - does not.

It's a marathon, not a sprint. — Advice from DeSimone's mentors, oft-repeated

Off The Clock

DeSimone picked up tennis late in life and treats it as a lens for learning - the sort of hobby that offers a legibly measurable version of getting a little better, week over week, a thing that experienced executives quietly crave. He cites Billie Jean King as a personal hero, admiring her fearlessness and her insistence on inclusivity. This is the sort of detail that either explains a lot about someone or explains nothing, depending on how you read it.

A small artifact of the past: his Twitter handle is @couchcommerce. That was the name of a mobile-commerce venture from a previous chapter, since long absorbed into what became NewStore. The handle stayed. Somewhere on the internet, in a URL, is a piece of DeSimone's earlier taste for the phrase "commerce on a couch," which is what mobile commerce was, before it became the default way people bought things.

What He's Building For

The stated aim: keep NewStore's position as the leading unified-commerce platform for enterprise retailers, execute concrete growth strategies, and expand the platform while empowering the partner ecosystem that installs, extends and resells it. The subtext, given DeSimone's track record: get to a bigger commercial outcome. Whether that outcome is a much larger private company, a public company, or a strategic sale is not something a CEO is going to declare in advance, especially not one who has been on all three sides of that transaction.

What is clear is that DeSimone is very good at the specific job of running a mid-scale commerce-technology company toward a bigger number, and that NewStore, as of 2024, needed exactly that. The founder, Schambach, moved to Chairman. A year-long succession process concluded. And South Street got a new occupant of the corner office who has, at this point, effectively rehearsed the entire film reel of enterprise commerce software - global cross-border ecommerce at Borderfree, mobile POS at ShopKeep, integrated stack under one roof at NewStore - across a career whose consistency is more impressive than any single line item on it.