Former Whole Foods co-CEO Walter Robb is doubling down on cannabis.

The natural foods industry veteran will serve as retail advisor to e-commerce company Jane Technologies, bringing with him decades of experience in natural and organic foods — an industry he says felt similar in its early days to the cannabis industry now.

"The natural food business … at the beginning it was very small — just a few players on the fringe. It took a long time to gain acceptance to get the mainstream shopper. And now natural and organic foods, everybody's talking about them," Robb said. "It's a parallel with [the cannabis industry] that's [in its] early days. It's finding its way."

In his role as retail advisor, Robb will guide Jane Technologies' executives in forging strategic partnerships, crafting data-driven e-commerce solutions, and scaling their online cannabis marketplace iheartjane.com or I Heart Jane. Jane Technologies co-founder and CEO Socrates Rosenfeld said he's grateful to have someone to turn to with strategic, big picture questions, and who has a tremendous track record with e-commerce, technology, and fostering a healthy company culture.

Jane Technologies was born of Rosenfeld's own less than ideal experiences shopping for cannabis. A veteran of the U.S. Army, Rosenfeld began using medical cannabis but was forced first to turn to the illicit market in his home state of Massachusetts and ultimately to dispensaries once he relocated to California. As a medical marijuana patient living in cutting edge Silicon Valley, Rosenfeld found it frustrating that the cannabis shopping experience was so outdated. He created Jane Technologies and I Heart Jane to give cannabis shoppers the same kind of purchasing power available to shoppers in the market for virtually anything else.

"If I want to buy a plane ticket to New York, I go on Kayak. I decide when I want to take off when I want to land, what airlines I want to fly — and in a matter of minutes I have made a very well-informed decision," Rosenfeld said. "When it came to cannabis ... I wasn't afforded that same level of curation and convenience. I was not afforded that same level of purchasing power."

Today, I Heart Jane supports more than 1,300 dispensaries across 28 states and offers an Amazon-like shopping experience to consumers and a Shopify-like experience to businesses. By inputting their location or address, shoppers can browse products on shelves in brick-and-mortar stores nearby. Purchases made through the platform can be picked up or delivered, depending on local regulations. And because the platform drives business to local shops, Rosenfeld said, it has the added benefit of supporting and empowering local business.

"It's enabling small businesses to showcase their products digitally, and to transform themselves in a digital standpoint without burdening them to hire MIT engineers to build out their own e-commerce," said Rosenfeld, who earned his MBA at Massachusetts Institute of Technology. "We are a little like Shopify, we are a little bit like Amazon, but at the end of the day we are trying to find our own voice, and that's the voice of Jane."

Rosenfeld and Robb initially connected through a mutual friend who worked at Whole Foods, where Robb spent the better part of 25 years. What started as a social connection turned into mutual respect and, ultimately, a business opportunity.

"For me first and foremost, it was because I really liked Socrates. I liked who he is as a person and, for somebody as relatively young compared to me, [he is] a pretty strategic thinker, a pretty disciplined thinker," Robb said. "I think he's done the right things to put himself in a position to have Jane be successful."

When considering whether or not to hop into cannabis, Robb took a similarly meticulous approach. The more he researched, the more he found similarities between the current state of affairs in cannabis and the early days of the natural foods industry.

"Cannabis and hemp — it's a little Wild West out there," Robb said. "It's not unlike the early days of the natural foods industry in terms of the guardrails being set, the quality being established, the brands emerging to the top level."

When it comes to pre-eminent brands in natural foods, there are perhaps none as powerful as Whole Foods, and Robb was crucial to the company's growth and success over the course of his career there. But natural and organic foods weren't always as socially acceptable and mainstream as they are today.

Robb founded his first natural foods market in 1978, a year when the industry was still considered "fringe." He joined Whole Foods in the early '90s after selling a different natural food store to the company. Over the next 25 years, as he worked his way up to co-CEO, he helped build the brand into what it is today: a household name with a footprint in 42 states, the United Kingdom, and Canada. He stepped down in 2017 when Amazon acquired Whole Foods but was closely involved in striking the deal. It's no coincidence Robb knows a thing or two about e-commerce and the digitization of shopping.

"In today's world, you digitize and the customer expects to be met in that space. To the extent that joining with Amazon allowed Whole Foods to digitize much faster, in the same way, Soc is allowing the dispensaries to digitize through their partnership with Jane," Robb said.

And as with organic and natural foods, Robb eventually became a true believer in cannabis, too. In addition to his role at Jane, Robb sits on the board of Canadian cannabis producer Aphria ($APHA), a company chaired by Hain Celestial founder — and friend of Robb's — Irwin Simon . He assumed the seat in April 2019.

As for Jane Technologies, the future looks bright. The company scored $21 million in funding last July, and Rosenfeld is looking forward to continuing to scale the business and grow with the still-young industry. But unlike the early days of natural foods, this time around, the cannabis industry has technology on its side.

"We now have some wonderful technical tools we can use to accelerate the 'mainstreaming' of this product," Rosenfeld said. "The regulations are keeping us in the early innings … it's a challenge and something that we welcome, particularly as a tech company in the space trying to do the right thing by advancing and extending the online footprint of both brands and dispensaries."