Like so many direct-to-consumer digital-first startup brands, the women’s clothing maker Ayr spent the past few years expanding its brick-and-mortar retail presence. Last year, says CEO Maggie Winter, who cofounded the company with Max Bonbrest and Jac Cameron back in 2014, a third of Ayr’s business came from its stores. But then came Covid, and this year 90 percent of sales have been digital.

Ayr, which spun out of Bonobos as its own company in 2016, has relied on one big strategic advantage in this unprecedented year: Rather than ride the cycles of the ever-changing fashion seasons, Ayr offers what Winter calls “seasonless apparel.” (The name Ayr stands for “all year round.”) “When the economy hit a standstill in March, retailers found themselves sitting on spring and summer products that they weren’t going to be able to sell later in the year; you can’t sell a sundress in November,” explains Winter, who got her start at J. Crew under retail legend Mickey Drexler. “But our business was built for year-round sales, so we were able to manage inventory very quickly.”

On top of that, Ayr’s clothes offer a casual, non-showy look that played well in the pandemic. (“It’s about the women who are wearing it, not about the label or the logo,” Winter says.) The result: Despite everything, the company has actually grown this year.

The company has built some of those same attributes into the way it works. After laying off some of its retail employees, Ayr has been hiring in a different way. “We’re a lot less confined to hiring to a title and a role and more open to getting flexible contributors and collaborators, so we can allow resources to flow where they need to go at any moment,” Winter says. She expects that to be a new normal. “We are probably going to experience more change in the next 12 months than in the past ten years. And we want a team and a culture that is built to be adaptable.” -- Tom Foster

How do you convince San Francisco’s top designers to join your company when you have little money, a primitive website, and an ecommerce strategy that’s mostly focused on fidget spinners? This was the challenge facing Katie Witkop when she joined Faire as its founding designer. The company aimed to become a major online wholesaler of boutique gifts across the United States, and needed an elegant merchandising, marketing, and web strategy to match. But it was still early days, and her co-founders’ early version of the online store was still limited to selling faddish, mass-produced items. This had become a recruiting challenge, and Witkop needed to figure out how to help prospective hires feel her vision for the brand in small ways before they went big.

Witkop wanted shopping on Faire to feel warm, bespoke, almost antique — reminiscent of handpainted signs of shops on cobblestone streets. Her initial recruitng tactic: printed dinner invitations. Witkop invited designers she admired to join her for intimate dinners in private rooms of restaurants like Octavia, a Michelin-rated farm-to-table restaurant which is owned and operated by a female chef. With no expectations, she let the food and wine flow and let her guests enjoy one another. “All of a sudden, I didn’t feel like I was pitching anyone,” she says. “it was a really great way to lower everybody’s guard and just have good conversation, to find where peoples’ hearts are.”

She clicked with several of them, soon wooing them to join her little company. At the end of 2019, Faire was valued at $1 billion, but Witkop still takes the same care in recruiting talent —meeting for coffee around one of the office’s Parisian-style bistro tables, then mailing handwritten thank-you notes along with bags of local candy to candidates after job interviews. “All these little things draw you away from the [mainstream] current and help you steer toward your own vision of a brand,” she says. “Think through all these little steps and hurdles, attract the right people with the biggest brains and hearts, and then the brand replicates itself with every new hire.” Today that thoughtfulness is behind even the choices around the company swag — canvas tote bags with custom illustrations themed around the cities where Faire has offices, and simple, black high-cut crewneck sweatshirts that say Faire. Tech-bro hoodies are strictly verboten. – Burt Helm

In her early 20s, Carloyn Witte she had set of frustrating healthcare issues that showed her just how depersonalized and fragmented our healthcare system has become. That experience became the inspiration for Tia, which is a reimagining of what healthcare would be like, work like, and feel like if it were designed with women at the heart of it.

Tia started as a digital platform with a pre- and post-doctor's office tool, and has evolved into something more comprehensive. Last year, Tia launched its first physical clinic in New York, which now includes 15 physicians, physician assistants, registered nurses, therapists, and other treatment providers. The shelter-in-place order forced the clinic to close its doors, but Tia very quickly pivoted into telehealth and virtual services. Witte's goal is to eventually open offices in other cities around the country, delivering integrated women's healthcare that includes gynecology, primary care, behavioral health, and acupuncture.

Despite recently raising $24 million, Witte says funding is secondary to creating the right product. "Female founders and getting funded is very much in the spotlight right now for a good reason, but I think sometimes there's a little bit too much focus on the raising money part and not enough focus on building a product and getting product-market fit.” That fit, she says, is “the best thing women can do to get funded."

Sarah Paiji Yoo knew she was facing an uphill battle: Rather than selling customers something they already knew how to use – such as razors or tampons or liquid dish soap – Blueland would be selling them tablets. Customers would need to pop the tablets into glass bottles with a bit of water, wait for them to dissolve, and then use the resulting hand soap or window cleaner just as they would any other. Blueland’s tablets would mean less fuel and carbon emissions during shipping, and reusing the same bottle would keep disposable bottles from piling up in landfills. But would customers get it?

That question guided everything from which products the company launched first (cleaning sprays seemed the most intuitive way to introduce the concept, and easily illustrated that it didn’t make sense to ship water across the country when it’s already piped into homes), to the chemical composition of its cleaning tablets (the faster they dissolved, the better).

All that work paid off. When Paiji Yoo and co-founder John Mascari finally launched Blueland in 2018, there was only a smidge of work involved, and customers seemed happy to do it. When the team launched its hand soap a few months later, with a tablet that could take up to 20 minutes to fully dissolve, they got exactly zero complaints.

The experience reminded Paiji Yoo, a serial entrepreneur, that trying to anticipate every hurdle before the product is even launched is a fool’s game. “Things will never go according to plan,” she says. “And until you put your idea out there into the real world, you can’t know what people will have a problem with and what won’t be a big deal.” – Kate Rockwood