Annie Dean and Anna Auerbach (Left to Right)

Working on Wall Street is not an easy job. Nearly 50% of employees will quit within three years, and it’s well known that some firms’ investment bankers work upwards of eighty hours per week. For Annie Dean, a wall street attorney, there were some other factors that complicated her experience.

For starters, she was pregnant with her second child, and her body did not want to follow the rigid schedules set out by her employer. As the days passed, even though she was working just as hard pregnant, she began to feel burnt out as if the system was designed for her failure. And so one day, she asked a friend to introduce her to the smartest woman she knew for some advice and landed on a fateful phone call with Anna Auerbach, a graduate from the Harvard Business School.

Anna came from the consulting world, and through her experience from both business school and her career, she made a few observations. Around 50% of her classmates at school were women, yet somehow, only about 16% of CEOs and executive officers were women. Troubled Anna also came upon an article by The New York Times called “The Opt-out Generation Wants Back In that perfectly summed up the issue that many women in the workforce faced: structural barriers. The piece detailed the trend of high achieving women having to leave their jobs because of juggling familial obligations and work duties.

Ultimately, this led Anna Auerbach to look for what was causing so many women to drop out of their jobs. The path had to lead somewhere, right? As she mulled over it, she began to develop an idea of a common framework of flexibility as the future of work. The statistics confirmed her beliefs. A 2010 study from the Center for Work Life Policy found that of the women who dropped out of the workforce after having a child, 69% said they would have stayed if there was some flexibility policy implemented.

So on that serendipitous phone call between Annie Dean and Anna Auerbach, connections were being made, and thoughts and ideas were being exchanged. Even from the beginning, it was a partnership waiting to happen. Both had similar values, had come to be disillusioned with the 9-5 workday, and had bonded over shared grievances. So when Anna blurted out that she had a business idea built around streamlining the workday and creating a common framework of flexibility for employees, Annie’s interest was piqued.

They talked a few more times, and within months had developed a business plan.

Their business revolved around some of the key issues they saw in current companies and how they addressed flexibility. The first issue to work around was the 9-5 structure. Almost everybody who has worked a job has encountered a schedule similar to this, and it, by and large, wasn’t flexible. Even when businesses decided to implement some measures of flexibility in their company policy, it usually ended up being more one size fits all. Individual workers still didn’t have the freedom to decide how they were going to allot their daily eight hours. And for companies that hadn’t done anything yet the question was, did they even know how to implement flexibility policies?


From these common problems arose three different areas where they thought flexibility existed. The areas were

  1. Location
  2. Time
  3. Set Schedule vs Ad Hoc

With these three facets of flexibility, they built their general framework: The Six Distinct Types of Flexibility.

The first type is Remote, which means being flexible to work location independent from the company headquarters.

The second is DeskPlus, or the ability to be partially location independent. For example, if something was to come up, they could leave the office and continue to work. On the other hand, it could also mean that some days you have to stay home to take care of your kids so you would take a DeskPlus day there.

The third is TimeShift which is the ability to break up the workday into blocks of time that you can work or move your schedule up and down. TimeShift can be used from avoiding rush hour to splitting the day so you can pick up your children.

The fourth is MicroAgility, the ability to step out from work for brief increments of one to three hours to take care of the unexpected. If your children have an emergency or a someone is coming to repair your roof, MicroAgility would be useful. It’s a no questions asked system.

The fifth is PartTime. This type of flexibility doesn’t necessarily mean less work, but it is usually reserved for senior members who can do the same amount of work in shorter periods of time. It’s just a modified schedule that requires fewer hours per week.

The sixth and final type is Travellite. This just means knowing whether or not the job requires more than 2-4 travel days per month. It’s great to know this ahead of time if you are a parent or caregiver.

These six types of flexibility weren’t completely arbitrary. They were rooted in the problems that Anna and Annie encountered in the workforce. With a common framework of flexibility developed, they set out to build their business. Their startup’s central idea had always been centered around this fundamental concept of universal flexibility for all workers. In order to touch both the employer and employee side of the market, their business utilizes two strategies. The first involves their enterprise products. They use their product FlexMatch to determine what areas the company offers flexibility and how well it is implemented. Afterward, they help them assess areas where they can improve and develop a plan moving forward. They also use their e-learning module FlexCert to help teach the six types of flexibility and how to use them. On the other side of the market they have a job board where members use the Werk platform to find jobs with pre-negotiated flexibility. They can apply right then and there.

The business plan was there. The structure and framework were there. The minds were there. So why was it so hard to get funding? Anna Auerbach and Annie Dean’s search for venture capital funding led them to experience firsthand a lot of the sexism involved in VC money. For example, they received many phase inappropriate questions. When they were in their pre-seed round, they would be asked questions about parts of their business that should be asked during Series A funding. Furthermore, their seriousness and capability were called into question. After they had raised $1 million in their first round, there were still investors asking if they were just making a lifestyle brand. Even the assumptions that the investors made tended to be biased. One investor who was interested in leading the round eventually declined because of an assumption that they were competing with another company that was doing something unrelated.

These situations were not enough to bring the two down. After much persistence, they got funding from a women-run fund, ReThink Impact. That’s not to say that they think that all female run startups should be funded by women, but after all the struggle they faced to snag funding, they believed the values of that particular VC fund matched their ideas.

Money in hand, Annie Dean and Anna Auerbach finally had the company that they had envisioned. Besides giving their own employees the flexibility they had wanted so bad, they also sought to build an embracing company culture where different beliefs and dissenting opinions would be welcome.

For example, they have a strategy called “let’s try to fail by Friday” where they attempt to poke as many holes as they can in a product to see if it will fail. The tactic has worked by and large. Many of the failed products go into the trash bin while ones that survive the meetings go on to be successful. But Werk isn’t just focused on creating products to bring flexibility into the workplace, it’s also focused on building a brand that people can rely on.


They have a presence on most large social media platforms, and not only do they preach the benefits of flexibility, but they also spread awareness for other things in the workplace that matter to them like sexism and racism in peoples’ careers. Moreover, they try to be as responsive and as transparent as possible. Everything about Werk is out there, and every email will get a reply.

For any startup, doing all this would be tough. In fact, it would be more than tough. Annie Dean and Anna Auerbach are attempting to change the workplace by using a completely untested strategy. No other company has attempted to use a framework of flexibility to modify the workday. But the synergy between Dean and Auerbach is palpable. As Werk’s head of marketing put it, “they complement each other in really interesting ways.” While Annie will be the big picture thinker with an eye for beautiful design, Anna will be the master with numbers, quickly making sense of any data.

This Ying Yang dynamic has allowed them to not only implement flexibility in the most interesting ways but be flexible about what they say as well. From a company that was built on the premise of helping women in the workforce with better flexibility policies, they have spread out their message to encompass more people as they begin to envision an adaptable workday as the future for all professions.

Their website puts it best: “they’re rewriting the rules of work, so they work better for everyone.”

If you want to learn more about Werk, you can find their website here. To read our last article about the business Eight Sleep, go to this linkContact us to get your story heard!