The Future of Work is Flexibility: A Chat with Anna Auerbach of Werk

What is the future of work? 

It’s a question that has been pulled into the limelight from every direction. Whether it’s concerns about gender and minorities in the workplace, technologically driven displacement, or the existential question of purpose, it’s one topic that will only continue to grow in prevalence. 

Today much of our focus has been on corporate culture, re-skilling labor, the intersection of success and fulfillment, and even the gig economy. What has been historically left out of the conversation is flexible work. All that is about to change according to Werk Co-CEO, Anna Auerbach:

"I would argue that jobs with flexibility will ultimately swallow all W2s and gigs. It all becomes gradients on the same scale… For us, flexibility is probably a dominant job category, long-term."

Anna knows her way around the workplace, after founding Werk with her Co-CEO, Annie Dean, to address the career progression gap between men and women by building flexibility into work. To Anna all the commonly attributed causes of this progression gap, just didn’t make sense. Rather, she identified the issue to be far more systemic, pointing out that our current work structure breaks down with the advent of parenthood (or care-giving): 

"That is when it all came together for me. I saw the articles, the data, and it all clicked. You have this massive exodus of women, because they can’t find a way to make it work. The reason they can’t find a way to make it work is their current work structures demand face time and long office hours. Those things are fundamentally incompatible with parenthood, and not just motherhood, but parenthood more broadly."

Anna and Annie’s impetus for founding Werk may have been to eliminate the progression gap but they see flexible-work as the future for everyone regardless of gender, identify, and status. As Anna states: 

"The market we address today is the people that are failing without that flexibility. These people are about to leave the workforce unless they get access to flexibility. That is a large chunk of the market, but that is not the whole market. The whole market is everyone who benefits from having work-life compatibility… It’s people who have hobbies and interest: they want to work out, they want to be healthy, they want to have other pursuits. For all those people, flexibility is not a deal breaker but it is an important life improvement, and to me, that becomes the future because all people ultimately benefit from it."

It’s clear their onto something. Nothing illustrates this better than the technology industry. While far from perfect, tech companies were able to poach workers from all the ‘traditional’ industries by offering the promise of a completely different lifestyle. One in which work is fun, individuality is emphasized, red tape is almost invisible, and nobody is constantly looking over your shoulder. While some prefer the clear separation of their personal and professional lives, many others thrived in this ‘mixed reality’.

However, as Anna points out, flexibility goes far beyond the culture set-up and perks: 

"We openly address the fact that flexibility is not a perk, it is about compatibility.”

In some ways, it sounds obvious but the reality is that, today's workplace is not set up with flexibility in mind. Anna points out that it comes down to an issue of trust:

“Today, flexibility is earned. The way flexibility functions today, is you only get access to it once you’ve been at a company for a certain amount of time, or once you’re a certain level of experience… When you take this to its logical end, which is about greater trust between employee and employer, it needs to be addressed at all levels.”

When you think about work from this perspective, it’s clear that the employee-employer relationship is in desperate need of an overhaul. It’s the basis of Reid Hoffman’s Tour of Duty framework, which looks to create win-win situations for employees and employers by moving past the ‘lifetime employee’ model, to looking at work as a series of multi-year tours designed to help employees learn critical skills and ensure companies have high-caliber, engaged talent at all times. 

Where Reid’s framework addresses the purpose and tenure of work, Werk looks to re-imagine how work is structured and what it means to be an ‘employee’. Do we really need to have set office hours? Do we need to be on-site a certain percentage of time? Do we need to work the same hours every week?

In Werk’s vision of the future, the answer is absolutely not. As Anna states:

"The ultimate logical end, is the idea of result-oriented work, which is just get your primary shit done, no matter when, how, and where. There’s a reason that that’s not part of our flexiverse today, and the main reason is we felt companies were not ready for that yet. But that is the logical end of all of this: people who have autonomy to actually just get their jobs done in a self-aware way, where they know how they work best."

As Anna is quick to point out, we’re not quite there yet. We have years of unlearning to do around what is means to work and the structures that define our workplace. As with any movement, it starts with a shift in mindset, something Werk has been able to do by highlighting the strategic element of flexible work:

"Actually, some research shows flexibility has more bottom line benefits to the company than to the employee, and that ultimately, this does not mean a reduction in scope, ambitions, aspirations, promotion potential. It is about modifications to the workday and work structure, to make somebody actually perform better and stay longer.”

As companies begin to understand the value of optimizing for an employees life, it completely changes the way people will approach work and the level of alignment between an employee and an employer. This is the future that Werk is driving toward, and in this future where your workplace is designed around your lifestyle, workplaces will instinctively become far more inclusive. That means there will be an (relatively) equal playing field irrespective of your identity, marital life, and status. It is these types of win-win situations that drive embed systems to change and Werk is certainly playing its part in leading that shift. 

The future of work is yet to be determined, but I think it is clear that a flexible future works better for everyone.

A huge shout out to Anna Auerbach for interviewing with me, both Anna and Annie Dean for hosting me, and Lindsay Dreyer for helping coordinate. Finally, thank you to Erin Jones for helping me transcribe this interview. I found out about Werk from Dalberg’s Big Bet Initiative and immediately reached out to connect. They were kind enough to oblige and Anna and I had a terrific interview. We chat about topics ranging from the future of work, to leading a company, trends in the workforce, 'parenting' a team, and more. Check out the full excerpt below:

SG: Anna, you do a lot of different things as co-CEO of Work. How do you describe your job.

AA: Oh, this is a good one. I think the way I describe my job is to be the leader for the organization, and specifically the way I view leadership is as the parent of the organization. In that mindset, it’s particularly interesting, since Annie and I are co-CEOs, we’re actually co-parenting this organization.

If you think about parenting philosophy, which I obviously think about all the time right now, the best sorts of parents make sure they set the right direction for their kids. They equip the kids for success, but then they give the kids space to do what they do, to make their own mistakes, and to carve their own path. You course-correct when needed, and you sort of give them their north star. But ultimately, if you helicopter, there are huge costs of that in the long-term, for a child’s life. That’s how I view my role in the organization. As a parent of the organization, my goal is to make sure nothing the children do (the organization) will mess up its life permanently, and that ultimately, things are going the right direction, and that my child is growing up with the right values, guiding principles.

SG: That’s a very appropriate analogy for the company. Avoid the giant crater but otherwise, a few bangs and bruises is ok.

AA: Yes, and ultimately, all the research shows is you can only do so much, and ultimately, your children take on their own life, and in the same way, your company does, too.

I don’t personally believe that command and control is a good long-term strategy. It might be a good strategy in a time of crisis or pivot or whatever it is, and in the same way, I think that relates to parenting, where the really commanding, controlling parent actually can do a lot more harm than good, and ultimately you need to let your child take on their own life and set the right principles, values, and end points, but let them run with it.

SG: What is it that really sparked you to found Werk? What was the experience or the series of experiments that led you to decide to do this?

AA: It’s interesting. I moved here as a refugee from the former Soviet Union, and so growing up, I was extraordinarily motivated to work hard, but also to do things, create opportunities for others. The only reason my parents got to this country is because others created opportunities for them.                 

In my family, there were lots of problems in Russia, but both men and women worked. This whole idea of a stay at home mom was an American thing. I didn’t quite understand that until I moved here. In fact when we moved here, my mom found her job first. She not only found a job, but she went back to night school to get retrained, because she’s always wanted to make a career pivot, and she did that in America.

For me, it meant I had an incredible role model in my mom. I never thought any differently of my own path. When I started off at McKinsey after I fought my way into that job, I was so thrilled to be there. I would say one of the most jarring moments was recognizing that although the entry level classes were pretty close to 50-50 men and women, senior leadership was under five percent women. That number (I left 11 years ago) hasn’t shifted one bit. That was my first eye-opening experience signaling there’s something going on around women and work. Honestly, in high school and college, it's something I never thought about.        

In fact, couldn’t quite understand it at first. When they do corporate women’s retreats- It was all about you need to speak up for yourself, you need to take credit, you need to take a seat at the table. For me it was one of those moments where you think: ‘Are you actually talking to me? I don’t have problems with any of those things.’ I was really confused as to what they were talking about. They were attributing these things to the reason that women were not succeeding, so I never quite connected the dots until, I was in business school and some of my friends began getting married, having children, and I followed suit having a child a few years after business school.         

I recognized that the problem really had to do with parenthood. I never had really thought about how much your life changes when you become a parent. Some people freak out before they become parents, but the majority of people don’t recognize how much it’s going to change. I was one of them.              

Before becoming a parent, my pattern in my career, and I think a lot of successful people’s pattern is if you don’t know something or you’re struggling, you just work harder. You just put your head down, you work harder, you get help. When your baseline is a 14 or 16-hour workday and you have the reality of being a parent, it’s not a problem you can work your way out of. Hard work is not going to solve this problem. It’s actually going to make the problem worse. It’s like one of those Chinese finger traps where if you struggle more against it, the more stuck you are in it.

That is when it all came together for me. I saw the articles, the data, and it all clicked. That you have this massive exodus of women, because they can’t find a way to make it work. The reason they can’t find a way to make it work is their current work structures demand face time and long office hours. Those things are fundamentally incompatible with parenthood, and not just motherhood, but parenthood more broadly.                 

The reality is, there’s a really quick, easy fix, which is just to have more trust in people and give them flexibility, but that is not commonly accepted. That’s, where this idea of Werk was born, is I found it completely unsatisfactory and unacceptable that the most talented women were dropping out of the workforce, and these are the women that had the greatest chance of making it into leadership. We still have only five percent of women in the Fortune 500, CEO class, same with the S&P 1500, the same across everything you look at. I felt as though it was maddening that the structure was really the problem, and not all the things about communications and credit and mentorship and sponsorship, which are all the symptoms of a deeper root cause.

SG: From our earlier conversation, as you build Werk, are there any ‘negative externalities’ you have had to consider?

AA: Yes and a lot of them have been written about. The unfortunate thing, is that flexibility gets a bit of a bad rap. That’s one of the reasons we wanted to create new language. When something has challenging associations or emotional baggage, the best thing to do is to try to break the frame and try to shift someone’s perspective.                 

That’s one of the things we tried to do: move away from the old way of looking at flexibility and give it a new life, to break some of the negative associations. But there was just an HBR article over a month ago, that talked about the fact that flexibility might make women more vulnerable to bias.Their argument is women ask for flexibility disproportionately than men, and it perpetuates gender bias and a perception of being not serious. Our response to that is the fear of gender bias should never be a disincentive for action. The fact that we’re afraid that somebody is going to persecute us for something that — all the research shows it has no down-sides, it only has upsides—means it’s purely based on bias.

Flexibility is often stimulus response. We’re having these stimulus responses to flexibility because it is not convention. The more we make flexibility a common convention, the more everybody has access to it, the less we will have stimulus response to it. To me, that is one of our goals, and so I guess the externality we worry about is are women going to be perceived as less serious? Well, that might be unless a company has the right contact. We try to make sure that we treat our sales process as an education process, and we openly address some of these issues.

We openly address the fact that flexibility is not a perk, it is about compatibility. Actually, some research shows flexibility has more bottom line benefits to the company than to the employee, and that ultimately, this does not mean a reduction in scope, ambitions, aspirations, promotion potential. It is about just modifications to the workday and work structure, to make somebody actually perform better and stay longer.

SG: In a perfect world, where would you want Werk to be, in five years? What’s the big picture vision?

AA: In five years, we want Werk to become - two things. Number one: we want flexibility to become a generally accepted dominant market category for work. Today, we have a black and white world of there’s W2, and there’s a gig, and there’s nothing in between. We actually think Werk occupies the entire grey area that is shades of W2 and shades of gig, and everything in between. We want it to be essentially a third dominant job category that is equally accepted and equally used by men and women. That’s about flexibility in general.                  

Number two: for Werk specifically, we want to become the source and ecosystem for content, expertise, and the central hub for jobs with flexibility on the entire internet. We want to become the number one job site, when it comes to flexibility.

SG: That leads right into my next question: in the future, do you see a situation which all work is flexible work?

AA: I would argue there is a potential – I mean, let’s get a little crazy. I would argue that jobs with flexibility will ultimately swallow all W2s and gigs. It all becomes gradients on the same scale. Even with our six offerings today, you would be hard pressed to think of a job that doesn’t qualify for at least one of them. The reality is, there should be a flexibility slice across all job descriptions and all jobs. For us, flexibility is probably a dominant job category, long-term.

It’s all about what type of flexibility you are able to offer within the job. The ultimate logical end, is the idea of result-oriented work, which is just get your primary shit done, no matter when, how, and where. There’s a reason that that’s not part of our flexiverse today, and the main reason is we felt companies were not ready for that yet. But that is the logical end of all of this: people who have autonomy to actually just get their jobs done in a self-aware way, where they know how they work best. 

The market we address today is the people that are failing without that flexibility. These people are about to leave the workforce unless they get access to flexibility. That is a large chunk of the market, but that is not the whole market. The whole market is everyone who benefits from having work-life compatibility. There’s this whole category of people where flexibility is the nice to have, but it’s an optimization. It’s people who have hobbies and interests... they want to work out, they want to be healthy, they want to have other pursuits. For all those people, flexibility, it’s not a deal breaker but it is an important life optimization, and to me, that becomes the future because all people ultimately benefit from it.

SG:  Interesting, I almost take flexibility as a necessity. If you’re hiring me you know I’ll do whatever it takes to get it done, but I’ve got to have the space to be creative, to be thoughtful, to build my – I guess lifestyle design. That’s really it for me.

AA: Yes, and it’s interesting because I think it can take a bit for our work cultures to catch up, because I think what is embedded in making us work is trust, and the reason we started with clocking and clocking out is because bosses didn’t trust our employees, and they wanted to make sure people were actually working when they said they were working.

I think that’s why today, flexibility is earned. The way flexibility functions today, is you only get access to it once you’ve been at a company for a certain amount of time, or once you’re a certain level of experience. We don’t believe that that’s right, or that’s the way the world should be going. But that is when companies are much more comfortable offering flexibility because it has a higher degree of trust when that person is credentialed. When you take this to its logical end, which is about greater trust between employee and employer, it really should be addressed at all levels. 

Obviously, I’m sure there’s lots of naysayers for entry-level work, shift work, et cetera, who say you can’t have full flexibility. There are things that require certain hours, like you can’t have your barista at Starbucks work remote, unless we have a machine. There are the realities. But you can still have flexibility in those jobs, and to be honest, for hourly workers, it’s actually much more about stability than flexibility. The challenges for those workers are the opposite, they have infinite flexibility in the most terrible way. They need more stability. When we talk about flexibility today, we still are talking about more corporate jobs, salaried jobs, things that have office hours, which is a little bit different than other structures of work.

SG: Great call out. I was just doing some work around hourly workers, and the number one retention factor for a lot of hourly workers was flexibility. Whether they could swap shifts. be flexible with when their hours are, etc. which I didn’t expect to be the number one retainer.

AA: Exactly, and what’s interesting is that a lot of this centers around parenthood. Not everybody becomes a parent, but data shows most people become parents at some point in their life, or caregivers. Almost everybody becomes a caregiver in some way. You might be a caregiver towards a dog or to your parents, your siblings. The reality is, most people do become parents or ‘parental' at some point. The reason I say parenthood is parenthood comes in all sorts of forms, not just motherhood or fatherhood. There’s all sorts of families, all sorts of situations, and I think in some senses we devalue parenthood as a society.

That’s the plight of people who are hourly workers who don’t find out their schedule until the day before. How do you arrange childcare? That’s insane. It changes week over week. I think what’s interesting is flexibility – obviously, like I said, there’s people who are failing without it, which do tend to be parents and caregivers. As a society, when we don’t support our caregivers, we destroy the care-giving fabric in our society.

SG: What is the biggest misconception people have about what you do, the work as a company, or just the field in general?

AA: Historically the number one misconception has been that flexible work and gig work are the same thing, and they’re not. One is about work-life compatibility, the one is about project-based, fractionalized work. They’re totally different things.

Over the last year, we’ve gotten fewer and fewer of those questions. I’d say the number one misconception, today, is that flexible work is something that is a perk, that it’s not something that is strategic. It’s something that you dole out as a nice reward or when somebody’s about to leave, and not something that you do proactively. Most people think of flexibility as a reactive, like sales desk in a call center, as opposed to a proactive offer to really set companies up to attract high caliber worker talent and to better retain their employees.

SG: Very interesting. Other than flexibility, what’s a work trend that we should be paying more attention to?

AA: There’s a number of things that I’m watching. I’m watching the fact that we are trying to develop more AI in curation and talent matching and talent acquisition, and yet all the research so far shows that if a human can barely choose a product themselves, forget about curation for help. How do you match human to human? We can barely match human to product. Imagining human to human is exceptionally difficult, and so to me, I’m watching to see what happens with all the AI that is supporting talent acquisition and talent matching.

SG: Now digging more into the platform: Has it been more difficult to get women on the platform as job seekers, or to get employers onto the platform?

AA: I think both are equally easy and equally hard. The reason I say that is they’re just different. Women are naturally drawn to the message, but it’s about getting to them in the right way and getting to the right pockets of people. In the same way, with companies, our conversion rate on phone calls is crazy. 

The companies get it right away. I think both are a matter of just reach and scale. A wonderful and exciting for us is that in both sides of the marketplace the appetite is there. Women clearly need this, and companies are willing to offer it. Companies just need help in understanding how to communicate it, categorize it, and support it. I would argue they’re both the same. They’re just a little bit different. Maybe companies are just a little bit harder, because it’s contacting one company to make one sale versus when we write one article and we get a couple hundred women. But ultimately, in terms of interest level and excitement, it’s actually equal.

SG: That makes a lot of sense. Okay, and so from an employer, what is the biggest pushback that you get?

AA: Honestly, we haven’t had a lot of pushback. The companies that have not posted jobs, it’s because the jobs haven’t matched the criteria. We do require a certain level of experience. You have to focus on certain verticals for the sake of liquidity. But, very few employers have had actual pushback on flexibility.    

I think, more often than not, when there has been pushback on flexibility, it is a symptom of a broader root cause in the culture. There are some companies we’ve talked to that don’t quite understand it, and really believe this is just about remote work, and they don’t offer remote work. For us, flexibility is much broader than that. There are some companies that really require facetime, and I think that’s fine for them, as a strategy today. I think their challenge long term will be remaining competitive in the war for talent, because the reality is our current conceptions of facetime are starting to phase out, and flexibility helps with that.

But there are some companies that still are very, very strict on facetime. That’s some of the pushback we get, and ultimately, I think our last battleground will be professional services, the client services. That’s because there’s essentially two parties you have to convince. You have to convince the company you actually work for, and you have to convince your client. You have to convince them that you’re going to be working in a slightly different way, and things might feel a little bit different, but the quality and the product of the work will never change. I think that will be a slightly longer battleground. For a consulting firm or a law firm where it’s about billable hours and facetime, it might take a little bit longer for these things to change.

SG: On the flip-side, are there different industries or types of clients you can put into early adopter buckets?

AA: Yes, and it’s actually interesting, because it is a corollary and a mirror image of what I just answered. First of all, the mirror image: startups are the first ones to jump on board, because they’re so hungry for talent and they’re growing so quickly that they’re willing to be flexible. Half of the time, they don’t even have office space, anyway.

Flexibility is not a problem for them. Most startups are built by millennials. This is a top three factor in a millennial’s job search, agnostic of gender. A lot of startups are built with this as a principle, and for most, flexibility is implicit in their culture. The corollary to what I said before, is professional services. If you look at the 50 best places to work list, or the 50 best places for working parents, there’s a couple consistent professional services firms that are on there every year. They really have been leading the charge, and they offer a lot internally. I actually don’t know how much I can share about the companies we’ve talked to personally, but I’ll tell you, there’s financial services and professional services firms that really are best in class. It’s just not all of them. Hence the corollary.

SG: Do you still face challenges around stigma and employer unhappiness, due to the flexible schedule after they are hired? Is there still stigma internal pushback?

AA: If we have talked to a company and we’ve trained them even through our sales calls, we don’t believe there is any more stigma. I think some companies get it right away, and others are surprised to understand how strategic flexibility can be, particularly given that it costs them nothing but delivers so much benefit to them. We believe that in the longer term some of the work we’ll be doing is around training and certification. If a company understands flexibility well, then there will be no penalty to the employee. What has been challenging, historically, is that a lot of companies have not understood flexibility well, nor implemented it strategically, and I don’t blame them. We’re giving shape to this job category, and so I would only measure bias against flexibility and implementation of flexibility going forward. Everything that happened before, I would discount because it is not implemented strategically, and people didn’t really understand what this (flexible) meant. Even a year ago, some companies thought flexibility meant gig work. Any historic articles or research you read about, the data is not valid, just from a few pure statistics standpoints.

Going forward, we definitely have to keep an eye on this, as it is one of those negative externalities we watch out for. We are going to be checking with our users, we are going to be checking in with our companies, and we want to ensure that not only is the employee feeling like the flexibility that they signed up for is there, but that they’re still able to get promoted and progress in the job. What companies are going to start seeing is that employees with flexible schedules outperform the rest of their employee base, purely because these people are the happiest, feel the luckiest, and are the most fulfilled by having those sorts of roles.

SG: Final question. What is the number one personal or professional skill you’re working on now?

AA: Great question. I’ll tell you about the one I have been working on and my new one. What I had been working on is not ascribing intentionality to action. For instance the moments when you get frustrated with a friend because they did something for some reason, and then you realize you’re crafting this whole narrative that may have nothing to do with why they did that thing. It’s the same with work, not ascribing intentionality to things that happen to your company internally. Even in the fundraising conversation, not ascribing intentionality to a lot of these things helps immensely. 

What I am shifting focus toward moving forward is providing context. I have found that the reason why sometimes somebody is doing something really well or, on the flipside not doing really well, actually comes down to context. I’ve realized that, as a leader and as a parent of the company, the most important thing I can do is share more context. It’s been a challenge, because I always have to remind myself to not just give people answers. I want to give them context.

Similarly, as the company is going through its own growth, positive and growing pains, one of my lessons have been it’s not just to protect my team, because my instinct is, I want to protect my team and I want to make everybody feel like everything is going so well. But the more I do that, the more I actually hurt the company and hurt their performance. What’s most important is sharing its context. Sharing, ‘Hey, we’re doing this with investors. Things are going well, or things are not going well,’ or, ‘Hey, we’re getting this sort of feedback,’ instead of keeping that information to yourself. If you keep it to yourself, you’re actually doing a disservice to others. But the big thing is, in short, what I’m working on is understanding and providing context.

 A big thank you to Anna Auerbach for taking the time to speak with me. For more of Anna and Werk check out their website, an essay they've written here, or a video from them below.