Going into investment banking right out of college just felt like a really good training ground.

I didn't think I wanted to be an investment banker for the rest of my life but being able to get into a discipline and an organization where you would just learn such good business basics was the plan.

I didn't know where I was going from there but the entrepreneurial idea was not even in my head.

I feel like I got a lot of the fundamentals of the learning of business already and I would have learned some of the fundamentals of growing and scaling businesses probably better in seat than necessarily in a classroom but what I got from it were amazing friends and connections and the reason I ended up going over to startups was because of those connections.

I was sad that it was limited to just two years, and in some ways wanted to create the ongoing version of that with Chief, but if I did it all again I'd want to get to startups faster for sure.

Mark is somebody that continues to be an inspiration for me and the way that he leads organizations, no matter what industry or what competitive environment he's in, I've never worked for somebody who gives so much autonomy to people.

I walked into that company with zero qualifications to be doing what I was being asked to do and yet he gave me just complete full reign.

I remember at some point we were working through our initial buys of inventory before we were about to launch and I was like, “If you want me to hit the breadth of assortment that you want me to hit in time for us to launch I'm gonna need to spend a lot of money and not necessarily the minimum buys that we have. I don't know that we're gonna turn through that in great speed.”

He just pulled out a piece of paper, did a very quick contract between the two of us, and it was millions and millions of dollars sight unseen. [He said] I trust you, go.

That was really empowering. I had never worked, at that point, as hard as I did in that moment because of the trust that I felt from him and the thing I took most was the leadership qualities that he demonstrated and how much that drove everyone in the organization to truly be their best selves.

We are actually very different and very the same all at the same time.

I encourage anybody that is thinking about starting a business and thinking about getting a co-founder, you should never get a co-founder who is exactly like you. Always make sure that you have just this really nice balance of skills, and that was very much the case for Lindsay and I.

I am much more of the operator. I think about: how is this experience going to be run? How do we think about scaling this? What is our strategy long term?

Lindsay is the creative, and she is the one who is maniacal about any experience that we’re launching, how that will actually resonate from a brand standpoint.

But at the end of the day, the thing that is most clear is that our values are aligned and that’s the thing that’s similar about us that allows for those differences to play out in a way that is playful as you described it.

We have a good dynamic in that way because we trust each other and we can come at things from totally different ways.

I grew up playing team sports my whole life, I love teams, it was a dynamic that I personally wanted and I knew when I was starting chief that when you say a “women's professional network” unfortunately the image that comes to mind is not one of a big aspirational brand.

You often go to a very corporate, stodgy feeling, and so it was really important to me as we were building Chief to invest in a brand in a way that could break through.

Lindsay was at Casper, she was one of the first employees there, and a mattress company is also not exactly an aspirational brand, but she had done such good work in helping to create that brand and I was excited to partner with her to do a similar thing here at Chief.

The idea of Chief, it came from a very personal place of getting more senior in our careers and spending all of our time managing teams and mentoring others.

There’s the old adage of, “It gets lonely at the top,” but for women, it gets lonely a lot earlier.

I think what was unique about what we wanted to build was we wanted to focus on senior executive women.

There’s 5.5 million women who are VP and above in the U.S., and they are so often the speaker and so often the mentor, but they don’t have a great community or resources for themselves to continue to grow as leaders.

We felt like the ripple effect that could have of getting just more of those women into true positions of influence and leadership, the ripple effect that could have in all of the companies that they are employees and leaders of would be really impactful.

I remember very early days of even just trying to get a lawyer to help us establish the company and I was talking about wanting to be VC funded and I literally could not get a lawyer to work with me because they were like this should not be a VC funded business, this is a very nice lifestyle business.

I think that there's a real challenge that you have as you are fundraising and it should just be something that you recognize is going to be a challenge going into it of trying to educate people on a very new business model.

I think the ability for people to say we're going to be the Warby Parker of X category or we're going to be the Uber of Home Services or whatever it is there's just such a benefit that you have of creating that analogy for people for them to be able to put it in a construct and we didn't have that.

It was really difficult then to educate people on that and I think one of our biggest challenges was you say that you are for women and automatically people think “oh well then that's half the size of market” and then you say “we’re for senior executive women” and they think “oh well now you're slicing it even further,” that was the challenge that we were always faced with was is this a big enough market for Venture Capital dollars?

There were a lot of people that as I started to talk about it would go into a place of this feels like a non-profit not a for-profit business, but for me, we live in a capitalist society, I looked at how much companies had made, statements about wanting to drive representation, how much they budget for investing in their top talent, and thought there is a real business model here where companies should be supporting their female executives as they are are making these statements and I don't see why this can't become a for-profit big scale business.

There's also 5.5 million women who are VP level and above in the U.S. alone and so as we were focused on senior executive women, that's a $30 billion market. It's massive.

I wanted to be ambitious about the impact that we could have on the world and I thought the best way of realizing that ambition was to go and get VC dollars that really allowed us to think bigger and move faster.

It was not just our closest friends, we definitely sent some cold emails out to people that we had never met before.

I remember some early VC conversations where we were showing them our first members and they were like “oh so are these just all your friends and Lindsay's friends,” we were like “actually no that's not the case.”

It was amazing. A cold email to C-Suite executives at Fortune 500 companies and people were excited to join.

We started very in-person. We always knew that we would have this extension to kind of democratize the access and allow for more virtual connection, but the pandemic pushed us there a lot faster than we ever expected, because everything we were doing was in-person in March of 2020 when the pandemic hit.

We had actually raised our series A at the second half of 2019, we had signed a bunch of leases for spaces in LA and Chicago. We were actively going through build-outs, and the pandemic hit. We were definitely top of the list of every single one of our VCs, like what’s going to happen with this business.

The amazing part of it has been that all engagement with our community went up threefold.

Women needed this community more than ever. They were trying to lead through social unrest and business challenges that nobody had ever foreseen.

They were also mothers that were trying to figure out how they were going to balance homeschooling with being that leader and there was no playbook.

So something like Chief became needed even more and it completely changed our model that we were able to expand the number of cities that we extended into over that time and provide this value for more women in a time when I think it was needed most.

Word of mouth has been by far our dominant channel which is great because that means that we can continue to use the capital that we’re raising to invest in the experiences and not invest in a bunch of marketing channels.

Product and tech is where the biggest investments for us really are. Our platform in some ways is LinkedIn, MasterClass, and a dating app all in one.

There's a lot of investment that you want to make when you're kind of in all three of those categories and I think the unifying thing across all of it that we're trying to focus on is that personalization, that if somebody is coming in because they are trying to navigate a career change, that there's a very clear path of how they go and tap into this network to help them with that.

If there's somebody that's coming in because they were just promoted to EVP for the first time and they're just trying to step forward in their own leadership journey in this new role, that there's a very clear path for them.

If you have an entrepreneur that's looking to tap into this network as they are building a business for the first time… all of those are very clear use cases of all of our members that join, of what they need and want from this community.

I do not think that I would have any regret with the way in which we are going because I think we're impatient of trying to build a really meaningful powerful network for badass women that need this.

At the heart of the mission is to drive more women into positions of leadership and keep them there.

It's over 200 years before we get to gender parity in senior executive positions and if a little bit of dilution means that we can go and execute on that mission faster, I'm game.

There's a lot of people that have a tendency to get very five-year planned focused and “I need to hit this milestone by this date” and the thing that made me successful was that I just jumped to the thing that most gave me passion next and ultimately found the right place for myself.

The advice I would give for people is to not get so focused on needing that next promotion, that next thing, but to really focus on the learning and following what makes you excited.

I actually think that the failures and the hard parts, the things that you didn't know, are actually where you learn the most about your business.

If you have too much capital that you are in some ways able to ignore the things that aren't going well and muscle through it by just putting more money into the picture, you don't learn what's working or not working for your organization… [Advice] I would give to anybody that's at a specific stage, whether it's unicorn status, their Series A, anytime that you get that influx of capital, it's to make sure that you really stay true to what's important and stay focused.