Navigating Culture in a Scaling Startup

Michelle O'Connor, VP Brand & Global Communications, TaxBit

Today’s edition is slightly different from past interviews. As the podcast launches, these notes will be a more condensed version. I met Michelle O’Connor, VP Brand & Global Communications at TaxBit through the NYC Fintech Women. I coached her for over a year as TaxBit scaled. I was thrilled she wanted to be part of the series. We talked about how she dramatically reduced her # of hours of meetings, how she thinks about hiring and what she’s learned about guiding culture at scaling startups. 

Can you introduce yourself? 

I'm Michelle O'Connor. I'm the Vice President of Brand and Global Communications at TaxBit, which is a cryptocurrency tax and accounting software provider. I work in the wonderful world of Web3 and have worked in this space since late 2013. I've been navigating the wild west for quite a while now.

What drew you to startups? 

I am a builder and you hit this on the head very early on when we were working together. I enjoy having no rails, no guardrails. I like to get in, I like to ask a lot of invasive annoying questions. I like to understand the who, what, where, when and why from A to Z. I like to know the what and the why behind it to make sure that if I'm going to put my brand and my weight and I give everything my all when I'm building something if I'm going to give my all, I want to make sure there's a there there.

I love the velocity of startups and the passion. A lot of people want to join a startup. A lot of people stay at a startup when they're bought into the passion and they're part of the frenzied chaos. Because it should be very chaotic. If a startup isn't chaotic, it's not a startup. I love that. I love those early days when you're making mistakes and changing quickly when you're learning when you have that moment where you hit and you have success. There's nothing better than that feeling. Maybe I'm chasing a rush. I enjoy taking something new and watching it grow. It's so satisfying for me.

You make a good point. It’s why I like leadership and I like leadership particularly at startups and scaling startups because of the chaos. Not everybody enjoys chaos. For people like you and me, I think it gets me into action. I think, "Ooh, what's happening here? 

I love it. When there's a lull, I kind of start getting that itch of, "Okay, what do I need to go do? What's next? What's happening?"

The phase of business matters so much and people who are good at startups may or may not be good at scaling startups and those who are better at later-term businesses are not good at scaling startups, and it matters because the task of leadership varies quite differently at those different phases of business.

100%. It's a different beast at each phase.

You've worked at two companies that have gone from a small scrappy startup to an established company. Could describe them to give context?

When I started at Uphold, there were 10 to 15 of us in San Francisco and then a team of developers in Portugal. San Francisco skewed mostly the executive team, myself, and four or five other kinds of different levels of the team, but it was a lot of former investment bankers and folks that had come over, myself coming from my world. What was interesting is we were only a US-based product at that point so we were serving a smaller market in an emerging industry. When I left, we grew to over 200 people serving 120 countries. We had launched groundbreaking products in Latin America offering US equities tokenized to people in Latin America.

We were remote from the onset. We had an office in San Francisco, but most of us were remote. It was great because you're working across multiple time zones. You had the autonomy to have a work-life balance, but also to be working at a very fast-growing startup that was lean. I watched us grow into a people org, a sales organization, legal, and all of that in different regions and different countries. So totally different cultural differences trying to come together, and in the US, we are unique in how we work. I lived in Italy and learned that the US lives to work while the rest of the world works to live. I think of that often even now as I'm kind of looking at my work-life balance and it's true and we're just kind of programmed that way. 

Then I moved to TaxBit already knowing them because I was their first customer. I knew the founders and the team of 10 at the time. I was the first remote hire and the first female executive hire. It was interesting navigating cultural nuances after being at a big startup, and going back to a smaller one. I move very fast. I'm incredibly direct to the point of sometimes being a little sharp-elbowed, I've been reminded at times.

Culturally I had to figure out how to navigate that and shift myself back to that very early stage 10 to 20-person startup and how that works and wearing multiple hats. Love it, I thrive in that, but I had to remember that muscle, which I had forgotten being at Uphold for about six years. TaxBit had this incredible journey where when I joined, within six months we went out of stealth, had huge rounds of funding, we then were a hundred people, we were then 150 people, we then had multiple offices, we then got to 200 people in a year and a half. You say hockey stick, this is hockey stick plus. That was a lot and we also as a brand, I'm very mindful of who we are and how we scale and not losing the culture of the company, the culture of the product in that scaling.

It's hard because we went from being a Utah-based company to having offices in Seattle, San Francisco, and New York, DC. All cultural differences within each of those different chasms of space. So how do you work with a team in Seattle that had mostly come over from Microsoft, Amazon, et cetera. They work very differently than folks in Utah were used to or folks in DC were used to. How do you find that commonality, which is the goal of the company and our mission, and make sure in conversations we get reminded that so when you're moving fast and there's that hyper velocity, you don't lose your mission?

What's been most gratifying about being at a company that's in the scaling phase?

I was Taxbit’s first customer. When I met the founders, they didn't really have a product built yet. I knew that what they had was going to solve a problem for this industry, cryptocurrency. I really believed in it. They were bringing the regulatory tax bridge. Everyone knows taxes. If you don't pay your taxes, that's when they get you. We've seen that. The founders were a CPA and a tax attorney, very hungry, and very passionate and I said, "Okay, I need to help them build." That's the builder in me. When I decided to join, they were still in stealth mode. They'd had some movement and they were growing but weren't known too much in the market yet. They were building, they were focused on their product.

I came in quickly, I was like, "No. We're going to be the biggest, we are going to be the best, hold on," and strapped on the rocket ships. We had a significant funding announcement within the first six months of my joining. We had amazing founders that people hadn't gotten to know them and their why. You have a CPA and a tax attorney that are brothers that that built this now industry-leading product in a garage. If you don't love that story, that's why they built this company. So I told the story and then in telling the story, built thought leadership and SEO we started getting traction and then got media. All of that started snowballing really quickly to this trajectory where we went from stealth to a record-breaking hundred million series A in six months and then after that, six months later, another 133 million series B and hit unicorn status. That was in less than a year.

If you look at that, it's incredible, but it speaks to the power of taking a story and positioning how you tell that story and who you're telling it to.

As a leader in a scaling startup, what's been most challenging?

For me a challenge and I've seen my peers in leadership, there's a velocity, so how quickly something gets turned out, but also the quality of that velocity while working across the org. You need to move fast, but you can't lose quality. You can't ship products, you can't ship code, and you can't push send on a tweet or a blog or an email if it doesn't hit the bar, especially at a tax and accounting company. We're held to a standard because we’re accountants…we’ve got to be accurate. I think that the biggest challenge I faced as a leader and continue to refine is communicating that triangle. 

You have to have velocity, you have to have a high bar and you have to ensure that you're communicating cross-department because if you're moving in silos, it becomes challenging and there's duplicative work.

I think that was my biggest challenge – moving a million miles a minute. How do I step back, and communicate what needs to be communicated to relevant peers, parties, my boss, and who matters, but then also my team and then the wider team that what I'm doing is impacting? 

It was hard for me to slow down to be able to speed up. I still remind myself to slow down to speed up. 

When I started working with you, I had eight to nine hours of meetings a day every day of the week. I realized I needed to slow down to speed up. I got a lot more protective of my calendar. I slowed down so I could speed up communicating across departments. I make sure that stakeholders know what's happening, why it matters, what their takeaway is, and what to communicate. To do that, I have to slow down, look at my calendar, make sure I'm planning out ahead, and make sure relevant parties are engaging. Because we're all moving quickly.

When you say slow down to speed up I think you mean taking attention away from shipping which is what we’re focused on in startups. Is that accurate?

That's accurate. One thing I'm guilty of is that I know the million things that need to happen and they're all in my head. If I'm in a meeting and within 10 minutes of that meeting it's not engaging me, I will start multitasking. The challenge is there when you are multitasking, everyone does it. If you're in a company-wide meeting, you see heads start going like this, you see their profile because they're doing it. I was doing that because I didn't have the time to have a work-life balance because I had so many meetings. 

For me, slowing down meant that I don't need to be in every meeting. I need to look at my calendar and understand if is that a catch-up with that stakeholder in 10 minutes where I will be like, "What do I need to know?" or do I need to sit in a 30-minute meeting?

From there it was looking at the work and the emails and what I'm doing. I need to slow down when I'm thinking of sending something because if they get my shorthand it might not make sense, and not everyone's in this dome thankfully for everybody, so I need to make sure what I'm communicating, it's still concise to the point, but it has a takeaway if there's takeaway or it's actionable

I want to address the cliffhanger. What’s your average of meetings a week now?

Okay, let me look. This is where Google can tell me all of this. I am at about 12 to 15 hours now.

Incredible. Still producing at a high level and leading even more.

I am more engaged as a leader. In hyper-growth, it’s not sustainable to be involved in everything. If you go from being involved in everything to stepping back and not being in everything…that's a weird feeling. I enjoy control. I had to do some internal work to get past that. I realized I need to be in the areas for myself and for the business that is enjoying, that is showing value, and that is scalable. To step back and realize that was that moment of, "Okay, I am enjoying my job more", which means I'm producing better quality, which means I'm representing the brand better, and when I'm fully engaged and giving the best that there is to give and get.

That was very different from being a bazillion hours of meeting a week plus having work to do, plus trying to be a mom and a partner and all of that. There was a give-and-get that had to happen or it was going to just be total burnout.

Culture is always a challenge for leaders and the stakes are higher when you're in a scaling phase. What’s been the most challenging aspect of guiding culture as you scale so rapidly?

It's something I haven't perfected, so I don't have the solution, but I have a lot of learning. The biggest lesson I have ensuring that when you're interviewing, you're interviewing for different things based on the team they're joining and the leader they're going to be joining under. This is something you helped me land on, but the type of leader I am who does well in a startup. I do well in a startup, but I also need to interview a particular type of candidate to ensure they'll be successful and our relationship will be successful.

You refine who you are as an interviewer and who you interview as well as feedback and following your intuition, which is something that you've helped me remember to listen to. It's the hardest thing if you bring someone in who isn't a culture fit from the start. People can evolve to an extent, but to your point, if you're not built for a startup and you're joining a fast-growing startup and you expect to have a very narrow swim lane, a fast-growing startup isn't for you. I think those are the things you can identify where especially as we had a lot of funding and we're becoming this sexy tax and accounting somehow brand, we had become one of those companies that people wanted to work at – fast-growing, unicorn growth, great cap table. 

A lot of interviews came in where you hear what you want to hear because they want to get a foot in the door of the brand, and a lot of times when you would press on, "Well, you've never been at a startup or you've done this, why do you want to take a step back?" you'll hear what people want you to hear so they can get in the door, but nine times out of 10 it wasn't right. It wasn't the right fit. I think that's one of the biggest ones. 

The other thing is that I knew everyone until we had about 50 people. When we got past 50 people, it became a lot harder to know who everyone was. It became important to build relationships outside of your direct team as the company grows.

Hiring is so important. When we mis-hire it impacts the culture.

I once hired someone who on paper was great, had all the right questions, and checked all the boxes. My intuition reminded me it didn't feel right, but I was not slowing down to speed up. I had so much to do and on paper this person was amazing, so we hired the person and within two months, my team went from happy, engaged, and working well to unhappy, disengaged, and producing a lower quality of work. It became this toxic cloud. 

I quickly identified through multiple triangular points that the problem was the new hire. I was like, "Okay, how did this happen?" I went back through the interview notes and went back through everything. It was a traditional case of just not being a cultural fit. You have to be okay with someone you hired not working out.

I think we are programmed that you have to keep hires. Yes, hiring new people is expensive, but it's far more expensive to keep the wrong hires.

What advice would you give other leaders about guiding culture during a period of rapid scale?

Find your board of directors – peers, people you respect, people in the industry at a similar career level, and one or two that are a bit more senior. When I'm hitting a wall or something doesn't feel right, I have a small group of people that I'll go to and say, "Hey, this is my hypothesis, good, bad, or otherwise, what's your feedback?" I know exactly the tone that I'm going to get from the different people. But at the end of the day, if I can reach a consensus that I have a decision to move forward when I can't follow my instincts without some feedback. That's the biggest thing.

The second thing is finding who you are and finding a company and a leader who supports, empowers, and believes in you. I couldn’t have achieved what I need to achieve at the level and the pace without a leader who believes in me and kind of gave me the crazy wide swim lane. Without that, it becomes really hard because you are trying to do all these things. You're moving fast, you believe in it. But if you don't have that support from peers and leaders, it can get really hard. You get tired, you get burned out, and you question if you're doing the right thing.

It’s a great reminder that there are leadership team cultures too. We need to make sure that leadership culture fits us, that we get the support we need, and that we can be ourselves.

Exactly. 100%.

Did you know that before? Was that something you thought about before you took the roles or something you recognized later?

I did not give it a second thought at all. I jumped because I liked the product, product, or story. Later I learned the importance of actually having a seat at the table was important to me, my voice being heard was important to me, and my voice being respected and supported was important to me. Those are things that have come out of maturing myself as a leader and exploring and hitting some walls and realizing I don't like hitting walls all the time, so I want to find someone who helps move the walls out of my way.

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