GV’s Kate Aronowitz and Vanessa Cho on leading through design

Two decades later, these two women are blazing trails in design leadership. Both are design partners at GV (launched as Google Ventures in 2009 as the venture capital arm of Alphabet, Inc.), where they help a robust portfolio of startups find their way.

I hosted Kate and Vanessa on the podcast, where we talked about everything from scaling design teams to how to earn a seat at the decision-making table. If you enjoy the conversation, check out more episodes of our podcast. You can subscribe on iTunes, stream on Spotify or grab the RSS feed in your player of choice.

1. Adaptability is key. What gets you from A to B is not necessarily what’s going to get you from B to C. As a team lead, you need to be prepared to steer.
2. Seats at the table are earned, not given. Ask yourself how you can use design to help build a better company and culture – that’s what shows you as a real leader, rather than just a design leader.
3. Great designers have superpowers. They’re great at facilitating discussions. They can bring people to decisions faster. They can help visualize what a room is thinking. These are the ways you can prove your worth to executives and get them to lean on you.
4. If you’re successful, it’s because someone has helped you get there. It’s up to you to pay it forward. Support is how the industry grows.

Stewart: Vanessa, Kate, welcome to Inside Intercom. It’s a real pleasure to have you here. To set up our conversation today, could you give us a brief rundown of your careers to date?

Kate: I graduated with a graphic design degree in the late ’90s before there was anything like “user experience” and really got my start in graphic design, advertising, branding, and that kind of stuff. I was at an agency for a while and then moved to the Bay Area in 2001. That’s when I really jumped into tech, and I was at eBay for about 7 years. I did interaction, visual design, and then got into management. From there I went to LinkedIn, where I became their first Head of Design, helped add user research, and built out their design discipline. From there I went to Facebook where I’ve spent the bulk of my time out here, helping them grow and define what design means at Facebook. I did a little bit of consulting along the way and was also at startup called Wealthfront for a while. I’ve been at GV now for about a year.

Vanessa: For me, it’s a very similar story. I also went to college in the ’90s, and at that time interaction design was not a thing. I was lucky enough to actually go to college where you could choose a lot of your major, so I ended up experimenting with psychology and cognitive science classes, computer science and then traditional art, which now when I look back I realize I was building my major. After graduating, I worked at a lot of web design shops, mostly in New York – very small stints. I ended up coming to the Bay Area and getting a call from Walmart, which I had never heard of before, growing up in Europe going on a school in the East Coast.

It was an incredible place for me to learn: about ecommerce, about scale, and just in general about management practices. Then I moved over to GoPro, where I started and headed up the design team. I learned about how hardware and software work together. Then I moved over to Google and ran their Apps team. Google Apps covers anything for communication and collaboration – it could be Gmail, Calendar, Drive, Docs, Sheets, Live – both for personal and for enterprise. I didn’t have any enterprise experience until then, and it was something I was really interested in. I was lucky enough that I also had done some consulting (some of which was for the GV portfolio), so when GV called and asked if I wanted to make my part-time job into a full time job, I said, “absolutely”.

Advising startups

Stewart: Let’s talk about your work on the GV portfolio. What types of conversations are you having with these companies and what types of advice are you giving them?

Kate: On a functional basis, GV has about 300 companies in our portfolio. We obviously don’t work with all of them. I took stock when I hit my year anniversary, and I think I’d worked with about 40 companies. We hold office hours every week so people have access to us and can ask us any kind of question from: “I’m interviewing a designer on Thursday. What should I ask them?” to “I’m having to influence my product manager. What do I do?” After working with all of these companies, I’ve fallen in love with helping on the team-building side.

Our goal is to think about establishing design management as a discipline and help these newish leaders build and scale their teams to meet the needs of their companies. If GV a couple of years ago was mostly in seed companies that were thinking about hiring their first designer, we’re now spending a lot of time with companies that all of a sudden have three or four designers. They’re discovering that design is a thing: it needs to be a group and have a function. They’re asking, “Do we have the right person as the executive there? Are we thinking about scaling the team and do we have them working correctly in the organization?” We spend a lot of time on that.

Vanessa: The second bucket is really just focused on the product strategy. Our goal is to figure out how we can accelerate these companies – but first and foremost when we meet with these companies it’s just asking whether they’re working on the right problem. We have to help them define what is the right payback. Who are the right customers they should be talking to, and what can we do that will add the most value? We spend a lot of time talking to CEOs or heads of products or even design leaders.

Once we’ve identified that, “Yes, this is the problem that will help differentiate you,” we roll up our sleeves and work with them on the most complex problems to see how we can help them accelerate. It’s partially the identification and the prioritization but also the hands-on design work which is really satisfying for us. That’s probably one big thing that drew us to GV, because we really value the idea that it’s not just a check from GV that will make a startup be successful. It’s really having this fleet of operating experts that come in and work with you.

Scaling design

Stewart: I imagine that you’ve both seen companies that you’ve worked with before scale really fast—perhaps at Walmart, Vanessa, and at Facebook, Kate. You’ve experienced firsthand how rapid growth happens in those companies and what kind of problems and opportunities it brings out. What lessons did you learn that you apply to your portfolio companies?

Vanessa: I have a lot of tips from things I’ve done pretty poorly. They’re all war stories. Once, I was scaling a team, but I don’t even think I realized I was scaling. I was just constantly looking at the team and thinking, “Okay, if I just tweak this one thing, put this person here, or start another project there, then the team will be perfect. The team will be done, then.” But I came to realize that was a really narrow-minded mindset, because how the team is designed really does need to be fluid, and it needs to be responsive to the company’s needs.

What gets you from A to B is not what’s going to get you from B to C

We ended up having a leadership change that really disrupted the whole organization. The team and I were really resistant about it, and we tried different things, but we realized with hindsight that it was time: time for us to move on as a company, time for us to grow. I said, “It’s been a wonderful ride for you doing it this way for this long, but we really need to shift, and it’s okay for you to decide this is not the right organization for you. But this is what we need to do for design to actually be successful.” It was important for me to learn is just what gets you from A to B is not what’s going to get you from B to C, and as a team lead you need to be prepared to steer.

Kate: The other thing with scale is that what works for one company will not always work for another. You can look at a Facebook. You can look at an Airbnb. You can look at a Pinterest. You can look at Google. Too often, I’m seeing really small teams saying they want the same thing. They want a print shop. They want a design ops team. I’m thinking, “You’re four people.”

Embrace what you are now and make it about what the company actually needs and what you need to do your job better – not an obsession with an organizational model. We’re often talking around where should the brand be, where should marketing be, where should product design be. But the answer is really that there are trade-offs any way you scale and looking at one single organizational structure isn’t going to get you all of your wins. It’s knowing the trade-offs and focusing on the business and culture you’re building first.

Vanessa: It’s actually a pretty common pattern. Kate and I often say that there really aren’t shortcuts. Sure, you can read a blog post from one of these incredible companies, but you should use it as a possible direction, not a thing you must do right now. If you find out Steph Curry wears size 13 Under Armour shoes, going out and buying size 13 shoes won’t put you on his level. Under Armour shoes might be great, but you have customize them for who you are and what you actually need.

Kate: At Facebook, we started this new form of front-end engineering and design called UI engineering. It hadn’t been done before. It was born out of a business need. We had to get something out faster. We ended up with a print shop at Facebook, because it was something very specific about the culture. It doesn’t work everywhere.

Earning a seat at the table

Stewart: How can designers champion for a seat at the decision-making table, and what should they do with if they’re given the opportunity?

Kate: I love the idea of design getting a seat at the table, but I believe it should be earned. What I mean by is only having design at the table because it makes a material difference in the business. Paul Adams, who runs the product team here at Intercom, recently gave a wonderful talk called The End of Navel Gazing. He starts by talking about how as designers, we’re always running around having this existential crisis: “Why am I here? What am I going for?” Then in the next breath we’re asking, “Why isn’t anybody inviting me to a meeting?”

One of the cool things about being at GV now for a year is that we’ve seen patterns over time. Now I can design these “purpose workshops” to help walk teams through these kinds of existential crises. When designers come in we regularly get questions like: “How do I get more influence? How do I get to be more of a leader in the company? How do I get involved earlier in the process?” I ask, “Have you been able to communicate how design makes a difference to the business, how design aligns with your mission?” And the answer is, “Oh no, I haven’t been able to do that.”

So, we literally write the mission on the board, and we figure out how design aligns, moves it forward, and gives designers real purpose at a company. Now, a design leader can go back to their CEO or their founder and say, “This is why design matters at the company, and these are the results I’m going to deliver for you.”

Vanessa: It’s really transformative. So often, even if you do get a seat at the table, you realize you’re at the kiddy table. You’re just there as a figurehead. People will ask us, “I’m leading a design team. Why don’t I have a seat at the table?” I’ll reply, “Because you’re spending a lot of time asking yourself that.” You should really not think about design with a capital D.

How are you a leader for the company? How are you using design to help you lead?

You should really be asking: How are you a leader for the company? And how are you using design to help you lead? They could be really tactical questions like how can you use design to help drive the bottom line? How can you use design to actually help with product strategy mapping? How can you use design to build a better culture? That’s what shows you as a real leader, rather than just a design leader.

Kate: Getting the seat at the table is a blessing and curse. We’re all in the room, but it actually puts more pressure on us to deliver. I remember being at Wealthfront, and it was the first time I was told, “You now have to go to all the board meetings, and you have to speak up”. I was trying to figure out what to say and looking through the board deck and thinking, “I’m going to bring the story of the brand and the sequence of how we go to market and how that makes sense to our users”.

From the board’s perspective, that made a tremendous difference. But one of the things Vanessa and I are very passionate about is trying to prepare the current and next generation of design executives to really think like business executives. If you just go into the room and narrowly think about “design, design, design,” and if you don’t value the business or understand why you have to move to market quickly, your contribution will not be felt.

What got you to the executive table is design, but that is not what’s going to keep you there

Vanessa: It goes back to the A-to-B-to-C conversation we had earlier. What got you to the executive table is design, but that is not what’s going to keep you there. It’s really important to become a company leader. That’s one of the huge advantages we have working with t the GV portfolio: we can try to mimic and to role model what it looks like to be a design executive at a company because a lot of them do not have the opportunity to have an executive there.

Practical advice for real companies

Stewart: So how does this play out on a practical level, when you visit one of these companies?

Kate: There is a company that we’ve been working with for just about a year where we’ve actually deployed all of our services – they’ve gotten the full suite of benefits. They have a design team about four or five people, and they came to us and they said, “We want to sprint”. Everybody thinks they should sprint first. We carefully examined what they were thinking about, and it was going to be a new app that they were going to launch. It had to be somewhat novel in the marketplace and differentiated and we were decided that sprint was a good idea. We got the team into the room for a week. We did a fantastic sprint, but what we quickly realized that while a sprint can focus on a product problem, sometimes there are organizational and team issues you need to straighten out as well. So, we’ve evolved sprint to not just be about the product but about leaving the team with really good habits to be able to implement learnings from the week. While the team is in the room for the sprint, we role model what a successful design executive looks like. How do we interact with the Head of Product? What questions do we ask? How do we lead and facilitate conversations? How do we make decisions faster? We carried on with coaching with the head of product after that. We even had a debrief with the CEO where we told him, “Hey, your project strategy is actually off”. We helped them rebuild the team back into what it needed to be.

They’ve been working on the new app now based on the sprint for about four or five months. They’ve just come back to us. We’re going to help them with the naming and brand sprint, and we’re also helping them with their launch plan. So, this company ran the gamut: everything from one-on-one coaching sessions to talking to the CEO about product strategy and sprinting in a room for a week. We’re trying to do deeper engagements because if a team just jumps in with us for a day or two, they don’t really fully get to see the benefit of what we can provide. But we’ve got a handful of companies right now that we’re giving them everything, which is really fun.

Stewart: You can form a proper, ongoing relationship with them and really be part of that journey.

Kate: In week one, we were role modeling what it was like to be a design executive. By month two or three, you see them stepping up and doing it. And then we give them the next guidance. So it’s really fun to see these teams evolve over time and like you were saying, build strong relationships with them and see them grow which is a lot of fun to see. Both the business and the teams grow.

Vanessa: We often say, “We need to teach the teams how to fish,” because that’s where we’ll really see the hockey-stick growth for these companies. Maybe we can go with a sprint as a Trojan Horse, but when you’re there, you’re really getting to know the product itself and seeing if there are any gaps in terms of talent or people that you really want to accelerate.

Stewart: What are those common gaps that you sometimes see in these organizations?

Kate: I would certainly encourage executives to push on the design team. Invite them to the table, and really try to immerse them in the business and see what they can bring. The other thing is thinking about design outside of how we think about it everyday, not just pushing pixels or doing user studies or being the quality police.

Great designers have a lot of superpowers. They’re great at facilitating discussions. They can bring people to decisions faster. They can run to the board in visualizing what a room is thinking. They can prototype and get things out faster. The facilitation, the visualization, the prototyping, the faster decision-making – executives should lean on their design leaders that way. For instance, we were in with a group yesterday that had this giant product road. I’m looking at the design lead and thinking, “You should be facilitating this conversation”. This is the power of being a design leader: you know how to read a room, how to get the best out of people, how to have a good conversation.

Paying it forward

Stewart: Sam Altman tweeted this week:

If you are successful, it’s almost always because some people went out of their way to help you. You have a moral obligation to pay it forward.— Sam Altman (@sama) August 21, 2018

What are some ways that designers and design leadership can pay it forward in the community?

Vanessa: I loved that tweet. I think Kate would agree that we’re in the position we’re in because a lot of people took a bet on us. Maybe it was the leaders we had, or our peers. For me, my teams were what helped me significantly. I feel like it’s my moral obligation to actually pay it forward, and I don’t want to disappoint them. If somebody from my old team calls, I’ll pick up the phone.

We’re in the position we’re in because a lot of people took a bet on us

I encourage any senior designers to do the same. Be available for different designers during their times of transition. Pick up the phone when they call. Write them an email. Give them a really good design crit on their portfolio. We need to teach each other, and we need to support each other, because that’s how we as an industry will grow. But it’s not quite a scalable model. You should see our calendars; they’re completely full. So we’re thinking, “How can we actually make our impact grow even more?”

I remember when I was running design teams; I felt like my calendar was burning. It just was too full, and I was burning out. I was trying to give back in a scalable way and asking myself, “How are design leaders making a bigger impact or giving back and handling these problems?” I think we’ve realized that the way to pay it forward to is offer a really safe community for these design executives – a place for them to actually share some secrets and best practices.

In the fall, we’re actually going to host a small get together with the top 20 design executives who are still in the weeds. They’re running some of the largest teams in the industry and have probably 20 years of experience, and we’re just going to offer a very neutral place for them to have a conversation and build a community. We need to invest in them, because their impact is significant.

Kate: I’m super excited to get this group together. It’s my geeky dream to have these 20 people in a room, and I also feel like we can offer them a great place to connect because it can be lonely when you’re leading a design team. You look around your company and think, “Nobody else is sharing my problem”. But also selfishly, we want to talk to them about what’s made them successful and what they’re thinking about next. Then, we can take that back to the portfolio companies we’re working with, too.

A lot of this first year for both of us has just been heads-down. We joked that we’d try to say yes to everything for a year and see what breaks – see what bubbles up. I feel like we’re coming out of this first year really strong. We have a passion for pushing design executives and leaders forward, so you can certainly look for more of that next year from us.