Invincible Career podcast transcript: Career Success with Irene Au, Operating Partner at Khosla Ventures – Issue #259

Please enjoy this transcript of my interview with Irene Au, Operating Partner at Khosla Ventures. The newsletter version is available here.

We discussed her career path and what helped her become a successful design leader. She shares advice that is useful for people just starting in their careers, but also individual contributors who are considering a move into management and leadership.

Note: Transcripts may contain a few typos.

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Google Podcasts, or on your favorite podcast platform.

Note: Larry Cornett owns the copyright in and to all content in and transcripts of the Invincible Career podcast, with all rights reserved, as well as his right of publicity.

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Larry: My guest for this episode is Irene Au. Irene is a Design Partner with Khosla Ventures. We're going to hear about how she got her start at Netscape and then made the decision to move into management. Eventually became the VP of user experience at Yahoo and the global head of user experience at Google.

She shares some of her advice for folks that are just started out in their career and. Making that really interesting decision of, do I move into management and leadership or do I stay on the individual contributor path? Irene also shares some advice towards the end of this episode that I think everyone will find useful.

This is Invincible Career and I'm Larry Cornett.

Welcome to the show, Irene! It's been a long time since we've seen each other.

Irene: Thanks for having me. Good to see you.

Larry: I want to start with sharing with the audience who you are, and for those that don't know you and what you're doing right now.

Irene: My title right now is Design Partner. I work at Khosla Ventures, which is a venture capital firm here in Silicon Valley. And my role is to work with the entrepreneurs and CEOs in our portfolio to help them be successful. We have various. Operating partners inside the firm. So, you can think of venture capital firms as having investing partners and operating partners.

And the operating partners are the ones who get involved with the startups. Once we decide to invest in them. And we have various operating partners with a wide range of functional expertise, deep expertise in particular. Fields that are part of a company's journey from like AI to PR and communications, marketing, et cetera.

My background is in user experience and design. I work with our portfolio companies on all matters related to design.

Larry: Fantastic. Let’s go ahead and look back across your career history and talk about your career path. Maybe even going back to your degree in HCI, which is cool.

That's what I studied too. Call out the key events that kind of paved your way. Let's start with your experience as a UX leader. Cause you've been a UX leader at some of the most notable companies in the Valley. Let's talk about your background and the path that got you to where you are.

Irene: Sure. Yeah. I studied electrical and computer engineering as an undergraduate and had originally intended to get a PhD in the field, focusing on chip design in graduate school, and then realized that a lot of my peers were building technology for the sake of technology. And no one was thinking about how to direct technology towards people's needs and interests.

And in my quest for finding something that really resonated with what my heart wanted to do. I discovered this whole field of human computer interaction and human factors, engineering, psychology. So that's what I studied in graduate school. And coming out of graduate school, I joined Netscape communications as an interaction designer.

So maybe some of your listeners are too young to even know what Netscape was, but that was the world's first commercial internet web browser. And so, we were really the first company on the planet to think about how to deliver internet content to people in a user-friendly graphical way. And almost as soon as I joined Netscape, so I worked on Netscape’s client products.

So, like the web browser, mail and news, product, the calendar, product, page editor, things like that. And almost as soon as I joined the company, that was around the time when Microsoft started integrating Internet Explorer into its operating system. So, a couple of years later when Netscape decided to open source.

It's browser code. I decided to join Yahoo. Amongst many places that I had considered joining, but I loved the energy and a sense of mission and purpose that people had at Yahoo and also the irreverence and the fun and the joy that they had in doing what they were doing. So, I joined Yahoo as their first interaction designer.

They were just moving from a place where they started out with a directory of web pages, websites, and they were starting to offer. Web-based services and products like Yahoo mail and my Yahoo. And they wanted somebody with my background to figure out how to develop products that were easy to use and useful in a systematic way within the company.

So I was at Yahoo for eight years and, whereas I started as their first interaction designer, I ended up becoming the VP of user experience and was responsible for UX. Back then we didn't even call it UX, but I was responsible for user experience for all of Yahoo's products. And then in 2006, Google came knocking on my door and they were looking for a design leader.

And so, I took that on and was responsible for UX for Google for six years and helped kind of transform Google's relationship with design while I was there. After that I did a double stint where I was in executive in residence at a venture capital firm called Trinity.

At the same time I was consulting and advising for a startup called you Udacity, which was the world's first like MOOC, so massive online open courseware company. And eventually I joined them full-time because I was having so much fun with them and was a VP of product and design there.

Then later, joined Khosla ventures as the design partner. So that was kind of my journey. And you know, even though it wasn't necessarily deliberate each step along the way, each a path that I took paved the way for the next step.

So, it just kind of serendipitously happened that way.

Larry: Right. So, I mean, you've had an incredibly successful career. Everybody rises to become a VP of user experience at big companies like that. What do you think helped you transition? Well, I guess moving into management, it was a decision point as well, deciding, “Hey, I don't want to be an individual contributor. I want to move into management and leadership.” But what do you think made you so successful and able to, to see those opportunities and be the person for the role? Because yeah, it's very impressive.

Irene: I think there's a combination of factors. I mean, one is that I always followed my heart and chose the path that I thought would challenge me to grow in ways that I wanted to grow.

Like, what am I curious about and what are the places that are going to feed that curiosity? Where am I going to be really excited to go to work every day and see these people and work on really hard problems with them? So, as an example, I'll just draw upon several decisions that I made along the journey just to kind of illustrate my points here.

When I was leaving graduate school, I was trying to choose between Netscape and another company called Bellcore, which was in New Jersey. Bellcore doesn't even exist anymore, but they had a well-established human factors group, and I would have gotten a lot of mentorship there and would have learned a lot.

And they were also advertising that there was like a lower cost of living and I could buy a bigger house in New Jersey. But I really wanted to be at the heart of Silicon Valley and the heart of where the internet was happening and being made. So, I just knew that was where my interest was. I couldn't believe that I got paid to do that job.

And similarly, when I went to Yahoo, I couldn't believe that I cut pay to do that. I mean, I would have, I worked long hours because I loved it. Not because I was doing it for the money. I chose Yahoo above the other choices I was considering because the people there just have really great energy, and I'm not talking about energy in the sense that they could stay up all night or do a lot of things.

It was more just a feeling of joy and passion and they were having fun. And I wanted to be with people who were very positive in that way because I knew good things would come out of it. And, the choice that I made to go to Google was a little bit more complicated. I mean, that was one where it was a famously challenging role to take on.

In fact, I remember a lot of my colleagues and peers had looked at that role and either did not get offered the job or, or just shied away from it because Google was notorious for being a very engineering-driven culture, and some might say hostile to design at that time. But, I feel like we define ourselves by the challenges we take on.

And I felt like even though the role at Google. Would be very similar to what I did at Yahoo, that it would be under very different and extraordinary contexts and circumstances. And that I would, I would be challenged to learn and grow in ways that I hadn't before. And that definitely proved to be the case.

By the time it was time for me to leave Google. I had a hypothesis about the possible role and value that I could play in venture capital because I was getting a lot of inbound inquiries from executives I had worked with and entrepreneurs that were complete strangers who reached out, asking for advice.

So I thought, you know this is really fun and interesting to advise all these companies, but the sum of all these coffee dates… my time is worth more than that. And so maybe I should turn this into a job. So, I went around Sandhill road pitching my idea to a lot of different venture capital firms.

And at the same time, just coincidentally, a headhunter contacted me about the opportunity at Khosla Ventures. And it turned out to be a great match, like my vision for what I wanted to do and how I wanted to contribute exactly aligned with what Vinod was looking for. So that was kind of a really nice match.

In my two-year stint at Udacity and then also concurrently at Trinity was also just sort of a —it wasn't very deliberate — but it was just sort of a learning opportunity and like a follow your passion kind of thing. At Trinity, my intention with being an EIR there was not necessarily to move into venture capital at the time, but just to see how the world of venture capital worked and to see, is there a need here?

Like I had this hypothesis, I thought there was a role that I could play, but I just wanted to test that out. And so that was a chance for me to try before I commit. Cause when you go into venture capital, it is like a marriage, like you're committing to that firm for. A long time. And with you Udacity that was like just totally serendipitous.

I ran into Sebastian who was the founder at breakfast, and it was my last day at Google and I, I told him it's my last day at Google. He said, come help me with Udacity. And I was just… so I love Sebastian. I was so intrigued by what he was doing and loved the, the mission and the opportunity to work in education.

Also the office was two blocks from my house and two blocks from the yoga studio where I was teaching. So, it was just like very convenient and easy. So, I'm a big fan of designing your life. You know, you choose paths that like feed your curiosity, feed your soul, feed your happiness, and also fit into your life in the way that you want it to.

So those have been like guiding, guiding points of inspiration for me in my career.

Larry: No, I liked it. I love that. Designing your life. Yeah. I tell people design your career, especially if you're a designer. It's like you design systems all day long. Your career is a really complex system. You can design it, right?

Irene: Yeah. I would say for me, it was not as top-down, as very bottom up, you know, putting one foot in front of the other.

Larry: Nice. I also noticed, you know, we've been connected for a long time that you took a break and you were focusing on yoga for a while, which I think is amazing that I've found that in tech it's easy for us to kind of neglect ourselves a little bit because we're working so much and neglect our health and it looked like you were taking some time to kind of reconnect and think about what you wanted to do next and taking the time to invest in yourself a little bit.

Irene: So, my foray into yoga happens concurrent to all of this. I didn't actually take any break. I went through yoga teacher training,  while I was at Google and I had a very supportive husband who took care of the kids on the weekends. For several months, while I went through this training, I had no intention of teaching yoga.

When I went through the teacher training, it was purely just to feed the curiosity and when I came out of it, I was so transformed that I felt compelled to teach just to pay it forward and to push myself, to continue to learn because we teach what we need to learn and to hold myself accountable, to continuing to do that.

It definitely informs every aspect of life. So it's not an “either or,” it's an “and.”

Larry: I like that. Nice. So, if you look back at your entire path and it seems like it kind of went the way you wanted it to, but is there any moment or anything that you think, you know, I wish I'd done that differently, or I wish I'd taken this path instead of that path.

Irene: I have no regrets about that. I think like in every moment that we take, we just do the best we can with what we have. There may be mistakes that are made along the way, but I also think that compassion and forgiveness are also really key. And to not beat yourself up over mistakes that might've been made along the way, but to learn from those and to understand yourself well enough so that you don't fall into the same patterns over and over again.

So, yeah, I have no regrets.

Larry: Good that's even better! So, for the young listeners, especially the folks in UX, what advice would you give them? The folks that are kind of earlier in their careers.

Irene: Stay curious and find opportunities to feed your curiosity so that you're always learning. And then, I think it's really helpful to build and nurture relationships with other people.

Like I would say one of the key factors that was a part of my success was my ability to work with a wide range of people. I think my background in engineering really helped me work with very difficult engineers. That's one attribute that set me apart from my peers, at least at Netscape early on in the career.

And that, that in turn led me to opportunities that I might not have otherwise had. So it was a launching point. But I would say like throughout my journey, there have always been, you know, people very different from me that I've had to work with and negotiate with and to win over like the landscape's really different now, but I would say that over the last 20, 25 years, like designers were not often in a position of authority.

Where you know, whatever we said should be done automatically. So, it just means that you have to have enormously high emotional intelligence and powers of persuasion and more importantly listening and understanding. So, I think like my ability to listen and understand and see the other side and then to bring people on board with what I thought was crucial. So I would say that's another thing. Stay curious and also listen.

Larry: I like that. So I want to talk a little bit about the decision point when you moved into management and leadership, because I was recently talked with a bunch of folks who are, they're kind of that crossroads they're individual contributors.

And they're trying to decide, do I continue to go up this path of craft, which goes into like the principal track and so forth, or do I move into management and what are the pros and cons of those and how did you decide what made you think? You know what I do want to take the management path?

Irene: I always had a really clear vision for the kind of organization I wanted to build at Yahoo.

And I felt like I was the best person to do that. So it was just baby steps, you know? I started off by proving that this whole area of design and user research was valuable, important so that the company would invest more in it. And then as the company chose to invest more in it, they trusted me.

Because I was proving that it was worthwhile. They trusted me to build out that team. And so, it was just one hire at a time, but I had a very clear idea for what I wanted to do. I mean, in fact, that in a sense that was designing, I was designing the organization and the future for how design would fit into Yahoo.

So I don't think that management is the best path for everyone. You have to deal with a lot of stuff that is pretty yucky. And for me, like my approach has really been one of servant leadership. Where I see myself as an enabler and somebody who's building a team that can achieve something that's greater than the individuals themselves.

And that you're bringing as bringing in a lot of different perspectives and disciplines to create something. But in order to do that, I also had to pave the way for people to do great work. And that means I have to get the yucky stuff out of the way. So that's not for everyone. So, I think it's really important to understand your motivation.

Why do you want to do this? And what are you going to get out of it? Because actually in a lot of companies going up the ranks of management does not necessarily lead to more power or more pay. That certainly wasn't the case at Google. There was no thanks in becoming a manager at Google at the time that I was there.

So, you know, like for me it was like I had a vision for the organization I wanted to build, and I wanted to serve that team. And make a great team that could do great work. And so, I felt like I was the best person for that job. That's my story. I think other managers or leaders have different motivations.

But I think it's important to know thyself, and to be genuine and authentic about it and hopefully virtuous as well. Because I think, these days, especially with organizations, people choose who they want to follow. Like, just because you have a title doesn't mean that people are naturally going to follow you.

Larry: Absolutely. Yeah. I tell people, choose your next boss. You can choose the right person you want to work for and learn from makes a huge difference. One of the things that I've noticed has changed. I would say in the last 10 to 15 years, is that it seems like startups have an awareness that they need UX earlier than they did.

Certainly, when I was a young designer I was interested in startups way back when, but it was like, they're like, if you're not an engineer, we're not that interesting. But I've certainly noticed a change. And I don't know if you're experienced this with your portfolio and the founders that you work with.

Are they bringing UX on earlier into the organization than they did in the past?

Irene: Absolutely. And it's a big reason why I have a job because I think entrepreneurs understand that design is as, as critical to their success as technology and business and sales, you know? So, people really do see it as, you know, one of the legs of a three-legged stool.

There may still be some naivety around like, how to do it, or what's the right talent to get because you need a lot of different kinds of skills that are embodied under the rubric UX. I think there are a lot of different factors that are driving that. So one is that like we're at a point now where technology is good enough.

You've got so many off-the-shelf components that it doesn't take a lot of capital for people to create a tech startup. So you get a lot of competition out there and, therefore, design can be a differentiator. So that's one factor that's driving it. I think also people just have elevated expectations for what a good user experience should be because we have a generation of people now who've just grown up with the internet and consumer experiences.

So, you know, they don't want to use products that like we're historically designed as enterprise software. And even in terms of enterprise software, like we see this whole wave of the consumerization of it. Like people are demanding to have like the. Tools that they use at work to be at least as good as the tools that they use in their personal lives.

So all of that is driving a rise in interest in design, even in unexpected companies like historically enterprise companies have under-invested in design and that's actually not the case anymore. In fact, I think a lot of enterprise companies see that when it comes to having productive, efficient, end users of their software.

It's not so much the technology or the software that is the limiting factor, but it's actually the quality of the user experience that makes or breaks, whether people can be productive and happy. So for several portfolio companies I work with, that's a big driving factor for why they prioritize design.

Larry: That's fantastic. No, it's very promising. It gives people more options and I think everybody should have a startup experience at some point in their career. I think they learn a lot. I mean, I certainly did and I'm glad that it's open to more people now.

So, one of the things that I've been trying to understand is: what does the future hold for us given the current situation? We've been impacted by the pandemic. It certainly impacted how teams are functioning. It's impacted how teams are organized co located. More people are working from home. What guidance are you giving to your founders in terms of where they're finding talent, working with talent, collaborating, working as teams now?

Irene: Well, it's really interesting because companies that I've worked with who were historically reluctant to hire people who worked remotely are now very open to the idea. And so, there's just a lot more access to talent now. And this goes for companies that are based in historically expensive areas where there's like a shortage of talent.

They're trying to hire people who want to live somewhere else and now they have access to those people. They're also startups that are in cities that are not necessarily hotbeds for talent, and now they have access to top talent because right now they're open to working remotely.

So, there are a lot more opportunities now I think on both sides. So that's really interesting. Early on in the pandemic and the lockdown I had seen, like for some consulting agencies and freelancers, like they were starting to. Lower their rates maybe because they were worried about companies tightening their belts and there was like a shortage of work.

But actually I, I'm not necessarily seeing that now. And at least for our portfolio companies they're most of them are not really that affected by the pandemic because they're in businesses that if anything might benefit from more people being online and working remotely I would say for, for UX people you know, like I mentioned, the ability to work with a wide range of people and forging relationships and nurturing those super important.

And I think that's something that people need to do more consciously now because you can't just like swing by and run into somebody at the cafeteria or the water cooler or whatever. So it takes an extra effort to stay in touch with people and to. Build new relationships. And then, to the extent that designers and user researchers are facilitators of collaboration across functional teams, I think this is an interesting area that needs perhaps more exploration and maybe more pedagogy around it is like, Okay.

We did a lot of work to figure out what's the playbook for running an effective brainstorm or running an effective design sprint, but all that done, all that was done in person. And so now it's like, how do we do that online effectively? Like, what is a five day design sprint look like when it's done remotely and people can't all stand up and look at the whiteboard and put sticky dots on the best ideas.

I think those are some of the new areas of opportunity.

Larry: Yeah, I think it's exciting. I'm excited. Cause I remember way back in 93, when I was at IBM, we thought that remote collaboration and all of this was just around the corner. There was so much excitement and energy in the Valley around it.

And I think it's taken us this long to like finally embrace it, let go of the physical workplace and say. Okay. We have no choice. So we have to make these tools work, and I'm hoping we're going to see an increase investment in these collaboration tools and the digital whiteboards, improving video check communication, the, the sense of telepresence, all this stuff that we had thought we was right around the corner.

I think we're not going to start to see. In the next two to three years, which, you know, it makes me excited cause I work remotely too. So fun, fun to see. Well, I just want to thank you for making the time to come on the show. I really appreciate you taking some time to talk with me.

Irene: Sure! Thanks for having me.

Larry: I want to call out a few points from my conversation with Irene that will help you as you create your own invincible career. First, you may have noticed her theme of curiosity and deliberately seeking challenges. She pursued companies and experiences where she could learn something new, be challenged and grow a career is more fulfilling when you're excited to go to work every day.

See your coworkers and solve hard problems with them. Next nurturing relationships is so important, intelligent networking matters. And now we have to be more intentional about that than ever before. The longer I live, the more I realize how tightly your success is tied to your relationships. She mentioned her serendipitous encounter with the CEO of you Udacity.

When she bumped into him at lunch one day. And how that conversation led to her joining the company as their VP of design. Finally, she defined her most recent role and proactively pitched firms. She thought would need it. That's how she ended up at coastal ventures. All too often, we accept would exist and we settle for what is offered.

One of them, most invincible careers that you can have is the one that you define and troll. Thanks for listening. I hope you enjoyed this episode. And if you would like to follow upcoming releases of the show, please subscribe.

And as always, I appreciate your ratings and reviews. Thank you.

If you would like to learn more about invincible career and the podcast, you can visit invincible career.com

Until next time, I wish you the best of luck and becoming an opportunity magnet for the best things in life.