“Redefining Failure”: Tiffany To, VP of Product at Atlassian (Video + Transcript)

March 8, 2022

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Sukrutha Bhadouria: So we are moving on to Tiffany. Tiffany’s the VP of Product at Atlassian. She leads the product team for Jira software, Jira Align and Bitbucket. Tiffany joined Atlassian in 2019 and moved from the [San Francisco] bay area to Sydney, Australia, where she resides today.

rutha Bhadouria: She brings her operator experience to support enterprise startups as an advisor and as an angel investor. By the way, we’re going to have to play her prerecorded talk today because Sydney is experiencing weather issues that is affecting the connection for Tiffany.

Tiffany To: When you are introducing yourself, you are inclined to highlight your biggest successes. But given my talk is about how we can redefine and normalize failure, I’m going to set the tone by starting with some of my career low lights.

Tiffany To: So let’s start by rural winding to my second job out of university. When I joined what I thought was my dream company, Silicon Graphics. For those of you too young to have heard of it, SGI was famous in the late 90s for bringing to life the CGI dinosaurs from Jurassic Park.

Tiffany To: At Stanford, I programmed on SGI boxes we named after raptors and I was so excited to be a PM for a company responsible for so much innovation in graphics and super computing. I was building software being used by NASA. So, a girl geek dream come true, right?

Tiffany To: Well, SGI was my biggest lesson in tech and business. This was when x86 boxes from HP and Dell were blowing into the market and SGI’s final move to switch from their proprietary MIPS to Intel’s titanium processor architecture was simply too late.

Tiffany To: While numerous classmates went to this new company called Google, here I was seeing my stock plummet below a dollar. From this brutal failure, I learned a lesson that would stay with me for the rest of my career.

Tiffany To: In tech, disruption happens fast – for even the biggest predators in the food chain and understanding the interplay between technology, innovation and the business landscape is critical to survive and thrive.

Tiffany To: My second failure hit me psychologically more than others because it was the first and only time I’ve been fired. Ever the overachiever, being fired was not a failure that had ever fathomed, but at my first startup 10 years into my career, I put in 110%, thrilled with the startup excitement of working all hours to make impact.

Tiffany To: My job was building a go to market strategy for a new cloud storage technology, launching the product and convincing analysts, we’d created a new product category every CIO needed to buy. Now, my strategy was ultimately successful. The company reached IPO. The market category today is over 10 billion dollars.

Tiffany To: However, the CEO and I had not seen eye to eye on numerous issues, and this experience taught me how important culture fit is. Most startups are under high pressure to succeed and do it quickly. So not all leaders are going to invest in creating a sustainable culture.

Tiffany To: You need to do your diligence to get the real story and understand if it’s an environment you can personally thrive in. I had not, and jumped in without doing my homework. So market success, but personal failure.

Tiffany To: I went on to launch three more startups, including a spectacular failure that purred through 50 million dollars before I came to my current role at Atlassian as VP of product. But I’m the leader I am today because of the lessons learned from all of these failures. And I’m so excited to be here with all of you today, to talk about why I believe embracing failure has the potential to change the trajectory of women in leadership.

Tiffany To: Now, recognition of the value of having female leaders is thankfully becoming much more widespread as study after study proves out the bottom line benefits of diversity. But organizations and women themselves are still struggling to find ways to correct the leadership in balance.

Tiffany To: There’s been a lot of focus on how important the role of advocates play in this ecosystem in supporting women and creating opportunities.

Tiffany To: However, now as a mother with both a son and a daughter, I started to recognize the differences in how society and I, myself perceive success and failure differently based on gender, because of this unconscious bias, I believe there’s an opportunity for a mindset shift around risk and failure for women without deeply examining our personal and collective expectations of perfection in our careers as women, we won’t be able to increase our risk tolerance to seek out the opportunities that I believe will truly challenge us.

Tiffany To: First, do women even want these leadership roles? The answer is yes, BCG and Hendrick And Struggles, an executive recruiting firm, surveyed more than 750 female and male senior tech leaders last year on a range of career topics. They confirmed what I believe we all collectively feel, which is there’s no ambition gap.

Tiffany To: Women in tech want to seat at every table all the way to the top. So what are the steps along the way where men and women deviate in their career paths that results in this leadership divide?

Tiffany To: Well, one of the most interesting stats from this study is around career pivot points, both men and women agreed that changing employers was critical to career advancement.

Tiffany To: But interestingly, while 80% of the male leaders surveyed had been at more than three companies, only 53% of these female leaders had. Why are men making the moves necessary to advance their careers?

Tiffany To: While most female leaders are staying put and trying to earn those opportunities over longer tenures with the same employers. Maybe the answer is in risk tolerance differences. That study also found that there was a 15% gap in risk tolerance between gender, for leaders in R&D functions but interestingly, no difference in the business leaders.

Tiffany To: Maybe this is because women in tech are often fighting this perception that they have lower technical skills. I know I felt that throughout my career, I had to triple check that I was right on anything technical before I shared my opinion.

Tiffany To: But the insidious power of this pattern of upholding perfection then translates into how often we aim for promotions in or inside our company. This same study confirmed that 41% of women’s surveyed went for multiple promotions where they didn’t meet all the qualifications compared to 51% of men.

Tiffany To: So you start to see where that gap opens up. After looking at these stats, are you wondering if I’m telling you to start job hopping, doing a whole stringing of failed startups? Absolutely not.

Tiffany To: Please do not let the takeaway be that more jobs automatically equals more success. You need to take a path that’s true to you, but I’m hoping with this talk that by having more awareness about our views on failure, we can all more consciously consider the opportunities we choose or don’t choose to go for.

Tiffany To: In the last few years, there’s been a lot of discussion about how the most valuable employees will increasingly need to be T-shaped to adapt to quickly changing opportunities and environments.

Tiffany To: Companies need to be more agile as every company becomes a software company, and that means they need their teams and leaders to be as well. T-shaped knowledge means you have this deep level of knowledge in one area and a wider array of knowledge across other areas to support that deep core competency.

Tiffany To: Essentially, you’re a generalist with a specialization. And I think I unknowingly built my career this way because I had a couple key things I understood that I did well early on. And those were areas that I honed with each opportunity I took on.

Tiffany To: And I had a lot of curiosity about technologies and business that I’ve had through the different companies I joined over the two decades of my career. In high school I was torn between my love of journalism and programming, but I went down the CS path. University, I couldn’t decide between software and hardware. So I studied both CS and EE and I realized, I love learning about all kinds of tech and my knowledge.

Tiffany To: As I started working, I realized I was good at communicating complex concepts to many audiences, for example, new technologies to analysts or customers through various roles that started in software development, but then spanned across product marketing, product management, and a bit of everything in startup land.

Tiffany To: I honed my ability to create new categories of B2B products and consider that my specialty or the vertical part of my T. The horizontal part of my T spans technologies that include everything from wireless networking to supercomputers, cloud infrastructure, security and now DevTools.

Tiffany To: I’ve also spanned business models and company types, from huge tech companies like Intel to 10 person startups and rocket ships like VMware and now Atlassian. My startup rollercoaster was tumultuous, four companies in 10 years. And my resume could be read in very different ways.

Tiffany To: Having worked at so many companies can be a flag that someone has failed a lot and a negative factor for recruiters. On the other hand, two of the four startups I launched have reached IPO or multi billion dollar valuations, which is a much higher hit rate than the average of 90% failure.

Tiffany To: I chose to trust my own definition of success based on lesson learned, but that doesn’t mean I didn’t out myself a lot, but ultimately that scrappy startup drive is why the best manager I’ve had in my career recruited me to join him at Atlassian to help scale the company’s growth.

Tiffany To: At Atlassian, I lead a really awesome team of PMs that drive our agile DevOps portfolio of products to help all companies build great software.

Tiffany To: My personal challenge though, in coming in as a senior leader, is that I felt like I was expected to know all the answers to help my team perform at their best. In a startup, managing with ambiguity was necessary for everyday survival.

Tiffany To: My last startup as COO, I handled everything from our product strategy to sales calls and leading our fundraising. I was perfect at zero of these things, but I had to move it all forward to give us a fighting chance. So I just did the best I could.

Tiffany To: In Atlassian, as with any multi thousand person tech company, roles become more specialized and there’s overwhelming amounts of data. As a company, Atlassian is ranked one of the best places to work year after year.

Tiffany To: And what I found is a large part of that is a strong philosophy based on empowered autonomy, built around our core values you see here, that I can attest people live to, every day.

Tiffany To: Teams work as triads, product management, design and engineering. And are expected to build their own strategies, goals, and plans. That means leaders above these layers aren’t directing work or micromanaging their plans. So what’s their job? I asked myself this a lot the first year.

Tiffany To: Wasn’t I supposed to come up with brilliant strategies for them to test and execute? What I found was that empowered autonomy isn’t magic.

Tiffany To: Teams needed to feel aligned to larger goals and understand the bigger picture of where we were going and why. In an agile organization that’s moving fast, coordinating work across all these teams created complex challenges.

Tiffany To: Working with an executive coach and with a lot of support for my team, I’m proud to say I’ve been pushed to grow a lot as a leader at Atlassian and embrace failure in different ways.

Tiffany To: I’ve learned that easy problems don’t make it up the chain.

Tiffany To: I learned I needed to feel comfortable putting out ideas that may be wrong and not measure my worth as a leader by their success.

Tiffany To: Earlier in your career, you’re rewarded for great execution, but as a senior leader, my job is to push for thinking and likely fail a lot as I help my team solve more and more complex challenges.

Tiffany To: I share my experience candidly, because embracing failure is hard I think at every stage of your career.

Tiffany To: When I started working with that coach I mentioned, who has a background in neuroscience and psychology, she helped me better understand the struggle was shared any other female leaders and how much gender can actually play a role.

Tiffany To: Women look at failure sometimes in a different way. We’re the first or the few oftentimes in our company or team, so we feel more pressure to nail it.

Tiffany To: We owe it to the women who pave the way or we’re paving the way, or we think there are others around us expecting us to fail who we need to prove wrong.

Tiffany To: If we choose to have children, we’re often the ones taking more time off during prime career years. So we need to plan our moves out more carefully for an abundant set of reasons.

Tiffany To: My own viewpoints on failure and success were formed at an early age with my front seat view of my parents’ immigrant experience. I picked this Darwin quote because my parents were the ultimate role models for using failure to adapt.

Tiffany To: They were forced to leave their home country Vietnam in 1979, due to a situation sadly not too unlike current events unfolding in the world. And they eventually escaped to America after near death experiences on the open ocean.

Tiffany To: I was born soon after they made it to wintry Minnesota with all their hopes and dreams in a new country. And I saw them start over again and again, every time they saw a chance to do better. Without high school diplomas, they did everything from hourly tailoring work in Minnesota to working at a textile plant in North Carolina, and then relocating to California for the new opportunities springing up in Silicon valley in the 80s.

Tiffany To: They leapt at the chance just to escape East Coast winters. You can’t tell from this happy photo, but my parents hated the cold and it was just the one thing they just couldn’t adapt to.

Tiffany To: My parents found jobs eventually assembling hardware for the first generation of Silicon valley companies, including Amdahl, a big IBM mainframe company. They would sometimes bring home discarded parts for my sister and I to play with.

Tiffany To: And this early presence of computer hardware in our home started my interest in tech, which led to high school programming classes. They lectured me very little though on what classes to take, but encouraged me in every activity or sport I wanted to try, whether it was guitar or math club. I saw in how they built their careers, that mistake failures weren’t things to be ashamed of, but an opportunity to learn and build from.

Tiffany To: They’ve actually became successful, small business owners and funded my pricey university education. But the priceless lesson they taught me was the necessity of failure in that messy path to your full potential.

Tiffany To: One memory that has always stayed with me was a time when one of my uncles asked my dad, why not have another kid? So he might have a son.

Tiffany To: My dad’s reply was that girls and boys are the same in America. From the experiences I know we all share, we know things are not equal yet. And there are many challenges for all underrepresented groups.

Tiffany To: Though progress has been made, there’s still a long road ahead for my dad’s dream to be true and even bigger challenges around the world. But we do need to celebrate the progress we, and all the women before us have made, so that we can keep inspiring each other to push for better.

Tiffany To: So maybe my dad’s granddaughter will experience this equality.

Tiffany To: In this spirit, I ask several women leaders in tech that I’ve had the privilege of working with throughout my career to share their stories.

Tiffany To: The first woman I’m sharing about is Betty Junod, an amazing product marketer I’ve known now for over 16 years, since our day sharing an office at VMware. She’s now to senior director of product marketing there, and her second stint. Similar to me, she had some rocky starts early in her career.

Tiffany To: Betty entered the job market in the initial rise of dot-com boom, but witnessed first hand the graveyard that followed with the crash. She shared that she and her teams were being asked to apply winning playbooks from brick and mortar go to market. They simply didn’t work. Several of her companies went under and the key lesson she learned was that playbooks and tech have to be updated constantly as the markets change.

Tiffany To: Being part of those failures though helped her shape how she built business strategies the rest of her career.

Tiffany To: Her second big failure came much later in her career in the guise of one of the first open source unicorns, Docker. She started there as the VP of Marketing. They tried to do too many things too early from having a developer business, open source community, enterprise business.

Tiffany To: She and her teams were stretch way too thin and didn’t deliver enough on any of those fronts, burning out the team and damaging ecosystem relationships.

Tiffany To: Her lesson learned was that as a startup focus on one thing at a time, test for success or fail fast and then pick a milestone for when to figure out the next business strategy. Wise words.

Tiffany To: The second woman I’m honored to share about is Cathie Metcalfe. She’s a Program Director at Atlassian and my right hand woman. In 2010, she’d already had an extensive career in the banking industry in Australia,

Tiffany To: Cathie then took on an ambitious project to make it frictionless to move between the four main banking institutions that dominate Australia. The idea was to give consumers a lifetime unique address that could move with you, but what started out well then fell apart when one and then all the four banks backed out.

Tiffany To: She showed us a huge learning on how two sided network markets operate and the power of an oligopoly. Cathie needed that lesson for the next time her team took a run at this with a real time payments product, eight years later, with more wisdom and determination from that initial painful failure experience, she and her team were much more successful.

Tiffany To: Sometimes you need multiple attempts at big changes, was her takeaway. So look at that failure as a necessary stepping stone. Then a few years later recognizing the passion she had for tech businesses, she sought to join the biggest tech company in Australian ecosystem, Atlassian. She did her due diligence and even networked with the VPs and execs before applying.

Tiffany To: Unfortunately, there wasn’t a fit with the PM roles open at that time, but she was offered a program manager role. She initially wasn’t sure if it would be right for her, but she ultimately decided that the learning she would do in Atlassian was more important than the job role or title and she took that job.

Tiffany To: Cathie ended up tripling her team over the next two years and is an amazing chief of staff to me and our business unit of over 600 people at Atlassian. I also couldn’t live without her. So I’m so thankful she didn’t stop at her initial job application failure.

Tiffany To: What a privilege for me to be able to share Betty and Cathie’s stories and what great examples of how failure can actually drive success throughout your career. I can only imagine how many more stories we have in this audience today.

Tiffany To: So I want to end my talk by encouraging all of you to help me in redefining and destigmatizing failure by telling your stories.

Tiffany To: We must crush these expectations of perfection we put on ourselves as women in tech by showing the full picture of how we’ve arrived, where we are through the scrapes and bumps.

Tiffany To: I’m not talking about citing every little failure you’ve made and being hyper critical of yourself, but share when you’ve learned something from a failure and normalize these critical parts of our career growth.

Tiffany To: During job interviews, highlight what you’ve learned from failures, not just the successes.

Tiffany To: Second, I want all of us to be more aware of how fear of failure plays into our risk tolerance, ask yourself how you can play it less safe, whether it’s small things or big things, take a small but habit forming risk.

Tiffany To: Make it a point to share your ideas in a forum at work that scares you.

Tiffany To: If you love your current company or role, ask for more responsibility or more visibility, for example, a one-on-one with a leader in your company, other than your manager.

Tiffany To: If you suspect you may be approaching a plateau where you are, start mapping that T for yourself and actively network to build relationships that you can tap into for future adventure.

Tiffany To: As women in tech, we all know innovation requires failure. Your career is about innovating the best of you. So embrace and welcome failure into it. Thank you so much for having me and I look forward to connecting with many of you.

Sukrutha Bhadouria: Hi, everyone. Thank you so much to Tiffany for sending us this video over so that we could like make sure that we didn’t have problems despite all the weather issues that she was dealing with. 

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