The Art of Executive Shifts: A Conversation with Stash CEO, Liza Landsman

Authored by Hannah Doherty

Liza Landsman is arguably one of the top tech executives in New York City. She brings a remarkable blend of operational prowess and venture capital experience. Her distinguished career encompasses key roles at Citigroup and BlackRock, alongside a pivotal tenure at E*Trade. Notably, Liza was a founding executive at Jet.com, where her strategic leadership powered the company towards its colossal $3.3B acquisition by retail giant Wal-Mart and further solidified her standing as a leading figure in the city’s tech industry. Following this, she spent over half a decade as General Partner at New Enterprise Associates (NEA), a global venture capital firm with a staggering $25 billion in assets. Her investment focus was on consumer, ecommerce, and fintech sectors. These diverse experiences uniquely positioned her for her current role as CEO of Stash.

Stash, a fintech pioneer, is on a mission to democratize investing and savings for everyday Americans. Liza took the helm nine months ago during a founder-led transition, a change that earned the accolade of the 'most seamless CEO transition' from Lynne Oldham, Chief People Officer at Stash and former Chief People Officer at Zoom.

With Liza at its helm, Stash is charting a new course of expansion. In the past year, the fintech company’s revenues surpassed the $100 million mark, gross margins surged past 70%, and two million subscribers have set aside nearly $3 billion in assets under management. Under Liza's astute leadership, Stash continues to thrive, empowering its customers and redefining consumer fintech.

Having spent about 15 years at renowned corporations such as Citi and BlackRock, you later ventured into the dynamic startup ecosystem. Could you share with us your experiences and insights gained from this significant transition?

My career trajectory often reminds me of the narrative in the book, A Prayer for Owen Meany, by John Irving. Just as Owen Meany's life was characterized by a series of seemingly peculiar habits that eventually coalesced in an unforeseen way, my journey to Stash mirrors a similar pattern. The choices I made throughout my career, which may have seemed random or haphazard at the time, now make perfect sense in retrospect. Each decision provided me with a different window into diverse aspects of the financial services industry. From credit cards and retail banking to retail brokerage and asset management, these experiences allowed me to explore various niches within the overarching umbrella of financial services, ultimately paving the path to my current position.

Many startups hesitate to hire seasoned professionals from large corporations, questioning their adaptability and drive in a resource-limited setting. What traits do you believe signify someone’s potential for a successful transition?

Before joining corporate giants Citi and BlackRock, I cut my teeth in the startup world. This 15-year detour through Fortune 500 companies has not only enriched my perspective but also shone a light on the bias against recruiting big-company talent into startups. Yet, I'm a firm believer that there are unmistakable signs of an individual's potential for a successful transition.?

The ability to deftly navigate the intricate labyrinth of bureaucracy in a large organization, while keeping the wheels of productivity turning, is indispensable. When I interview candidates, I zero in on the nitty-gritty – their unique contributions and direct involvement. I also hold in high regard those who've made impressive cross-divisional leaps, akin to vaulting from a director role in the cards business to a senior role in retail banking. This kind of rapid advancement signifies the recognition of talent and the speedy movement of individuals within companies. To truly grasp the significance of titles like VP within various organizations, it's important to familiarize yourself with their implications. Fortunately, your clients have professionals like you at their disposal to assist them with such matters.

But the ultimate litmus test lies in how candidates voice their aspirations. I'm drawn to those who speak passionately about what they yearn to build, rather than just the outcomes they seek. They have the roll-up-your-sleeves-and-get-dirty mentality and a readiness to actively fuel a company's growth that I find irresistible. I'm not on the lookout for someone to merely navigate the ship; I want a visionary capable of constructing a whole new vessel within the organization - a telltale sign of a focus on the journey rather than just the destination.

Throughout your career, you've taken on a multitude of roles; from Business Development to CMO, ascending to the role of President, then transitioning into an investment partner, and now, at the helm as CEO and Board Member. Talk to us about these pivots -? were these transitions a natural progression, or an ultimate end goal that you were striving towards? Furthermore, how would you advise those contemplating similar monumental career shifts?

When I set out on my career, I certainly didn't have a rigid plan or mindset where X must follow Y. However, my approach has always been focused on building a diverse portfolio of skills, as I didn't want to confine myself to a single skillset. But the through line for me has always been data. I’m a big data geek, and a big reason why I got into marketing in the first place was because at the time, it was being transformed by data. Then, I started getting interested in operations because call centers started becoming more informed by data, and that was the transferable skill I brought between functional areas as I made that very intentional pivot.?

What I think about when I talk to people who are earlier in their career is, get yourself over the mindset of something being a “lateral job.” For me, some of the best learning opportunities I got in my career were from things that, from the outside, may have seemed like taking a step back. An example of this is when I went from managing a team of 500 to managing a team of 4 because I wanted to learn operations and do something that was radically different. You have to have the belief that your skills will be transferable, that you'll eventually acquire the knowledge you need, and that it will make you more valuable on the whole.?

Throughout your career, you'll often take on roles you're not fully qualified for. Ideally, you should be able to handle about 70-75% of your role proficiently, learning the rest on the job. The value equation between employer and employee should reflect this, with you contributing 70-75% value to the company and the company contributing 25-30% value to you. This balance can shift depending on career stage and experience. For instance, as an investor, my balance was more like 60/40 due to my limited investing knowledge. As your career matures, you may feel more comfortable taking risks, but companies might be less willing to let you do so.

On the other side, as the hiring manager, you shouldn't hire someone who can do 100% of the job when they get there. The likelihood that they are going to stay engaged and stick around for a long time just isn't that high so it doesn’t ultimately end up being that advantageous for the company.

Having experienced both the investment and operational sides of business, can you shed light on the advantages and disadvantages of each??

I think this goes beyond just a matter of advantages or disadvantages as they are qualitatively very different experiences. What I loved about being at NEA and what I love about being an investor is that, in addition to the great people you get to work with, it affords you a kind of intellectual promiscuity that almost no other career does. You get to look at a ton of different industries, dive deep, then pull yourself out, and meet some amazing founders along the way. If you are a person who has intellectual curiosity and is an explorer of the world, there's almost no better career than investing. It's just so much more diverse than almost any other role you could have. As an operator and especially as a senior executive, you certainly get a wide purview, but it's like a wide purview within the swim lane.?

As an operator, the analogy I like to use is this: the company is like my third child. I worry about it all the time, I go to sleep thinking about it, I wake up in the middle of the night thinking about it. The worry is deep, profound, and persistent. As an investor, I’m like the aunt or grandparent; I’m emotionally engaged, I care deeply, but at the end of the day, I get to give the baby back to the parents and have a restful night of sleep.?

I definitely think that having been an operator made me a different kind of investor - one who has a healthy dose of both empathy and skepticism towards founders and operators. It certainly gave me an appreciation of the challenges around execution, and also altered my perspective on the amount of time required for due diligence. Having been on the other side of the table for a significant portion of my life, I do not want to waste anyone's time if I genuinely believe we won't invest. And having now made the transition back to operating, I definitely think differently about value creation than I did before I was an investor, which has been helpful particularly in the CEO seat. It helped me understand what to articulate as the strengths of the business much more clearly, and gave me a better understanding around identifying lack of interest, consequently saving a lot of valuable time by avoiding prolonged engagements with individuals who were reluctant to commit.

Pivoting to your present role at Stash, could you share the driving forces behind your decision to join this company? How did you perceive Stash's unique advantages compared to other consumer fintech firms and investment platforms?

Stash captivated me as it perfectly married my desire for positive change with my capitalist inclinations. I saw in it a unique opportunity - a company that not only should exist, but could make a significant impact, helping people achieve something meaningful while also boasting huge commercial potential. Despite this, the decision to take over from its beloved founders wasn't straightforward. Drawing from my investor experience and awareness of how such transitions can go horribly wrong, I had to meticulously consider this move. So, while it felt like a no-brainer due to Stash's impact and potential, it required serious thought and extensive due diligence.

There were a couple of factors that heavily favored them. Firstly, the founders themselves initiated this decision; it wasn't imposed by the board. They expressed genuine love and concern for the company, while recognizing its potential for even greater success. They acknowledged their own limitations and sought someone better equipped to lead the company towards that future, which really reflects their sensibility and humility. Having spent significant time with both individuals, I can attest that despite our contrasting skills and approaches, we share a strong foundation rooted in shared values, which has proven to be a crucial bond between us. We also genuinely enjoy each others’ company. When I spend time with them, it’s not just me with these really smart guys; we actually have a lot of fun together.?

As just one example, the co-founder/former CEO, Brandon Krieg, also gave himself an entirely new role and mandate within the company– Head of Business Development for our B2B business, StashWorks. There's a great Harvard Business School article that discusses when these CEO transitions are successful, and it’s when the founder finds something specific to pursue, whether it's within the company or outside the company. Everybody in the company knows what Brandon is focused on so they go to him for that specific thing vs. everything else.?

Lastly, I will just say that Brandon and co-founder Ed Robinson have been unbelievable. We all have very direct conversations all the time where I can very honestly be like, “Hey, it'd be great if you stopped grabbing engineers” and Brandon will say, “you’re right, I’ll back off.” Or Ed will pull me aside to say, “hey I think you need to pay more attention to this area, this is what I'm hearing.” So I really appreciate both their willingness to make the space for me, and their comfort in being super transparent with me. You can talk a lot about the structure, but at the end of the day, it ultimately comes down to the humans.