Latest / Chief in Tech Deep Dive Shortcast / Chief in Tech S1E18 - Raji Subramanian, Heather Natour : Leading Through Change & Uncertainty

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Chief in Tech S1E18 - Raji Subramanian, Heather Natour : Leading Through Change & Uncertainty · Chief in Tech Deep Dive Shortcast

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  Welcome to the Deep Dive. Today, we're cutting
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  through the noise. We've got a fascinating mission
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  to really understand how top tech leaders manage
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  strategy, manage their teams, when the whole
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  economic landscape is just, well, fundamentally
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  shaking. That's exactly right. Our source material
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  today is focused on this incredible playbook
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  from a high -impact leader, the CTO of Opendoor,
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  Raji Subramanian. And she stepped into that role
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  at a truly unique point in history. We're not
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  just talking about a normal market downturn here.
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  No, not at all. The frameworks we're looking
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  at were forged while navigating two huge simultaneous
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  disruptions. First, this this rapid, dramatic
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  40 -year interest rate shock that just completely
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  upended the real estate market. And at the same
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  time? And at the same time, the accelerating,
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  absolutely transformative rise of AI. Wow. So
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  navigating a massive economic contraction while
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  steering toward the next technological revolution,
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  that's pretty much the definition of managing
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  uncertainty. It is. And the sources detail these
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  concrete experiences, these really robust leadership
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  frameworks that she relied on. It all draws on
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  her deep experience from Amazon, AWS, Yahoo.
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  So this is less of an anecdote and more of a
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  functional roadmap for transformation during
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  genuine chaos. OK, so our goal is clear. We're
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  going to unpack the specific frameworks from
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  the four operational necessities you need when
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  uncertainty hits all the way to the five core
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  leadership principles, the things that allow
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  companies and really individuals to innovate
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  and thrive, not just, you know, survive. OK.
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  Let's unpack that operational reality. The immediate,
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  and I mean brutal, challenge was that macroeconomic
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  shift. The real estate industry was just fundamentally
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  affected by the speed of those mortgage rate
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  hikes. Affordability just plummeted. But maybe
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  more critically, the sources point out the market
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  completely froze because so many homeowners were
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  locked into those low 3 % rates. It was a profound
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  liquidity trap. Sellers, who were almost always
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  buyers too, just decided not to move. I mean,
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  the cost of capital had doubled or even tripled
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  almost overnight. So when uncertainty is that
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  high, You just can't rely on your business's
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  usual assumptions. They're out the window. The
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  source has outlined four essential operational
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  reactions. And they apply to business, but also
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  to your own career strategy. The first necessity
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  is focus. Focus. Okay, so controlling the controllable
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  variables. Precisely. you have to be ruthless
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  about prioritizing what you can actually influence
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  and focus on the fundamentals. For a company
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  like Opendoor, that meant making sure the underlying
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  business model could actually work, could generate
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  value across wildly different economic climates,
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  not just in a low interest rate world. You had
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  to prove the core physics of the model were sound.
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  Exactly. That makes sense. But when you're forced
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  to focus, to tighten budgets, the conventional
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  wisdom is always cut costs, right? Especially
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  R &D. So that leads to the second pillar. Innovation.
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  How do you innovate aggressively when... every
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  single dollar is being scrutinized. This is such
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  a great counterintuitive point. The sources really
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  emphasize that during these periods of high uncertainty,
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  being bold, breaking barriers, it's a need to
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  have. It's not a luxury. If you freeze innovation
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  during a shock event, you basically guarantee
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  that you will fall behind the seconds the market
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  thaws. The companies that innovate through the
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  downturn are the ones that survive and thrive.
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  The others. They just, they become irrelevant.
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  So it's not about reckless spending. It's about
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  strategically shifting resources to things that
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  are true differentiators. And I guess that innovation
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  needs flexibility, which brings us to the third
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  necessity, optionality. Absolutely. Optionality
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  is just about creating diversity everywhere you
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  possibly can. That could be diversified businesses,
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  diversified positions, different customer bases.
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  or even just making a conscious effort to have
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  employees who bring a whole range of thoughts
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  and experiences to the table. We actually saw
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  a great real -world example of this in Open Door's
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  pivot. They used to be all about the direct cash
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  offer model, but when the market froze, they
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  pivoted. They started letting customers sell
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  their way so you could get the certainty of a
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  cash offer but also have a listing option. That's
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  a perfect illustration. They used optionality
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  both defensively and offensively. They diversified
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  the product to meet the customer where they were.
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  Some people needed speed. Others really needed
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  to maximize their price in a super tricky market.
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  It created structural resilience. And the fourth
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  and final pillar is adaptability. Correct. Your
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  nimbleness, the sheer speed of your adaptation
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  that determines if you ride the wave of disruption
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  or, you know, drown in it. Those four things
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  focus. innovation, optionality, and adaptability.
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  They are the core requirements for a global business
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  or just for managing your own career. So beyond
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  the operational strategy leading teams through
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  this kind of change, it requires a really specific
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  leadership philosophy. What's the fundamental
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  value system here, especially when the stakes
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  are so high? The core driver and it's very unapologetic,
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  is value creation. The whole philosophy is about
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  creating value and caring deeply about three
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  stakeholders. Customers, employees, and shareholders.
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  And critically, in that specific order. In that
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  order. Yes. The belief articulated is pretty
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  stark, actually. If you fail one, you fail all.
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  I want to just dwell on that order for a second.
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  In so many public companies, the fiduciary duty,
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  it dictates a shareholders first mentality. So
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  why put customers and employees ahead of the
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  shareholders? Because it forces you to use a
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  long lens. If you serve the customer brilliantly
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  and you empower your employees to succeed, then
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  sustained shareholder value becomes the inevitable
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  outcome. It's not the starting point. It's a
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  sustainable model. It prevents that kind of short
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  -term decision -making, which is exactly what
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  a company needs to survive a major shock and
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  a multi -year tech transformation. That structural
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  shift is key. Okay, so this philosophy, it's
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  supported by five specific operating principles.
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  Let's start with the first three. The first is
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  to create long -term value over short -term gain.
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  This is so crucial in volatile times. It requires
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  leaders to apply a much larger lens, thinking
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  years out, not just next quarter. And this commitment
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  relies on two supporting ideas. Having a beginner
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  mindset, and treading with courage. Let's break
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  those down. Why is the beginner mindset so critical
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  for long -term thinking? Because without it,
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  you just fall victim to your own success bias.
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  A beginner mindset means you are actively listening
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  to new opinions. You hire for skills you don't
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  have. You seek out ideas that actively challenge
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  what you think you know. You can't innovate if
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  you're just looking for affirmation. And treading
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  with courage. That phrase was specifically emphasized
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  particularly for women leaders. It suggests a
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  real need to step forward, to take visible credit
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  for high -impact work and be willing to take
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  calculated risks, even when the path isn't perfectly
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  clear. The second principle is bring clarity
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  in times of ambiguity. Absolutely. When the market
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  is uncertain, everyone defaults to their own
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  unspoken assumptions. Building a shared understanding
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  is essential because alignment is never given.
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  You have to build it. and that shared understanding
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  lets the team make high -velocity, high -quality
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  decisions. Without it, you have five teams pulling
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  the shit in five different directions. It's just
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  a waste of energy. And the third principle, earn
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  trust by being trustworthy. Yes. And the key
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  insight here is that trust is an outcome. You
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  don't focus on it. You focus on being trustworthy.
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  by being relentlessly honest, highly reliable,
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  and demonstrably competent at what you do. But
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  crucially, this all starts with being self -critical.
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  Having hard conversations with yourself first
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  about your blind spots, your weaknesses, that's
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  the prerequisite for having respectful but still
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  hard conversations with your team. So that self
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  -criticality ensures that when you do have to
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  confront a difficult issue, your position is
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  based on rigor and competence, not just emotion.
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  Exactly. And while those The first three really
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  define the value system. The final two are about
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  execution and culture, generating energy with
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  passion, which is about creating psychological
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  safety even amidst cuts and delivering success.
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  despite the odds, a mandate for flawless execution.
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  It's fixed both the soft and the hard things
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  at the same time. Okay, so if the interest rate
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  shock was the immediate crisis, let's pivot now
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  to the generational opportunity. This is where
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  it gets really interesting. The conversation
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  shifts to the next great disruption, AI. What's
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  the perceived magnitude of this technological
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  shift? The conviction here is immense. This isn't
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  just seen as an evolutionary step. It's viewed
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  as being bigger than the internet revolution,
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  and potentially as consequential as the industrial
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  revolution. It's happening incredibly fast. And
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  the belief is that it will fundamentally change
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  how companies interact with people by introducing
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  something the sources call automated intimacy.
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  Automated intimacy. That sounds like a contradiction.
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  Automation usually means distance, right? What
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  does that look like in practice? Well, it refers
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  to a future where these customized intelligent
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  experiences are just the standard. Think about
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  personalized doctors, financial advisors, or
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  specialized teachers, all driven by highly individualized
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  AI. The level of customization will be so tuned
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  to you that the technology actually feels empathetic.
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  It centers the customer, providing high -touch
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  service at a massive scale. So moving beyond
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  theory, how are tech companies applying this
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  now to serve customers better, especially in
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  a complex market like real estate? So Opendoor
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  detailed three specific areas of immediate AI
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  investment. First, creating a 247 highly personalized
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  experience for every single user, making the
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  digital storefront feel like it was built just
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  for them. Second, enabling seamless intelligent
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  transitions from the technology to a human with
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  context. So if an AI can't fully meet your need,
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  it hands you off to a human agent, but it gives
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  them all the information so you never have to
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  repeat yourself. That addresses a massive customer
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  service pain point. It does. And third, using
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  generative AI in the discovery process, using
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  it to transform the currently commoditized home
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  buying search into a genuinely intelligent guided
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  experience that anticipates what you need. The
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  ultimate goal... is to enable the company to
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  feel and act on behalf of customers, to invent
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  the future before the customer even asks for
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  it. But implementing that level of change, it
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  requires tough organizational tradeoffs, restructuring,
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  shutting down legacy product lines, potentially
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  layoffs. How should leaders approach those decisions
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  with both humanity and rigor? Right. For those
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  unavoidable hard tradeoffs, the source introduced
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  this EE framework. Efficient, effective, and
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  empathetic. We usually default to... The task
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  -oriented, just get it done quickly approach.
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  Exactly. But that's only one third of the solution.
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  If you only focus on efficiency, you risk damaging
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  the culture and you miss the long -term impact.
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  The second E is effective. This means being holistic,
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  balancing competing needs, making global trade
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  -offs. And crucially, as you climb the career
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  ladder, effectiveness shifts from driving the
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  task yourself to enabling others to perform.
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  So effectiveness becomes less about my personal
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  output and more about the leveraged output of
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  the system I manage. That's the key distinction.
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  And the third component, empathetic, is described
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  as the table stakes in tough times. It means
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  putting people first, looking at both sides of
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  a hard situation, and being transparent about
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  why a decision had to be made. And when you're
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  innovating this fast, failure is basically guaranteed.
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  How do you manage that? Leaders have to turn
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  failures into learning opportunities. Embrace
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  a growth mindset. They advocate for this principle
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  of failing often, but failing fast, and maybe
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  the harder part, not getting emotionally attached
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  to ideas when the data says they're not working.
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  The anecdote cited was powerful. A famous category
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  -creating Amazon product required 16 distinct
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  prototypes to get right before it ever saw the
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  market. 16. Wow. Failure is just necessary data
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  collection. So to wrap up this entire playbook,
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  let's focus on personal career strategy. If you're
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  a senior leader or you're aspiring to be one,
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  what's the final advice for achieving high impact
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  in this volatile new world? There are four key
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  pieces of career advice here. First, and this
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  is especially for women leaders, is the mandate
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  to focus on visible results. The source material
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  explicitly warns against falling into the trap
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  of doing horizontal stuff where the results are
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  invisible. Horizontal stuff? What does that mean
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  in this context? It's typically that internal
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  work process improvements, mentoring, cross -functional
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  organizing that supports the business, but, well,
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  it lacks a clear, quantifiable metric that's
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  tied to revenue or a product launch. In these
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  high -stakes environments, leaders have to deliver
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  measurable, tangible impact that other people
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  can see and attribute directly to them. That
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  is extremely actionable advice. What's next?
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  Second, work backwards from outcomes. Just like
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  you build a great product by working backwards
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  from the customer, you need to set personal and
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  career outcomes. Where do you want to be in five
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  years? And then work backward from there to define
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  the steps for today. Right. Third, get mentors
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  who kick your butt. The best mentors are not
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  therapists. They are critics who push you out
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  of your comfort zone, who highlight your blind
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  spots. They force you to develop the competence
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  you need to be trustworthy. You need a challenger,
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  not a cheerleader. Exactly. And finally, and
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  maybe most importantly, do stuff that matters
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  and be your authentic self. If you're not passionate
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  about the problems you're solving, you just won't
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  survive the volatility required to succeed. What
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  a phenomenal deep dive. To summarize the core
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  takeaway, leading through a 40 -year shock and
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  an AI revolution, it requires this intense commitment
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  to clear operational frameworks, focus, innovation,
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  optionality, adaptability, and a customer -first
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  value system that dictates every single decision.
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  And remember, the strategies we talked about
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  aren't just for C -suite executives. That challenge
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  of being effective is universal. It's about moving
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  beyond just executing tasks and instead focusing
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  on enabling others, on balancing competing needs,
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  and making holistic trade -offs in your own work.
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  We heard today that earning trust requires being
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  ruthlessly self -critical, having hard conversations
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  with yourself before you can ever have them with
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  others. So here's a provocative thought for you
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  to chew on this week. What is one assumption
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  you currently hold about your work or your life
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  that you really need to challenge? And where
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  are you going to start that hard self -critical
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  conversation this week?