Olivia Nottebohm, former CRO and advisor at Notion, discusses immigrant assimilation, balancing accountability and empathy as a leader, growth vs. profits vs. product, collaborative creativity, what CEOs care about, community-led growth, screening for Grit, and finding focus in an engaging conversation.
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Quick takeaways
The importance of balancing accountability and empathy as a leader and respecting personal journeys of team members.
The evolution of go-to-market approaches from top-down to community-led.
Grit is not just about perseverance, but also having a passion for what one is doing and pushing oneself out of the comfort zone.
Deep dives
The Importance of Making an Impact
The speaker emphasizes that the impact we have on others is what truly matters in life. It is not about the titles or achievements, but how we make people feel and the kind of person we are.
Different Waves of Go-to-Market Approaches
The summary explains that there have been three waves of go-to-market approaches. The first wave was top-down, targeting CIOs and focusing on selling software to companies. The second wave was bottoms-up, with a product-led approach where users adopted the software on their own. The third wave was community-led, where companies fostered communities around their product, engaged with users, and listened to their feedback.
The Size of the All-in-One Software Market
The summary highlights that the all-in-one software market, including companies like Notion and Coda, is significant and has a large user base of hundreds of millions of people. The market is driven by the desire for better productivity and work experiences, as well as the need to support hybrid work models.
The Importance of Empathy and Accountability
The summary mentions that the speaker is known for balancing empathy and accountability in her leadership style. She strives to understand her team members' experiences and perspectives, and sends monthly gifts as a reminder of her care. She believes that people's personal milestones and experiences are crucial and should be respected and acknowledged.
The Value of Grit
The summary defines grit as having a purpose and striving to achieve impact over a sustained period of time. It emphasizes that grit is not just about perseverance, but also about having a passion for what one is doing and pushing oneself out of the comfort zone.
As a veteran of several high-powered organizations — including McKinsey, Google, Dropbox — Notion advisor Olivia Nottebohm has learned the importance of respecting her teams’ personal journeys. She believes none of the 10 most important milestones in any person’s life will be career-related, and it’s important for leaders like her to strike a balance between accountability and empathy. “Before I need to have a tough conversation,” she says, “I try to put myself in their situation and think, ‘OK, how would I best receive something? ... [And] how is this person different from me?’”
In this episode, Olivia and Joubin discuss immigrant assimilation, the joy of learning, college vs. startups, stepping away from work, growth vs. profits vs. product, steep learning curves, working through a restructuring, collaborative creativity, what CEOs care about, community-led growth, screening for Grit, finding focus, and the only things people will remember about us when we’re gone.
In this episode, we cover:
Olivia’s parents and how she became a grammar stickler (01:00)
Small-town ice hockey and playing with the boys (03:54)
Why her parents didn’t want Olivia to go to Harvard, and what she wants for her own kids (08:49)
Choosing to go into business instead of science (15:32)
What changed for Olivia when her brother passed away unexpectedly (18:42)
“Grow Fast or Die Slow” (24:29)
Who doesn’t believe in growth in 2022? (31:37)
Leaving McKinsey after making partner (35:32)
Six years at Google and one year at Dropbox — starting right before COVID (39:34)
How Olivia got to Notion, the crowded “all-in-one” space, and its enormous addressable market (42:36)
The evolution of go-to-market strategies (49:43)
Accountability, empathy, and the biggest milestones in everyone’s life (58:36)