Dear hustlers, founders, operators and visionaries,
Today's episode is with Olivia Elf, VP of Operations at Sana, the Stockholm AI company that Workday acquired in November 2025 in a $1.1 billion deal. Olivia joined as Chief of Staff three months before Sana's Series A in 2021. She held the same seat through five rounds, three offices, and the close. This conversation goes after the operating decisions Sana made when there were 20 people in a room, not the strategy memo the press release wrote afterwards.
🎧 Tune in now on Spotify, Apple, YouTube and share your thoughts! In the meantime: Follow the Gradient and stay tuned!
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Why you should listen
You should listen to this if you are running an org that has scaled past 20 people and still looks the way it did at 8. The conversation maps the playbook that took Sana from a vision document to a $1.1bn exit while rebuilding the entire org around the strategy every six months.
As the conversation unfolded, the real tension emerged between keeping a culture intact and demanding that every new hire actively rewrite it.
What we talk about
00:00 Introduction
01:41 Three Months Before Series A
04:29 Vision Before Product Existed
07:05 Building the UK From Zero
11:16 The 666 Rhythm and DIBS
14:11 Strategy First, Org Second
15:47 The Hire She Wouldn't Make Again
18:02 Generalists Beat Specialists
21:41 Deploying AI Inside the Company
26:15 When Sana Stopped Being a Startup
28:04 Every New Hire Rewrites the Company
30:12 Inside the $1.1B Workday Acquisition
31:28 Staying Sane While Scaling
Our main take away's
Sana rebuilt the entire org around a new strategy every six months for almost five years. Olivia set the rhythm when she joined in 2021. It runs on a 666 cadence: six years to dream, six months to set the strategy, six weeks to execute. "Every six months is almost like a lifetime in itself," she said. "You can think back at that era and you can say, that's when I built the UK with this person." The company that closed the Workday deal in November 2025 went through almost ten of those eras.
Strategy shapes the org, not the other way around. "You shouldn't shape your strategy based on your org. You should do it the other way around. You should shape your org based on the strategy. Because otherwise you end up in these local maximums where you say, Christian really wants to do this thing, so then he should do that. But that might not be the most important thing the company should do." This was the bet Sana doubled down on through every funding round.
Specialists push you toward a local maximum. Sana's most contrarian hiring decision was to lean on generalists. "Specialists risk pushing you toward a local maximum because they're going to optimize for what they already know and they're going to reframe the problem to fit what they know how to solve." The exception that proves it: when Sana did hire specialists, they were asked to unlearn the playbook. Olivia screens for the willingness in interview.
The UK expansion mistake she would not repeat: hiring senior leaders into the new market. "We had never hired leaders in [Stockholm]. We've always hired ICs that grew into leaders. When we came into new markets we told ourselves we should hire leaders into them instead of growing them from within. I wouldn't do that again." Her current playbook: ship a core team of three to five people from a working market and ask them to stay one to two years. Culture does not transfer over a video call.
Every new hire is told their job is to change the company, not preserve it. "If you joined the company, I would expect you to change it. That's the expectation." The opposite of the standard onboarding script. Combined with the closing principle of the episode — "defy gravity," the assumption that everything decays into mediocrity unless you fight it daily — it produces a culture where ownership is distributed by default, not opted into.
How to reach out to Olivia
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