Ep. 564 - Asana COO Anne Raimondi - How to Conquer Imposter Syndrome and Lead Powerfully
Second in Command: The Chief Behind the Chief with Cameron Herold
Second in Command with Cameron Herold
4.9 • 225 Ratings
🗓️ 24 March 2026
⏱️ 49 minutes
🧾️ Download transcript
Summary
Ever question if you’re truly moving the needle in a high-stakes, fast-growth role or just treading water in chaos?
In this unfiltered replay, Cameron Herold gets radically real with Asana’s COO, Anne Raimondi, a powerhouse operator with a track record scaling iconic SaaS brands from eBay to Zendesk. Their candid conversation delivers hard-hitting truths and breakthrough strategies for COOs, VPs of Ops, and ambitious seconds-in-command. From conquering boardroom friction to onboarding at scale, and from navigating imposter syndrome to wielding conscious leadership, this episode is your no-nonsense roadmap to building culture, resilience, and runaway growth.
The window for operational greatness closes quickly. Don’t risk getting left behind as your competitors dial in these proven systems. Press play now for a front-row seat to rare, real-world tactics you won’t hear anywhere else.
Timestamped Highlights
[00:00] – Why this Asana episode is a record-breaking, fan-favorite comeback
[00:03:02] – The one skill that built Anne’s “uncommon” career and why she doubled down on curiosity
[00:05:33] – A dot-com crash, a diamond startup, and how obsession with customer pain points kept Anne in the tech arena
[00:07:47] – Is product obsession really the COO’s unfair advantage? Anne reveals what sets true ops leaders apart
[00:13:14] – How Anne’s onboarding at Asana destroyed all her old assumptions about exec transitions
[00:15:10] – The joy of “extra delights”—what most SaaS products miss about human motivation
[00:25:34] – The real source of company politics (and how transparency kills it dead)
[00:44:38] – Anne’s most vulnerable answer: How she faces down imposter syndrome and wins
About the Guest
Anne Raimondi is the Chief Operating Officer of Asana, a global leader in work management software empowering teams to orchestrate their work with clarity and impact. With 20+ years scaling technology giants, including senior roles at Zendesk, TaskRabbit, SurveyMonkey, and eBay, Anne brings deep boardroom and operational wisdom to fast-growth SaaS. She’s also a lecturer at Stanford Graduate School of Business and has served on the boards of Gusto, Patreon, and more. Anne is renowned for her mission to build workplaces that blend high performance with humanity.
Mentioned Resources
- Microsoft Project
- Blue Nile
- eBay
- TaskRabbit
- Guru (knowledge management)
- SendGrid
- Gusto
- Patreon
- Block
- ThredUp
- 15 Commitments of Conscious Leadership (framework/book)
- Stanford Graduate School of Business
- Kozmo (Seattle delivery)
Important Links
- Connect with Cameron: Website | LinkedIn
- Explore the COO Alliance - The World’s Leading Community for Seconds in Command
- Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
- Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
- Chat or video call with AI Cameron via Delphi
Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.
The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.
Transcript
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| 0:00.0 | Just a quick note before we dive in. |
| 0:01.9 | This is actually one of our older episodes, but we're bringing it back because it's one of the most downloaded ones we've ever released. |
| 0:07.8 | Clearly, it struck a chord with a lot of listeners, and I know there's so much value packed inside. |
| 0:12.9 | So whether you're hearing it for the first time or revisiting it, enjoy this fan favorite. |
| 0:16.7 | I do think it starts with that, which is like, what does great look like and what does |
| 0:21.9 | excellence mean for that company at that stage with that board? And then where are the gaps |
| 0:28.7 | today? From even just like board meeting and time spent standpoint, the friction points are |
| 0:34.3 | like, gosh, we're not getting as much out of, often is because that hasn't |
| 0:38.5 | been clearly defined or redefined, right? Which is like the precious time we all spend together |
| 0:43.4 | and the time that the management team spends preparing for these meetings, what does a good |
| 0:49.0 | outcome look like? You know, and what does the company need over this next arc of its journey? |
| 0:59.8 | Welcome to the Second in Command podcast, produced by the C.O. Alliance and brought to you by its founder, |
| 1:07.2 | Cameron Harold. In the Second in Command podcast, we talk to top COOs who share the insights, |
| 1:13.4 | strategies, and tactics that made them the chief behind the chief. And now, here's your host, |
| 1:19.7 | Cameron Harold. Our guest today is Asana's CEO and head of business, Anne Ramundi. |
| 1:28.3 | Anne first joined Asana's board of directors in 2019 and is an industry veteran with over 20 years of experience leading various product and business functions in fast-growing SaaS companies. |
| 1:38.3 | Prior to her role at Asana, she was the chief customer officer at Guru, senior vice president of operations at Zendesk, |
| 1:45.4 | chief revenue officer at TaskRabbit, and held senior positions with SurveyMonkey and eBay. |
| 1:50.7 | With a strong commitment to fostering innovation in the technology sector, |
| 1:53.9 | Ramundi is also a lecturer in management at Stanford Graduate School of Business, |
| 1:57.6 | and she served on the board of directors for Gusto, Patreon, guru, Sendgrid, Block, and Threadup. |
| 2:03.3 | Anne holds a BA in economics and sociology and an MBA from Stanford University, and you |
... |
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