The Official SaaStr Podcast – London: Scaling SaaS, Picking Winners & Leading With Authenticity

Date: December 24, 2025
Guests: Maggie (OpenAI, ex-Slack, ex-Webflow), Host: Eric

Episode Overview

In this engaging episode recorded in London, Maggie—seasoned SaaS leader with stints at OpenAI, Slack, and Webflow—joins Eric to dive deep into leadership, talent, hiring, career strategy, and culture in high-growth SaaS companies. Maggie’s insights balance tactical advice with personal revelations, touching on her recent battle with cancer and how it affected her perspective on life and leadership. Key topics span picking the right rocket ship, building standout sales teams, non-traditional commission structures, optimizing pilots, thriving as a working mom, and the future impact of AI on healthcare.

Key Discussion Points & Insights

1. Developing an Eye for Talent and the Realities of Hiring Salespeople

• How Fast Do You Know?
  • Maggie says, “About a week.” ([00:14])
• What to Look For:
  • Red flag: Blame-shifting in interviews.
  • Seeks humility and self-reflection over blame:
    “What I want to know is did they own up to that mistake and what did they learn from it? And that’s a really big signal.” ([01:20], [21:39])
• Challenge:
  • Salespeople are the hardest to hire because they can sell themselves exceptionally well, even if skills don’t match.
  • True talent often stands out by owning imperfections and learning from mistakes.

2. Life-Altering Events & New Leadership Mindsets

• Maggie’s Cancer Diagnosis ([03:46]):
  • Diagnosed with early-stage pancreatic cancer during an OpenAI world tour.
  • Learned the value of compassion (“You never know what someone is going through.”) and the importance of advocating for oneself in the medical system.
  • New intolerance for mediocrity and a strong belief in self-advocacy and delegation:

    “It created this intolerance for people who do not give everything their all... I just don’t have time or patience for people who are not going to give it their all.” ([04:49])
    “The reason that I was able to have a very success is because I advocated within the American health system.”

  • Recognition that everyone is replaceable, no matter how driven.

3. Career Decisions: Picking the Right Company

• Lesson from Kevin Egan:

  “Pick the rocket ship, not the seat. If you get on a rocket ship, your career will go places you could have never imagined.” ([07:10])

• Titles Matter Less Than Trajectory:
  • Maggie left a director role at Webflow, joined OpenAI as an individual contributor—betting on the company, not a title.
  • Powerful example of running toward opportunity, not away from discomfort:

    “I was only at Webflow for two years, but I was running towards OpenAI... I’ve never run from something.” ([23:45])

• Creators vs. Disruptors:
  • Categorizes companies as either category creators (e.g., Slack, ChatGPT) or disruptors (e.g., Webflow, Eventbrite) and weighs opportunity by their ability to outpace competition or innovation.

4. Early-Stage Sales Cultures: Rethinking Commissions

• No Commission at OpenAI and Slack (Early Days):
  • “What I love about no commission... is it creates a different culture. You are incentivizing them to do what’s right for the company and not for themselves.” ([10:20])
• When Not to Do It:
  • Acknowledges it doesn’t work for underfunded or very early companies that can’t match market salaries.
  • Advocates for equity and management-based objectives (MBOs) as alternative incentives.

5. Standing Out & Scaling Fast Inside a Company

• Be Invaluable, Be Helpful:

  “The single most important thing any of us can do is to be the most helpful person possible. To have no ego and to be helpful.” ([14:08])

• Anecdote:
  • On her fourth day at Slack, volunteered to be the point of contact during a major security breach—earning exec trust and propelling her career.
  • “People remember how you made them feel, and if you inherently are helpful to them, you will make them feel good.” ([15:37])

6. Work-Life Balance for High Performers & Parents

• Integration, Not Balance:
  • Maggie: “Most days I will work seven days a week and I will work bizarre hours... I leave the office by 4:30 every day, but you better believe I’m on from 7:30 to midnight.” ([16:57])
  • Non-negotiable: Never misses important family events, sets an example for her team to do the same.
  • Open dialogue promotes healthier work environments, especially for parents.

7. Characteristics of Top Sellers

• No Ego & Willingness to Start Small:
  • Tells the story of Molly, an MBA who took a junior SDR role and quickly advanced:

    “She said, ‘You know what, is being an SDR ideal? No, but I believe in myself…’ Within a few months, Molly was leading and building out an entire global sales dev organization. That’s because Molly had no ego.” ([18:26])

• Detecting False Positives in Interviews:
  • Success lies in identifying those running toward an opportunity, not just away from a problem.

8. Beating Incumbents & Perfecting the Pilot Process

• Distribution vs. Innovation:
  • “Can the startup acquire distribution before the incumbent acquires innovation?” ([09:47], Alex Rampel, Andreessen.)
• How OpenAI Wins Pilots:
  • Executive buy-in is non-negotiable for pilots.
  • Clear, repeatable playbook for evaluating success.
  • Focus on ROI and customer experience during the pilot:

    “We give our customers a taste of what it is like to work with us when we’re doing a pilot... most companies just flip the switch and say, hey, two week free trial, good luck.” ([27:25])

  • OpenAI boasts a 100% win rate on pilots by sticking to these principles.

9. Future of Sales and AI

• Need for More Women:
  • “I want more women in it. There’s not enough women in sales right now. And I actually think it is getting worse over time.” ([29:57])
• Large Enterprises Can Move Fast:
  • “Large enterprises can't move fast... when they know that a small startup could eat their lunch, they will move fast.” ([31:04])
• AI’s Impact on Healthcare:
  • Maggie’s main focus and excitement: AI reducing time to market for therapies, streamlining clinical trials, providing support for overworked doctors, and enabling better patient outcomes.

    “Every single day that we can get a therapy out to market faster is going to be more lives saved... All of a sudden [doctors] essentially have a co pilot now to turn to.” ([32:17])

Notable Quotes (with timestamps & attribution)

• About hiring and talent:

  "What I want to know is did they own up to that mistake and what did they learn from it? And that’s a really big signal."
  — Maggie ([01:20], [21:39], [22:24])

• On career moves:

  "Pick the rocket ship, not the seat. If you get on a rocket ship, your career will go places you could have never imagined."
  — Maggie ([07:10])

• Work ethic and boundaries:

  "I will not miss those most important moments in life for my kids, for my family, for my friends."
  — Maggie ([16:57])

• Starting at the bottom:

  "She said... I believe in myself and I believe I will come in and crush it."
  — Maggie (on Molly) ([18:26])

• About culture:

  "You are incentivizing them to do what’s right for the company and not for themselves."
  — Maggie ([10:20])

• On sales and gender diversity:

  "I want more women in it. There's not enough women in sales right now... The number one thing that I want to change is getting more women into sales and into AI."
  — Maggie ([29:57])

• On the future of AI and healthcare:

  "Every single day that we can get a therapy out to market faster is going to be more lives saved... All of a sudden, they essentially have a co pilot now to turn to. And I think that is the biggest thing that we will do to change the future of the world."
  — Maggie ([32:17])

Timestamps for Important Segments

• [00:14] – Knowing when a new hire is a good fit (a week!)
• [03:46] – Maggie’s cancer diagnosis and impact on leadership
• [07:10] – Kevin Egan’s “pick the rocket ship” advice
• [10:20] – Commission-free sales cultures in early stage SaaS
• [14:08] – How to scale quickly inside a company: be helpful, not egotistical
• [16:53] – Maggie on navigating work and motherhood
• [18:26] – Characteristics that make top sellers stand out (Molly’s story)
• [21:09] – Interviewing and detecting true sales talent
• [27:25] – OpenAI’s unique approach to pilots and winning enterprise business
• [29:57] – The importance of bringing more women into sales and AI
• [32:17] – Biggest excitement: AI's transformative impact on healthcare

Memorable Moments

• Maggie sharing how she returned to work just one month after major surgery, only to realize that rushing back wasn’t worth compromising her health. ([05:15])
• The “Pick the rocket ship, not the seat” principle—betting on company trajectory over job title, a move that defined her career transitions. ([07:10])
• Molly’s journey from Stanford MBA to account associate, proving humility and grit trump ego in early-stage scaling. ([18:26])

Conclusion

This episode is packed with practical SaaS leadership insights and candid reflections on life, ambition, team-building, and personal growth. Maggie’s story serves as a blueprint for navigating modern tech careers: prioritize opportunity over status, build a culture around collaboration and humility, and, above all, never lose sight of what truly matters both at work and at home. The future, especially with AI in healthcare, is both more demanding—and more promising—than ever.