2025 Pod edits - London - Harry And Maggie.prproj

Summary

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

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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.

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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.

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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.

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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.

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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.

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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])

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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.

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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.

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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.

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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])

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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])

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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

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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])

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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.

Transcript

[Eric]

Welcome to the official Saster podcast where you can hear some of the best Saster speakers. This is where the cloud meets up. Today on the Saster podcast.

How quickly do you know if someone's not any good?

[Maggie]

About a week.

[Eric]

About a week?

[Maggie]

About a week.

[Eric]

Oh God, that's an awkward first week.

[Maggie]

It's. Yeah, you start to have the inklings, you know, right away if someone's got it or not. And here's the thing with interviewing salespeople. And I hear this from all of my founders. Every single founder says salespeople are the hardest to hire because they're so hard. I, I think that salespeople show up so well when they're interviewing that it's really hard to tell a good one from editor. You have to be a really skilled interviewer. And I actually think one of my superpowers is picking great talent.

[Eric]

How do you do that then? If someone is a great seller of themselves, which a lot of people are, how do you unpick true quality versus facade appearance?

[Maggie]

The first thing that I look that sends off the absolute red flags is blame. So I'm okay that people lose. I'm actually okay if someone wasn't the top rep, if they were the second to third or third or fourth. But what I want to know is why weren't they the top? Do they have humility? Are they self reflective? Can they, do they say, you know what, Harry, he outworked me, he outperformed me, he was better at discovery. Those are the types of things that I want to hear in the interview cycle. And more often than not, sellers tend to blame. When you dig into why did you lose a deal, they blame, you know, the competition, they blame the product, they blame something else. And what I'm actually looking for is did they own up to that mistake and what did they learn from it? And that's a really big signal.

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That's quite an entrance, isn't it? I feel like I'm at a pop concert. You see now I'm so old before my time. So we were talking, we had dinner last time. We're doing that. What's boring start to any conversation you can have in this regard and it's like, tell me, how did you get into sales? So we're not going to start that. We're actually going to start with something really quite personal, if that's okay, which is last year when you were actually in London, you were diagnosed with cancer and you got the call in London and I actually wanted to start with that. I know you well enough so I think I can. How did that experience change how you live and how you lead?

[Maggie]

Yeah, so I'll start with I'm cancer free now, but a little over a year ago. Yeah, what an entrance. A little over a year ago I did a preventative MRI just for fun and they found a suspicious tumor on my pancreas which turned out to be very early stage pancreatic cancer. Never the thing that you think that you are going to get when you are, you know, a mom and in your mid-30s. So it's completely changed who I am today as a person, as a mother, as a leader in quite a few different ways. It has been probably the greatest and the harshest teacher that I've ever had. The first is I approach life with a lot more compassion now. You never know what someone is going through. So I was here in London, we were doing essentially an OpenAI world tour. We had these huge conferences, our very first ones in New York, London, San Francisco. We were just going back to back city and in the middle of this I was diagnosed with pancreatic cancer. And then I had to go up on stage the next day and speak to a room full of executives such as this. So you never know what someone is going through. And I've now realized that as I go through and lead, however, kind of maybe the more interesting thing here is I have no tolerance for mediocrity anymore. When, when, when you are stared in your life with something like this, what is. Which is probably one of the worst things I will ever go through. And then I was able to beat it. It created this intolerance for people who do not give everything their all. And being at OpenAI, being in just this world, in this generation of AI, is such a privileged place for all of us that I just don't have time or patience for people who are not going to give it their all. It also taught me self advocacy. So without getting into all the details, the reason that I was able to have a very success is because I advocated within the American health system. I realize you guys have a different health system out here. It's not great in America. And I had to advocate like hell for myself. The other thing that I learned is that we're all replaceable. I rushed back to work a month after surgery. Even Stanford was like, no one's ever gone back after a month. But we had a new chief customer officer at OpenAI and I wanted him to know me. He'd been already been there for a month and I just needed to make sure he knew me. And in hindsight, it didn't matter. It actually compromised my recovery because I rushed back. And so there were so many different things that I learned. From compassion to very high expectations, to advocate for yourself and then also, you know, set up your teams for success and delegate. But you are still replaceable at the end of the day.

[Eric]

Speaking of replaceable, I think Jason's trying to replace me with an AI every single day. I'm waiting for the day I'm turning out to a podcast. He's like, no, don't worry, quality's here. Don't worry. Across your career, you've done Slack, you've done Webflow, you've done OpenAI, and you've picked companies at a moment in time where it's non obvious to the world, but it's obvious to you the trajectory, which is brilliant for your stock options. I'm thrilled for you first. But the question then becomes, how do you consistently pick which companies to join at the right moment in time? And if you were advising people today on the same, what would you advise them?

[Maggie]

Yeah, there's a few elements to this. The first is a lesson that I learned from Kevin Egan. But Kevin Egan, for those of you who don't know him. He's currently the CRO at Clickhouse. He was the CRO at Atlassian. He was the VP of Sales at Slack, at Dropbox, at Salesforce. He's had a pretty incredible career. And he gave me a lesson early on when I was working with him, and that was pick the rocket ship, not the seat. Because if you get on a rocket ship, your career will go places that you could have never imagined. But if you're so fixated on picking, am I in the captain's seat, Am I in the driver's seat? It just doesn't matter. And because when you take a big step back, what people want to know is they want to know what you saw, what you built, what you learned. They want to know how to drive that rocket ship. And you don't learn how to drive a rocket ship. If you're sitting on the outside of that rocket ship, you learn nothing.

[Eric]

It's so interesting. I remember when you joined OpenAI and I said, what title are you? Maggie? This is fantastic. And you're like, well, we don't have titles and you had great titles before. I remember being like, well, what do I put on the podcast?

[Maggie]

And I.

[Eric]

Well, just like gtm.

[Maggie]

Gtm.

[Eric]

And it didn't phase you?

[Maggie]

No, no. And what's funny about that is when I went to OpenAI, so many people in my network said, why would you go to this small company? Go to market was only seven people. And I was going from leading an org of 50 people@webflow as a senior director to being an individual contributor at OpenAI. And many VCs, many mentors said, don't do it. Why would you give up this great management career? But you have to believe and you have to bet in yourself. And then the other thing I look for when I'm looking at companies is two categories. Are they creators or are they disruptors? So if you look, for example, at Slack or ChatGPT, those are category creators. Now, maybe Webflow or my first company, Eventbrite, that was a disruptor. Clay Harun, who spoke earlier today, is a good friend. That is a category disruptor. And so as I'm thinking about, do I want to go to a creator or to a disruptor? There's a couple different things. The elements that go into it, creators, can they build a product that will move fast enough that people will love and people will jump onto? Because if you are a creator, you better bet, if you are a good creator, there is going to be competition. People will come after you and Incumbents like Microsoft and Google will also probably go copy you. If you are a disruptor, you better have a good enough product that is leaps and bounds ahead of everything else in the market. And then you have to move fast before the disruptors or before the incumbents go and catch up.

[Eric]

There's a brilliant quote from Alex Rampel at Andreessen and he says, can the startup acquire distribution before the incumbent acquires innovation? I think it's very prescient. Speaking about picking companies though, one thing that's attractive for salespeople is commission people. I don't mean people say salespeople are coin operators. You have commission at OpenAI. Can you just talk to me like, should founders listening here go? We don't need commission either. Is this a special case and how do you reflect and advise them given no commission?

[Maggie]

Yeah, yeah. We also had no commission at Slack for the first few years as well. So I'll only talk about this in terms of building early stage companies because I do think you need commission as the company gets larger. It's a very different type of a profile that you're hiring for. What I love about no commission, I realize this won't work for everybody, but it creates a different culture. It creates a culture. Let's say you have commission. Let's say every hour that you spend closing a deal or working with customers is money in your pocket. Every hour that you spend onboarding or training someone else or doing some other project is quite literally money that you are not making, that you could have been making. So it's at a true cost to yourself as an individual if you are doing other things to benefit the company versus benefiting yourself. So with OpenAI, with Slack, many other Airtable, Figma, New Relic, there's tons of companies out there that all started with this model of full salary. And it's, you know, a normal living salary like you would give to any other product manager, marketer, engineer, and decent equity for the first, you know, earlier hires. You all of a sudden are incentivizing them to do what's right for the company and not right for themselves. At OpenAI, we reorg all the time, we pivot all the time. We're always doing new things, shifting teams. And I never have to worry of, oh, if I go help this person out over there with this really important initiative that we're doing, is that actually going to be money out of my paycheck?

[Eric]

Totally understand that. Is that only applicable to OpenAI? Because you're OpenAI because you know that your stock is getting more and more valuable with every day or can that be applied to a startup in London where they don't have commission?

[Maggie]

I think it, it's nuanced. It depends on how much money they've raised. Right. If you have not raised a lot of money and you can't pay everyone, you know, a normal competitive salary, you probably need commission on top of it. I mean there's, I advise a lot of founders and there's founders that are just paying insane amounts of money with commission and that's also not scalable. All of a sudden you can't have one of them. Their rep made $4 million a quarter. It was like an estimate prep because the commission plan was so high, that's also not scalable and that's going to be really hard to reverse that. Whereas at OpenAI, at companies that maybe don't start with commission and maybe start with a management based objectives plan. So MBO's is what I call them, maybe it's, you know, you close 10 logos, you get this amount of money, there's, there's other ways to factor it in that aren't just pure. You get 5% of every deal you sell and all of a sudden you're going to have a lot more of a collaborative culture. I've talked about this a lot on LinkedIn too. I believe that OpenAI and Slack and Stripe's culture, that kind of these leading pioneer lighthouse companies that all started with no commission, they're all known for having the best and the brightest talent and so much of that comes from the people that they hire. And so again, I think that to kind of wrap that up, the early stage mentality of the builder is maybe not quite as money motivated as someone who's going to a Salesforce or a Google or a Facebook, you know, much later on in their career. Yeah, isn't that insane?

[Eric]

Not buff.

[Maggie]

It's dangerous. I know. I'm like, I should quit my job and go for it. There kidding.

[Eric]

Did they do it for many quarters?

[Maggie]

I retired after their most recent quarter. Wait, I'm still tab for lp.

[Eric]

What company is it?

[Maggie]

I'm not gonna say.

[Eric]

I wasn't expecting that. Well, I mean, how do you stand out inside a company? Make 4 million in a quarter is the freaking answer. There's jokes aside, you have continuously risen inside companies very quickly. If you were advising people today on how to scale quickly once inside one of these companies, what would you say is the cheat sheet hit list for how to scale fast inside a company?

[Maggie]

Yeah, this one's pretty quick. The single most important thing that any of us can do is to be the most helpful person possible. To have no ego and to be helpful. So I always want to be that person that if a cross functional partner needs me to help execute a strategy or needs me to be on their interview panel. Just today I was asked, will you do the leadership chat for the SDRs that we're hiring? I don't have to do that. That's time out of my day. But I want to be the most helpful person. People remember how you made them feel and if you inherently are helpful to them, you will make them feel good. I'll actually, I'll share a quick story here. This is a. You've probably heard this before, but, um, my very first day at Slack was 2015. I was the first seller hired out of headquarters and Slack had a huge hack and we thought it was going to take the company down. Um, what we needed, what Stuart needed is for someone to be on the phones on the front line for all of the customers that were hacked. And so I raised my hand. This is literally day four, March 23, 2015. And I was like, I'll do it. So we emailed all of the customers that were hacked. I won't share how many, but these were, you know, some of the largest companies in the world because that was what the hackers were going after. And I was the very first phone call of basically, you know, Fortune 10 companies being like, wtf? We just got this email thing to call because you were hacked. And that was me. And you know what, the exact team loved me for it. And I would say I had a pretty incredible career in Slack.

[Eric]

You're like, my bad, sorry.

[Maggie]

But again, it goes back to be helpful, right? Just like do things for other people. Now you also have to learn boundaries. That's something I really struggle with, is saying, no know, but be helpful. Always think, what can I do for others? And it will pay back in dividends.

[Eric]

You know, how I build trust in people. I see them work incredibly hard and people know that I talk about 996, but then they meet me and they're like, oh, he's not joking.

[Maggie]

No. You're like 7, 7:15.

[Eric]

Yeah, absolutely. Is why I'm in therapy and other resistance. Do you agree with me in that or do you think you can have outperformance, excellence, crushing with balance.

[Maggie]

What do you mean by balance?

[Eric]

Crushing family as well.

[Maggie]

So I'm a mom to two kids. I have two little girls. They are the single most important thing to me in. In my world they. We just spent a week in London together. They are so incredible. I wish I was there more for them. But I am there enough that they will always remember that. I will never miss a dance recital. I will never miss. Next Monday we have a two o' clock singing performance. You know I'm gonna have to leave the office at one o' clock but I'm not gonna miss it because in.

[Eric]

The grand school do you have to sing?

[Maggie]

No, no, no. My daughter. It's Disney Pop Princesses.

[Eric]

Oh, we're all grateful for that.

[Maggie]

I'll have you recording five year old kindergarten class. Singing pop princess songs is actually going to be the cutest thing in their little uniforms. I will not miss those most important moments in life for my kids, for my family, for my friends. However, what that means is most days I will work seven days a week and I will work bizarre hours. And if it's, you know, Tuesday night watching TV with my husband, unfortunately that just doesn't happen. Like we. I leave the office by 4:30 every single day, but you better believe I'm on from 7:30 to midnight every single night. And I think that's just the world we live in and that is the choices that, you know, we. I think you all probably wouldn't be here if you weren't in the same kind of hustle. SaaS rapid growth mindset. I have learned how to prioritize my life and my work around what matters the most. And something that I'm really proud of is I don't hide this like my team knows I put it on my calendar. Disney Pop Princess dance recital or singing lessons. And I think as a mom, as a parent, it's important that we show up so that those who are looking up to us or those that are someday hope to be parents can feel okay doing that.

[Eric]

I have the same Disney Pop Princess on my calendar.

[Maggie]

But that's you performing, right?

[Eric]

Yeah, absolutely.

[Maggie]

No kids Winter Wonderland on the same.

[Eric]

None. Yeah, yeah. Meaning the Wicked recital is personal highlight. Other than just like sheer hard work. What else do the best sellers have that others don't have in terms of characteristics, traits?

[Maggie]

Yeah. It's going to be different for early stage and later stage, but let's focus on early stage. I think that's what we're all here for. Let me start actually with a story. The way I'm going to answer this one. This was May 2023 at OpenAI. I was making my first hire and my first hire was an sdr. We were in A fortunate position that we had a lot of inbounds and we needed somebody to work the inbounds. We had no salesforce set up. We had nothing. So I decided I didn't want a 23 year old SDR. They're wonderful. But I wanted someone who had many years of career experience, who had an mba. So I started scouting from Stanford and from Harvard. I Talked to probably 50 different candidates and every single one other than one said, I don't want to take a job as an SDR at OpenAI. And then there was Molly. Molly had eight years of experience from Google and then she went to Stanford and was top of her class in GSB in their MBA program. And she said, you know what, is being an SDR ideal? No, but I believe in myself and I believe I will come in and crush it and just absolutely blow out the expectations. Within a few months, Molly was leading and building out an entire global sales dev organization. And now she's one of our top sellers globally. She then wanted to go move into sales and, you know, close some of our top, largest customers out there. And that's because Molly had no ego. Those 49 other people that I spoke to, they all had an ego. They said, I'm not willing to go be an sdr. And we had even rebranded it, we called it account associate. And they still said, I don't want to go be an SDR. When I have been, you know, a manager somewhere else. I've had no less than 40 of those people reach back out to me over the years wanting to come back to OpenAI. And unfortunately there hasn't been room for most of them. So it's put your ego aside. And that's what I see the best sellers have in common, is they believe in themselves.

[Eric]

How quickly do you know if someone's not any good?

[Maggie]

About a week.

[Eric]

About a week?

[Maggie]

About a week.

[Eric]

Oh, God. That's an awkward first week, isn't it?

[Ad Voice]

It's.

[Eric]

Yeah, you're the end of the year.

[Maggie]

Well, you start to thank for coming.

[Eric]

There's a short stay. Didn't make the first cliff. Bad luck. We're all vesting millions and you're.

[Maggie]

You start to have the inklings, you know, right away if someone's got it or not. And here's the thing with interviewing salespeople, and I hear this from all of my founders. You know, I've made over 35 investments with 20 sales and made many personal angel investments. Every single founder says salespeople are the hardest to hire because they're so Hard? Well, hey, no, I think you'd be a lot harder to manage. But I, I think that salespeople show up so well when they're interviewing that it's really hard to tell a good one from editor. You have to be a really skilled interviewer. And I actually think one of my superpowers is picking great talent.

[Eric]

How do you do that then? If someone is a great seller of themselves, which a lot of people are, how do you unpick true quality versus facade appearance?

[Maggie]

Yeah, the first thing that I look for that sends off the absolute red flags is blame. So I want to hear, for example, Harry, tell me about a time that you lost an investment. Why'd you lose it?

[Eric]

See, the VCs are brilliant because whenever we lose an investment, we always go, we lost because of price. And that's the.

[Maggie]

Sounds like some blame is a total.

[Eric]

Game of like, we didn't really lose. Someone just paid more. When did we lose an investment? We lost Translucent pretty recently. And it's because founders wanted Silicon Valley brand and a halo effect from Andrewson.

[Maggie]

Is there anything you could have done differently there?

[Eric]

No, I literally got a tattoo of the company. No, seriously, I got a tattoo of the company here. And, and I thought, like, you know, we're going to show that we love this company. What I didn't anticipate was being on TV the next day and I was like advertising that I was chasing this business.

[Maggie]

Wait, really?

[Eric]

Yeah, literally there's pictures of it and. And we lost to Andrewson. No, I actually quite like losing. There's this masochistic element of me which is like, we just need to get better and better and better.

[Maggie]

Yeah, exactly. So I'm okay that people lose. I'm actually okay if someone wasn't the top rep, if they were the second or third or fourth. But what I want to know is why weren't they the top? Or do they have humility? Are they self reflective? Can they. They say, you know what, Harry, he outworked me, he outperformed me, he was better at discovery. Those are the types of things that I want to hear in the interview cycle. And more often than not, sellers tend to blame. When you dig into why did you lose a deal, they blame, you know, the competition, they blame the product, they blame something else. And what I'm actually looking for is, did they own up to that mistake and what did they learn from it? And that's a really big signal. Something that I, I look for and I stand by is, unfortunately, job hoppers are typically going to struggle Quite a bit.

[Eric]

When you say job hoppers, just get some clarification. Is like two years enough time? Is this six months?

[Maggie]

So I want to know why. I dig pretty hard in the story. If you see someone that has a consistent record of, you know, every year, every six months, every two years, it's not necessarily about the time, it's the why. And what I want I'm really trying to understand is were they running towards someone, towards something, or were they running from something? I was only at Webflow for two years, but I was running towards OpenAI. When ChatGPT hit the scene on November 30, 2022, I was like, I am going there, I gotta go there, whatever it takes.

[Eric]

One running away from webflow.

[Maggie]

I wasn't running away. I literally got promoted to senior director and quit three days later. It was not ideal to do that. My boss was not thrilled. Not a good look. But I was running towards it. And I've never run from something. I've always run towards something and that's what I'm looking for. And if someone is running from something, why were they running from something? What? What was it? Was it because their performance was bad? The leader, the company, what was it?

[Eric]

So can you tell me a story of when you lost a deal at OpenAI and what your reflections are on it now? I'm a good.

[Maggie]

Yeah, yeah.

[Eric]

Now we're going here. So we earn the money. Thank you.

[Maggie]

So the main reason that we lose is we lose to people who just do nothing. They're. They're thinking too narrowly or in full candor, they decide to go with a large incumbent and they just flip it on. You know, they say this is free, this is subsidized. They don't look at the quality of the product, they are looking at the price point.

[Eric]

Large incumbent. Because people would say that OpenAI is.

[Maggie]

An incumbent, which is crazy to me.

[Eric]

Crazy after raising 200 billion, 351 billion. But how could we be an income.

[Maggie]

Where a smooth startup feels like a startup inside, doesn't it?

[Eric]

Yeah, there's seven offices around the world. So cute.

[Maggie]

Such a jerk.

[Eric]

Everyone just grinding away for every million dollar contract. And it was like, oh, we just signed, you know, the government.

[Maggie]

Ministry of justice on OpenAI.

[Eric]

Yeah, there we go. Fantastic. And so sorry, Moon. Incumbent is Microsoft. It is Google. Okay.

[Maggie]

Yeah, basically. And same thing with, you know, with slack Microsoft, teams flip on a switch and today, you know, I help to oversee our large enterprise business. Majority of them are on teams. I'm no longer a slack employee. If I'll just say this, I think teams is severely inferior product to Slack. I still think Slack is a world class product. But you could argue that we did not win in the large enterprise and Microsoft won because of their distribution power.

[Eric]

Yeah.

[Maggie]

And that's going back to startups is all of you founders in the, in the audience are thinking about this. It's if you are going up against an incumbent, how are you going to outrun them? I actually think clay does a really nice job of this is they have a whole strategy called Clay gencies. They're basically partnerships for them. I don't know if run talked about this today.

[Eric]

So what are they called?

[Maggie]

Agencies. Yeah, so basically different agencies that are always going out there and doing videos and TikToks and Instagrams and YouTubes about how to use Clay and they're just creating this massive network of distribution as fast as they can. They've also built the best product on the market at OpenAI, we pretty much run go to market on clay. It is infused into everything that we do. They've built an amazing product and then they've also built an amazing team. And I'd say that's actually probably why we win the most amount of deals at OpenAI. And for all founders in the audience, I would take note of this. It's again going back to how you make people feel. People want to have a trusted partner that teaches them something. My goal of my team is to always understand what did you teach the customer when you were working with them? And if you're learning, if I'm learning from you, I will automatically feel respect for you.

[Eric]

Totally agree with you in terms of how you make people feel. Speaking of like losing to incumbents, part of the win is how you get them over the line. And sometimes a pilot can help with that. You have quite a contrarian view of so what is that contrarian view? And how do you think founders should think about pilots today?

[Maggie]

So I run our pilot program, I created it and I helped to run it. At OpenAI we have a 100% win rate on pilots and there's many different ways to think about a pilot. And I'll kind of walk you all through this. There's, you know, piloting software, buying a small purchase and just flipping it on. And then there's what we do for our largest customers, not for everyone is the very well thought out, baked out pilots. And there's a couple things that go into our recipes for success and this works across the board. Whatever size company you're at first there needs to be executive buy in for a pilot. I hear all the time from my founders. We did three months on a pilot and then we lost the deal. And I say, well, who are you working with? The IT manager. And it's like, well, yeah, they didn't have authority so you should not be doing a pilot. Should be a heavy investment of time. You should not be doing a pilot unless you have that executive buy in and sign off. In our case, we make sure that executives are sitting through a training of ChatGPT, otherwise we're not doing a pilot. They have to be involved in it. The second thing is to have a repeatable playbook. So we go to our customers and you all should do this too. And we say this is our playbook that we've done across hundreds if not thousands of pilots. And we ask that you follow this playbook and you trust us. If they try to deviate, which they will, and they'll say, oh, we do pilots this way, we want to do it that way. It's pretty much a nonstart. Little tweaks here and there is okay, but we have a very well thought out formula. The third thing is we need to understand really the ROI and the results from this. So we need to work together on what are the metrics of success that typically comes with doing pre and post pilot surveys across the board for the people who are involved in that pilot. And then finally, and I'd say this is where we really do well is the team we bring. We give our customers a taste of what it is like to work with us when we're doing a pilot. Most companies out there, they just flip the switch and they say, hey, we're going to give you a two week free trial. Good luck, let us know how it goes. And then that company's surprised when they didn't win the business. Whereas we show up and we show them what it is like to have that partnership. And there is no frontier lab in the world that has as much experience as us deploying AI and transforming companies. We just announced that we've had a million businesses on our technology. There's nobody else that's at that scale.

[Eric]

Love that as an endpoint. Subtle flex. I'm going to do a quick firearound with you now. Short statement. And you don't know any of these, so this should be interesting. What would you most like to change about the world of sales today?

[Maggie]

I want more women in it. There's not enough women in sales right now. And it, I actually think it is getting worse over time. It's getting worse and I don't. I genuinely don't know why. And I think that's why I feel so much passion about showing up as a mom, as a leader. If you go to my LinkedIn, you'll see half my posts are something about motherhood or parenting. I was at a dinner with a very well known VC recently and the dinner was 13 men and two women and I don't know why this is but the number one thing that I want to change is getting more women into sales and into AI.

[Eric]

Totally agree with you there. I would love to have more on the podcast as well. Actually it's something that we could do much better on. I completely agree. Okay, fantastic. What have you changed your mind on most in the last 12 months? Again, Maggie had no idea about these, so forgive the pauses. We edit these out of podcasts and people have no idea. Edit a lot out of podcasts.

[Maggie]

What have I changed my mind on? The Large enterprises can't move fast so everyone thinks of large enterprises as slow as stodgy, is hard to sell into. And they are. They absolutely are. But when a large enterprise knows that something is coming after them, when they know that there is a small startup that has the potential to eat their lunch or take a significant journey, they will all of a sudden start moving fast. And I'm seeing this in our results. I mean we're selling to oil, gas, energy, airlines, government. You know, everyone goes oh, if government, Ministry of Justice piloted us for a couple months and then bought like that's actually not that long. And in fact we often see large enterprises can move now faster and smaller. Kind of digital natives, because digital natives are so busy piloting and testing everything. Where a large enterprise is getting pressure from the board saying what's your AI strategy? And the CEO says we gotta have an AI strategy.

[Eric]

Final one, what are you most excited for in the next 10 years?

[Maggie]

So I'll bring this to AI related, but the single thing I'm the most excited for, which is a huge focus of OpenAI, is how we're going to change healthcare. Spending about 80% of my time focusing on healthcare. Kind of naturally after last year, there are fewer things. Honestly, there's nothing more uniting in the world than health. Every single person wants to live longer, to have their friends and family live longer. Every single person in this room probably knows someone who has had cancer or passed from some sort of an illness. In my case, my dad has Alzheimer's, your mom has Ms. And I really believe that AI can change this. And I'll share, I'll actually share how, and kind of how we're thinking about this first is in the life sciences world. So right now to get a drug or a therapy through, I think it's called EMA over here, it's FDA for us in America, it can take five to 10 years. And we're working, you know, with the amgens with some of the largest pharmaceutical companies in the world. And part of the reason it takes so long is because of all of the data, all of the document authoring, all of the protocol amendments, all of this time that people have to spend spinning their wheels. And Harry, imagine if someone said to you there is a therapy out there right now that could reverse your mom's ms, but you don't get it for five years. That's the reality of where we're at today in health care. So we are spending a lot of time. We just announced a huge partnership with Thermo Fisher where we want to redo their entire clinical trial process and we think we can bring it down significantly. And every single day that we can get a therapy out to market faster is going to be more lives saved. And then you look at healthcare, you know, doctors, physicians, nurses, everything. When we look at the queries that come into ChatGPT, we get hundreds of millions of healthcare queries every single week. People are turning to our tools saying, I have a rash on my kid, you know, I have this, I was diagnosed with this. What do I do here? And we have been putting so much work into that to make sure that people are getting better and accurate answers and prompting, saying, you're going to the doctor, you know, here's the questions you should think about asking, which is so incredible. And actually just recently we, we shared that we now have in America, it's hipaa. I'm not sure if it's the same out here, but a HIPAA regulated version of our technology and we are already selling this to physicians, to doctors, ucsf, it's a top leading hospital in America. Every single person there has access to the technology. So you think about doctors who are often burnt out, they're tired, they don't have time to keep up with the latest inventions in medicine or the latest practices. 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.

[Eric]

I just want to say, you know, Maggie is one of the hardest working. I'm fortunate to interview some of the best CROs in the world. One of the most talented, most hardest working sales leaders in the business. I so appreciate the friendship. I so appreciate you. Thank you so much for doing this with me and you've been fantastic.

[Maggie]

Thank you. Thanks Eric.

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