SaaStr 814: How to Build Top-Performing Sales Orgs with OpenAI's GTM Leader Maggie Hott

0:01Welcome to the official Sastr podcast where you can hear some of the best Sastr speakers. This is where the cloud meets. Up today on the Sastra Podcast. And at OpenAI, we held and we always hold the line, even when it slows us down, because one exceptional hire is better than three average hires. And exceptional people tend to know other exceptional people that they can refer in. Hiring mistakes early on are incredibly costly. A mishire can cost over a million dollars. And this is because if you think about it, it takes time to hire them, time to ramp them, time to get them in front of the customers, and then probably not close deals.

0:43And then you have to start all over again to hire. So let's look at some of the common hiring pitfalls that lead to mishires. The first one that I recommend is avoid the logo trap. Don't confuse a big company brand with startup readiness. You need to understand if they were at a big company, what did they do? Hey, everybody. Saster AI is coming to London December 2nd and 3rd. It's Christmas with Saster and thousands of the best in AI and B2B will be there. The biggest names, the best networkings, and most importantly, the best playbooks to scaling in AI and SaaS. Early adopter tickets are selling like hotcakes.

1:24Use my code Jason20Pod for exclusive savings. Get your tickets now at podcast.sasterlondon.com or just use jason20pod at checkout.

1:39Hey, everybody. The best dot coms are taken or overpriced. I was literally looking for a domain name the other day. It was$10 ,000 just to make an offer. So you settle on a workaround domain for your website. Don't compromise. Get a clean sharp dot tech domain that instantly says it's a tech startup. Grab yours at get.tech slash SASTR. That's get.tech slash SASTR or on domain registers like GoDaddy. Stop compromising. Get the domain you need. .tech. Please welcome GTM Leadership OpenAI, Maggie Haad. All right. Hi, everyone. Thank you so much for being here. I come to SASTR every single year, and it has always been a career goal of mine to be speaking here.

2:24So being up here on the main stage is a little bit of a pinch me moment. But that's not what we're here to talk about today. What we're going to talk about is how to build top performing sales orgs. I have had a really lucky and fortunate pleasure of working for four different unicorns, helping to build their sales team at all four of them. I started my career at Eventbrite as the second SDR, spent five years there scaling it until about 2015. And then I made my move over to Slack as the very first sales hire out of headquarters, where I spent six and a half years in a variety of different roles.

3:04Then I made my way over to Webflow, where I was director of sales, overseeing sales dev, SC, SMB, mid-market enterprise, helping to take the company from$40 to$140 million and a$4 billion valuation. A couple of years ago, I made my way over to OpenAI. They hired me on to help build out ChatGPT Enterprise. So what I am going to do today is to take as many of the lessons that I have learned from scaling these companies over the past 15 years and distill them into a tactical playbook for you. My side hustle is that I run a small venture fund alongside seven other amazing women, and we have collectively invested in over 30 founders.

3:46And these are some of the top founders of this next decade. So I'm also going to take all of the lessons that we've been learning from mentoring and coaching them and distill them. So this entire talk is meant to be no theory, but all tactical. We'll cover four key areas. The first one, hiring. How do you build your A-team? The second one, how do you build teams that thrive? So you've got your A-team, but how do you create alignment and accountability? Then we'll move into scaling. Scaling is one of the hardest things that a company can do when they're going through hyper growth. So we're going to look at some sustainable growth strategies.

4:24And then finally, we're going to wrap it up with a rapid fire playbook of some of the most common mistakes that I see founders making as they build out their companies. I'm excited to jump in. You'll be able to take all these takeaways immediately. And a small disclaimer, these are my personal views, not those of OpenAI. Let's jump in on how to build the right team. as fewer things matter for. It was early 2023, and OpenAI had just released the fastest growing consumer app the world had ever seen, ChatGPT. We were about 200, 250 people, and we had reached a pivotal moment. We had to scale quickly.

5:07We had to end the year at somewhere close to 1 ,000 people. And this wasn't just growth for growth's sake. We needed to meet the demands of our market. And quite frankly, we needed to service our customers. Sam often says that hiring is the highest leverage thing that you can do. And great companies will always have great people. But for us, it wasn't just about finding the great people. It was about finding and hiring the right people. So let's look at three key principles that we follow at OpenAI as we hire. The first is to hire for clear, measurable objectives. A mission alone isn't enough.

5:47You need people who can explain exactly how their work and their skills will help you achieve that mission. So we looked for candidates who could clearly articulate how their skills would move us closer to our mission, which is to create AGI, artificial general intelligence that benefits all of humanity, not just those who are excited by the vision. The next is it's important to build teams, not just talent. You can have 50 top performers, the best 50 people out there, but if they can't collaborate and they can't work together, you're going to get bottlenecked and stuck. So the most simplistic way to think about hiring teams is to think about them as a puzzle.

6:29You need multiple different pieces that will all fit together, and everybody will have something they bring that is distinct and complementary. Their skills, their roles, and culture all need to fit together because trust and collaboration matter just as much as individual excellence. and then finally and maybe most importantly and one of the hardest things to do especially in hyper growth is maintain a high bar when you are growing fast i know it's tempting to compromise i know it's painful because you just need a body in that seat sometimes it feel like a warm body would be the best and quickest possible outcome that is not the case and at open ai we held and we always hold the line, even when it slows us down, because one exceptional hire is better than three average hires, and exceptional people tend to know other exceptional people that they can refer in.

7:24So these three principles help to scale with clarity and conviction. So let's shift gears a bit. Let's get right into the tactical, and what I think will probably matter to many of you, go-to-market hiring. Hiring mistakes early on are incredibly costly. A mishire can cost over a million dollars. And this is because if you think about it, it takes time to hire them, time to ramp them, time to get them in front of the customers, and then probably not close deals. The cultural disruption that a mishire brings, then you have to pit them, then you have to severance them, and then you have to start all over again to hire.

8:02So now you're looking at about a million dollars and probably a year of wasted time. So let's look at some of the common founder hiring pitfalls that lead to mishires. The first one that I recommend is avoid the logo trap. Don't confuse a big company brand with startup readiness. I'm not saying that you shouldn't ever hire someone that comes from a big company because big companies have great people, but you need to understand if they were at a big company, what did they do? What did they build? What did they scale? So that way you can really understand if they can bring these skill sets over to your thriving startup.

8:40You don't need someone who can just operate the machine. You need someone who can build it. The next one that I see founders do very often is they promote too early. Your first AE is very likely great, but that doesn't mean that they should be your first head of sales. You must give them mentorship, but you also need to be thoughtful about how and when you level them up. And to go on this a bit further, what I often see is founders, if they end up promoting someone who doesn't have management experience, they will have to spend a lot of time coaching them, which is just time they don't have. Or they will not spend the time coaching them and this hire will flounder.

9:20So neither of those are great outcomes. on the flip side i also see founders trying to hire someone who's senior way too early they come to me and they say maggie i have two aes i think it's time for a cro no it is not time for a cro you need to make sure that you have clarity on how the repeatable motion works they need to make sure there's strong playbooks in place otherwise they will be flying blind so founders you are the head of sales until you have a repeatable motion. You must own it until the motion works, and then you can hire to scale. So essentially, a repeatable motion means that a non-founder can sell and close.

10:01You know your ICP, you know your pitch, you know where your leads are coming from, and you know that they can move predictably through the funnel. No one is going to sell with the same urgency and conviction that you do, so you need to make sure that it is possible for you to hand off the sales cycle to someone else before you go build out a sales team. So let's look at what we should be looking for. I love to hire what I call chaos translators or people who embrace the chaos. These are basically people who just thrive in ambiguity. You can throw them on a renewal. You can throw them on an outage.

10:39You can throw them on a crisis and they're going to take it with a smile. These are the builders that you want to hire. I also love to prioritize generalists early days, someone who can wear a lot of hats. So that's a versatile generalist that can jump in right away. Also, early days, you want to avoid lone wolves. I actually love lone wolves. There's a time and place for lone wolves, but that time and place is not your first hires. You want folks who are deep collaborators, not people who are just going to put their heads down and sell. You must be meticulous. Do deep interviews, back channel thoroughly and trust your gut.

11:16Off is usually off. So let's take a look at some interview questions. Founders often ask me, how do I interview salespeople? They all seem like they are great at interviewing. I think the easiest thing to do is to distill it into two clear buckets. Look at tactical and look at behavioral. So when you're looking and asking for questions that are tactical, you're really looking for skills and experience. What did they build? What process did they invent? How did they mentor and train others? How did they help hire and scale the team? When you look at behavioral, you're really looking for mindset and you're looking for character.

11:55Asking questions like, describe a painful deal that you lost. What did you learn? Is going to show, do they take accountability? Do they have a growth mindset? It's also really important to understand who were their closest cross-functional colleagues. Early days on in building a sales machine or just a company machine, people have to work very closely together so you want to make sure these folks are strong collaborators. Let's take a look at some red flags to watch for that tend to come up during sales cycles and if I see these, I am always an immediate no. The first is blaming others for failures.

12:33You want to make sure that somebody can take ownership of the mistakes that they've made or when things don't go wrong and they don't just blame others. The next is frequent job hopping without progression. We've all seen those people that seem to have a year at a whole bunch of different companies, maybe a more senior title at each one, but what you really want to look for is growth within their current company. People who are primarily motivated by titles or money. Look, we are all financially motivated, but it is so important to make sure that if you hire someone, they're not going to jump ship if somebody comes along with a$20 ,000 hire offer.

13:11And finally, a lack of humility or unwillingness to make mistakes. We've all made so many mistakes within our careers, and so it's so important that you find someone that can admit to these mistakes and most importantly, learn from them. Early hiring is high stakes. Hire mission and objective aligned talent. Folks that have the skills to get you to where you want to go. Never skip interview steps. Interviewing is so painful, but what's more painful is cleaning up a bad hire later on. Trust your gut early. Off is usually off. Act quickly on mistakes. You will make hiring mistakes. It's just part of the game.

13:54But the best and kindest thing you could do for yourself, your candidate, and your company is to move fast on that person. And finally, don't go it alone. Leverage your network, leverage your investors, leverage your advisors and people who have hired go-to-market before. At 20 Sales, one of the most common things that we do is we help our founders look through who should be their first sales hires, and we even help them interview. So make sure that you are leaning on people that can help you guide through this process. So I'm going to leave you with a piece of advice from OpenAI's CFO, Sarah Fryer.

14:28She fundamentally believes that if you get the right people and you really let them fly, and that evolves, giving them a lot of autonomy, encouragement, and tough love, then the A team with the B idea will always beat the B team with the A idea. I hope this section helps you build your A team. So let's take a look at how to build teams that thrive. You've hired the right team. You've got your A players. Now let's talk about how do you set them up to succeed. it was march 2015 i walk in the doors at slack first sales hire out of headquarters ready to jump in slack has just become a silicon valley darling we're about 50-ish people at the company i walk in and all of a sudden the tension in the room is very obvious it feels off it feels weird my then boss pulls me into a conference room and says i have bad news slack was hacked and it could be crippling for the company.

15:28That afternoon, Stuart stood up on a desk. Again, remember, we're like one small room and he addressed the whole company and he says, this is going to be challenging. This is going to be tough, but we will make it through this, but it is going to take hard work from every single one of you. The trust and respect that the employees had in Stuart was so clear. And this was really the first time in my career that I had seen what it looks like to have a culture of accountability. So fast forward four days later, and we decided to let the world know about this hack. And they put me on the phones for every single person who was hacked, basically got an email that said, really sorry, you were hacked.

16:07Call this phone number. So that was me on day four. It was trial by fire at the very best. The lesson here is that alignment isn't tested in the good times, it's revealed in the hard ones. And I bet most of you probably don't remember this breach. But what stuck with me wasn't the crisis, it was how the team responded. This moment reinforced three powerful lessons. The first is that authentic leadership matters. People follow leaders that they trust, especially in moments of uncertainty. Culture is your strongest defense. A unified culture will empower teams to navigate even the toughest challenges and emerge stronger.

16:51And finally, alignment drives outcomes. When teams rally around shared goals and values, they move faster and they deliver more. So with these three things in mind, let's get practical. How do you actually build alignment, accountability, and speed into your day-to-day? First is that you need to encourage real debates. You need to make sure that every single person in the company feels comfortable speaking up from the SVP of marketing all the way down to the SDR. I'm a big believer in no meeting after the meeting. Avoid those side chatter conversations. Once you've decided on something, move forward and you can always revisit with intention.

17:37Second, make priorities obvious. Founders and leaders, this one is on you. You need to set clear priorities and ownership. You must use async transparent communication to connect everybody's daily work to goals. Our CPO, Kevin Wheel, at OpenAI, every single Monday morning does a post to the entire company that tells us what's coming up for the week. What are we launching? What are the key things to be aware of? And that's how we've helped to build this culture of alignment. And then finally, speed up decisions. In this world of AI, you don't have time to wait. Empower decision-making at all levels.

18:14In just the last year, I had an AE come to me wanting to test out a new vertical, another one wanting to test out a new pricing strategy, another one wanting to test out a pilot motion. We did experiments on all three. All three were wildly successful, and they've changed how we sell today. I am a big believer that those who are closest to the business have the best ideas. And that's typically the ICs. So frontline managers shape your team's daily experience. They are essentially your organization's pilots. And you wouldn't get on a flight with an untrained pilot, right? I hope not, at least. Yet, unfortunately, this is what happens in most companies.

18:55They underinvest in their frontline manager leadership and development. I also like to joke that frontline managers are also untrained therapists because it's so common that they are shouldering the weight of those that are reporting to them. So you must overinvest in their leadership development, in executive coaching, in emotional intelligence training. Equip them to manage not only people, but conflict and culture. They are not just managers. They are your cultural backbone. Customer obsession is everyone's job. Success isn't just on sales. Every team owns the health of the customer. You must build this mindset from day one.

19:36We actually did this really well at Slack. At Slack, we took our largest customers and we assigned non-sales DRIs, directly responsible individuals, to be in charge of each customer. So our VP of engineering, Michael Lopp, was in charge of VMware. Our CTO, Alan, was in charge of Nike and so on. And all of a sudden, we started seeing the customer feedback start to come into our roadmap a heck of a lot faster. We also at Slack, Webflow, and OpenAI have built out customer wins and customer losses channels. If you don't have these, go build these immediately. The customer wins channel is awesome. It's a feel-good channel.

20:14Everyone loves to see the new customers that are coming on board. But the customer losses channel is really where it's at. As soon as that thing lights up, everybody swarms in because they want to know why we lost the customer. I often see our COO Brad in there jumping in, offering support, asking questions, trying to learn from what we could have done better. Bake customer obsession into your DNA. So this picture that you see up here, that is OpenAI's go-to-market team about two months ago. In two years, we have gone from 10 to 500 people, and we are going to keep on going. And the reason that this is working today, while it hasn't been easy, is we are built on transparency, trust, and accountability.

20:58We invest in our leaders so they can grow with the company, not out of the company. And we embed customer obsession into every single function. Do these things well and your teams will thrive even in the toughest of moments. so we've hired the right team they're all swimming in the right direction let's now jump in to how do we scale without breaking let's dive in in 2016 Stuart Butterfield came to the sales team Ed Flack and said we're going to hire an SVP of sales Bob Fraddy many of us myself included raised our eyebrows. And we wondered why a thriving startup needed a hotshot corporate executive.

21:44We were completely wrong. Bob came in. He brought structure. He built scalable systems. He helped convince and teach our executive leadership why enterprise and sales mattered. He brought in season judgment because he had seen the movie before by scaling Salesforce. And he mentored and elevated internal talent. He didn't just replace us. The result of this is Slat grew from$50 million to a billion. We went public, and then we had an outcome of a$27 billion acquisition by Salesforce, one of the largest acquisitions to date. And I honestly shudder to think what life would have been like without Bob.

22:23Without his external expertise, we probably would have played it too safe. we would have stayed a modest growing consumer app and we probably would have never been the enterprise powerhouse that we became. The lesson here is that sustainable growth comes from internal momentum and external perspective. And this is why for founders and senior leaders, it is so important to give away your Legos. Giving away your Legos, which is one of my favorite terms, it's coined by Molly Graham, essentially means to hand off parts of your job or your full job with as you scale. At OpenAI, we've done this really well.

23:01In just the last year, Sam has brought in a new chief product officer, Kevin, a new CEO of applications just announced last week, Fiji, and an amazing CFO, Sarah Fryer. And what this does is it unlocks bigger impact. Rather than the CEO managing everything, they're able to give away parts of their job to these seasoned leaders who can run it wholly. This is all about scaling impact, not about losing control. You must build repeatable systems and then hire someone who can elevate them. And I've got two tips for giving away your Legos and how to think about this. The first is you must give them away.

23:38This is not about loaning your Legos. You cannot hire someone and then micromanage them. You have to give them away. And then secondly, the first Lego to give away should be the one that drains you the most. So let's say you've built that repeatable motion in sales, but it's draining you. Now, hire on a head of sales or a CRO, and you can focus on other areas. This is how you grow and how you help the company grow. So we've just talked a lot about how great it is to bring in external executives, but it's also really important to talk about how to blend external and internal talent. Your internal talent is the people who got you here today.

24:18And let's be real, they know where the bones are buried. You don't want to lose your internal superstars. So you must balance both of them. Internal promotions create cultural continuity, loyalty, and retention. But when you are layering and bringing in external hires, it is important to be transparent. It's always going to be painful to be layered, no matter what. So share the why. Share why you're excited about this person and what you expect them to bring the company to help reduce the friction. And finally, prioritize clear career paths. Growth drives retention. I stayed at Slack for many years post-vesting because I saw a strong future ahead.

25:02Take care of your early believers because they are the ones that built your foundation. Help them grow with you and not out of the company. Companies rarely use compensation as a strategic lever. And I genuinely think it is one of the best things that you can do for motivation. I'm going to give you some hot takes in this one. I believe the entire company should be on a bonus plan, not just the sales team. They should all be aligned to your core metrics and your North Stars. We did this at Slack. We put every single employee on a bonus plan, and we tied it to ARR and customer adoption. All of a sudden, the product team saw if they launched EKM, we could get, you know, another X millions in revenue.

25:44And lo and behold, those features shipped a lot faster. It's important to rally everybody around the same goals. But let's say you're an early stage startup and maybe you don't have the funds to put everyone on a bonus plan. That's okay, but it means you really need to lean into recognition. Recognition matters. If you're a CEO and you see someone grinding late at night, send them a$50 DoorDash gift card as a thank you. That little amount of money is going to mean so much to this person that their CEO sees them and acknowledges them. For early sales teams, I am a big believer that you should always start them on full salary.

26:22We did this at Slack, Webflow, OpenAI, and I know many other greats have done it like Calendly, New Relic, and Airtable. I actually have a whole LinkedIn post on this from a few months ago that went a bit viral if you want more takes on this. But the main reason for this is you want the sales team to be acting in service of the company and the customer, not acting in what they need to do to be able to make the most money. Your early sales team is also effectively user researchers. Have them focused on building and scaling, not focused on their paycheck. It will emphasize strong foundations, mentorship, and great process.