How Sierra Went From $0 to $400M ARR in 2.5 Years | with Reggie Marable (Chief Customer Officer, Sierra)

0:00AI is going to change everything. It is changing everything. This is going to be bigger than the internet.

0:04Reggie Marable: Reggie Marable, Chief Customer Officer at Sierra. He was the first sales hire. If you hire Sierra to do a job and we can't handle it or it has to go to a human, we don't get paid. We just surpassed$400 million and then we did$150 million in ARR just this quarter alone. I remember sitting right here when they made me the offer and it was a tremendous pay cut. And my wife was like, are you insane? What are you doing? What did that founder to sales hire transition look like? What's really cool and unique about Sierra? Everyone is in sales. This is the most collaborative selling motion that I've been a part of my entire career.

0:39Reggie Marable: How are we growing at such a crazy pace?

0:56Reggie Marable: Reggie, welcome to GTM Now. Awesome. It's exciting to be here. Really appreciate you having me on this incredible podcast today. Absolutely. And you come bearing exciting news. Sierra just surpassed 400 million in ARR, adding more than 150 million in Q3 alone. So first, a huge congratulations. Are you and the team doing anything to celebrate? Yeah, actually, we do a big thing for end of quarter close. We get everyone together in the respective offices and we kind of do a big party, big celebration. This one is incredibly exciting because we just surpassed$400 million. And then we did$150 million in ARR just this quarter alone.

1:39And we're really positioning ourselves to be a generational company. And it's all driven on the value that we're driving for our customers, the power of our technology, the power of our agents, and then our just amazing team. So this is a great day for Sierra, a great moment, and it's really exciting that I'm on this podcast to share this amazing news.

1:57Reggie Marable: Yes, very excited to have you on sharing the news. And I heard for the party, when you guys get together, it's like a double denim theme. Yeah, yeah, double denim. I'm a little bit out of costume today, but yeah, it's double denim, and we use that to close the quarter. and this was started by Logan Randolph and Natasha Clare way back when we were a tiny company coming out of stealth. So this is a Sierra tradition. We have a lot of traditions at Sierra and this is one of them where we rock denim when we close the quarter. Big milestone. Very exciting. We're going to dissect how you hit this milestone and how you're doing so while growth is accelerating.

2:35Reggie Marable: But to get the full picture, let's start a little bit earlier in the journey, closer to the beginning. After leadership roles at Salesforce, Slack, you joined in January of 2024 as employee 23 at Sierra and the first sales hire. That was just a month or so before Sierra came out of stealth, that$110 million raised from Sequoia and Benchmark. So when you joined, was there any kind of revenue? What was the state of affairs? Yeah, when I joined, we were in a small office above a coffee shop in downtown San Francisco, and I was employee number 23. And I had the privilege of working with Brett Taylor, who's an incredible friend, mentor at Salesforce for eight years.

3:15Never imagined I'd ever worked for a startup, but I was so inspired by what Brett and Clay were building. I got a chance to get to know Clay. And then I just felt that this technology was really going to change the world and it was going to change how people interact with brands and this could be a generational company. So I joined. I remember sitting right here when they made me the offer and it was a tremendous pay cut. And my wife was like, are you insane? What are you doing? So I had to get my wife comfortable that we were, this was going to be, one, I was willing to bet on myself and bet on the founders and bet on the space.

3:48But this was going to be successful, and I was going to do everything within my power to make sure that we were successful. So I joined very, very early. And to answer your question, that was a long-winded answer, but we had design customers. And essentially, they were paying for a proof of concept. We hadn't converted anyone to a long-term contract just yet. So right when we came out of stealth, we were very, very early. I believe we had like seven design customers, but we hadn't really started to scale and prospect and look for new business just yet.

4:17Reggie Marable: Very cool. And that conversation with a partner around going to the startup space or starting a company is a very common, challenging conversation. Was there a key to actually having that conversation for just anyone else that's looking to make that jump or start a company? And it is quite a lifestyle adjustment. Yeah, I would say for me, I just anchored on the why. Like why would I leave something very, very comfortable and safe and successful to go to the unknown? And it came down to just four things. Number one was the founders. Once again, I said Brett and Clay are brilliant, but they're humble, hardworking, just great human beings.

4:55And I really wanted to partner with them. The second was the space. I felt and I still feel AI is going to change everything. It is changing everything. This is going to be bigger than the internet, bigger than social, mobile, any technology we've ever seen. And I wanted to be a part of that. The third thing was to really have an opportunity to work with incredible people and build a generational company from the ground up, which was really exciting. And then the fourth, which was more personal to me, I just didn't see a lot of minorities getting these kind of opportunities. So I almost felt obligated to take this chance and be successful because if I'm successful and people can point to, hey, they have a successful minority leader that's part of the leadership team of this amazing company, I felt that it would open up doors for other people to get these kind of opportunities or even to consider taking these risks.

5:50But I just think if you can anchor on your why and just pour all of your energy into the why, that will lead you to the right decisions. The last thing I'll say is the great Muhammad Ali says if your dreams don't scare you, they're not big enough. So every big decision like joining a startup is a very scary decision. But usually the most uncomfortable, scariest decisions you make in your career are the best ones.

6:14Reggie Marable: That is great advice. And for anyone unfamiliar, can you just quickly explain what Sierra does in very simple terms? In very simple terms, Sierra makes customer-facing AI agents that help our clients power their customer experience and also help drive revenue. That includes customer service and sales conversations for many big brands, 50 % of the Fortune 50, I believe. And you actually only get paid when an agent resolves an issue. Is that correct? And first of all, Sophie, we want to power the entire customer experience, not just customer service. These agents have advanced memory, intelligence, so they can actually handle tasks over days, months, weeks, even years across all modalities.

6:59We can answer the phone. We can make outbound phone calls. We can respond to text messages, emails. We can be integrated inside of apps. We can be integrated inside of customer experiences. So think of Sierra as the front door of the customer experience where we power revenue when we improve and elevate the customer experience. Yeah, so what's really cool about what we did when we launched the company, we knew that clients no longer want to pay for seats, consumption, tokens, the right to use the software. They don't want to pay implementation fees. People want to pay for business results and business outcomes.

7:36So when we launched Sierra, we oriented our entire company around what's called outcome-based pricing. And what that means, Sophie, is when you hire Sierra, if we resolve a customer issue or we close a sale, we help someone refinance their mortgage, we get paid. And if we do that on our own without human intervention, we get paid. If we have to transfer to a human or you call back tomorrow with the same issue, we don't count that as a resolution and we don't get paid. So you hire Sierra to do a job. If we do our job and we do it well, we get paid. If you hire Sierra to do a job and we can't handle it or it has to go to a human or we don't resolve the customer issue, we don't get paid.

8:17That's a completely new business model. Our clients pay for business outcomes and results.

8:22Reggie Marable: That was a pretty bold bet in 2024. Now you see a lot of businesses shifting over to outcome-based pricing. But when you actually joined, curious, what surprised you most about joining Sierra? It's a couple of things. How fast the pace of innovation was happening. You know, Sierra, we do board meetings every six weeks just because the technology changes so fast. Fortunately, we have founders that can think five, six, seven, eight steps ahead of where the technology trends are going. So we've evolved our platform eight times since I've been here. So just the pace of innovation has been like shockingly, I didn't realize how fast this place moved.

8:57And I think of AI in terms of a day is a week, a week is a month, a month is a year, and a year is 10 years in the space. So that's the first thing. And then the second thing is when you work at a startup, I mean, you have to be humble. You've got to be willing to wear multiple hats. Like since I've been at Sierra, I've been a sales rep. I've been, I pretended like I was a sales engineer. I've been an office manager. I put dishes in the dishwasher. We, at one point we had one executive assistant, Allie, who's amazing. She went on vacation. So I was Brett and Clay's EA for a week. So the way I look at working at a startup, which I didn't realize until you actually get here.

9:36You have to be humble. You have to be willing to wear multiple hats. Whatever is required that needs to happen, that is your job to go figure that out. You see a problem, fix a problem.

9:46Reggie Marable: So you have board meetings every six weeks. You mentioned model development. Timelines are a big part of that. Brett Taylor chairs the OpenAI board. Does that give Sierra an edge? Brett keeps his engagement with OpenAI completely separate from his work at Sierra. So we call it his like his the greatest side hustle of all time. But he keeps those completely separate. So they don't they never intertwine. So hopefully that answers your question. But I'm just when I when I talk about like their ability to think so many steps ahead. I just think it's just their understanding of the technology, their research and how much they study.

10:23And they put in efforts into understanding what's happening in the space. talking to customers. Like I think our founders, they're running multiple customer meetings a day. So they're talking to early States customers. They're talking to customers that are in proof of concept. They're talking to our OG long-term customers. So talking to customers and then studying and being a steward of what's happening in the industry is what gives them the ability to think way, way ahead of where the technology is going.

10:49Reggie Marable: Interesting. Okay. And so when you join your early employee 23, first sales hire, You wore a ton of different hats, like you mentioned. But as the first sales hire, you were kind of taking over sales from Brett or any of the founders running it. What did that founder to sales hire transition look like? That's a very common question that a lot of startups ask and also grapple with getting right. Well, first of all, what's really cool and unique about Sierra, everyone is in sales. This is the most collaborative selling motion that I've been a part of my entire career. So saying that because I showed up as head of sales for a sales hire, that I'm like taking the reins from Brett.

11:32That's not what happened. Brett is still involved in sales. Clay is involved in sales. I'm involved in sales. When I joined, my onboarding buddy was this guy named Logan Randolph, who is now our head of expansion. Logan onboarded me, and he and I were in sales. So what's cool about Sierra is there is never a point of handing the reins off. Everyone is here. Everyone here is in sales. Everyone talks to customers. If there's a customer issue or need, we drop everything we're doing to support our customers. Customer obsession is one of our corporate values. So everyone's involved in sales. So when I came on, my role was to just continue to add more horsepower, but then build out a team so we can start taking on more customers and having more customer conversations.

12:20But everybody at Sierra is in sales.

12:23Reggie Marable: Is that challenging as you scale? What is Sierra at now? How does that scale with volume? Yeah, we have over 1 ,200 employees in the company. And then me, my role as the chief customer officer, I'm heavily involved in a lot of our most important strategic customer relationships, serving as executive sponsor. We also have a president of field operations, Eric Eichensleiter. He's involved in a ton of customer engagements. We have an incredible senior sales leadership team that's heavily involved in customer engagements. Our agent development team led by Paul and Sue, they're heavily involved in customer engagement.

12:57So we have enough horsepower. We have enough people that get involved in the day-to-day aspects of making sure that our clients are getting the full power of their investment behind Sierra.

13:06Reggie Marable: Very cool. And when a few months ago you shifted over from head of sales to chief customer officer, congratulations, by the way. How did that shift your role and how should other people think about that connectivity between sales, kind of the pre-sales process, and customer success, almost the customer ownership? Yeah, so once again, my first chapter was building, leading, and scaling the sales organization. And then about two months ago, our founders and then Eric Eikensleiters, who's our president of field operations, asked me to take on the strategic role as chief customer officer. My role now is to get involved in our most important customer relationships across all aspects of the customer lifecycle, whether that's early to you're in a proof of concept to you are a customer to, you know, we're expanding and growing with you.

13:56So this role gives our leadership team leverage and scale. Once again, right now, this is a really, really exciting, cool role for me because I get to interact with all of our customer relationships from very, very early to our OG customers. That's why the role was created to help us scale and continue to grow. As we add more sellers, we add more customers. My role is to help ensure they get the full power of their investment.

14:21Reggie Marable: Well, let's dive into a couple of the growth moves that helped you go from pre-revenue essentially to$400 million in ARR. Now, you come out of stealth February 2024 with$110 million and a handful of design customers that you mentioned. By October, so the same year, you have$20 million in revenue. What did that first growth chapter look like? How did you go and get$20 million in revenue the year you launched? It started off with, one, we have an incredible product. The second thing is we have an incredible selling motion that allows our clients to test out our technology with very, very little risk.

14:58and it gives us an opportunity to prove ourselves and approve of concept. The third thing is we have a great business model where our clients, we only charge when our agents successfully resolve issues, cases, closed deals. And then another aspect is we have a forward-deployed engineering model. So for every engagement, we have a dedicated team of AI experts that work with the client and approve of concept to put the agent, build the agent, do all the back-end system integration work and put the agent in live production. And then those resources become integrated with the client's technology, business, and operations team.

15:36And then they stay on the engagement through the life of the customer relationship. So they have intimate knowledge on the inner workings of the client, how they like things, what it's like to work with us. So they're able to add tremendous, tremendous value because we have this dedicated team of experts that get their MBA in the client's business and can add tremendous value. And then the last thing is we hired some incredible sellers. We hired a nationwide team of sellers. We started off pretty small. By the time we got to October, maybe we had like 15 to 20 sellers. But these are some of the best sellers in the world.

16:11So if you've got a great product, you've got a great culture, you've got a great selling motion, you've got a great business model, you've got a way to prove your technology, and you hire great talent, it, you mix all that all together. That's how you grow a company.

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17:00Reggie Marable: That's Z-E-R-O dot I-N-C forward slash GTM and O-W. That is a great combination. And let's dive a little into the selling motion itself. So you've got a pilot, proof of concept, then forward deployed engineer combination. Obviously, you have to generate interest. And then once we do some discovery, then we'll build like a demonstration, like an art of the possible of what this technology could look like based off the use cases you want us to handle and the challenges you're trying to solve. And then once the client sees the art of the possible, then the next step is to get them to commit to a paid proof of concept.

17:38So in that proof of concept, that's when we assign the dedicated team of AI experts. and then the proof of concept, we'll pick three or four customer journeys or use cases and then we'll build an agent and put the agent in live production. We'll do all the system integration work, meaning that the agent will need access to knowledge, the systems of record to handle those use cases on their own without human intervention. And then we'll put the agent in live production. Before we do that, we'll simulate traffic, different personas, so the agent is battle-tested and ready before you put it in live production.

18:14And then we slowly ramp the traffic and we do what's called hill climbing. So you handle 5 % of the traffic. We'll make adjustments. And then we'll make the agent harden, make the agent better, and then we'll take on more traffic. And those POCs can run anywhere from a month to four months. Some customers that are ambitious and aggressive will do a POC for a couple of weeks and they're ready. They've seen enough where they're ready to enter into a long-term contract. So that's the motion. And then when you're in the proof of concept, they get a chance to see the power of the technology, how we can handle the use cases, how you manage the agent, all the AI that goes into building the agents and all the analytics work you can do to make the agent better, to get a feel for your customer traffic.

18:59What are your customers asking for? What do your customers need? And then what it's like to work with our incredible team. How responsive are we? How fast do we move? What value are we driving? Are we being a strategic advisor? So by the time you're done with the proof of concept, it's a clear way to know Sierra's the right partner. They've got an incredible team. Their technology says it's doing everything that they say they're going to do. There's a clear ROI, and they sign a long-term contract. We have a very, very high conversion rate for when someone commits to a proof of concept to converting to a long-term contract.

19:32It's an incredibly high conversion rate.

19:35Reggie Marable: That's amazing. I mean, that's great to have the ability to actually go in, work directly with them before, show the value before actually committing. And so that helped create that$20 million revenue off the gate. What did that next version of growth look like? Was it continuing that system or was there anything that you layered on top that you feel like was a real key unlock for your go-to market and your growth? It started off with just scale, adding more sellers, adding more agent development teammates. We started to get more customer stories where our customers loved the results that we were delivering and they were happy to share the success that they're having with Sierra.

20:12And then we also continued to innovate the platform. We launched Voice, which was a huge unlock for the company. It was a lot of volume. And we were the first, I believe we were one of the first companies to launch Voice. So it's a combination of scale. It's a combination of innovation. And it's a combination of execution. We have this thing called lessons learned. So if you lose a deal, we have a bad engagement, we swarm it, we do a postmortem, we figure out what can we do to get better. So we're constantly learning from the mistakes that we make. And then you add all that together, more people, incredible talent, incredible platform that's innovating, continuing to hone and tighten up your motion.

20:53That's just putting gasoline on what you've already built.

20:55Reggie Marable: And as you scale a sales team, how do you organize it? Great question. One of the key decisions we made early on in our construction of the go-to-market was to orient around industries, meaning we figured out who our ideal customer profile was. And essentially, it's where people live, work, and play. Who would need to speak to a brand on a consistent basis? And that is financial services, that's healthcare, that is retail, that's media, travel, tourism, hospitality, telecom. So we oriented our company around supporting and executing in those industries. And that's from our agent development team, our sales team, our marketing, our product, everything that we do is built around industries.

21:39So what that means, Sophie, is I can show up with institutional knowledge of what's happening in the industry, the trends, the use cases, the challenges. I have a strong point of view. So our team, our sellers and our agent development teammates are not only getting their MBA in their specific client's business, but they're getting their MBA in the industry. So now we can show up as strategic advisors. And that was a huge decision that we made early. And it's paid off dividends because we are now adding so much value within these industries because we show up as strategic advisors.

22:14Reggie Marable: That completely makes sense. What are the biggest industries that you serve? Yeah. So financial services, healthcare, retail, media, travel, tourism, hospitality, telecom, and then business services. We're actually now expanding into the government. So we have our FedRAMP high certification. So we're now starting to work with the federal government, state and local governments. And there's a lot of value that we can drive to the way that government services are delivered to constituents. So we're really excited about the work that we're going to be able to do within the government space. So that's key areas that helped skyrocket your growth.

22:48Reggie Marable: I think it was about November 2025, you guys announced 100 million ARR. And that was only seven quarters after launch. So about 5x in 13 months, which is incredible. Fast forward to February 2026, out over 150 million ARR, first 50 million quarter. So you can see this acceleration of growth. And then recently with your news, you announced that it took you six months to double from 100 million ARR to 200 million. and then only five months to double from 200 to 400 million ARR. Like, how are we growing at such a crazy pace? Yeah, it just goes back to the key elements that I alluded to before. It's one, continuing to scale, you know, hiring more sellers, hiring more agent development teammates.

23:34That's like one of our secret sauces is the people. The second is we expanded internationally. So we are now operating in 60 markets. We have a pretty large operation in Europe, in Asia-Pac, so we're expanding internationally, which is also helping to contribute to our growth and our expansion. And then I keep going back to the innovation in the platform. Once again, we launched Voice. Then we launched this incredible, powerful innovation called Ghostwriter. And essentially, think of having your own teammate, your own AI agent that is helping you build agents, helping you make the agents better 24-7.

24:13And then we continue to invest heavily in putting more AI innovation into the platform to provide proactive insights into making the agent better, providing better reporting and more insights to our clients. So Ghostwriter was a massive unlock for us to be able to work with our clients to build agents, build them faster, build them better, have these agents constantly improve faster. And then we're actually using AI to automate the way we run our business. So we have this cool platform called Pinecone, which essentially is leveraging all types of different large language models. It's using some of our own fine-tuned models.

24:53It's tapped into all of our systems of record. So if I'm a seller, it's helping me sell faster. I'll have my own chief of staff. I'm able to sell 10 times faster. It's helping with strategic prospecting, with meeting prep. It's helping me get my MBA faster in my industry and my client's business. it's automating a lot of the mundane tasks. So I don't have to worry about that stuff. I can focus more on seeing more customers, finding more prospects. And then if I'm an engineer or if I'm a product person, if I'm a marketer, we have all this innovation built inside of our company. We're actually using our own technology to make ourselves more productive and be able to move faster with automation and better intelligence.

25:31So you add that with having more people, incredible talent, incredible innovation, and then we're expanding internationally. Those are just some of the ways that we're able to grow. But most importantly, it really comes down to the value that we are driving for our customers. Our customers are getting tremendous value out of their investment with the Sierra, which means they want to continue to invest with us. They're also graciously sharing the success that they're having with other potential customers. So when you have happy customers that are getting value out of your technology, and then the other factors that I just mentioned, that's how we've been able to grow.

26:09Reggie Marable: You mentioned people being a core part of that. Sellers, high quality. What are you looking for when you're hiring? We look for intellectual curiosity, beginner's mind, intensity, craftsmanship, creativity. I call it swag persona, the ability to go talk to the CEO, but treat the receptionist with the utmost respect. And I say beginner's mind and intellectual curiosity, just because of the pace of innovation. And then we look for operational excellence. We look for executors. And then we also look for nice people, like cool people that are humble, that are just great teammates. As I said before, this is a very collaborative selling motion.

26:50So being able to collaborate and partner with your teammates is something we find really, really important. And we just like, I mean, you're around your teammates a lot. So we want to hire nice people, people that are fun to be around. So that's what we look for for sellers and just in general, like just people that we hire at Sierra.

27:07Reggie Marable: I love that. We talk about that a lot internally also at GTM Fund. The number one criteria for the community above operating experience is good human. And then of course, get into the specifics. We've had a great, great success with hiring from referrals. So if you hire a great person, guess what, Sophie? They know other great people and they surround themselves with other great people. And that's been a great way for us to really build talent that are just humble, like hardworking, nice people. How do you measure things like intellectual curiosity when you're in an interview process? Yeah, we have a pretty detailed interview process.

27:43So I always call it like I may get happy years. I may like someone. I may not. I may overlook something. But when you have to talk to seven other people in the interview process, it's hard to fool someone. So I think it's a combination of there's multiple people that you'll have to talk to. We hire by consensus. So if we don't have consensus, we don't move forward. And then whoever's involved in the interview process, seven could very well be, you know, it could be five. I'm not sure the exact number, but it's and we try to have our folk come on sites. We can meet them in person. And then we actually have like them, they do a presentation, we give them a prompt so we can see how they present, how they prepare, how they think.

28:26So there's multiple ways you can do it. But I think if you have multiple people involved in the hiring process, someone is going to find something if it's not a right fit for your company. And that's something that we do really well here.

28:37Reggie Marable: And so you've got an incredibly high quality team of sellers. How do you actually allocate how much pipeline that they are carrying in an outcome-based model? And how does that differ from past experiences you've had? One thing that I think people get caught up in is like with technology and changing industry, it still comes down to just basic fundamentals, like prospecting, getting meetings, creating pipeline, and then tracking, like, are you converting that pipeline into actual POCs? And are you converting those POCs into long-term contracts. Even though we are selling somewhat of different technology and it's a different business model, the fundamentals of sales still remain.

29:18We track meetings, we track pipe generation, we track POCs. Those are leading indicators into the success of a seller at Sierra. So it's a little different. And unfortunately, I can't share the exact metrics that we use to how much pipeline should a seller have. But what I will tell you is it's selling mobile phones, selling water, selling AI agents, selling CRM software, the basic fundamentals of what you need to do, the hustle, the grit, the grind, the focus on prospecting. That's not going to change. I don't care how much AI you infuse into your business. You have to have people that are willing to prospect every single day, show up prepared, show up with craftsmanship, show up with their MBA as a strategic advisor.

30:06They know the client's business, they're the industry, they can add value. That's not going to change. So I know that was a, I didn't directly answer your question, but the fundamentals of sales, whether you're selling AI agents and selling software, it's the same.

30:20Reggie Marable: That's great. And maybe this actually transfers to my next question, which is actually from a founder and the audience who asked, what is the biggest unlock and also biggest mistake that you see AI startups making when selling to the enterprise? The biggest unlock is if you're early, I would say if I'm a founder and I'm going to hire like my first few sales hires, I'm looking for people that can scale. You know, Brett got me, Brett and Clay got me to come on as head of sales and I had a tremendous amount of deep experience, But I was a seller. Like I was a first line sale. I was a individual contributor carrying a bag my first few months at Sierra.

30:58But I was quickly going to help scale the company. So when I started hiring my first, we call it the Elite Eight, these were all sales leaders. People that were willing to take a step back, come in because they wanted to be part of Sierra. And those sellers, like some incredible folks like Kylie Maddox and Mandy St. Ledger are now super senior leaders at the company. So my advice to a founder, if you're going to hire, you need to hire sellers that can scale and people that are humble, that don't have an ego, that are willing to wear multiple hats, do whatever it takes to be successful. That would be my piece of advice for the first round of people you're going to hire.

31:34And then you've got to look for a track record of success where they already know how to sell into the enterprise because selling in the enterprise is very, very complex. And if you don't know how to do that, you don't want to hire someone and try to learn on the job. You need someone that can scale and then someone that has a proven track record of success selling to the complex enterprise companies that you want to go after.

31:55Reggie Marable: That's really good advice. Yeah. And I would also say like the founder for the first wave of growth is going to need to be involved in deals and talking to customers. But if you've got a great teammate or a great counterpart that has a tremendous amount of experience selling to the enterprise, then they can take some of the burden off of you. But when you're early, everyone's in sales. Even to this day, at our scale of 400 million AR, everyone is in sales. So that would be my advice is the founder needs to be involved in the first early stages. They need to be involved in deals, talking to customers, helping to close deals.

32:28Reggie Marable: Love it. And you mentioned Elite Eight, first eight that you hired. Was that a framework that you went into it with that you think other founders or anyone else should think about? Or was that once you hired them, you realized how elite they were and they became a name? I'll give myself credit. I came up with the Elite Eight because I love basketball. I love it. I love basketball and football. And I was trying to find, like, I knew we were going to hire eight sellers. I was trying to find, like, an acronym. And, you know, in the NCAA men's and women's basketball tournament, when you get to the Elite Eight, that is the best eight teams in the country at that period point in time.

33:02So when I hired the first eight sellers, I knew they had to be the best in the world because they were going to be the foundation of how we scaled to go to market. So I was looking for the best sellers in the world. and I was also looking for people that I had been in the trenches with. I had seen their work ethic. They trusted me. We trusted each other. They have a proven track record of success. So those eight hires had to be elite because we were going to build the go-to-market infrastructure on their success.

33:29Reggie Marable: Completely makes sense. Love how you coined the term. And Reggie, help me finish these sentences. I've got two for you. The first is, the thing nobody tells you about leadership is? Service. I think people get into leadership for the wrong reasons. They think that they're to be a boss, to be like it's this figurehead position. But in my humble opinion, I had to learn this the hard way, Sophie. Leadership is about service to others. And I'll quote the great Dr. Martin Luther King Jr. Life's most urgent and persistent question is what are you doing for others? And when you put people first and your success is derived off of their success, that is a great leader.

34:10A great leader is someone that's patient, that listens, that's a coach, that's a mentor, that's a friend, that's a counselor, that is someone that's pushing. So you've got to wear multiple hats. But the number one priority of a leader is service, service to others. And if you can think about the best leaders you've ever worked for, worked with, are the folks that put themselves, they devalue themselves and they put you first. and that, in my humble opinion, is the best leadership, is when you're a servant leader and your job is there to challenge people to be more successful, to help them achieve their financial goals and their business goals.

34:48Reggie Marable: Beautiful. And help us finish this sentence. The most underrated piece of go-to-market advice is? Don't make it complex. Keep it simple. In my humble opinion, go-to-market, it's about hiring elite talent, creating a culture where they feel trusted respected, and they can bring their authentic sales to work. It's creating an incredible sales process that you can teach them when they come on board. It's giving them a great product to sell. It's giving them a great tech stack to use and obviously put innovation into that. And then it's getting them, it's setting clear expectations and challenging them to get up every day and go find new customers and prospects.

35:31And they take care of the ones that we have, grow the ones that we have. And lastly, show up with your MBA, that you understand the client's business better than they know, and that you know your industry and you can show up a strategic advisor. Everything else to me is noise. It's fluff. You need to focus on those things when you build a go-to-market team. It's everything that I just said.

35:54Reggie Marable: The fundamentals. We love it. And zooming out, could be go-to-market, could be anything under the sun of life. what is the best advice you've ever received and who gave it to you? The best advice that I've ever received is from my parents. My dad would serve 30 years in the U.S. Army, retired as a full colonel. He was an Army Ranger, 82nd Airborne, Special Forces, Green Beret. My mom worked for the government most of her life in HR. And the biggest advice they gave me, and I'll quote Steve Martin, is be so good they can't ignore you. Say it again, be so good they can't ignore you. And that goes into your work ethic, to your preparation, to your brand, the way you show up, the way you treat people.

36:37And if you're able to do all of those things, no one's going to be able to like wave you off or disrespect you or ignore you because you're offering value and you're the best at what you do. And I learned that from my parents.

36:49Reggie Marable: Now, last question for you here, Reggie. forward-looking, if we think about customer service as a category overall, how many of today's human customer service jobs will exist in, say, five years? That's a great question. I can't predict the future, Sophie, but what I will tell you is I think the power of the AI agents that we're building for our customers that are up-leveling the customer experience, we are allowing the customer service reps to handle the really complex fun cases that they really want to work that require like deep thinking and gets them excited. So we're basically taking away a lot of the mundane stuff that a customer service rep didn't want to do anyways, and that's being handled by AI.

37:32But it's allowing the customer service reps to really handle the complex fun customer interactions. That's one. The second thing is we're actually creating new jobs and I'll reference SiriusXM. A lot of their customer service agents have now, they've now moved to a new job category called AI Architects. And essentially what they're doing is because the AI agent that's powering their customer experience named Harmony, she's an incredible agent. I encourage everyone to try her. She'll help you negotiate a great rate. They are managing this agent now. They're making the agent better. They're improving the agent.

38:06And that's a new job category. And those teammates are called AI Architects. So I think customer service will evolve. There'll be new jobs created for the folks that are handling the traditional customer service. They're going to have more fun because they're going to deal with the more complexity. But I can't predict what the landscape is going to look like. I also think with the emergence of personal agents, with Muse and Instinct and folks using these personal agents, I think that's going to be a shift. I'm really excited that Sierra is leading the pace there. We're basically building the protocol to manage how you interact with the personal agent.

38:41We're calling it POPI. It's the acronym is Personal Agent Protocol. We're working with Muse, Instinct, Genesis, Walmart, Rocket, Okta, OpenAI, and many, many other companies to build this protocol. So brands do know that, hey, this is an AI agent. It's someone's personal agent. How do I authenticate that user? What kind of permissions do I give it? So we're really working on that protocol because I do think there's going to be a wave of more personal agents are going to be interacting with brands and we want to make sure that those interactions are safe and secure. So we're really excited about that.

39:15But to answer your question, I have no idea, but I'm excited. I think it's going to create new jobs.

39:20Reggie Marable: Lots of exciting things ahead. And if people want to stay in touch with what you're doing at Sierra and yourself, where can they find you? Yeah, they can find me on LinkedIn. I'm big on LinkedIn. And also Sierra's on LinkedIn as well. I actually also too, Sophie, every Sunday night, if you're looking for some inspiration, I do a motivational quote to set the tone and motivate me for the week. I share that out on LinkedIn. I've been doing this since I first got into outside sales. And I know how challenging this profession is. And you need to pick me up. If you're interested in that, check me out on LinkedIn.

39:50Reggie Marable: Perfect. Everyone's got to turn the notifications on for those Sunday posts. And of course, all the other ones in between. Reggie, thank you. We appreciate you. And congratulations on the$400 million. Thank you, Sophie. It's truly been an honor to have this conversation with you today.

40:10Thank you.