Listen on YouTube // Apple // Spotify

Thank you to our sponsor partner:

Building software has never been easier. Selling has never been harder. And the CRM was built for a world before AI.

Zero is the go-to-market operating system that replaces your CRM and the tools around it. Its AI agents prospect, follow up, update your deals and flag accounts at risk. Your team spends the day selling.

If you’re a founder about to make your first GTM hire, start here. And if you’re already on something else, just drop in your data. One YC company moved over in three clicks.

Customers close 2x more new business with a third fewer sales hires. GTMnow listeners get 30 days free at https://zero.inc/gtmnow

Who you’ll learn from

Sierra just passed $400M in ARR, adding $150M in Q3 alone – they went 0 to $400M in 2.5 years. When it came out of stealth in February 2024, it had zero long-term contracts. It hit $20M by October, doubled from $100M to $200M in six months, then doubled again to $400M in five. Reggie Marable, Sierra’s Chief Customer Officer and first sales hire (employee 23), joins GTMnow to break down exactly how.

Reggie joined in January 2024 after leadership roles at Salesforce and Slack, a month before Sierra came out of stealth. He walks through the whole run: taking a big pay cut to bet on founders Bret Taylor and Clay Bavor, the outcome-based pricing model where Sierra only gets paid when its AI agents actually resolve an issue, the paid proof-of-concept plus forward-deployed engineering motion, how he hired his “Elite Eight” first sellers, why every single person at Sierra is in sales, and his counterintuitive advice for founders making their first sales hire.

Episode highlights

0:56 – Welcome, the $400M milestone, and the Double Denim tradition

2:28 – Joining as employee 23 after Salesforce and Slack

4:17 – The conversation with his wife, and anchoring on the “why”

6:14 – What Sierra does, and outcome-based pricing explained

8:22 – Why outcome-based pricing was a bold bet in 2024

9:46 – Board meetings every six weeks, and Bret Taylor’s OpenAI role

10:49 – The founder-to-first-sales-hire transition, and why everyone is in sales

12:23 – How selling scales at 1,200+ employees

13:06 – Shifting from Head of Sales to Chief Customer Officer

14:21 – From pre-revenue to $20M in the launch year

16:24 – Sponsor break

17:07 – The selling motion: paid POC and forward-deployed engineering

19:59 – The next growth chapter: scale, voice, and innovation

20:55 – Organizing the go-to-market around industries

22:14 – The biggest industries Sierra serves, and expanding into government

22:45 – The growth curve: doubling $100M to $200M to $400M

26:09 – What Reggie looks for when hiring sellers

27:36 – How to measure intellectual curiosity, and hiring by consensus

28:37 – Tracking pipeline in an outcome-based model

30:21 – The biggest unlock and mistake AI startups make selling to enterprise

32:28 – The “Elite Eight” framework for first sales hires

33:29 – Finish the sentence: the thing nobody tells you about leadership

34:48 – The most underrated go-to-market advice

35:54 – The best advice he ever received

36:49 – The future of customer service jobs and AI architects

39:20 – Where to find Reggie

Key takeaways

1. The scary bet is usually the right one.

Reggie left Salesforce and Slack to join Sierra as employee #23 and its first sales hire, at a “tremendous pay cut.” He bet on four things: humble, brilliant founders (Bret Taylor and Clay Bavor), a market he thinks will be bigger than the internet, the chance to build a generational company, and opening doors for other minorities. “If your dreams don’t scare you, they’re not big enough.”

2. Charge for outcomes, not seats.

Sierra only gets paid when its AI agent resolves an issue or completes a task with no human help. If the case escalates or the customer calls back, it’s free. “You hire Sierra to do a job. If we do our job well, we get paid.” It was radical in 2024, and the industry is following now.

3. A paid pilot plus forward-deployed engineers, then scale.

Sierra builds a demo, then runs a paid proof of concept for one to four months. A dedicated team builds the agent, tests it on simulated traffic, then raises live traffic from 5% upward. Those engineers stay with the account for life. Results: $100M to $200M ARR in six months, $200M to $400M in five, and $150M in a single quarter.

4. Everyone sells, and everyone is organized by industry.

The founders never stopped selling, so the company was never bottlenecked on founder-led sales. Sales, product and engineering are all organized around industries such as financial services, healthcare and retail, so reps show up as advisors with a real point of view.

5. Hire elite people willing to step back, and keep the fundamentals.

His first eight sales hires, the “Elite Eight,” were senior leaders who agreed to carry a quota again. Each candidate is screened by about seven interviewers, because “it’s hard to fool seven people.” And the fundamentals don’t change: “selling water, selling AI agents” is still prospecting, pipeline and grit. His parents’ advice, in Steve Martin’s words: “be so good, they can’t ignore you.”

Reggie Marable

Sophie Buonassisi (Host)

The GTMnow Newsletter (by GTMfund)
GTMnow merges go-to-market strategy, venture capital and media.
Build, scale and invest with the best minds in tech.

The media brand of VC firm, GTMfund – sharing the how and who behind company growth.

GTMnow

The GTMnow Podcast – subscribe to support

It would mean the world to us if you subscribe to the show on your platform of choice. This helps support our growth, which in turn helps us continuously bring on bigger guests and deliver the content that you want to hear most.

Subscribe on YouTube

Subscribe on Apple

Subscribe on Spotify

The GTMnow Podcast shares how the best in tech build, scale and invest.

Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.

The media brand, GTMnow, shares how the best companies get built, told from every perspective: founders, operators and investors, at every stage of company building. GTMnow is owned and operated by VC firm, GTMfund.

GTM 213 Full Episode Transcript

00:00 – 00:04

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

00:04 – 00:08

Sophie Buonassisi: Reggie Marable, Chief Customer Officer at Sierra. He was the first sales hire.

00:08 – 00:26

Reggie Marable: 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 just this quarter alone. I remember sitting right here when they gave me the offer, and it was a tremendous pay cut. And my wife was like, are you insane? What are you doing?

00:27 – 00:30

Sophie Buonassisi: What did that founder of sales Hire Transition look like?

00:30 – 00:38

Reggie Marable: 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.

00:39 – 00:42

Sophie Buonassisi: How are we growing at such a crazy pace?

00:56 – 00:58

Sophie Buonassisi: Reggie, welcome to GTM now.

00:58 – 01:03

Reggie Marable: Awesome. It’s exciting to be here. Really appreciate you having me on this incredible podcast today.

01:04 – 01:17

Sophie Buonassisi: Absolutely. And you come bearing exciting news. Sierra just surpassed 400 million IRR, adding more than 150 million in Q3 alone. So first, a huge congratulations. Are you and the team doing anything to celebrate?

01:17 – 01:57

Reggie Marable: Yeah, actually this is we do a big thing for for end of quarter clothes. We get everyone together in the respective offices and you kind of do a big party, big celebration. This one is incredibly exciting because we’re we just surpassed 400 million. And then we did 150 million in RR just this quarter alone. And 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 a great day for Sierra, a great moment, and it’s really exciting that I’m on this podcast to share this amazing news.

01:57 – 02:05

Sophie Buonassisi: 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.

02:05 – 02:28

Reggie Marable: Yeah, yeah, double denim. I’m a little bit out of at a costume today, but yeah, it’s double denim and we use that to close the the quarter. And this was started by Logan Randolph and Natasha Claire a 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. Uh, denim, uh, when we close the quarter.

02:28 – 02:58

Sophie Buonassisi: Big milestone. Very exciting. We’re going to dissect how you hit this milestone and how you’re doing so while growth is accelerating. 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 at 110 million raised from Sequoia and Benchmark. So when you joined, was there any kind of revenue? What was the state of affairs.

02:58 – 04:17

Reggie Marable: 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 was an incredible friend mentor at Salesforce for eight years. Never imagine I never worked for a startup, but, um, I just 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 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, um, 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. But 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, but we hadn’t converted anyone to a long term contract just yet. So right when we came out of stealth, um, we were very, very early believe we had like seven design customers, but we hadn’t really started to scale and prospect and look for new business just yet.

04:17 – 04:35

Sophie Buonassisi: Very cool. And that conversation with a partner around going to the startup space or starting a company is, 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.

04:35 – 06:14

Reggie Marable: Yeah, I would say with for me, I just anchored on the why. Like why would I, 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. And 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, like, incredible people and build a generational company from the ground up, which 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 in, 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, but 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.

06:14 – 06:20

Sophie Buonassisi: That is great advice and for anyone unfamiliar. Can you just quickly explain what Sierra does in very simple terms.

06:20 – 06:31

Reggie Marable: And very simple terms? Sierra makes customer facing AI agents that help our clients power their customer experience and also help drive revenue.

06:31 – 06:43

Sophie Buonassisi: 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 results in issue. Is that correct?

06:43 – 08:22

Reggie Marable: And first of all, SoFi, 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, we 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 and we improve and elevate the customer experience. Yeah. So what’s really cool about what we 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 in business outcomes. So 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 it 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. That’s a completely new business model. Our clients pay for business outcomes and results.

08:22 – 08:33

Sophie Buonassisi: 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?

08:33 – 09:46

Reggie Marable: So 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 um, has been like, shockingly, I didn’t realize how fast this place moved, and I think of AI in terms of a day as a week. A week is a month, a month is a year, and a year is ten years in this space. So that’s 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, well, 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, Ali, 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, you 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.

09:46 – 09:55

Sophie Buonassisi: 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?

09:55 – 10:49

Reggie Marable: Brett keeps his engagement with OpenAI completely separate from from his work at, at, uh, 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 I’m 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. And they put in efforts into understanding what’s happening in the space, talking to customers like, I think our founders, they they’re running multiple customer meetings a day. So they’re talking to early stage customers or 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.

10:49 – 11:15

Sophie Buonassisi: 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 or sales higher transition look like? That’s a very common question that a lot of startups ask and also grapple with getting right.

11:16 – 12:23

Reggie Marable: 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 sales higher, that I’m like taking the reins from Fred, that that’s not what happened. Brett is still involved in sales. Clay is involved in sales. I’m involved in sales. When I joined, um, my onboarding buddy was this guy named Logan Randolph, who is now our head of expansion. Logan onboarded me, and and he and I were in sales. So what’s cool about Sierra is there. There is never a point of handing the reins off. Everyone is here. Everyone adheres 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 is involved in sales. So when I came on, my role was to like just continue to add more horsepower, but then build out a team so we can start like taking on more customers and having more customer conversations. But everybody at Sierra is in sales.

12:23 – 12:28

Sophie Buonassisi: Is that challenging as you scale? What is Sierra at now? How does that scale with volume?

12:28 – 13:06

Reggie Marable: Yeah, we have over 1200 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, I consider he’s involved in a ton of customer engagement. 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. So 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’s.

13:06 – 13:25

Sophie Buonassisi: 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? And what’s the customer ownership?

13:26 – 14:21

Reggie Marable: Yeah. So once again, my first chapter was was building, leading and scaling the the sales organization. And then about two months ago, our founders and then Eric Aiken sliders, 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 your in a proof of concept. So you are a customer to you know we’re expanding and growing with you. Um so this role gives our leadership team leverage and scale once again right now. Um, 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, um, continue to grow as we add more sellers, as we add more customers. My role is to help ensure they get the full power of their investment.

14:21 – 14:48

Sophie Buonassisi: Well, let’s dive into a couple of the growth moves that helped you go from pre revenue essentially to $400 million in IRR. 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 revenue the year you launched?

14:48 – 16:24

Reggie Marable: 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. And it gives us an opportunity to prove ourselves and a proof of concept. The third thing is we have a great business model where our clients we only charge when our agents successfully resolve, you know, 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 a proof 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, and 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 and the client’s business and can add tremendous value. And then the last thing is we we just we hired some incredible sellers. Uh, we hired, uh, 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 were some of the best sellers in the world. Uh, so 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. You mix all that all together. That’s how you grow a company.

16:24 – 16:34

Sophie Buonassisi: 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 for deployed engineer combination.

16:34 – 18:53

Reggie Marable: Obviously you have to, you know, generate interest. And then once we do some discovery, then we’ll build like a, um, 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 handle the, you know, the 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. So in that proof of concept, that’s when we assign the dedicated team of AI experts. And then the proof of concept will pick maybe 3 or 4 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. And 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 hard and 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, will do a PLC for a couple of weeks. And they’re ready. They’ve seen enough where they’re ready to in turn 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, the 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. What are your customers asking for? What are 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. They says it’s doing everything that they say they’re going to do. There’s a clear ROI and 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. It’s an incredibly high conversion rate.

18:53 – 19:17

Sophie Buonassisi: That’s amazing. I mean, that’s great to have the ability to actually go in and 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?

19:17 – 20:13

Reggie Marable: 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. And 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 we 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 know, you add all that all that together. More people, incredible talent, incredible platform that’s innovating, continuing to hone and tighten up your motion. That’s just putting gasoline on what you’ve already built.

20:13 – 20:16

Sophie Buonassisi: And as you scale the sales team, how do you organize it?

20:16 – 21:32

Reggie Marable: 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 health care, 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 Asian development team, our sales team, our marketing, our product, our everything that we do is built around industries. So 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 clients 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.

21:32 – 21:36

Sophie Buonassisi: That completely makes sense. What are the biggest industries that you serve?

21:36 – 22:04

Reggie Marable: Yeah. So financial services, healthcare, retail, media, travel, tourism, hospitality, telecom and in 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.

22:04 – 22:41

Sophie Buonassisi: So that’s how key areas that helped skyrocket your growth is. About November 2025, you guys announced 100 million IRR, and that was only seven quarters after launch. So about five X in 13 months, which is incredible. Fast forward to February 2026 at over 150 million IRR, first 50 million quarters. 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 AR to 200 million, and then only five months to double from 200 to 400 million IRR. Like, how are we growing at such a crazy pace?

22:41 – 25:28

Reggie Marable: Yeah, it just goes back to the the key elements that I allude to before. It’s one continuing to scale, you know, hiring more sellers, hiring more agent development teammates. That’s like that’s like one of our secret sources is is the people. Um, the second is we expanded internationally. So we are now operating in 60 markets. We have a pretty large operation in Europe, in Asia pack. So we’re expanding internationally, which is also helping to contribute to our growth in 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 over seven. Um, and then we continue to invest heavily in putting more AI innovation into the platform to provide like 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, um, platform called pinecone, which essentially is leveraging all types of different, uh, large language models. It’s using some of our own fine tuned models. It’s tapped into all of our systems of record. So it’s if I’m a seller, it’s helping me sell faster. I’ll have my own chief of staff. I’m able to sell ten times faster. It’s helping me with strategic prospecting, with meeting prep. It’s helping me get my MBA faster in my industry and my clients 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. So you add that with having more people, incredible talent, incredible innovation, and then we’re expanding internationally that those are just some of the ways that we’re able to to, 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 you’ve been able, that’s how we’ve been able to grow.

25:28 – 25:35

Sophie Buonassisi: You mentioned people being a core part of that sellers high quality. What are you looking for when you’re hiring?

25:35 – 26:26

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

26:26 – 26:39

Sophie Buonassisi: I love that we talk about that a lot internally. Also at GTM fund, you know, big the number one criteria for the community, the above operating experience is good human. And then of course get into the specifics.

26:39 – 26:54

Reggie Marable: We’ve had a great, great success with hiring firm 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 to really build talent that are just humble, like hardworking, nice people.

26:54 – 26:58

Sophie Buonassisi: How do you measure things like intellectual curiosity when you’re in an interview process?

26:58 – 27:56

Reggie Marable: Yeah, we have a we have a pretty detailed interview process. So 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. Um, 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, um, 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. Got it. It’s, um, and we try to have our folks come on site so we can meet them in person. Um, and then we 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. So there’s there’s like 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 the right fit for your company. And that’s something that we do really well here.

27:56 – 28:09

Sophie Buonassisi: 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?

28:09 – 29:39

Reggie Marable: 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 getting me prospecting, getting meetings, creating pipeline and then tracking like, are you executing, converting that pipeline into actual POCs. And or you can bring those pieces 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. We track meetings, we track Pi Generation, we track POCs. Those are leading indicators into the success of a seller at Sierra. So it’s a little different and unfortunate. I can’t share like the exact metrics that we use to how much pipelines today’s 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. They know the clients business of the industry. They can add value. That’s not going to change. Um, 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.

29:39 – 29:53

Sophie Buonassisi: 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?

29:53 – 31:13

Reggie Marable: 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 an individual contributor carrying a bag my first few months at Sierra, but 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 Saint Leger, 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. Um, and 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.

31:13 – 31:15

Sophie Buonassisi: Yeah, that’s really good advice.

31:15 – 31:46

Reggie Marable: 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 a year, everyone is in sales. So that 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, help and close deals.

31:46 – 32:00

Sophie Buonassisi: Love it. And you mentioned elite eight verse 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?

32:01 – 32:04

Reggie Marable: I’ll give my soul credit. I came up with the Elite Eight because I love.

32:04 – 32:05

Sophie Buonassisi: Basketball.

32:05 – 32:48

Reggie Marable: Love it. I love basketball and football. And I was trying to find like, I knew we were going to hire eight sellers and I was trying to find like an acronym. And, you know, in, 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. So 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 the 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 the on their success.

32:48 – 33:00

Sophie Buonassisi: Completely make 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.

33:00 – 34:06

Reggie Marable: I think people get into leadership for the wrong reasons. They think that they’re to be a boss, to be like, it’s a, you know, 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 doctor, 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, a great leader, 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 the most if you can think about the best leaders you’ve ever worked for, worked with are the folks that put themselves. They 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.

34:06 – 34:12

Sophie Buonassisi: Beautiful. And help us finish this sentence. The most underrated piece of go to market advice is.

34:12 – 34:29

Reggie Marable: 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 selves to work. It’s creating a

34:30 – 35:13

Reggie Marable: 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, and they take care of the ones that we have CRO, 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 like is is noise, it’s fluff. If you. You need to focus on those things when you when you build a go to market team, it’s everything that I just said.

35:13 – 35:24

Sophie Buonassisi: 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?

35:24 – 36:07

Reggie Marable: The best advice that I’ve ever received is from my parents. My dad would serve 30 years in the US 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. Um, and 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 of what you do. And I learned that from my parents.

36:07 – 36:19

Sophie Buonassisi: Now, last question for you here, Reggie. Forward looking. We think about customer service as a category. Overall. How many of today’s human customer service jobs will exist in say, five years?

36:19 – 38:38

Reggie Marable: It’s a great question. I don’t 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 the customer service rep didn’t want to do anyways. And that’s being handled by AI, but 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 Sirius XM. 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. And 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, you know, 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 calling our we’re basically building the protocol to manage how you interact with the personal agent. We’re calling it Poppy. It’s the 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? Um, so we’re really working on that protocol because I do think there’s going to be a wave of, 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. But to answer your question, I have no idea. But I’m excited. I think it’s going to create new jobs.

38:38 – 38:44

Sophie Buonassisi: 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?

38:44 – 39:08

Reggie Marable: Yeah, I can find me on LinkedIn. I’m big on LinkedIn if and also Sierra’s on LinkedIn as well. I actually also to Sophy 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.

39:08 – 39:19

Sophie Buonassisi: 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 and honor 400 million.

39:19 – 39:23

Reggie Marable: Thank you Sophie. It’s truly been an honor to have this conversation with you today.