20Sales: Sierra: Inside Silicon Valley's Fastest Growing Sales Machine & How to Prospect, Outbound and Close Enterprise Deals in AI

23:03How has the process been in terms of introducing really a relatively new pricing mechanism to traditional enterprise customers who aren't used to it? This is the most fun I've had as a sales leader in my entire career because I'm selling a business model that people get immediately. They no longer have to pay for the right to use software. They don't pay for seats. They don't pay for consumption. They pay for outcomes. Did our agent solve a problem? Did our agent convert a sale? Did it make the right product recommendation if so we get paid? And oh, by the way, it's a fraction of what you're paying human beings to do this work.

23:37So people get it. We don't charge implementation fees or any integration work. We absorb all of that. So when you partner with Sierra, you're paying for outcomes. You're paying for results. And it's just the fun model that people get. And it's fun to be in the space. And we're creating a brand new category of software where in the way we price it and the way people consume it. It's really fun. And so funny when I was young, you watched an Entrash TV and they would have adverts for lawyers, for car crashes or whatever, insurance stuff. And they would be like, no win, no fee. And you're like, well, great.

24:08And that's when I'm getting money, I'm not paying you. And it's the most obvious win win for the customers. Exactly. The software today, the power of this technology, it actually delivers results so you actually can pay for the results that you receive. Is there a challenge in terms of contention around attribution? And what I mean by that is, say you prevent a turn of a customer. And then one of the CS reps actually goes, well, not really. I actually went for dinner with Reggie last night, and I saved the deal. It wasn't really Sierra doing that work. It was me going for dinner with them on a Saturday evening to reassure them.

24:44How do you think about ambiguity and resolution? It's fairly simple. I mean, it's a fairly simple definition that it's possibly different for each client, but we partner with our clients of what the definition of a resolution is and then how we measure it. And we get alignment with our clients. So we're both fully aligned when we go into a long -term contract. How do you think about the volume of resolutions? In other words, we're 90 % of resolutions or 85 % whatever it is versus we solve the really, really difficult ones. Our vision for all of our clients is to be the front door and the contiers of their experience.

25:19So we can handle the easy stuff, but we can also, where we really, really thrive and shine and excel is the really complex things. Like, for example, if you're a sonos customer and your sonos system stops working, our agent is sophisticated enough to figure out, is it your Wi -Fi? Is it the software on the speaker or is it the hardware? So it's got the ability to handle that kind of complexity. if you're a serious XM customer. Not only can we tell you what station Shade 45, hip -hop music is playing on, but we can also, if your radio stops working in your car, our agent will call the satellite and resend the encryption keys back to your car to get your satellite radio working.

25:55So this technology, it can handle very, very sophisticated things. So our job, our goal is to put, once again, your best sales rep, your best customer service agent in front of your customer's 24 -7. And so that take, then, on outcome -based, ticketing pricing, whatever we want to call it. It must differ dramatically because different customers worth different amounts in different fields. A financial services customer is worth a lot versus in maybe immediate, they're worth less if they churn. How do you think about how you'll take varies by sector? It depends on what the client wants to accomplish, what use cases they want us to handle.

26:28We can customize our outcome -based pricing to fit their needs. We have one customer that actually pays us a commission when we upsell someone's membership or we get paid when we prevent you from cancelling. Some customers we do a revenue share with them on preventing from someone from cancelling their service. So there's different models that we can implement and partner with our clients on, but at the end of the day, once again, people want to pay for outcomes, they don't want to pay for the right to use software, and that's the fun thing about partnering with the Sierra as we can customize our alchem base pricing to meet your needs.

27:00Do you think we will have per seat pricing in three to five years? If I had to look at my crystal ball, not sure. Yeah. The expectations of clients are going to change. And I think outcome -based pricing is to way to catch on to the new way where people really want to pay for results and they don't want to pay for the right to use the software. But I can't predict the future, but if I had to guess, I would say I think that's going to change. Do you think sales teams will get dramatically smaller with the increasing advancement of sales tooling, which means you can bundle so much intelligence into one sales rep that actually you don't need teams of A's, BDRs, SDRs, and actually one is just a superhero that has amazing tooling.

27:39How do you think about how the structure of sales teams change? If I had to look at my crystal ball, I would say sales people are gonna be better and more efficient because they're gonna be using the technology to help them. Work smarter, is it gonna decrease the number of sales people and BDRs and SDRs not really sure yet? I still think there's always gonna be a place for a salesperson in human interaction, but what that looks like in the future, I'm not really sure. Has the way that you lead in sales changed in a world of AI? In terms of the tooling that you use, how you use ChatGPT or any of the models to actually write emails, write monthly updates, write sales forecasts, has how you work changed with AI?

28:17Absolutely. I pretty much stay in ChatGPT all day long. I try to use, and I think our teams, one of our modules at Sierra is use the technology to make the way we operate better. So helping me executive briefings, you used to take hours to do that, now it takes less than a few minutes. Can I ask, I don't know, it's weird, but we have so many people who literally really listen with note pads. What do you put in a prompt for an executive briefing? I'm going to talk to the Nobu collection of hotels. I would just put in there going to meet with XYZ executive. Ed Nobu please tell me about the company, their business, their challenges.

28:54What is this particular executive interest in? And valuation, revenue, and then three minutes later it's got this beautiful executive briefing that used to take me or someone on my team hours to create. It's now taking minutes so that time can be reallocated to do something else. And by the way, this information is really accurate, it's really good. It's unbelievable. Honestly, when I click deep research and then I love it when it goes away and shows you all the different sources and you were just like, wow, I used it the other day for an incredible show that I did and it went back to a show that the guest did in 2017 in French.

29:29Well, that's amazing. And I was like, well, that's better than I could ever have dreamed of. Okay, so we use it for executive briefing. Anything else but it's really cool. I also like the fact that I use it a lot for email. Like I still like writing my own emails but I use it for just making it shorter, more concise, is crafting it, that's another good use case. And then we use it to help with like the way we run our business with some of the forecasting that we do, it's pervasive throughout Slack. Just being able to use the technology to move faster and then take that time and reallocated more to being in front of customers.

30:01But has the way that you sales force change over time. And when you look at today, do you sales force with the error? Still absolutely. Okay, people say that it is a data repository and we just kind of throw the data in and respectfully. I know that that's the insulting thing in some terms. Do you think that the relationship with Salesforce changes with it potentially becoming a data repository that agents just cruel over? Possibly, we still live in Salesforce quite a bit. Yeah, I mean, I just part of my DNA from running our forecast. Did the reps like it? Yeah, I mean, I think if you set clear expectations and then you tell them what information we need to be inputted in there.

30:38And a lot of our team, most sales organizations use Salesforce. If you do it right and you make it simple and easy for people to use people like love using it But we pretty much use it frequently the way we run our business So I want to go back to you joining and your employee number 23 and your toss with building out a sales team correct What were the hardest elements of building out the sales team as Sierra when you joined as employee number 23? Well, when you join a startup when you come from a you know traditional company There's this thing called a pay cut So one of the jobs that one of the challenges I had was convincing...

31:13I've only got significant. Very significant. Convensing highly compensated, super talented people that were successful in other companies to take a pay cut and come join our pirate ship. So Jason Lamkin, a dear friend of mine says, don't do it, it's not possible. A question that I have for you is, are you a unique situation respectfully? Because your brat Taylor and the team is so stellar. If you're like a normal team with great founders, but you're 25, you're 30, whatever, do you think this is a nice, latest system? Well, basically you can get people like you because of who the founders are. The Bretton Clay Factor obviously definitely helps, but I still think it's a startup and there's a lot of uncertainty, a lot of unknown.

31:53And what I sell, I don't sell, I just try to teach people what the vision of where this could go. And in my heart and soul, I believe Sierra is gonna be one of the most important companies in AI. and I tell people that you have an opportunity to be on the ground floor of one of the most important technology companies in the world. And also, this is an opportunity to carry real generational wealth for your family if we execute. And then also, I look at it too, the reason one of the reasons I came is like, I wanna be a legend, man, I wanna be a trailblazer. I wanna help, you know, make Sierra a generational company, and then open up doors for other, you know, minorities to get these kind of opportunities and take these kind of risks.

32:29And I always go back to this quote from Muhammad Ali, If your dreams don't scare you, they're not big enough. So the most important decisions I've made in my career is when it's scary and when it's uncomfortable. If you can convince people to see where potentially this company is going to go, then it's much easier to recruit them. You mentioned generation and wealth there. Often sales reps, teams are suggested to be coin operated, more mercenary than other functions. To what extent do you find sales people? And I know it's Jan on S. So if you give me for it, but it's a podcast, mission driven versus money driven.

33:06It's a great question. That's like the million dollar question about sales. Obviously everyone wants to go into sales. People want to make money because there is unlimited compensation. But I also think people like being part of something special. I think people like being creators and trailblazers and helping to build something. So I think that's an aspect. People love recognition. You get into sales for recognition. But I think also people get into sales because they're intellectually curious. They love how companies make money They want to help these companies be successful So there's a lot of other reasons why people get into sales I also find that a lot of former athletes get into sales like myself.

33:39I was a former. I played college American football And I played no way did you know I was looking at gas I'm still trying to stay in shape But I also think sales professional sales is one of the most competitive things you can do It's wins and losses. It's accountability. It's what have you done for me lately? and I think a lot of people like being in those environments. Because you get rewarded for it. I totally agree with you. Do you think we demonize the money chasing? I think it's great. If you want to make money and you're like, I want to make a lot of money and I'm here to crush it. I'm great, but I think a lot of people go, oh, they're not here for the mission and they're not here to have impact.

34:14Fine. It's quite okay to want to make a lot of money, but I think it's more of what I try to do when I interview people is connect, like what is your why? Like what motivated you every day? Why do you get up and why do you get after it every single day. And what you'll find is not the money, it's what the money can do. It's like providing a better life for your family, sending your kids to college or private school or being able to get on a flight and travel first class. I think it's not just about the cash. It's about what the cash can do. So I always try to connect with people's why and what's motivating them.

34:45I totally get you. I think that's so important. It's a very good addition. When we just go step back in the hiring process, where do you find the best candidates come from. Is it network? Is it outbound? You're very targeted in wanting a specific type of person. Is it from old companies that you've worked with before? Where do you find the best sales talent comes from when you look at who you've hired? Referrals all day long. Really? The best hires I've ever made is either through my network or my colleagues networks or my friends networks. Obviously you're looking for the certain things like intellectual curiosity, Hustle grit proven track record of success, you know energy swag But you want to be able to have someone that knows that someone that can vouch for that person This is a good person.

35:31They're a humble person. They're a great teammate They're gonna come in and add like value to the company So the only way you can really do that is through referrals and completely agree And I also think you can have a short suck at years of experience working with someone and so when someone says like what was Raji for six years He was incredible and hit hit hit and hair versus someone else where I was like I met them and they seemed credible great But six years against someone I really trust who worked with them. It's a no -brainer So we have that referrals is where we get our best candidates from How do we structure hiring processes again?

36:02You had to build out your team We have them in do we first meeting it's all personal second meeting it's about sales How do you structure that process? Well first of all we have a phenomenal recruiting team that's led by this gentleman named Greg Marsh So they usually do the qualification first and then we'll have them talk to one or two of our sales leaders And if there's mutual agreement to move forward then we'll have them come visit our company for half a day Where they do a presentation and they meet senior leadership and then if all that checks out Then I have a one -on -one with that particular candidate the presentation.

36:33Sorry just to dive in there All they about Sierra or they about a company they've worked with before how do you choose which material to give them? It's a general prompt and it's really explained who are you, tell me about your background, you know, walk me through a deal that you closed, and then how do you think about, you know, certain things that we're looking for, we have corporate values that we really hone in on, and we try to evaluate like their craftsmanship, their track record of success, what kind of teammates they're gonna be, how they think about their sales principles, how they execute deals, what's the complexity of the deals that they sold?

37:06And I think if you, throughout that process, you'll figure out if this person's a right fit for the company or not. When someone doesn't get it, what's the most common area where they fall down? Craftsmanship. In what way? It's the way that they show up. It's the way that, you know, are they concise or they compelling in their verbal communication? And I think when someone does a sales presentation, do they have like errors on the slides or the slides formatted correctly? Are they a storyteller? I think you can find out a lot about someone but their craftsmanship by how they prepare for the interview process.

37:37And I think that manifests, Yes, if you're not going to put the time and effort into delivering a really nice presentation, how can I trust you to do that when you actually become part of the company? Spelling in slides is the worst. I see. When I see that on my slide too, and you're like, really? That's what you came up with. Spell check. It's also like, do you just open a chat GPT this now? This is just lazy. I totally agree with you. Do you have hiring panels? We do. Do you find them helpful? Very helpful. I'm very fortunate to work with some incredible sales leaders like Mandy St. ledger, cali -matics, lily -skolnick, leewayfer.

38:12I could go on and on and on. Scott Townsend, Matt Joshi, and these folks have a innate ability to identify talent. So you may be able to fool me and I get happier sometimes, but throughout the process, these are some really sharp evaluators of talent. You're not going to be able to get past these folks. Do you need consensus? Absolutely. Do you not think the best people are often spiky or controversial? So like Inventure, often the best deals or investments are non -obvious and right, which means that three out of five want to do it, but two don't want to do it. In people, do you find consensus -driven decision -making is best?

38:48I think so. Over my, if I look at the statistics of folks that I've taken chances on, it didn't work out. I always go back and look. I remember debating in that room, and there was two people that were like, I'm not sure. And we still did it anyways, and it came back to Vitus. So I think at least now I really rely on the team and we make decisions on consensus. Now, if someone here itself, someone is really passionate and they're an outlier, we'll listen and we'll take that into consideration, but we try our best to do it by consensus. When you review your hiring mistakes, what did you not see most often that you should have seen?

39:21Well, we saw that we saw things, we just overlooked them. What did you see? Crassmanship issues, communication issues. and you overlapped them because they had, they were stronger in certain other areas or someone, they had a great referral that someone I trusted, they gave this person a shot or they were really, really strong at one particular prospecting and at the time, we really focused on that solving that particular problem. But I think you're gutting your instincts and your heart always tells you the truth and you should listen to it. And I think a lot of times, I've had instincts like that person's not gonna make it but let's give them a shot and it's usually you always end up being correct with your initial instinct.

39:59So let's give them a shot, right? Let's do it. And there's two parts where I find really telling of a candidate in terms of how they think, which is salary and title. How do you learn about the candidate from salary and title? So is it bad if I come in and say, I want to be a VP of sales? That's here. What we do is everyone comes in as an individual contributor for a certain period, even if you're in leadership. Like myself included, once again, as I said before, when I started, there was no sales team. So I was in AE, I was an SDR, I was a BDR, took the trash out, I kind of like earned my right to kind of lead his team.

40:33And all of the sales leaders that we brought into Sierra, they came in for a period of time to be an IC. Then that takes humility. I mean, you've got to like master your craft. You've got to learn how to prospect. You've got to learn how to run a deal. You've got to learn how to negotiate a deal. And I think that's important and powerful. So when you do start running a team, you know how to lead your team, especially when this is a brand new category of software, where a new company, so I think it's important for people to come in and kind of earn their leadership. And Michael Jordan says, like, earn your leadership every day.

41:00I still feel like I'm earning my leadership every day. That's just how we approach it. Now, over time, that may change. Do you find it bad then if people all very, very focused on a title? I think so. For a startup, you need to be focused on the mission on building something. And one of the cool things I love about our company, no titles, no egos, everyone's aligned on this mission of building an amazing company, everyone's humble and hardworking. I think that's really important. What about the focus on money, the salary? Hey, listen, Reggie, I know you want me, but I'm a doctor now. And actually, I'm paid like, you know, 250 base.

41:32And you're paying me 175. Like, come on dude, I need you to help me out here. If you have the vision to see that this is gonna be one of the most important companies ever in software and you believe in yourself and you believe in our team and you believe in what we're doing, there is unlimited commission so you can make as much money as you want, but you have to come in and earn that. But once again, I'm looking for mission -driven people that want to help us build something special. but they have to be able to take risks because they can make that pay cut back in commission if they execute, but they have to be able to believe in themselves and see the vision of what we're building.

42:03Don't laugh. It's a bit of a stupid question, but I'm a British and a podcast, so it's kind of within my rights. You said unlimited commission there. If you would have really crushed it as a salesperson at Sierra, really crushed it. How much could one make? Is it like five million dollars? It's quite a bit. It's quite a bit. How about that? I won't get into the specific numbers of what people are making, but I would just say if you have aspirations and you're an A -player and you want to make a ton of money, there's room for you at Sierra to help us build an amazing company make lots of money.

42:33Why do you think athletes make such good sales people? Discipline, work ethic, being part of a team, being coachable, mastering your craft, all those things, just having like a never -can -say -die attitude, holding yourself accountable, I think. All those things that make athletes successful translate well into professional sales. I think it's also like the willingness to do a lot of work for no perceivedly obvious gain. You know what you're in the gym and it's like you can train for a week really hard. There's no gain at all. There's none. Two weeks. Some of the three weeks. And slowly, slowly you start to see the games, but you have to at the start not get anything for it.

43:10That's a hard mindset. Yeah, especially when you start out and you've got a prospect, you've got to build your business from scratch. That goes into like the discipline, the work ethic. I think about Mark Cuban's quote, work like there's someone working 24 hours a day to take it all away from you. You gotta have that mentality as an athlete, and you gotta have that mentality as a professional seller. And I think professional sellers, I consider them athletes. You said they're about kind of learning to run deals. What are the biggest mistakes you see team members or other professionals make when it comes to running a deal while?

43:40What should we watch out for? I think great enterprise sellers are leaders. They're natural leaders. They know how to galvanize like resources to get them excited about working their deal. I think it's listening to your team, directing your team, including like the co -founders and the executives. You're the quarterback of the deal cycle, and I think if you're running a tight deal cycle, you're learning more about the client they know about themselves. You're asking great questions. You're deploying your resources. You're giving them guidance and instruction about your strategy. I think that's how people succeed in enterprise sales.

44:10Should A's be responsible for tomorrow and Gen, or should they be fed by marketing? A .E.'s in my humble opinion should be responsible for their own piped in and I'm going to quote one of my sales leaders Matt Joshi He says pipeline is lifeline. I think marketing can help you BDRs can help you but at the end of the day The sales professional is accountable to generating their own leads. I always say like you know what? It's like ice cream with sprinkles hundreds and thousands. That's like the marketing what they can give you But you need to be doing the ice cream. Do you batch time or do you advise your team members to batch time for for outreach, prospecting, filling pipe, or is it much more natural throughout the week?

44:49No, I think in my home loop, I try to tell my team, put it on your calendar, like it's a customer meeting, put like an hour, two hours a day on your calendar for prospecting. Every Friday, we have like a quote -unquote old school like prospecting blitz where the team will block off a couple of hours, they'll do it together as a team to go out and prospect and try new strategies. Can you just take me to that? What's the prospecting blitz? How do you guys work together in this time? What does that look like? By lunch, because obviously we're a global company, we have folks in here in London, all over the East Coast, Central, West Coast.

45:21And we just pick a time and we'll buy lunch and we'll come up with a theme that everyone will just, they'll come up with a list of what they're gonna target that day. It's more fun because prospecting is hard here. You're getting your teeth kicked in, you're getting rejected. But when you do it as a collective group, it's fun. You kind of exchange war stories, you find out what's working, you share information. and we've been doing that consistently and it actually really works. And people look forward to it. Do you record your sales schools? Not yet. Not yet. Not yet. We're gonna probably invest in some technology to do so.

45:50We haven't done that yet, but in previous roles, obviously, yeah, we used all types of different technology. Did you find it helpful? Understanding what worked, didn't work, the messaging, you could go back over your old schools. Ah, I wasn't so good there and that was where I fell apart. Do you find it or not really? We have emphasized it. Yeah, I think it works. Yeah, I think it works. I would go back even presentations I'm a perfectionist. I'm gonna go back and watch this podcast and see what I did well and not. But I think recording yourself, like it's just helping you master your craft and get better.

46:17So that's when you hear and see yourself. We also add brush, wonderfully helpful. I listened to it after my brilliant editing team who've done it and I'm like, wow, I'm so good. And then I hear the roar and I'm like, oh shit. So yes, I totally get you there. You mentioned that global company team around the world, well done on London, thrilled about the team here. I don't believe that remote sales teams work as efficiently. How do you think about that versus the raw, or of having people in person? We're at an office culture. Right now we have a large office in San Francisco where our corporate headquarters is.

46:48We have a big office in Midtown, Atlanta. And then we obviously just open an office in Soho. We're going to open office in New York. We have an in office culture, I think, being in the office together, collaborating, sharing information. I think it's really important. It builds community, it builds culture. Now, we do have offices that, or people that work from home that don't live in those major cities, but I bring the sales team together once a month. Oh, wow. Yeah, and we do team building, we do a customer event, and then we do, like, some training, some enablement. But I try my best as we get bigger and bigger, and we have a more dispersed team to get everybody together so they can meet their teammates, they can build relationships, they can collaborate and share information.

47:28And I think it's the power of having a strong sales culture is when people like know each to each other, trust each other and they collaborate. So you've hired me, right? I've finally found Game From Employment after a decade, my mother will be thrilled. I love for you to come over to me. That's very kind of you. I do care about salary. I'm not taking a pick on. On the big commission, that's so kind of you. I'm not that good of salary. My question to you is, when you think about knowing how good someone is quickly, how quickly do you know if I'm good versus I made a mess high? Within a few weeks.

47:59Is it really? Yeah, within a few weeks. And then we have a certification process that you have to go through and you have to present. What is my first week? Like, first week we usually have all of our new hires come out to San Francisco and we have a curated first week where you kind of go through some of the boot camp where you learn about like our sales process, our technology, our platform, our products, our sales process. You also learn like the technology. We have like a, we call it an agent boot camp where you kind of learn how to build an agent. So it's a first week. You get a chance to meet the team, meet the co -founders, meet the entire, everybody in San Francisco.

48:29It's a good vibe. We do some team building and then within a few weeks we actually have you certify Present to us the first call deck and I think after a couple weeks You know if you've made a hiring mistake or if someone's good when you've made a hiring mistake What does show up in other words? What are the signals that then all to get fit? I was go back to the same guess for I'm ready to go Harry cross -smanship Craftsmanship and you see that pretty clearly very clearly It's it's something we truly believe in at Sierra's craftsmanship the way you show up the way you prepare the way you communicate the way you show up the customer meetings, the way you engage with clients, your teammates.

49:03How quickly do you get my own tools with customers? First week. Really? Yeah, actually, you're not going to run a call, but we'll have you shadow teammates. And what's really cool is our co -found, Bretton Clay, they heavily involved in meeting with customers. So they get a chance to see how Bretton Clay and a rack of clients, how I do it, how our sales leaders like Manion Kylie do it, how our solutions engineers do it. So they get a wide variety of different people. And then within a few weeks, they certify and they're off and running. But we're trying to hire the best town in the world. So a lot of these folks have great instincts.

49:35They just need to learn how to sell our products. I totally get you, but it's still pretty cool to have that exposure to see a founder sell as early in your journey as that. So that's amazing. So fantastic. Can I ask you then, when we have these deal cycles and we're in a team setting, how do we do post mortems? What do they look like? How are they structured? It's a difficult thing to do well. Yeah, they're pretty impromptu. We always usually collaborate immediately after calls whether they went well or they will do it in real time real time Gochis real time whether if we're in person into in person me We'll just huddle right after or if it's a virtual We'll just jump on a slack huddle and do it But we do it quick and we provide each other feedback good bad and ugly and it's two way It's not like sales leadership is giving you feedback.

50:17You're also giving us feedback Hey, Reggie didn't like how you position that you know next time do it this way It's a total team effort and we share. Do you have any lessons? I find this hard actually as a leader's day. Do you have any lessons in how to give feedback that's hard, but in a way that doesn't discourage some moving forwards and kind of make sure they leave in spot with their head up? Yeah, so it starts off with, I think, the leadership style in your principle. So I start off with, I'm open, I'm honest, I'm transparent, I lead from the front, I treat people with respect, I would never ask someone to do something, I wouldn't do myself.

50:48But I also have high expectations and I'm very clear about what's expected. So I think if you lead with that type of energy, people know what to expect. So I think delivering feedback, because you're doing it quite often, is pretty easy. As long as you're respectful, but you're honest, and you also are open to receiving feedback, people will accept your feedback, and they'll also listen and action your feedback. If you're willing, you do it in a respectful way, but you're also open to getting feedback back. I get lots of feedback, not only from my colleagues, but also my wife and my children. your wife is always right, is the answer.

51:22Just never ever push back on that one. I'm sorry. Listen, I'm so sorry, Reggie. The deal just fell through. I wasn't expecting it, or it slipped to next quarter. I'm sorry, dude. It happens a lot. I've said on many boards where big deals, they just slipped to next quarter. What do we say as a sales leader, or me as a board member, when I hear it slipped to next quarter? I have the mantra of good news, And I got this from one of my mentors, Scottie Warren Wick, who's a superstar at Salesforce, learned a lot from him. He says, good news should travel fast, bad news should travel faster. And what I try to do is create an environment where people feel okay telling the truth and letting us know in advance if there's an issue, so we can also jump in the boat and try to help them, salvage a deal from slipping.

52:07But when it does slip, we just want to understand how it happened, what can we do differently, so it doesn't happen again. It's not like to beat someone up, it's just to learn. Is there something wrong with the product? Is something wrong with your approach? Something wrong with our process? What can we learn from this? So what doesn't happen again? We mentioned running deals, and then you said about negotiating deals, and negotiating is where deals can slip, and where deals can not happen. What are your biggest lessons on how to, and how not to negotiate large enterprise deals? That's great. There's different variations of enterprise sales negotiations, but it really comes back to, are you delivering value?

52:43Are you solving a problem? Are you talking to the right people? Have you done your homework? Have you built business value in or a return on investments of the client and see the technology they're investing and what are they gonna get out of it? And then are you talking to the right people? Are you leveraging the power of Sierra? Are you getting me involved? Are you getting Elliot Greenwald? Are co -founders involved? Like are you loading up the boat to make sure you have the right people helping you negotiate these deals? Where are you weak? Does someone else better at like negotiating like the financial structure of the deal?

53:13But let's get them in the boat with you. So do we need to get our general counsel, Jonathan Milar to involve? Like, you as all the resources, all these talented people to help you get your deal across, but just know where your strengths and weaknesses are and then know where to fill those gaps. What's an acceptable reason to lose a deal? What's an unacceptable reason? Unacceptable reason is you're not talking to the right people. You didn't deliver value or it was a craftsmanship issue where we didn't follow up on something, we didn't do something right. We didn't control the controllables. What I think where it's out of our control, like there's some type of financial issue with the company, there's some companies IPOing, they're not buying anything new from that three months while they're going through right today.

53:51Pandemic, whatever it may be. Like I think those are things that are out of our control, but what I can accept is you did not execute the controls. You didn't leverage the power of Sierra, you didn't get the right people involved in your deal. I can't accept that. I totally agree with you there. What's the hardest thing for you to stay about being a sales leader? There's so many challenging elements. There's so many shifting parts. What's the hard part today? Right now, we are in hyper growth stage. We have right product, right time, incredible co -founders. We've got really talented smart people.

54:22We have a product that delivers the best quality agents. So we have a tremendous amount of demand and we're growing fast. My challenge is hiring, hiring fast, hiring smart, maintaining the awesome sales culture that we've created. A lot of founders ask me, they go, hey Harry, I know everyone says, oh wait till you get that perfect heart. I need bumps on seats. I need to hit targets Harry. It's a luxury to wait for the perfect higher. What would you say to them? I would say if you hire fast and you don't hire smart you end up having to fire fast. I don't want to use the word fire but usually have an issue.

54:56So I think you have to be measured. You have to be aggressive and you have to move with urgency but you need to be smart about it because I think hiring the wrong people causes more problems than it's worth. So I think just being Being aggressive, but being measured and doing it smart. How do sales cultures break down in hypergrowth? You've seen huge scale sales teams across different organizations. Now you're scaling one in real time fast. What cracks could appear that you're aware of and looking out for? I think it's making sure people are part of an environment where they feel trusted, they feel respected, they feel supported, they know who their teammates are, they know where to go to get things done.

55:37when they are supported and ramped up fast, I think if you bring people on, and there's no structure there, there's no environment, there's no support, there's no help, I think that causes problems. I think if you don't really focus on building like a culture and building a really strong team, I think people feel isolated and disconnected. So those are two things that I really focus on is one, hiring the right people, and then creating a really positive environment where they feel trusted, supported, and they feel like they have the support they need to be successful. What do you advise on competition?

56:06You do have competitors, every space does, as well as something, or any. How do you advise founders on how to think about competition? And also just how to message about competition in sales cycles. We are in an ultra competitive environment. We're competing with big tech, we're competing with startups, we're competing with, I can build this myself, we're competing with, I'm too scared to put AI in front of my customers, so there's lots of competition, but I just think it is make basically understanding your message, understanding how to combat what your competitor is going to throw against you.

56:36Understanding your competition, respecting your competition, don't take your competition for granted, but know your strengths of how you can beat your competition and just making sure your team is enabled on that. And not don't be scared to compete. I love to compete. I love waking up every day, knowing that every client that I'm chasing someone else is chasing that client too. And I need to show up better, stronger, faster, more craftsmanship. Make sure my I brought, you know, we have an awesome product to sell. So that's kind of how I think about competition. I love it. It's always gonna be there, especially in AI, but just understanding your competition, respect your competition, and know how to sell against them.

57:09Which compassage you respect the most? I respect all competitors. I don't take anyone for granted. You don't. Do not. All these competitors we're competing with, by the way, they all have strengths. So we need to respect those strengths and just be aware of that and not be scared to compete, but I respect all the competitors out there. I'm gonna push you. But not a name, because names with tough and tricky don't want to be basically black. Do you think incumbents with distribution are more threatening than startups with speed and agility? I know this is like a vague answer. I think they're both incredibly formidable.

57:41Startups, they're unique, they're fast, they're nimble, they're aggressive, and the large incumbents, you know, the big tech companies, they have scale, they have marketing muscle, they have massive distribution, they have strong, powerful customer relationships, their respected brands, so their former will just like the start -up store. Dude, I could touch you all day. I'd love to move into a quick fire. I'd say, shoot a statement, you give me your immediate thoughts. So that's not okay. Let's do it. What sales tactic has not changed over the last five years? Prospecting. Going out, generating interest, getting meetings, and I call that corporate swag, having the ability to get a busy, important person to give you 30 minutes of their time that they don't have.

58:22That's never gonna change. You mentioned co -cool in the earlier. Do you actually co -cool? Yeah, absolutely. It's a combination of emails, phone calls, messaging on social media, but also inviting people to events. Does that work well? I think so. Yeah. What has died a death? A lot of the administrative tasks have changed because of the power of technology like chat, ept, building executive briefs. I think that's changed. I could do that in three minutes now versus spending hours creating stuff like that. I think a lot of the administrative tasks have changed with automation. And I think if people aren't taking advantage of the technology that are disadvantaged.

58:58Which I think is great because it just means you have so much more time to be creative and think about how you can prove your differentiation in a more creative way. Do you know what I mean? For some prospect. Yeah, like briefing, like it's not that creative in many ways. So I told you, talk to me about a deal you've closed where you've had to do something. I love this one. Out of the box, creative to get it over the line. I'll think about this company, one of the largest IT companies in the world. And one of my colleagues, one of the best sales professionals I've ever worked with Mandy St. Ledger and I worked together along with Brett and this guy named Andy Kofoy to close a deal when we were at Salesforce.

59:33They were Microsoft's number one reseller, which usually means that they have to buy Microsoft's technology. So we were in a very, very competitive environment and what we did unique was we sold the vision of creating their own SI practice where they could resell Salesforce and be an implementation partner which is high revenue, high margin. And that was how we were able to navigate the Microsoft reseller compete. And they saw the vision not only was our, at the time, you know, I felt our technology platform was better, but we also had this unique way that they could be a partner, not just a vendor relationship where they can actually resell Salesforce and add value there.

1:00:11So that was a pretty unique approach that we took and it was very successful. It was a fun deal to work. Wow. Is that the biggest deal that you've worked on? At Salesforce, yes, but I think based on the power of what we can do for clients at Sierra, I'm hopeful that we'll have much bigger transactions with AI. I'm sure you want my friend. What one piece of advice would you give to a sales leader starting a new role today? I'm starting tomorrow in my new position, named the company. What would you say to me? I would ask you, or the advice I'd give you are three things. higher the right people, build a powerful culture where people feel trusted, respected, and they love coming to work.

1:00:46And then three lead from the front. Be willing to get your hands dirty, be willing to jump in and work deals, and not lead from a glass tower, but lead from being the trenches with your team. How do you maintain morale when it goes amiss? It's really hard. You have that team meeting, and people are deflated if something hasn't gone. How do you maintain morale? What I do is I focus on inspirational leadership, making sure people always stay connected to their why, like what gets them out of the bed every day, why they showing up to work, why are they in sales? And it's usually something, some type of financial thing or it's something with their family or something personal where they want recognition or to advance their career.

1:01:22So I keep people connected to their why through tough times and I come up with the motivational quote every week. You're very good with quotes. Thank you. Thank you. So I think it's important actually, because in a lot of times you kind of draw on them. Yeah, and I think the sales leader is critically important because you're the only thing between the sale, the sales professional and the fire. And the fire is the rejection, you know, the tough part of being in sales. And it's your responsibility not only to be in the fire with them, but to keep them motivated to continue to run out into the fire.

1:01:52What's your favorite quote? I have a lot of great quotes. This is a quote that I found that I used this week and it's from, I don't know if you're into American basketball. The quote is, no one ever loses it anything as long as they don't quit. It's from the head coach of the Houston Cougars, Kelvin Samson, I don't know if you watched. They played Duke University on Saturday night in the first game of the final four. Duke bigger, stronger, more talented team, three of their guys and their starting five are all going to be NBA lottery picks. Houston was down like 15 points late in the game. I turned it off.

1:02:24Everyone thought that they were going to lose. But what this coach did was he instilled grit, hustle, griminess into their culture, never quitting. and they, oh, they battled back and they actually beat Duke, who was the favorite in one of the game. And I just, that quote really resonated with me. No one ever loses at anything as long as they don't quit. That's what you gotta have in sales. I totally agree. I love a general abnormal craven, which is the guy who says always make your bed in the morning. And if you've seen this video, it's probably one of the best ones. I have seen that. And he's never ringing the bell, which is exactly that.

1:02:56Never quit, essentially. Totally. I'll give you one more. I got this from my dad. my dad was a 30 year full coronally US Army 82nd Airborne Army Ranger Green Bray and one of the things that he embedded in my DNA's failure is not an option. If you're going to be part of this marital family failure is not an option. So I learned that that's kind of how I approached life. He's not put some necessary pressure on children. No, it just sets expectations. And I go back to Nelson Mandela. I never lose. I either win or learn. So when he was teaching us that it's like you're gonna fail but don't quit, figure out what you did wrong, how you can get better, but the overall failure of quitting, that's failure, is giving up and that's something that we don't do as marbles.

1:03:39Love that. Final one, what one company sales strategy have you been most impressed by recently? Have you been like, that was small other than Sierra? Can't be Sierra. If you wanna do a Sierra and it's granular. I love the fact that we allow our potential clients to test out our technology before they make a long -term commitment. I love that model. It forces us to be on top of our A game at all times and deliver results before you know customers make a long -term investment in us. So it gives you the opportunity to earn your keep, earn your value and demonstrate the power of what we can do and I love that model.

1:04:14I'm not saying that because I work at Sierra, it's just you get to compete every day. You get to compete and show customers the value that you can deliver. I totally agree. The other reduces the risk for them. It reduces so much of the burden on them. I totally agree. Reggie, I so appreciate you taking the time. I'm thrilled that we could do it in person. As I said, I spoke to so many, Larry, Frank, we mentioned Danny, so you've been amazing and thank you for joining me, man. I guess the bucket list more and especially live from London too. BELL RINGS My word, it was so great to have Reggie in the studio there in London.

1:04:43I'm so grateful to get to do these shows and meet just the best operators in their verticals. I hope you enjoyed the show. Let me know on Twitter at Harry's Debbings. But before we leave you today, If you're ready to leave rigid payment terms behind, capchase is here to change the game. Capchase brings B2C buying convenience to B2B software and hardware purchases. Capchase offers your buyers the flexibility they demand on annual and multi -year contracts. While you get paid up front every time, this means faster closings, higher deal sizes and a streamlined process without the hassle of discountual collections.

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1:07:10As always I so appreciate all your support and stay tuned for an incredible episode coming on Monday next week. We have an exclusive, a very special news announcement.