Three Reasons Why Sales People Fail

Yeah. I just kinda wandered into it, to be honest. Probably not too dissimilar from some of the other folks that you talked to that ended up at Dropbox at some point. I actually started in the wine industry, so I grew up in the middle of nowhere. I was able to go to college because I got a scholarship at a winery called Gallo Winery. So they offered me a scholarship and I had to work there for a year at school, and I ended up working there for three years.

And now it’s just kind of like a party trick that I know a little bit about wine, but back then it was a great place to start the career. My wife told me there’s no way she wanted to live in the country with me, so she made me move to San Francisco, and it’s hard to be in San Francisco and not be in tech. So I ended up at Dropbox maybe back in the early two thousand tens. From there, it’s just been an amazing experience.

Oh, yeah. Well, it’s a really amazing first year out of school job because one day you’re selling to grocery store managers, and the next day, I had this job where I was selling to US senators about the importance of why farmers are the most environmentally conscious people on earth. So you get this, like, insanely wide ranging group of people that you sell to, and it humbles you a lot, and it gives you a perspective on how to connect to people in different walks of life and be able to understand what’s really important to people.

That skill is something that has served me throughout my career.

The first one is from Dropbox. I think startups live and die by simplicity and clarity of thought. I would say that Dropbox did struggle at times with a core identity of whether it was a consumer company or whether it an enterprise sales company. So I think that we spent a lot of cycles and we missed a lot of opportunities because we didn’t have that clarity of conviction. Segment was really different. And at the risk of sounding trite, I think I learned in that role, the importance of becoming really great at hiring.

So I worked for Genya, and I hired 100 people plus just reporting to Genya. And he actually interviewed every single person and just rode me so hard on keeping the talent bar super high. You realize that a company is really just a combination of people and the way you do things. So it’s your culture and it’s the people that you have. As a leader, you’re not gonna have every single skill set, you’re not gonna be great at everything, you just can’t. So you get to a point where your only leverage is the people that you’re able to bring in, so how you evaluate talent.

And Segment taught me to do that. I learned that from Peter, I learned that from Genya. And a lot of these folks actually I worked with today still at Monte Carlo and they’re some of the most talented folks that I’ve ever worked with.

it means either.

with you. It’s not different than a CRO. So my remit is sales development, sales, CS, customer success partnerships, bunch of broad functions. But one funny thing about Monte Carlo is we managed to get to like a billion plus valuation, we managed to get to an 80% go to market team, and we still hadn’t hired a recruiter or head of HR. So we don’t have any formal titling or levels at Monte Carlo. And I think to your question, what we don’t know yet about what to call me is whether it’s CRO or COO, and I think that there’s a question in terms of remit and how we wanna our sales team to be oriented.

But it just hasn’t been really core focus to figure out what to call me. So head of revenue is fine for now.

So sales playbook is discrete steps that you take to accomplish five things. One is to help the customer understand what you do. And the second is to evaluate whether or not your solution is gonna drive some sort of critical business outcome for that customer. The third is to gain consensus across who members involved in that decision making process. The fourth is to agree and formalize their relationship. And most importantly, the fifth one is that sales process and that sales playbook should create a blueprint for a customer to be really successful and for you to make good on those promises that were made in the cycle.

So that’s all sales playbook is.

So I think that you’re gonna have dozens of versions of a playbook over time. I think there’s a v zero, and I think there’s a v 20. In the early days, those playbooks need to be really open ended, and they need to make space for all the things that you don’t know. In the later days, the problem that you’re trying to solve is I need to go hire and onboard 25 AEs, and they need to know specifically what to do. You’re getting very, very prescriptive around, like, what are scripts that you use?

What specific questions do you ask? And you’re trying to grow the company through making sure that people onboard really quickly. To answer your question, I think a 100% a leader of an organization, a founder is accountable for that v zero of that playbook. And that v zero should really only clearly document three things. They’re just the foundational go to market pillars. They are, what problem are you trying to solve? And who are you trying to solve it for? Also, by the way, it’s really important for that founder document who you’re not trying to solve the problem for, because that’s going to be a direction of how you actually focus the sales team that you go and hire.

Two, what are the wins, losses, points of resonance with the customer? What are the key things that are factors for success in your sales process? You should have a very clear point of view of what that is the founder and you should know it better than your sales team. And then the third thing is what are the two or three reasons why people wanna focus on solving that problem with your solution right now? Why not do it in six months? What are the reasons they came in?

It doesn’t have to be pretty. It doesn’t have to be precise. It doesn’t have to be formal. But I’d argue that no matter how successful a company is, the best founders in the world are accountable to answering those three questions in perpetuity, not just at seed stage, but at Series A, Series B, Series C. Now, eventually, your sales leader is gonna come in and they’re gonna be focused on okay, how do I make this like V1 or V2? How do we get more detailed and more dynamic?

How do I ask better discovery questions? You don’t need to do all that stuff as a founder, someone else can do that and they’ll do things better than you are. But those foundational things, I think you owe that to a sales team from a founder led sales standpoint.

Yeah. Great question. Who doesn’t necessarily need to mean who are the users within an organization? Who is the person that actually makes the decision from a monetization standpoint, because we’re talking about sales, we’re not talking about product adoption or usage? And who are the companies that are early adopters or the adopters at that stage of the product? So for example, if your notion, three or four or five years ago, whenever they started growing, you probably weren’t jumping out of the gate selling to banks, you probably didn’t have single sign on, you probably didn’t have all those things that like a notion needs to go sell to those companies.

The first reps that you come in probably shouldn’t be talking about million dollar deals with HSBC. Think who can be loosely defined, but you do have to focus people down. I think that’s the point of who. You have limited hours in a day, and you can only talk to so many people. Who are the highest value people that you should talk to? So I would divorce that out from the question of who gets value from the tool, because a lot of times it is different.

Yeah. The best gift you can give to a salesperson coming in is a subset of recorded calls. The second best gift is for you to continue to take calls and have that person shadow you. And I think those points of resonance, they come out consistently and you’re looking for themes. The few things that I would document is one, for every call that someone takes, a simple question is, hey, why’d you take this call? You have a million people reaching out to you. Like, why are you talking to me right now?

What did I say in my messaging that was resonant for you? You’ll find everyone takes calls for a subset of reasons. So Monte Carlo has three reasons why people even just got on the phone with us. And those three reasons why they got on the phone with us are eventually the three reasons they end up buying the tool. And you can map those things back to the problem that you’re actually solving for a customer. Hey, I took your call because boom, this made sense. This is something I’m thinking about right now.

Tell me more about that. And just open ended questions. And the more that you can document that and the more you can put them into broad categories, rules of three are very simple. Salespeople are very simple people don’t give them 50. If you can give us three categories of pay, this is archetype one, archetype two, archetype three, and here’s 20 companies that prove that archetype, that’s amazing for salespeople. They can run with that and figure out, okay, who am I talking to? And now I can ask this discovery questions or go down this path.

Well, it’s the end of our quarter, so I might be trying to make that excuse in a couple of weeks. We’ll see how it goes. But urgency just wasn’t important to them. All of those are subsets of pain. If you deeply understand a customer’s pain, then you know why they have to solve it. What happens if they don’t solve it? And why do they need to solve it right And if you can’t get to that pain for the person that actually is going to make the decision, if you can’t make that pain real for that customer and help them understand the consequences of not doing it, yeah, your deal is gonna slip every single time.

The backup plan is always okay, I will either give you an exploding discount. It’s 50% if you signed today and it’s no discount if you signed tomorrow, that’s a horrible customer experience. Or your option is to lean on your relationship. Hey, listen, this is really important to me. This matters to me. That second one is not to be underestimated. People buy from people, they think at the end of the day, customers if they value your product, they won’t start the partnership off on a good foot.

But I would say that if you don’t have that reason that someone’s gonna make money, save money, reduce risk or go to market faster, you don’t have that thing. It’s gonna be hard to push a compelling event on someone.

Early days, I don’t care at all about what price people pay. ARR doesn’t matter at all. There’s a hot take from a sales leader. Early days, I think the only thing that matters is that you’re learning and that you have good customers who are good fits that are gonna drive your product forward. So they’re either gonna say really good things about you in the market, talk to other customers, or they’re gonna give you really good feedback and your product’s gonna be be better because of it.

But man, whether they give you 50 k or a million dollars, that doesn’t matter. In the grand scheme of things, if you’re gonna be a big company, that doesn’t really matters. The way I think about discounting is I don’t care that much about it. I care about finding price to value and communicating upfront that, hey, we’re an early product and pricing is gonna change over time. I just need to make sure that you understand that. And I might put something in the order form to reflect that.

Later on in the phase where like Monte Carlo is at, for example, now, let’s say you’re at a 100 customers, pricing discipline becomes so important because customers talk to each other. And customers don’t wanna not pay a lot of money. They don’t wanna not pay you 100 ks, they wanna know that you’re not fleecing them. They wanna know they’re getting a fair price. So as disciplined as you can be around discounting, I think that actually leads to a better customer experience. You can have two customers, one gets a 20 k discount and one gets no discount.

That doesn’t mean the person with a 20 k discount is gonna get a better experience or be happier with you If they don’t feel like they got a good deal. Aligning price to value is really critical. You got to get to a point at some point where you’re okay with the fact that some customers based on their business models might not see value from your product, and it might not be at that price. So that’s a pricing and packaging problem. But solving it through just, like, excessive and wanting discounting, that’s super problematic from a customer experience standpoint.

Champion left is brutal. It really is. First of all, it depends on the size of deals that you’re and the complexity of deals that you’re operating on. It doesn’t make sense to build this multi threaded overly engineered go to market motion when you have a $4,000 ASP. So for those lower end of the markets, be single threaded, that’s fine, but just move quickly because time kills all deals. Compressing those deal cycles down is actually far more important than multithreading. You’re basically minimizing the window for something to go wrong.

On the upper end, you have to multithread. You have to have multiple stakeholders. You have to have a person. Even if you get the deal and the champion leaves, you’re still screwed by the way. You still have to go roll out that product and get it adopted and used. If your champion’s gone, guess what? You got churn risk on day one of the contract. So I think it is really critical to have a champion, to have a practitioner who’s going to deploy it, and to have an economic buyer in the organization and have access to all three of those parties and make sure that they are all on the same page.

Think that’s quickly becoming the role of an enterprise sales rep. And insofar as you can get multiple champions or even like a department being a champion for something, that’s a significant backup plan.

Yeah. And I’ve listened to the answer from other folks on this and they’re all, like, slightly different. But I think so much of hiring any sales leader, it comes down to two things, luck and timing, and two, what your business needs. I would always ask you if I was your angel investor, I would ask you, hey, what problem are you trying to solve with hiring a sales? Why do you wanna hire a salesperson? I think that’s the first really critical question of what are you trying to solve?

Because if it’s product market fit, you don’t have anything hiring a salesperson is gonna help. It ain’t. It’s not gonna help you. Don’t hire a salesperson. If you’re in a competitive market scenario, you’re fast moving market, you have like all these free signups and you wanna amplify the number of conversations and learning, or you wanna bring in an expert and that you hope that expertise could come and increase your revenue per lead, it’s probably time. The first thing that I would say is if you know Very

That wasn’t the third one I was gonna get to. That’s the other one. So let’s go straight to that one since that’s the one you hear the most. That’s a you question, not a sales question. Right? That has nothing to do with go to market. That’s where you wanna spend your time. And do you wanna spend your time building a product or in front of customers? Now I’d argue that they don’t think that you’re gonna hire a salesperson and go save a bunch of time. Maybe you have like a fast transactional deal and a bunch of inbound volume and you need someone who’s just gonna process and transact.

Okay. Go hire a sales leader, right, that’s gonna build out a junior sales team if that’s the case. But if you’re just trying to like step away from it because you have other things you wanna worry on, hiring people doesn’t make your life easier. We had a saying at Monte Carlo in the early days, every time you hire someone, you failed because you couldn’t solve the problem with the people that you had on the boat, so you had to go hire another person. And I think shifts people’s thinking in terms of how you think about solving that problem.

I would say that founder who’s like, I’ve got a million things, I just need help. Give a transactional business, yeah, you’re probably ready, you could probably go hire a senior or like a mid level head of sales that can go build out a team really quickly. Or if you’re like an enterprise motion, you could probably go hire a person that needs minimal supervision. But you’re still gonna spend 25% of your time with customers or prospects. That’s not gonna change for six or nine months. Just to set expectations, good luck walking away from sales.

Yeah. So the other two are one, you actually believe that by bringing in a professional salesperson, you’re gonna get more revenue per lead. I have a subset of leads. Know because there’s a person because they’re gonna process it better, you’re gonna get better results. I think there’s three things that you need. You need one, four or five customers that you’ve made successful that have paid you and said like, was worth the money. Even if it’s $500, doesn’t matter. The second thing you need is you need to be able to repeatedly generate, call it five to 10 leads a week.

And then the third thing that you actually need is you need to make sure that those leads are actually progressing from the discovery phase to the evaluation phase and those early leading indicators. If you have those things, you can probably hire someone and they were gonna actually do better than you’re doing as a seller. Now, if the other one that people will typically hire salespeople are in is like, you have a competitive market scenario, it’s a fast moving market, you might have things where you just need to transact or you just want like a lot of conversations start happening, you to amplify your message.

That person’s gonna be, like, kind of a marketer. That’s okay. Just have the expectation that person’s a marketer. But what problem are trying to solve?

Yes. So three variables to that. One is the complexity of your sale. Two is the degree of confidence you have in your go to market motion. And then third is the level of involvement that you want to dive a little bit deeper. If you have really transactional deals, your ASPs are, let’s say sub 12 k, for example, a year, it’s low and it’s simple, then you could probably go higher. It’s based on how many reps can actually handle the transactions. If only have enough transactions to support one rep and you just hire a junior rep, if you feel like you have enough for like three or four reps can go get transactions, then you hire ahead of sales.

Fairly simple. It’s your willingness and readiness to go and hire people because honestly, heads of sales, if you go too senior on a head of sales, they don’t know how to sell anymore. I haven’t carried a bag since 2012. It’s been ten years since I had like a individual quote on me. Everyone on my team is better at selling than me. I just wanna like call that out of hiring that head of sales. There’s some benefits to it. And so if you wanna grow a team really quickly and you wanna attract talent, that’s the right time to do it.

But if you just want a really good Salesforce, don’t just think you’re getting ahead of sales because it’s gonna be easy to manage. They’re gonna do things that don’t matter. They’re gonna, like, implement Salesforce or something stupid that you don’t need when you’re a five person company.

trying to solve a product market fit problem by hiring a salesperson. And I don’t think that founder would go into that hire and say, like, I have a product market fit problem. I’m gonna go hire a salesperson. They’re gonna say, like, revenue stalling or leads aren’t progressing. Maybe if I go but hire a sales person that will solve that problem. So I think that critical think what problem you’re trying to solve is probably the biggest one. But I think the second biggest one is I think sales and marketing are the two toughest groups of people to evaluate.

It’s so hard to attribute excellence to individuals. Let me give you like a dumb example. Let’s say I was the first sales rep at Twilio in 2009 or whatever. And I go close. What do I do if I’m the first rep at Twilio? Well, I go close like Uber and Lyft and Airbnb when they’re 15 person companies and they just need like a messaging service. And it’s like a transaction on a credit card or whatever. And then I ride that way for the next six years.

Those customers turns into 10,000,000, 20,000,000, $40,000,000 customers. You look at my resume, you’ll say, okay, this person’s at a great company and they’ve been number one sales rep for six years consecutively. Clearly, it would be a major coup d’etat if I could get this person to join my team. That person might not have done anything at all. And I think that is so true, especially in a product led sales era of understanding how someone actually got to the results that they did is a really critical thing.

And I think it’s really hard for founders to decouple the brand names on someone’s resume versus what that person actually did at that company.

Yes. So salespeople fail. I always approach things through the lens. Failure, it’s what drives me. So salespeople fail, it makes for a horrible night’s sleep. Salespeople fail for three reasons. They don’t fit within the organization. They maybe can do the work, but they might take the company in an entirely different direction than you want as a founder. They have a motivation problem. They don’t wanna do the work. They got there. It seemed cool to start join a startup. Then they came in, they’re like, oh my gosh, I have to do everything.

Third thing is they just not that good or the skill set isn’t aligned with what you actually need from organization. So you’re not able to do the work. Cultural fit and motivation, those are actually definitional things that you need to have set out ahead of hiring any human being much less sales, you need to do the work upfront to define how you do things and you need to care enough about what your culture is to see how like a person is going to positively or negatively impact that culture.

Starting with a clear understanding of who you are is paramount. Otherwise, this person’s going to drive you nuts, you’re gonna have no idea why. The second thing is motivation. And your questions like how do you structure an interview process? I think early on in that interview process, the temptation is to sell the dream of what the company could be. And I think that’s important. But you also have to sell the reality of where you’re at, you have to sell what’s hard about it. I start every first interview, I don’t know if it’s a good iron frags or a bad one.

But I say like, Oh, man, we have problems. Let me walk you through all of the things that are wrong at Monte Carlo and all the things that we need to fix in the next six months. And I just like lay it out. And the person whose eyes light up and is excited about that, that person belongs at Monte Carlo. The person who’s like, tell me like how many leads I’m gonna get a month. You’re not gonna make it here. Leads might come, they might not come.

We’re two years old. I think that telling people the truth, and letting them self select in and self select out and using what we call in sales negative pressure, letting them sell you on why they still wanna be part of this thing, even though it ain’t perfect is super critical. And then if you wanna get them pumped and excited, use board members like yourself to go sell them why this is gonna be the next like forty billion dollars company. Early on, I want people to see the dumpster fire they’re walking into.

That’s your job. That’s a great use of board. Then the third thing is the hardest one. So, and that’s like the skill set misalignment. That Twilio example that I just gave is the problem. What I think founders need to do is they need to make sure that they’re going very, very deep on past experiences. Jenny said this a few weeks ago, right? Like he said, like, I don’t do like the forward looking case studies anymore. I go really deep on a relevant experience. And what I mean by really deep is you are asking fourth and fifth and sixth level questions to that person.

Hey, I saw that you did 183 of your number in 2018. Tell me how you got to that number. What did you do? What did other people on your team do? How is that relevant to what other people did in the organization? What were the deals that made that up? And what did you do on that deal? What’s the deal that you’re most proud of? What are the things that you would have done different you could have learned from? Well, then I saw you dip down to 175% of your number the next quarter.

What happened there? Going like that in terms of what specifically they did. And then there’s like a key question that I think gets to all skillset that has been the most powerful question that I ask. It’s what was hard about it? Because that question gets to the root of what that person actually did and why their skills are relevant to your company. For example, the Twilio example I just gave, what’s hard about it? Like, I don’t know, I had to send a contract and there were 20 people and there was no legal department.

So it was hard to tell them that they had to 10x their contract. Like that was hard. That was a tough conversation. But the person that’s like, No, I had to go talk to like 15 different people. And I had to bring like engineering involved and I had to get my CTO involved. And there’s this one person who’s trying to buy a competitive product. And there were 15 different companies popping up at the time. We had no idea what their differentiators were and how we were differentiated.

That person is your person that’s made of gold. They went through some hard things, and they’re gonna come in and they’re gonna really perform well for you.

sales, candidly. We do a presentation, like a pitch at the end, and I hate it. I’ve been trying to kill the pitch presentation interview for like seven years. And my sales leaders just won’t let me do it. That’s the closest thing to it. But I’d say like 90% of our interview is looking back at relevant experiences and trying to find patterns in that person’s background and how they perform, how they relate to others and how they use the experiences that they have to acquire the skills that we know that they need to be successful in our company.

And case studies don’t really get that.

Yeah, good question. Maybe going back to that framework of culture fit, skills, and motivation. So the first interview, the screen is the motivation. Do you want to do this because this thing is hard? Like, there’s a lot of easy ways to make money. And so that’s kind of my like, I’m gonna try to scare you off and see if you wanna keep talking to us and if you’re still excited. So that’s the first thing of like, is there a motivation aligned to come to Monte Carlo?

Do we make sense for their career as much as they make sense for our career? If you don’t have motivation, this job sucks. Point blank. You don’t want to do it, it’s not fun. So I think that’s like the first interview. The second interview is their historical track record. Is it a track record of excellence? Now I said attribution is really hard in sales and marketing, but you still aren’t probably aren’t gonna hire someone who is middle of the pack or low performing historically throughout their career.

Eventually, life’s gonna turn right. And so you’re looking for someone who has had sustained success across their career, and then you’re going deep on that success. Did they actually do it? Were they just like on a rocket ship and on for a ride? That’s the first interview. That happens with the hiring manager before they get to talk to anyone else. So ideally, when they go to our on-site where they meet other people, the manager has vetted, is this person a cultural and motivational fit? And do I believe it’s possible that they are excellent?

If you get those two checked off, you’re gonna like half the people that end up going to talk to the rest of the team will end up getting hired because that’s the meat of it. Then the on-site is three interviews, it’s typically with one person who’s actually doing the job, a different manager who’s not involved in the hiring process, and then like a cross cross functional person, and you ideally identified two or three competencies that this person needs to have. And each of those interviews is focused on going really deep on one of those competencies.

So I might say, Okay, Liz, you need to give me a high degree of confidence that this person has tolerance for ambiguity. And there’s a structured interview and how she does it and there’s the score. So then when we all get together in that debrief, we’re like, okay, this person has the skills and competencies, they have the motivation, they have the cultural fit, then that last step, if we give a go, then they go to the presentation. And ideally, the presentation is giving them a good experience of what it’s like to work at our company.

So the presentation has worked for them. It’s a final test on motivation. It’s a final test on just like hard skills. But most importantly, we give them all the information, we say you can talk to anyone in the company you all the resources are yours. They can like see what it’s like to work with us. I let any candidate call me and say, hey, what’s the answer to the test? I’ll give you the answer. You get an A plus for asking the question. I’m not gonna get hit by a bus the day you start.

Like, I’m still gonna be here and I’m gonna be part of you being successful. That’s the last step of the interview process.

curiosity, ability to ask questions and hold court. No one wants to sit around and listen to someone talk for an hour. So if you’re able to ask good questions and get to truth and you demonstrate that you can do that in a presentation, and that’s like counterintuitive, because you’re presenting something, that’s the most important thing. The worst ones are, this is like a book report, and I wanna show you that I learned all the content. I wanna show you that I know the answers to the test.

You get this from all the Ivy League and for you, our friends across the pond, the Oxford folks, those are the folks that got the A pluses all day. They’re gonna give you the answers, and I want the answers.

So there’s probably two or three. The first one is veering from a high like, a very structured hiring process and letting bias creep into the process is always number one. And that can happen, I’ll pick on you. Like a board member says, hey, I heard this person’s like the best person in the company. I’m like a first time head of sales hire and I’m like, yeah, well, I want my board member to be happy and I wanna show that I can go get this person. So I’m gonna go just like skip a few steps in the interview process and try to win them, right, and just try to sell them.

So that’s one. And that happens all the time, right? Your founder is gonna say, I think this person’s world class, we need to hire up. Every time I’ve gone with that and veered off from my process, I’ve regretted it just deeply. So I think that’s one of like sticking to your process no matter what people say. That’s the first one. The second one was I didn’t adequately run reference checks. We’re pretty good at getting to the truth in the interview process. But those reference checks are just so valuable.

So running like two or three references, you have to do it. That’s the second one. And the third one is not having a clear idea of what you want and not having conviction on what makes the role. So what you do in those situations is you bring, okay, let’s bring like 15 people out of the hiring process and by some consensus, we will find the best person. That always goes wrong too. So it’s like slowing down in that one, getting really clear about what the person that you need in this organization, and then keeping that decision making group to less than six is the third thing that’s just so important.

You

Yeah. And what I imagine is even harder in your world because you also have the FOMO factor of investing. You’ve got four other VCs that are pitching this person. You don’t wanna be the skeptical one that’s telling them, your baby looks a little ugly over here. I can imagine that’s a hard skill. I couldn’t do that.

it to you after this. It’s a public notion doc. Yeah. So what I found is two things like one, working remotely and then having larger teams. It’s harder and harder for people to understand my motivations and why I do what I do. This is gonna sound trite, but like I work because I love working with people and I love the relationships that will come out of it. And I love being proud of something that we’ve built. But you tell that to a sales rep on their first day, they’re like, okay, but what happens when I don’t have my quota?

But I’ve tried to take painstakingly detailed effort on is to clearly document like who I am, how I work and what I do. One, I set really clear boundaries at work. I do work a ton, but from 5PM to 7PM, you will never find me. I sit and I have dinner with my wife and my three daughters. And I tell them, if you try to find me in those two hours, I will not show up. So just so you have an expectation, this is me. Don’t ever set a meeting for me from five to seven.

I won’t decline it, I won’t show up. So it’s expectation setting on how to interact interact with with me. Me. This is how long you can expect me to respond to something. Here’s my phone number if you really need something. You’re getting out ahead of those. Jordan isn’t responsive, or he doesn’t care about me, or he doesn’t think that my problems are the biggest problems in the world. I’m giving them a framework for how to communicate with me. That’s the first thing. The second thing is I’m telling them what’s important to me.

There’s seven things on the user guide that are really critical to me. And the things that I reinforce every single day, everyone starts, I get my user guide, I say, let me know if you have any questions and stuff for some folks for direct reports, I’ll actually walk through it with And then I also put in, hey, these are the five things that are just most important to me in life. This is how I make decisions in my life. What I found is for most people, it basically shortcuts the trust process, especially when you’re in an interview.

Someone’s like, well, hey, how do I know that you’re not gonna ask me to fly to San Francisco in the middle of a pandemic and work till 09:00 for two weeks when I have a brand new born? That’s what people expect from startups. And I can say, let me show you my user guide that I put together not just to convince you to come work at our company, but this is like how I operate and what I care about. It’s been a good shortcut for me to, like, have that identity of who I am and to give to people outside of the context of whenever that inevitable conflict is going to arise.

success starts in the sales process, employee success starts in the interview process. So deeply understanding what someone cares about and what their motivations are and making sure there’s a motivational fit for why Monte Carlo makes sense for them. That’s the why. We just don’t hire people that aren’t going to be happy. I appreciate what Eleanor said, but there’s like a little bit of selection bias that like I hire a very specific type of person that I know will be successful in our organization and will tolerate me as a manager.

But one, knowing what they care about. On their first day, I tell them all the reasons why I hired them and all the reasons they are going to fail. And I lay it out on day one, as much as you can take all that conflict and pull it out of the heat of a moment and set them right on the first day that just makes such a difference. So I sit down with each person, here are the things that your superpowers, this is why you’re going to be my boss someday, here are the things that are major derailers for you that came up in the interview process, and I want you to be aware of them, and I’m going to be watching them.

What does that do? That exposes someone’s blind spots on their very first day. And it can be like a little bit rattling, but it sets this tone of, okay, we’re gonna have a very direct and honest relationship from day one. And then I revisit those things every week, I revisit them. Generally, that’s how I approach nurturing talent.

I learned that from from Jenny. So my first one on with Jenny, he said to me, Jordan, you have a low hiring bar and you have bad judgment. And I was like, oh my gosh. I’m getting fired and I’m five days in. And he’s like, this is not a problem. We will fix it. And that was the most powerful that got me to change really quickly. It helped me focus. It, like, changed my trajectory at Segment for sure.

Yep. That’s true. Yeah. I think the comment that I’d make in reaction to that is I used to think that people just wanted to be supported and they like knew exactly what they needed to be supported and they just need like a cheerleader. I think that’s the version of me that worked for Genya. What I’ve learned is people need like a really clear understanding of what great looks like, and they need to be told how they’re progressing towards great. And I think that’s how you walk that path of caring for people, but being able to be objective and doing what’s best for them.

And learning that hard lesson, think everyone learns, which is like caring is is not being nice. They’re not the same thing. You can be, like, very uncaring and very nice. So that’s been the fun one to learn for sure.

I always think that onboarding should reflect the stage and maturity of your company. I didn’t create a super structured rigorous onboarding program when we had five employees. Because it’s not like you’re gonna be in this thirty day onboarding season, then you’re gonna move out and like everything’s gonna be hunky dory. You’re walking into like a disaster and you’re gonna continue to be in a disaster. So you got to figure it out. Early days, the onboarding was, hey, here’s the information that you need, go figure it out.

I ain’t got time. And then I’m gonna give you a ton of feedback, I’m gonna shout at you, I’m gonna put time into you, but there’s nothing structured. That works with like your first couple of sales hires, it needs to work with your first couple of sales hires, because that’s the reality of the company. Later on, as you’re trying to go onboard, like what we’re in right now, we’re trying to onboard and hire people in the borders of magnitude of 10s and 20s, you have to get really, really disciplined and structured, okay, what are the things that you need to know?

When do you need to know them by? And how do we demonstrate that you’ve actually known them? So we’ve put together a very rigorous onboarding program that checks off those competencies. And what are the levels associated with those competencies? And how do we know that that person’s achieved those levels? I put onboarding at this phase into the hands of those frontline sales managers, because it’s their job to onboard and enable their people. Someday when we have 1,000 reps, there will be a field enablement or a field productivity function that will own that.

But in the early days, it’s your managers. And I think that’s true for every function for what it’s worth. It’s incumbent on the manager to go spend third of their time with new hires in the first month.

First one is proximity. They’re not close enough to the person’s work. And they don’t know how to break out whether the person actually has a weakness or they’re new. Managers need to get really adept of what are the signals that someone just doesn’t know something because they’re new, or what is the Hey, there’s like an actual skill gap here. Maybe this person doesn’t move fast enough. Maybe they are shocked by our environment, and they don’t know what to do with it. They struggle to actually like parse out those things.

Unfortunately, the best way to solve it is through pattern matching and pattern recognition, but you don’t necessarily have a lot of that. What I always say to managers is like pick out one or two people that you think had the best onboarding, get really disciplined about those two or three things that that person needs to have and know that inside and out and watch that person like a hawk and support the heck out of them until they get there. And you should know within thirty days about whether someone’s gonna be a fit or not.

Now impact doesn’t mean that I’m closing a 6 figure deal with like JPMorgan Chase in my first month, but they’re actually having an impact. Impact might look like they’re on customer calls and they’re having an impact on that customer, or they’re looking at the sales process and they’re having an impact on that sales process, or they’re raising the bar on the onboarding process and they’re getting there faster than the people before them. If you’re not seeing that, but you’re seeing maybe people are like, oh, I developed five x pipeline coverage.

And we’re all of these, like, very soft things that TBD about whether they’re high impact or not, or I put together, like, my book strategy. Ain’t nobody got time for that. You need to come and you need have an impact immediately. And I think that you you can tell pretty quickly whether or not someone’s, like, actually jumping in and going in the right direction or they’re flailing in the organization.

Super fair. First of all, I think we focus in sales too much on the lagging indicator, and

lagging indicator is revenue. And of course, we’re gonna focus on revenue. Like, at the end of the day, that’s why everyone gets hired, fired or promoted. But a ton of stuff happens up until that revenue point. And the better you can build out your sales process and your gas sales playbook to have discrete measurable events, you can get signal on day one of a sales cycle. That deal may or may like 10% likelihood or 5% likelihood that it converts into anything that matters. And maybe it’s a year from now, but you can know what are they doing with those first interactions, and whether or not they’re actually a fit for the organization or whether they’re doing well.

And that comes down to how well you have designed and structured the sales process, and how discreet and measurable each of those steps are. Give me a tangible example. Alright, person XYZ, enterprise rep, they have two weeks where they learn the product and they go through a pitch presentation. This is a person with ten years of experience. So they go to that pitch presentation and they just flop horribly. There’s a very clear indicator that something’s not going right in the onboarding with a person of that level of experience.

And you have to understand what’s going on there. So that’s your first red flag. I wouldn’t fire someone because they didn’t do well at presentation. So they pass the pitch presentation, maybe they do really well. And then maybe that you release them into the wild and they go set up three or four calls. Good, all three or four of those calls don’t have next steps set with them, or don’t go anywhere, or don’t have that person talking to other people in the organization asking for introductions, but nothing comes out of them, you have a potential red flag on your hand.

Because what that person is gonna say is like, hey, it takes a while to build pipeline. But like, again, ain’t nobody got time for that. For our company, we’re two years old, you can’t ask me to worry about Q1 of next year. That is not guaranteed. It is not guaranteed that we’re gonna survive for that long. What are the things you’re doing right now to actually progress the company? And if that person has nothing to show for those first calls, then there’s something not right there.

How soon do you let reps meet customers? We’ve been doing it too soon. Lately, our entire team’s like ramp because we’ve gone from like zero to 80 people in a year and a half. So we just actually needed people on the phones like in week one, and it’s been too soon. I think people should meet a few customers in their first month on the job under close supervision from a buddy or a manager. And I think that’s more for their learning. And you have to expect that that prospect is not going to turn into a customer, you just have to like accept that that’s a potential outcome.

It’s more about that person’s growth and development. So I need them to be in front of customers pretty early on. But in terms of when they’re running a deal cycle, I think you need to wait, We’ve been doing it fourteen days, and I think the right answer is probably, like, thirty to sixty. And we’re trying to figure out how to make it faster, but I think it’s starting to hurt us a little bit.

mortem everything. Deals, POCs, top of funnel, everything everything gets postmortem. Because the only thing that matters early on in your company’s life is how quickly you learn. I told you revenue doesn’t matter what matters, how quickly you learn, how quickly you put it into action. So we do deal reviews. We do forward looking deal reviews once a week where we take our key deals and we actually go really, really deep on them. But we do retrospectives on every single deal where we invested significant resources, and we didn’t get an outcome.

Typically, that’s when something gets to POC. And if for some reason that POC doesn’t convert to a paid customer, it takes too long, we’ll do a postmortem. I do postmortems on deals that we’ve won that I don’t think we did a very good job on. I think what you’re looking for is you’re looking for cracks in the sales foundation, and you’re trying to extract all of the learnings from those. So I would say as many as possible. And I love if the rep can lead it, because making a safe space for them to lead with their failures, and to own it creates such a great environment for learning.

So you just can’t let those things turn into I’m gonna beat you over the head because you made these five mistakes. How do you create the safe space? Tough to do. Well, when you screw up as much as me, you have a lot of opportunities to demonstrate it. I try to be really open about my failures. And a lot of the mistakes that these reps are making are mistakes that I made when I was trying to figure out the sales motion, like two years ago. So like, I get it.

So I think one is I try to communicate to people that like sharing your failures and your mistakes is a sign of strength and not a sign of weakness. And I actually don’t trust you if you’re perfect. I say that like maybe on a monthly basis. People know if they have nothing to work on that I’m kinda giving them the side eye because I’m a little suspicious about like what they’re actually doing.

At the end of the day, understanding your customer will always be the most important component of sales. If you don’t understand your customer, what problem you’re trying to solve, you shouldn’t sell them anything. It’s not how you build a company. Two, qualification. If you can get sales to a point where it’s actually like an engine where you’re thinking about where I spend my time is the most important and most valuable thing where I focus actually knowing who’s gonna buy and who’s not gonna buy early on.

And putting all of your chips and resources towards the ones that are gonna buy is really critical. So what sellers can do is they can really take your company for a ride if they’re like, trust me, this person just love this person’s gonna do a deal. Like, I just know it. I know it. They’ve never bought software before. They just have this pain that’s so big. So let’s go like build this integration that’s gonna take us like two engineering sprints. That happens all the time. So discipline around qualification is I think something that is actually like ramped up probably in the last fifteen years.

And I think will stay for a long time. What sales tactics have died to death over the last five years? Pure tops down sale. I will never be able to go into a CIO’s office and show them a really spiffy deck and give them a customer reference and get a deal. CIOs, CTOs, VPs of engineering, they need to see that their teams are using and adopting the product because they’re actually realizing that getting humans to change behavior is as hard as evaluating software. That CIO making a unilateral they obviously are really important to the deal cycle.

Like, they’re critical, but they’re not the only piece. You have to make practitioners happy at the bottom.

all about your founder. You’re picking a partner. You’re picking a partner ideally for the next four to six years. How do you work together? How do you get feedback? How do your strengths and weaknesses complement each other? Having that open dialogue really early on is critical. Just a personal example, I there’s four pillars of great sales leadership. The one that I really suck at, like I’m not a product marketer, I don’t tell a story, I don’t create a neat analogy, I can’t like help anyone understand what this thing is.

I’m a systems and I’m a process and I’m a people and I’m an execution person, right? So I needed Barr who created this entire category and who understood how to tell like entire story of the problem that we’re trying to solve. I needed someone who was an A plus plus in that, because I’m like a D minus. And setting that expectation with her, hey, this is what I am. And if you’re expecting this out of me, don’t, because I’m not good at it. And I’m not gonna get good at it.

It. I think that’s like a really important early conversation between a founder and a sales leader because the reason you’re doing this podcast is because I think founders don’t necessarily know what to expect out of sales leaders. They don’t know what they’re supposed to be doing. They fill that void with assumptions.

shot at Merced, California, is it?

most like to change about the world of sales? I’d like to see customer oriented sales win out. I think that there’s too much distrust between sellers and buyers, but I think the best sellers and the best companies in the world are always trying to drive business impact for their customers. And they just care a ton about their customers who put their names on the reputation of the line buying the software. Those are the companies that matter. Snowflake’s a great example of this. Right?

I mean, growing from, like, no revenue to 8 figures in revenue in eighteen months is really freaking hard. Growing a team from zero to 80 is really hard. Maintaining simplicity and focus when an organization is becoming much more complex is a huge challenge. Something that I wake up and think about every day.

Communication is the obvious one. That’s a company problem. I think like 150 people is like a great number where just like everything breaks down from a communication standpoint. I think the second thing that breaks down, especially if you’re growing really fast, if you have more new people than core nucleus, which is a situation that we’re in at Monte Carlo right now, If you were to have a pure democracy, the people with three to six months of tenure would actually win the vote. The first thing to break is what works and what has worked historically and how do you empower and engage that nucleus to basically overpower the new people to help them understand why we do the things that we do.

That’s a really hard challenge that I think also think about every day.

I think about the ones that have, like, really hard problems to solve. You talked to Eleanor. I think retool’s a really interesting one. They’re selling all things to all people. They have no clear buyer or person that owns that problem, yet they still grow incredibly fast. And I think that they’ve created a very nuanced product led, but also sales assisted growth model, which I think is really interesting. I think the second one that impresses me is MongoDB has always impressed me. But to go from tops down enterprise led to product led sales in the last couple of years, that’s a really hard transition.

I don’t think I’ve ever seen anybody do it, and they’ve done it really well. So I think those two are really great companies to look at.