20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp
You don't need product market fit in order to sell in enterprise, especially as that first seller. What you need to find is product customer fit. Those first sales, I don't think about revenue as being important. In no circumstances do you really want to bring in a VP of sales before you have a seller. This is 20 sales with me Harry Stebings and I started these vertical themes for 20 VC because I thought founders really needed to be advised by the best operators in these specific verticals sales, product and growth. Our sales discussion state is so actionable and hands-on. I absolutely love doing it.
I'm thrilled to welcome Mark Goldberger, head of enterprise sales at Ramb. The fastest growing corporate card and bill payment software in America. Prior to joining Ramb, Mark was the first enterprise rapid trip actions now called Navane where he helped bring in more than $100 million of ARR as an IC and then sales leader. And then before trip actions, Mark worked at high five, a video conference in companies since acquired by Dialpad.
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Mark, I am so excited for this. I had so many great things from so many former colleagues of yours and current colleagues of yours. So thank you so much for joining me today.
Harry, my man, it is so good to be here. Thanks so much for having me on the show. Now we have a lot to dive into, but I want to start with actually the move to ramp and leading Rams and price sales teams. How did you make your way into the world of enterprise sales? And how did you most recently come to lead Rams and price sales team?
哈里,兄弟,来到这里真是太好了。非常感谢你邀请我参加节目。现在我们有很多内容可以探讨,但我想先谈谈你从事企业销售的经历,以及最近是如何成为Rams and Price销售团队的领导者的呢?
I came to the world of enterprise sales from the world of wine. I recognized that's not the typical journey one makes. So I was working in Massachusetts as a salesperson for a wine distributor ship while I was going to business school. And upon graduating, it was the great recession, not a great time to leave a good paying job for an unpaid internship somewhere. So I actually founded my own company. I bootstrapped the SaaS business back then knowing nothing about SaaS mind you, but built a cloud-based company with tools in the cloud specifically for the wine industry. Bootstrapped it, we had paying customers. It was a wild, incredible experience.
After a few years, ultimately I did decide to wind down that business. My wife and I moved out to Silicon Valley when she took a role with a little startup in Mountain View called Google. And so I found myself out here in Silicon Valley and I said, okay, I'm going to be an account executive now again for SaaS companies. And I sent my resume out to about 100 companies. And the response was there was no response. Literally could not get an interview. More than 100 resumes sent out. I'd founded my own company that was a SaaS company. I'd always been a top performer in sales. And yet no one was interested in even interviewing me. It was a frustrating experience. It was a humbling experience. But ultimately as someone who has already had a giant chip on my shoulder, it drove me to go out there and perform.
You're the master of also being a cold outbound being the enterprise leader you are. You must also self analyze that what was wrong with your approach and why did that happen? There's fault on both sides.
I think there's a challenge from software companies and sales leaders thinking too small inside of a box in terms of the profile of who they're looking for.
And there was also a challenge on my approach not having it lived in this world. It was a world that was far into me and I needed to find my way in. Ultimately after a couple of months, I connected with a terrific recruiter and ultimately taking a position with a video conference in company called High Five was backed by General Catalyst and Light Speed competing again soon. And this was before the pandemic when selling video convincing was maybe a little bit harder. Ultimately ended up getting recruited by trip actions now called Nivan and was their first enterprise account executive and really built the enterprise go to market there.
You mentioned the time at Nivan in such a transformational and kind of hypergurth time for the company. What a one to the biggest takeaways for you from that time and from being the first enterprise sales leader there. What have you taken with you to a time now is round the first lesson that I really took away and this comes from when I was an IC an enterprise account executive there.
I built up a massive amount of pipeline the first six to nine months. I had 87 opportunities in my name Harry and if you know anything about enterprise sales that's way too many opportunities. But I started to close deals about month six and what I recognized was you don't need product market fit in order to sell an enterprise especially as that first seller. What you need to find is product customer fit and so when you have a huge amount of pipeline like that you can really prioritize it and focus on the accounts that match best with the vision that you're building toward and where they're required capabilities match with your core competencies.
So when you focus on that 20% that's going to drive 80% of your outcome amazing things happen. And I closed about 13 million dollars of revenue that first year. My question is you said they're about going to product customer fit. I love it. I get it but we have those 86 companies. What do we do then? What does product customer fit actually mean? Help me and help sales leaders and wraps understand.
Yeah so it goes down to something that I built later on a qualification methodology I call the Lean Pivot Walk and essentially what you're trying to do is understand hey if the boxes that they're looking to check are the boxes that we check really well you should lean in you should be going after that opportunity full force. If what they're looking for is something that is not even on your roadmap and wouldn't be on your roadmap for the next five years you need to be honest with yourself.
So many reps out there have happy ears and just because someone wants to meet with them they think hey they've got an opportunity you need to be honest and be able to walk away and qualify that deal out and then there are other opportunities where maybe you check some of the boxes and not others and is there a world where they're willing to have two different solutions one for the rest of the world and maybe one for North America and so you start to understand these dynamics and you can play off of them and ultimately close a lot of business that way.
You said that you can get product customer fit without having a product market fit. I'm really intrigued. Does the salesperson need to be the one to create the sales book playbook or does the founder need to be? How do you think about that question in terms of the product market fit question as well?
Yeah for product market fit I think that is driven more by the founder being out in the field talking to customers talking to prospects really understanding their pain points and being able to dive in at that level but when you think about sales and a sales playbook I think that's originating from the salesperson and in some businesses the founder is that first seller in other businesses you want to hire a junior salesperson to go out there and figure things out but in no circumstances do you really want to bring in a VP of sales before you have a seller because they're going to come in with the preconceived notions that ultimately might not mesh with your particular business model.
I always think high the more senior because then they can build the team around them rather than hire the junior and then bring in a more senior who then adopts the team that they didn't actually hire. How do you think about that challenge?
I think about it a lot but where I come from ultimately if you have a sales leader who's coming in they have a playbook in mind they have processes in mind they have sales tools in mind and that playbook might not mesh with the product that they're actually selling it might not mesh with the people in that organization and so when you try to jam that square peg in the round hole you ultimately create thrash and for an early startup you can waste a lot of cycles and a lot of time having the wrong people in the wrong position. And he has a really good point.
I think you said that that's sometimes for a founder where they need to lead the case. When it is the founder leading the case what are the signals that they need to hire the first junior sales rep? Often it's like a million in a hour or is touted as the number which I think is bullshit because it means little.
What are the signals that the founder needs to make that first time do you think? I think they should make that first hire as soon as they have a product that they really want to be testing out in the market. I think it's a lot sooner than a million ARR to be honest. Those first sales I don't think about revenue as being important. The revenue or the currency that matters in those first sales are the logos.
You need to be acquiring logos. You need to be able to say hey this company works with us that gives you credibility when you're trying to make that sale for revenue. You want their feedback, you want the case study, you want them to be a reference for you. That matters a lot more than revenue in those early days. In terms of game about that single sales rep hire Jason Lamkin says about the importance of hiring too at a time so you can really determine quality and compare. Do you agree with that or do you think one was just as well?
The way that I think about it is I'm looking for sales people who can provide 10x growth, not 1x or 1.5x. When you find someone who can provide that 10x level of growth they're a rare find. To find two at the exact same time and to be able to recruit them and have them join at the same time is an exceptionally rare opportunity. If you do find them by all means you should hire them, you should hire them as fast as you can whenever you can. But ultimately if you are at scale it's easier to hire hey two sales people at a time you're going from 20 reps to 30 reps to 40 reps. Great, hire an incoming class. But in those early days where each additional player is going to have so much impact you need to be grabbing the best talent when you can.
I spoke to the best talent when I could who worked with you and so I have a lot of information about that you're so great at Mark. So I want to dig into some of the areas where you're taxed and I want to start with deal champions and multi-threading in particular. I think it's something that people university still do badly actually.
How do you confirm you have a deal champion in a cycle? There is only one way to know if they really are a champion for you. You have to test them and the way that you test them is asking them to take you to the executive buyer. Now that can result in two things. One they have the power and influence to be able to take you to the eb. Typically that's a CFO especially today. If they have the power and influence to do it and they're willing to take you there help present with you you need to be in that meeting on your behalf they're selling internally you've got a champion.
If they say no to you for whatever reason it means one of two things either they don't have the power and influence to take you to the executive buyer in which case you're dealing with a coach or just a stakeholder in the organization who really is not going to be meaningfully important for you or you haven't earned the right yet to have them take you to that CFO or to that eb in which case you have more selling to do. What is the right way to ask without seeming slimy or like you're asking for too much?
You need to set that expectation from the start literally in the first meeting where I walk through a pitch deck. I share with them why we exist, what we're solving for, and what it's like to be working with us. From everything from implementation and onboarding to hey part of our sales process is we're going to want to have an open dialogue between your executive team and our executive team. This is not a typical vendor customer relationship, but it's a partnership, and so we want to make sure there's that open dialogue so that what your CFO cares about, our CEO listens to.
When's the right time in the deal cycle to ask to go to the executive buy? Because you don't want to do it too soon where it's like whoa we've just met Mark and I'm not quite ready for that but then you don't want to do it too late. When's that time you need to be able to get to the executive buyer. There's a lot of different ways you can get there too. It's not just through a champion. You can leverage your network, you can leverage your board members, you can leverage your executive team to back channel into that executive. Typically, you want to be able to get some kind of a business value assessment where you're agreeing on what the value is that we can provide for an organization.
At that point, you're going to go with your champion and present those findings to the CFO or to the executive buyer. What should you provide your champion to make sure that they're equipped to sell your case back to the executive buyer on your behalf? But when you're not there, the phrasing of that question scares the shit out of me Harry. And the reason why is that you need to be in that meeting. There is not a world that I would ever become for a living in where I want to outsource my job to a champion and a prospect that is living very dangerously on the edge. I know a lot of sales people who will take completely wholesale what a champion says. Hey my CFO doesn't meet with anybody, my CFO is too busy, I will be the one to talk to them on your behalf.
We can't have that because what happens when the CFO asks you that question mr. Mrs. champion that you don't know the answer to? What happens when they question these numbers or they ask about implementation or have you talked to these different stakeholders and you don't know the answer? We have to be in that room with you.
Yeah, mark what a terrible question god silly no thank you for clarifying that. And by the way do ridicule any questions I love this. And you mentioned the importance of multithreading there and bringing the executive buyer, it's important that sales reps, the sales team see around corners.
What are some ways that sales reps can get better at seeing around corners during a deal cycle? A lot of people tend to wear rose colored glasses, they get happy ears. As I mentioned before people are meeting with them, they're excited rose colored glasses people are great fun at parties but they make for shit sellers. You need someone who is a lot more skeptical who questions everything. The way that you see around corners is you ask the hard questions, you run toward the danger and what scares you, not away from it.
Harry what are the reasons why you're going to lose this deal, what happens if your champion leaves, what happens if the CFO says this that or the other? If you ask yourself all of these questions and any possible way you could potentially lose this deal, now you have a map of all of the things that you potentially need to overcome, and in a worst case, you're overcoming objectives that might not actually take place and in the best case, you're really prepared for when that punch inevitably comes.
I think it's also actually incumbent a little bit on the founders to create an environment of safety where people feel they can ask the tough questions and then bring that information back and not be terrified because I think often it's fear that makes happy is multiply. I do want to ask you I think kind of sales qualifications a big problem and people still suck at it.
When you look at sales qualifications day, how do you coach and train young sales reps, and what do you see is the biggest mistakes that people make in sales qualification today? I think the biggest mistake that people make from sales qualifications standpoint is really not going deep enough. They'll ask discovery questions and then that first level of discovery question has been completed and they're already selling their solution.
You need to go deep you need to do some significant discovery where you get to secondary third level pain and really let someone stew in that pain. I'll give you an example Harry you're on a run this weekend and you scratched your arm right so I ask you about that and find out hey you know yeah kind of stings maybe you need a bandaid.
I don't know is there blood there we start to dig in and find out hey you've got some serious pain what happens if you don't address that pain right now maybe it'll get infected and now instead of a bandaid maybe you need antibiotics and if you don't do that what's the risk to you shit maybe my arm's gonna fall off or I'm gonna have to get it amputated well now this little scratch that you weren't really thinking about is a painful festering wound that you really need to address hey turns out I've got a bandaid Harry and I can solve this for you right now.
you have to be able to go deep on that pain and qualify what is it that this person or this organization needs from a solution standpoint to solve their pain and if what they need is what you have great you've got that match you should lean in but if what they're looking for is something that's completely different than what you provide you need to be able to walk away again it comes down to that lean pivot walk you can do med pick med pick is incredibly enlightening from a qualification standpoint it's me and my team.
I don't want a med pick filled out I actually want you to come in and we're gonna do an act of discovery together and I'm gonna ask you about your deal I'll ask you about this opportunity what's going well was med pick what's med pick are you kidding me med pick is an incredibly important qualification methodology it's really how you understand the deal dynamics you can look up the definition afterward but basically it's an acronym and what we want to find out are one of the metrics that are important the economic buyer the decision criteria the decision process paper process implicated pain not just pain we want to understand the implications of it for your competition as well as your champion that's what med pick stands for ultimately it's an act of discovery.
Harry what do you like about this deal what gives you pause who are there any red flags you've encountered okay if I could give you a magic wand Harry what are the five things you would want to know or see happen here that that you don't know or haven't happened yet great now we've got an action plan for what to do let's go out there and do it I love that my I'm also very ashamed that I haven't heard of this before I love any acronym as a vc it's what feed my soul but I do want to ask okay so we're going through this qualification process and I am leaning in okay I'm excited for what you've got to sell but I'm not quite converting what do you do to create a sense of urgency in a sale cycle to get someone over the line it comes down to pain Harry if you don't have enough pain there's not a world where I can get you to have the urgency you need short of discounting and that kind of cheapens what we all do what I would suggest is you got to go back to first principles you got to go back to discovery and if you Harry don't have enough pain I need to find someone else in the organization who has that burning pain I need to find other people and build groundswell again this comes down to multi threading and pipeline generation you want to get as high and as wide as you can in an organization because the only thing better than having a champion is having multiple champions.
does that mean that you would advise found is not to do discounting I think that discounting is an expectation that's spilt into procurement teams it's built into the way that sales operates today I think some organizations lean on it very heavily whereas others are able to sell the value and really hold the line more the more pain that you find and the more your solution matches with the pain that you're solving for the less you need to discount a lot of people say hey we'll give you the discount or we'd love for you to give us a customer a furl and allow you to use your logo how do you as a startup ask a prestigious company hey can we use your logo for validity what's the right way to do that without sounding need the install it up.
He yeah so one I don't ask for it the assumed clothes there is really important as part of working with us we want to support our customers we love to show off the great companies that are working with us and so we're going to have your logo on our sales materials on our website that's part of what we do oh we don't allow companies to do that okay it was great chatting with you good luck finding a solution that is going to solve for the pain that that you have today
you have to have confidence around it Harry do you feel enough people do you have confidence in sales today no not at all why is that it's a great question I think when you're a junior sales rep when you don't have as many bats you see things all the time that are new to you and that's scary as a junior salesperson hey I'm encountering something I've never seen before I don't know where this path will take me when you've done hundreds of deals like I have and you don't have that much hair left on on on your head and what is there is. graying quickly you have what one of my mentors Carlos Delatore he had a great colorful phrase for it's hot scar tissue and scar tissue is also known as pattern recognition and the more pattern recognition you have the better you're able to combat that because instead of living in your head and having to analyze every single decision and every single thing you do you can actually live by instinct you've seen it before what the proper response is
you mentioned your mentor that being Carlos what do you think sales leaders can do to better mentor this younger less confident cohort to be that best sales I spoke to some of your mentees what does great sales mentorship look like in require stage you think
I think the key to mentorship is helping people see their blind spots it so I'll give you an example now you spoke to a founder of a YC company who I mentor he actually reached out to me in a cold LinkedIn message and it cut through the noise and I responded to him and I've been excited to work with him and his team but he's not a sales professional and so he's going through this deal cycle and I shared with him what are his blind spots he thinks he's got an opportunity here what happens if it doesn't work out does he want to have all of his eggs in that basket no you got to build more pipeline right so I'm helping him as an example to see around his blind spots and ultimately to be able to close more opportunities with other reps with other people the dynamics can change the buttons you need to push will change but ultimately you're helping to make them more well rounded
I do want to talk about hiring this young talent which as we said needs more confidence and needs a lot of mentoring but can still be brilliant in terms of hiring we need to know what great looks like and you said to me before that it's about the four h's success in sales is the four h's I'm loving the acronyms today Mark what are the four h's
the four h's is something that I came up with that really is about saying the intangibles matter more than the tangibles first h hunger you need to want it more than anyone else if you don't have that burning desire to succeed that deep need to win that insatiable yearning to compete you probably won't win or compete or succeed hunger is an incredible motivator to get you through the inevitable challenges it's not enough to just be hungrier than everyone else you need to be prepared to outwork them too there's a great quote from john mcman who was a tremendous sales leader and it sums it up well the difference between winners and losers is that losers practice until they get it right winners practice until they never get it wrong and also applies to sports I always think about tom Brady when I hear that someone who was not the most gifted athlete of all time but certainly the greatest professional athlete of all time because he outworked everyone else watched more film than everyone was in the gym earlier than everyone no one would outwork him and so he was able to rise when it mattered the most
third age humility this is one that I will grant you a lot of sales people don't have they come in with bravado but I actually think humility is the approach you need to know that no matter how much success you've achieved there's always someone who's done more and there are always areas you can improve none of us are perfect certainly not me you need to recognize and embrace that you need to use that to fuel your growth the last age is heart it should be table stakes but instead it's more like special sauce think of it like grit what it takes to be a champion to be able to take a punch and keep fighting there's a great book by read hastings called note rules where he talks about talent density I actually think as important or potentially more important than talent density is grit density to have a team that just has a massive amount of grit
I do have to ask you mentioned there about hustle and the ability and desire to work all of them anyone else and put the hours in you said before to me you need to think outside the horse when it comes to hire and sales teams think outside the horse.
I repeated this to myself and it didn't become clear to me oh me out here what did you mean by this and how does that impact how you think about what you look for in the people you add to your sales teams.
It's a little bit of a mixed metaphor but let me tell you so from a product standpoint at ramp we think of the legacy state as a horse and buggy and do we want to build a faster horse and buggy or are we going to build an automobile on a slightly different vein.
I've heard guests of yours talk about the expression sales recruiting that fast horses run together right a players attract a players but if you want 10X productivity you need to think outside the horse you need a race car not a race horse let me give you an example here if you have a 10X better product and I hope you're investing in companies with 10X better products because they're amazing but if you have a 10X better product and a good traditional sales rep the best you can achieve is a 10X outcome it's a pretty good outcome but if you have a 10X better product and a 10X better sales rep you can achieve a hundred X outcome and the best sales people in my experience rarely fit the mold of what great sales people should look like and I'm not even talking about myself and my challenge getting into Silicon Valley the best sales people I've seen in the last several companies I've been in none of them would be hired today based on the rubric that sales leaders have you need to think outside the horse why what were they what did they have what did they not have that made them not fit in the rubric what made them that way for one thing they didn't come from the right companies or they didn't have the right linkedin profile or something about them would have canceled them out from even getting into the funnel from a hiring standpoint.
But the best sales people will have those four h's but they're also going to have creativity can you take duct tape chewing gum in a zoom link and mageiver a seven figure closed one deal right that takes creativity I've seen people do it it's extraordinary not everyone has that are they adaptable the two first sales people at ramp the first one now leads half the sales and str teams the second one is chief of staff to our CEO right they're adaptable you're hiring people not for what they can do today but people who have enormous growth potential that's how you get a 10x outcome but how do we determine what that 10x if we go to the interview process say we've let them into the interview process despite not being the traditional fed but therein we're sitting down with them what questions do we ask how do we know if that 10x is yeah you need to get really intimate you need to go deep in your interview questions get at the why not just the what so many interview questions are what did you do next what were you doing at that company what deals did you close I want to know the why I want to know the how I want to know them and get really deep to understand what makes them tick what was the reasoning behind decisions they made not just the performance
and a great way to test this is with a challenge so I know different organizations think about this differently I want them to sell to me not what they're selling today but I want them to sell my solution back to me because it shows if they can do research it shows if they can synthesize that information I know if what they're saying is correct or not I can see all of the gears turning and I can test them as well in that setting and say hey I'm a CFO we scheduled this for 45 minutes I actually only have 10 go are you adaptable can you take a punch can you give it really quickly go that's Hoshmock it happens in real life though I much rather it happened in an interview than with a real prospect I've had many sales leaders on the show say before
I like them to sell a product that they've sold before and they know because if they sell mine back to me there's this massive asymmetric knowledge one and there are two if you have any form of hiring committee who are involved they'll naturally respectfully intellectually look down on them because they just know way more given your experience compared to theirs how do you think about that pitch yours product versus pitch something they know much better I don't want you to be comfortable in that interview process selling me something that you could talk about with your eyes closed while you're sleeping I want you to have to think I want to challenge you it's a called a challenge for a reason I want to see if you can rise to that occasion enterprise sales is hard I want to see if you have what it takes to rise up and be able to perform in that setting
would you rather a rep that you're hiring has experience. selling at that level of ACV or has experienced selling to that segment of market in terms of finance tools for me I think it's about selling enterprise deals so that value the selling to organizations that size because the scale is so different I've seen mid market account executives get promoted into enterprise in my past and flame out pretty quickly and the reason is usually they're used to a certain level of multithreading hey I need three or four people in the deal now all of a sudden everything is magnified by an order of magnitude can you play 20 simultaneous games of chess it's great that you can play chess but can you play 20 games at the same time it's much harder
to what extent do you hand hold younger apps in these large deals like will see because you can't just let them run free to what extent do you do the kind of mental mentee going to all together so you need to create space for them to fail when the stakes are low so they can succeed when the stakes are high you have to be in the boat with them first of all as a sales leader my quota I've got a quota and my quota is a roll up of my reps so number one I'm in the boat with you because your performance is going to matter for my performance putting that aside I want to see everyone on my team succeed but I can't do the job for them all right I can't be in every deal in every place and every call at the same time so I need to give you the tools to succeed when I'm not there and I need to be in the boat with you and teach you mentor you throughout that process but what I've also found no matter how much you say the stove is hot people still want to touch it in order to find out that it's really hot and so it's my job to make sure the burners on simmer and not on high so it's not a catastrophic wound
If we're start up hiring what does that process look like? Is it like first interview, get to know you, then the why second, the case study? What does that process look like step by step? Do you think?
For me, I want to be able to qualify quickly. Is this person of the right caliber? Have they closed the right level of deals? Do they have the right experience? Do they have the right gravitas to be able to hold themselves in an executive meeting? That is usually like a 30 minute getting to know you call. Assuming that goes well, you want to go deeper. You want to spend an hour with them. You want to really go deep. You want to ask those why questions, those how questions. Really get to understand what makes them tick.
You want to have other stakeholders meet with them as well. Typically, in an enterprise, you're a quarterback. You're working with other people internally and externally. So how do those relationships form? Are you able to play off those dynamics? And then ultimately, yeah, you want to do a challenge with a panel of interviewees all the way up to your C-suite leadership.
We will learn a lot from making mistakes. I know I've made many in my time. What are the biggest mistakes you've made in terms of hiring and price sales teams and how did that change how you think?
I've certainly made mistakes. I think sometimes when you assume their experience, if you assume their fit based on where they've been or what they've accomplished in their career, you put yourself in a very risky situation where when they come in, if you haven't tested for that, they may fail. I've seen people who are extremely accomplished join organizations I've been a part of, and within six months, they're no longer in the company because they weren't able to cut it. The fit was wrong. And so you really need to test for that because the last thing you want is to waste six months of their career, of their time, and six months of your runway and six months of your time on someone who isn't a fit.
Before we dive into kind of that integration with the existing team, which is so important doing the onboarding, I do just want to close. We go through that process and we get to the deal itself of kind of the package. What are some of your biggest lessons and pieces of advice to founders on giving the right comp structure for those early sales repires?
I think when it comes especially to early sales hires, there's not enough emphasis placed on equity in sales. They give out equity for other roles, and I think equity is often something that founders don't really think of when it comes to salespeople. They really only think about cash compensation. That's the wrong approach. If you're hiring a 10x salesperson, someone who's going to be with you for a long time and drive an inordinate amount of impact in the organization, you should want to keep them for a long time.
And they're going to be able to see the impact of their revenue-generating activities on the company all the way up to raising funds. And we just need to get more creative and we need to find a path forward. And so when you have people who can drive an impact like that and put an entire team or company on their back, you want to reward them. Cash is great, we all like cash. Sales reps are coin-operated, I get it. But you want them to be bought into the long-term vision as well. And it needs to be aligned with what the company cares about. To hit those targets, they need to have targets in the first place.
How do you advise me on setting quota, especially in a year like this year where it's so fucking uncertain? I set a quota for the media company and we're like 250% over target now that in whatever four months in. Clearly, I was just shit at setting quota, to be honest. I didn't know what was going to happen. How do you advise founders on how to set quota accurately and efficiently?
You need to in the early days figure out what is the goal that the board is setting for you or that you're sharing with the board. Number one, is it realistic? Is it achievable? Work backward from that goal. Working backward is something that I often teach to my teams. Okay, here's the goal that we're trying to get to. If we're just driving toward it in a forward direction, we may drive off a cliff, and if you don't want to end up like Thelma and Louise, then what you need to do is work backward so you know where the cliffs are, you know where the landmines are, you know where the traps are, and you can find, hey, is there one path, is there no path, are there multiple paths to get there? And then you can move forward. If you work backward from that goal, regardless of how lofty it is, you can figure out the way to achieve it.
The other thing that's really critical here is pipeline generation. If you have a massive amount of pipeline, you are able to qualify deeply and make sure that you're going to hit the goals that you've set for yourself. This is something that I instill in my teams, and I'm proud to say that this quarter, the enterprise team at ramp is trending to hit more than 300% of their quota, which is pretty insane.
Do you think traditional sales outbound is dead, and why does no one in sales want to do traditional outbound anymore? Traditional outbound is the most important thing, Harry, and if you're not doing it, you are doing sales wrong. And the reason why is because pipeline is the most important thing if you want to hit your quota, as we just established, and the way that you build pipeline is throughout reach. The founder that I mentor, he pg'd into me, he called/message me, without that I wouldn't be mentoring him. We have so many opportunities that are in our pipeline because we did the hard thing; we picked up the phone, we sent out an email, we were persistent with it because usually it takes about five messages before someone is going to respond.
And ultimately, we feel good about it because we're providing a solution for them that helps them. We're not trying to sell them something that they don't need, and so if you think of it from that standpoint, what you're doing when you're picking up the phone is something that's good for you and it's good for the people that you're calling. So glad to hear people run away from things that are painful, and outbound can just be continuous punches in the face, and so I think it's nice to stay in the warm and cozy environment that is warm inbound.
Going back to the kind of integration into the team, I think onboarding is just chronically poorly done. How do you think about the right way to onboard new sales reps into your team and how do you do it today? I think it needs to be a mix of structured learning and unstructured learning, so asynchronous learning. I think there needs to be a fair amount where they're going to be shadowing the best reps on calls. I think you need to dig in with them and go deep on a daily and weekly basis, so one-on-one coaching as well, and you need to make them drink from the fire hose.
I know we try to limit that as companies get larger, where hey we're going to give them this nice kushy ramp-up period, but you're going to find out a lot those first few weeks about their ability to run at pace, if they can drink from the fire hose and start to synthesize that information. So I'm a big believer that the training wheels need to come off quickly. I do think there's benefit as well to giving them what I'd call t-ball opportunities.
So if you're an enterprise, you don't want to risk some massive deal by giving it to the guy who just or the woman who just started. You need to be able to give them a smaller opportunity that's safe, that's a safe place for them to iterate and figure out the motion before they're getting into these really large complex deals. What are the biggest red flags that you traditionally see in the first 30 days? I think people often say higher-fast fire-fast. I think we'd probably agree higher-slow fire-fast.
If we agree with that, what are the big red flags that like okay you need to step in and do something? I recognize that not everyone is a type 8 personality and gregarious even in sales, but if someone is not asking a lot of questions, if they're not vocal in that first month or two, to me that's a red flag that I want to at least dig into. It's not a sign hey we need to fire them because they didn't ask questions; it's hey are they not asking questions because they understand everything? Bravo brilliant, go forth and prosper.
Or they're not asking questions because they don't actually even know what questions to ask and is it an aptitude issue or an attitude issue? You need to understand that if you want to try to fix it, and in some cases, you're right it's higher slow and fire-fast if someone can't make it. The merciful thing to do is to let them go so that they can go to a place where they can be powerful, efficient, and grow their career.
How do you see the real quality of a candidate? What I mean by that is like I've had sales these on the show say before the person that sold Twilio to Uber when they were a tiny startup, it's probably the best deal in enterprise history, and it transformed obviously from a startup to an enterprise deal, but at the time it was a nothing deal, and it was probably stunned by a credit card. Almost like how relevant is deal attribution to you and determining quality of candidate.
I'm just too interested that it's why you need to ask those why questions, Harry. Some companies are great at product-led growth, and they're selling to an organization when it's an SMB. At what point did you sell to that organization? Was it a 10 person company that grew to a 10,000 person company, or did you sell to them net new when they were 10,000 people? Did you sell wall to wall? across the entire organization or was it a land and expand motion who else was involved with you in selling that deal you need to dig in to understand did they do all of the work did they generate that deal themselves was itself source or did an SDR make a cold call and that's how it happened where did marketing generate the lead and it came inbound in terms of I'm digging in on the deal and the deal dynamics that I think deal reviews are so important whether successful or not successful how do you do deal reviews how often do you do them who's invited who sets the agenda I'm an early stage founder educate me I think you should do a deal review for any deal that is going to be impactful toward you hitting your goal for that quarter or that year period and that means that you're probably doing more deal reviews than you're typically anticipating you need to give time for that if you're not digging in with your rep and understanding the deal dynamics what could go wrong what needs to happen the various stakeholders have you mapped the organization and getting really into the details then you're putting yourself at risk because that deal could slip that deal could end up as a closed lost and if you were counting on that if you were committing that opportunity man that is an unpleasant place to be I can tell you it has happened in my career a long time ago when you commit a big deal and then it doesn't come through that's a painful experience for everyone you don't want to be living like that what are the biggest reasons the delays today in my experience when you do lose to competition you can lose for a variety of reasons one it could be price and if you're selling something to someone who's really price sensitive and you haven't sold the value and articulated it you can have someone come in and offer a product for free or offer it for a really low price and that company may grow to regret that decision but ultimately they might make that decision you could get outflanked you have a champion but you know what they've got a champion that's more senior and so the more senior person who's got more influence in the organization is potentially going to win there are a variety of reasons you could lose but you need to map the organization you need to understand the dynamics at play
Final one, I promise. I'm just firing like interest questions. I don't know, but it's like when you do enterprise sales really well, it's this tailored boutique feeling for the customer. How do you do the handoff between sales wrap and enterprise sales leader to customer success team/customer experience team without it feeling like "oh good luck, off to mark?" Yeah, if you're doing it badly, it's "hey I'm handing you off over here, see ya." That's not the way it should go. You need to be introducing that implementation and that CS team before the deal is ever closed. Implementation onboarding, how we're going to make you successful as a customer, is part of the sales process, and so you want to bring them in to be able to walk them through what the implementation plan looks like, what does success look like, what are you trying to solve for, where are you at today, and what does good look like? What are your goals? And once we're aligned on all of that, and there's some overlap here between the sales team and NCS, now you feel more comfortable moving forward with us, and when you do, you already have this relationship formed with the team you're going to be working with to make you successful.
Should CS also get commissioned if their broadened pre-sales being concluded and a part of that closing mechanism? That's a great question. Typically, they end up being compensated in a slightly different way, which is that CS often in most organizations are going to be compensated based on adoption. At least in companies that are based on usage. Are you seeing that adoption curve? Are you seeing full adoption? So that's how they're going to get paid. Ultimately, by helping to bring in a deal and seeing that adoption happen, they are going to be compensated for it.
Mark, I've just so enjoyed this. I'm going to do a quick fire around with you now. So, I'm gonna fire questions at you very much like I have been doing for the last hour, to be honest. I'm gonna call it a quick fire round because I'm good at marketing, and you're gonna give me immediate thoughts. So, let's start with what sales tactics have not changed over the last five years? The fundamentals, cold calling, cold emailing, that pipeline generation, qualification, champion building, getting to the EB. It'll never change.
What sales tactics have died a death? It pains me to say it, but I think in-person meetings. It's not that it's died. I think it's on life support. Video conferencing, digital whiteboarding, sales intelligence tools, they're all built so we can collaborate and be productive in a remote first world. But it can sometimes create this soul-crushing reality where human interaction becomes transactional instead of deep. Really. So even for large six-figure enterprise deals, human interaction in-person is not required?
It hasn't been required the last few years. I miss it. I love it. I will take every opportunity to meet clients where they are, but I think it's a dying art. Does the CEO always have to be involved in sales to some extent if you have Amazon moving, that's a bold one, but Amazon moving to Ramp with 500 thousand employees, does Eric still need to be getting on a jet? I think so. I think with any kind of really large company trajectory-changing deal, you want not just the CEO, but you want the entire executive team to be involved.
What would you say is the biggest mistake founders make when hiring sales teams? I think again it's about trying to hire people who fit inside a box with their preconceived notions every time. That's going to end up biting you in the butt. What one piece of advice on the flip side of the table would you give to a sales leader starting a new role today? Always look to raise the bar. Don't settle for b-players. I've made that mistake myself. I now have a rule which is that each subsequent hire has to raise the bar for the entire team. If they don't have the potential to be as good or meaningfully better than everyone else in seat, why are you hiring them?
What would you best like to change in the world of sales today, Mark? The perception of it. There's science behind great sales. It's not some parlor trick. Sales is often deeply misunderstood by those and other roles, and I think if you step back and look at all of the processes behind it, there's real science. How do you maintain morale when goes a mist in a sales team? It's tough because you want to maintain morale, but you don't want to create a culture of accepting fate. You have to start with understanding why it happened, who's responsible, how do you ensure it never happens again, and the answer inevitably is pipeline coverage. And whose responsibility is that? Harry.
Final one, my friend. What one company sales strategy have you been most impressed by recently? I think anyone who's executing right now and exceeding their goals. Outside of generative AI, which I think has a very unique tailwind, they're doing something right. Starling's performance has been especially impressive, given they fly under the radar, which is on for a company that dots the skies.
I love. that night totally agree with you this has been such a joy to do thank you so much for doing this and I've loved having you on my pleasure Harry thanks so much.
I absolutely love that and if you want to see the transcript for the show stay you can sign up for the newsletter on 20vc.com or watch the whole show on youtube by searching for 20vc but before we leave it today you might remember in our amazing episode with Maggie hot she mentioned a tool she could not live without called focus.
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As always I so appreciate all your support my conway to bring you an incredible episode with Tom Tungers discussing his new incredible fund theory ventures.