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Mark Roberge

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2024-07-12
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2024-07-12
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  1. “That's really cool. So he started to learn about us. And Benny, I was like, Whoa, this is exactly what we need. So he's like, Benny Off looks at all the partner, all the different things that are in their app exchange, DocuSign, all this stuff, right? And Benny Off is like, we're going to choose 10 out of the 3,000 that our reps get quota relief on. It counts toward their quota. And HubSpot is one of them. And I'm going to talk about that at our sales kickoff. So Benioff gets up and says, hey, keep selling all of our child. We have really cool channel partners. 3,000. It's a huge app exchange. And there's 10 of them that you get quarter relief. And all the reps are like, whoa.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “It's a little like one off bonus, okay? I'll give you an example. So Salesforce.com was an early investor in our Series D, believe it or not, and actually became a big channel partner for us over time, about 10% of our customers before we became competitive. Here's an example of what happened. We had contacts really high up, George Hugh, I think it was, who was COO. And he eventually got us beneath year. And we heard at the time Salesforce wasn't in marketing yet in the marketing cloud. We also heard that the number one sales objection and reason for closed lost was, hey, cool, you organize my leads for me and my deals. My biggest issue is getting more leads. And the salesforce.com sales reps didn't know how to talk about demand generation. Benioff knew it. And he's like, okay, we need to find partners that can help us with demand gen and help us train our reps how to talk about demand gen. And George, like, I got this new company.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Like, you have to understand what the strategy at the C level is, make a case that your product aligns with that, and then convince them to spiff the crap out of their reps so they're motivated to pull it out of their bag. Hard,”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “Yeah, exactly what you said, Harry a complete underestimate of what it takes to actually mobilize that partner. Okay. And it's, I get why they're doing it. It's like we're going back to our product founder and they're like, yeah, we have like 10 design partners and 10 design customers and now we have to go acquire a bunch of customers. And I have two options. Option A is hire a big expensive scary sales team that's going to destroy my culture. I don't know how to hire salespeople. Or just go partner with Workday who already has 5,000 salespeople. And I'll just give them 20% of my profit. Why wouldn't they ever want to do that? It makes perfect sense. First off, do you even know how to get into workdays program? Like you need to like really have good alignment as high up as possible to do that. Second off, do you even know how to get the mindshare, the rep? Imagine being a workday salesperson. You worked for hours to get 30 minutes with a customer. What are you pulling out of your bag to show them some startups little product that I get a 5% spiff on? To really mobilize, you have to.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “I would say year four. We also built a vibrant channel partner program, a very fragmented channel partner program through like very small channels, channel partners. So I would say by year five, we were 50% inbound, 30% channel, 20% outbound around the IPO it becomes very blurry because at that point, you tend to just like go to territories. The brand becomes so strong that like it's really not clear what an inbound version out. Like someone does a cold call and they're like, oh yeah, I know you just cold called me, but I'm already HubSpot customer and you're like, what do you mean I'm a hub spot customer? Like, oh, I've been using your marketing grader, your free marketing grader product for two years. Like, oh, yeah, like you're not really a customer. Or like, oh, I heard about you guys. I saw you at an event. So it's like when you hit brand scale, the lines start to get blittered.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Ridiculously high. It's rare to see it that high. I think 100% of our customers came inbound for the first two or three years.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “10,000 employees. Those are red, you are not allowed to sell them. Yellow is you can sell them if they're inbound. So we're not going to coal call them, but if they come inbound, we don't have enough conviction to know that they're not a fit. We also don't have enough conviction to go outbound. So that's how I kind of try to think about it in that green, yellow, red mindset, least to start. And then over time, you can start to evaluate customer success, performances, et cetera, to get more conviction on it.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Good question. Like, do you have to be specific about your ICP? Now, very early, it's a hypothesis. So let's say if you take the whole world and ultimately your ICP is going to be, say, like 5% of that, well, I might be okay us selling to like 10 to 12% and drawing a little bigger circle because we just don't know. But like there's some folks, I like to do like a green yellow red. I have different attributes like, you know, how many employees were they located in the world? What sectors are they in? These types of things, right? And the green is like we have strong conviction that those are good fits between 50 and 500 employees based in the US in tech. That's green. And we're going to go after those all day. So when our SDRs are cold calling, they're the only cold calling those people. Then there's reds where we have strong conviction we will not sell. In fact, you cannot sell them. Okay. So that might be outside of English speaking territories. That might be healthcare nonprofit government. And it might be like greater than.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Not as much as people think. Case studies in general you throw a case study, well, that's a bank and I'm in healthcare. Okay, well, here's one from healthcare. Well, that's in oncology and I'm a dermatologist. Okay. Here's one incology. Well, that's in this type of oncology and I'm more this type. You know what I mean? It's like, or there on the West Coast or we're on the east. Like they're never satisfied. Yeah, it helps a little, but not as much as people think.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “Start doing that, and now of a sudden you have no sales because you don't know how to sell those deals. That was like a lucky inbound. Real big trap.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Yeah, I agree. You were actually in agreement, Harry. I probably didn't say it right. It's like they would say, you're not going to go unless you're pulled. But if you're being pulled, it doesn't mean you should go. You're on the same page with them, Harry. And like classic example, I mean, I think we're two, three million in revenue at HubSpot. And one rep brought Facebook to the table as a customer. It was like a $3 million contract. It would have doubled our revenue. And he said, no, we were being pulled. said no. Everything's going to go bad at that point. Like they're going to start controlling your product roadmap. We're not built for that. It's not going to go well. Things are going to get around. It's going to distract the company. And the other thing that happens too, Harry, is like if one of them, I had another company recently that did this where a friend of the CEO at a big company came in and bought. And it was like a huge contract. Up until then, they'd been selling $15,000 ACVs. And this one was like $200,000. And all the salespeople were like, whoa, look at that. I made my annual goal in one sale and everybody will.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Sell companies with 500 employees and 20 support reps. That's fine. That's not trying to close a huge bank. So you just have to carve out the smallest possible. And then I've asked a lot of people from Chris Degnan, one of LPs or the financier of Snowflake. And the answer on when is always the same from them. It's like when you get pulled. Because like, you know, you're making hay in the S&B. You're going 1 million, 3 million, 7 million. And like big businesses start hearing about you. In fact, you're probably turning away big businesses before you're starting to sell them.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “Both answers could be correct. I will say that it is extremely rare that you want to go into enterprise south of a couple million in revenue. Extremely rare. So it's a little bit of a trap for most entrepreneurs to want to go to the enterprise too early. A lot of my students do this. You know, like, oh, if I can just get that huge logo, everybody else will follow. Well, two problems with that. Number one, you really underestimate what it's like to get that logo. It's going to take a long time, maybe a year and a half. Whoever's your champion you might quit their job in that time. And by the time you get to the finish line, you're going to have to do sox compliance and show all the stuff and you don't have it. So it's like it's just going to kill you from a capital standpoint. Your better bet is to figure out what your product is, what your offering is, figure out your total adjustable market, and carve out the lowest part possible. Now, it's not always like a couple people. Like we have an AI company for support teams. It doesn't work if you only have two support wraps. It just does not make sense. You have to have at least 20. But that's fine. We can go.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “New software to new customers to grow by 10%. That is hard. Versus if you're at a billion and you have 100 10% never retention, you can do nothing in new sales and you're going to grow by 10%. So at some point, it just like you can't outsell our net revenue attention less than 100%.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “At some point, you need to get above 100%. Because if you're not above 100% net revenue retention, you have to, in order to grow, you have to outsell that gap with new customers. If you're at like 10 million in revenue, that's not that hard. If you're at 10 million in revenue and you have 90% revenue retention, that means that you start the year, your customers are paying you 10 million, and those customers will be paying you $9 million at the end of the year. And so you just need to sell a million dollars of new software to maintain flat and you need to sell five million of software to grow by 40%. That's not that hard. But once you get to a billion in revenue and you have a 90% net revenue retention, that means that at the end of the year, you're going to have 900 million. So you have to sell $100 million of new contracts to new customers just to remain flat. And $200 million of.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “I just worry that some customers don't know that. Like, I know this company is selling yoga software and they sell it specifically for more of multi-location yoga studios. But yoga own studio owners talk to each other. And when they're at like a retreat together and they're like, oh yeah, I tried that and didn't work for me. I don't think they were like thinking, oh, were they in ICP or not? I just think like. There's a reputation so”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “I think they're both needed. I probably put more weight in net revenue retention because at the end of the day, if you have 120% net revenue retention, you're going to grow 20% a year without acquiring any customers. That's really powerful. Whether that means you have 90% customer attention with 30% expansion, and that's how you get to the 120, or you have 50% customer attention, 70% revenue expansion. And that's how you get to 120. Either way, you're going to grow by 20% a year if you keep that up. That's why I think that's the most important. The problem with the latter of having 50% customer retention with 70% expansion, yeah, the customers that stick with you are seeing a lot of value and paying more. But that means half the world out there are being like, yeah, I tried Harry's product and it didn't work for me. That's not good. So that's why I want to look at customer attention, but like I kind of think.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “Get your revenue retention to be above 100%. It's doable in PLG. Most starting ACVs is zero. It's all expansion, right? And so only the people that have already seen value in your product start with revenue and that usually sticks very nicely and then continues to expand. So S&B is very doable. It's just like you probably have to start them on lowest ACVs and you have to have a really strong expansion mechanism.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “We do invest in companies that serve SBs. That's become like a really great starting point, and you can build a healthy business there, but more importantly, use that success to move upstream to the mid-market when your product and brand and your sophistication justifies it. And then eventually to the enterprise, potentially these are very common plays. But yeah, with three to four percent, not a lot. I mean, you have to have a lot of other things going right because actually you just don't have a business. Now, when you, if you do want to make your business work in SMB, you just need a really healthy expansion motion because like just macroeconomics because of like small business bankruptcy and budget sensitivities, if you're doing really well, you probably have an 80% logo retention in S&B. So you need to have at least a greater than 15% revenue expansion to get your business to be solid.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “Month, yeah, month, by the way. Yeah, it was high. It was the highest it hit in February of 2008. Throughout 2008, it was mostly between three and four, which is terrible. I mean, even at three or four, that's 40 to 50% a year churn. It's really bad.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “Know there's multiple ways to measure uneconomics, there's payback, and then there's LTB to CAC. For whatever reason the industry talks about or the LTV to CAC greater than three, it's a little bit of a farce, but it's not like a terrible measure. It's good to know what your LTV CAC is. That's where you could find that, Harry, and that's going to.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Yeah, so at scale, it's going to be like on your income statement the entire sales and marketing align is going to be the CAC. And you divide that by the number of customers that are acquired in that period, let's say in a quarter that you're evaluating. Now, that gets challenging at the Series A because if the founders are selling, well, then you have to attribute a part of their salary hypothetically. And if like you're throwing just general networking events for the company and that's leading to leads is that so there's always these squishy costs just to keep it simple. Everything you're spending on marketing and salespeople and sales leadership and sales ops and all that kind of stuff needs to go in there.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “At the IPO, less than 12 months is excellent, 12 to 15 is good, 15 to 20 gets concerning above 20. It's going to be a real problem. 20 months. At the series A, less than 12 is almost like you're probably being too efficient. We probably try to grow faster. 12 to 15 is really good. 15 to 20 is fine. It's kind of like, that's fine for now. We'll have to work on it later. Above 20, it gets concerning. Yeah, so you kind of have like some semblance, but there's a little more flexibility at the Series A because we know that there's a lot of improvement that's just going to come with scale potentially. And then there's a lot of opportunities and low-hanging fruit for us to get to that just isn't a priority right now.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “CV is only one part of that formula, Harry. The CAC is the other piece. The CAC for outbound sales teams is all over the place because it depends on like how many calls do you have to make to get an appointment, how many of those appointments turned into a demo, how many of those demos close, right? So there's a lot of different variations in there. Are you calling CMIOs of hospital systems or are you calling like landscapers of small businesses that pick up the phone a lot? It really comes down to like the absolute academic and practical answer is you have to have good unit economics, the CAC and the ACV have to match up, but it's not always like at 3,000 ACV, you can have a sales team and at 2,000 you can't.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “That was a really good question. Okay. So my approximation would be even in HubSpot, we started at like 3,000 a year. I would say that's on the lower end. Now that required a lot of inbound leads. There's a big missing part to that is like the ACV is only one portion. To answer like whether or not our go-to-market motion is working, whether we have a salesperson or PLG, or we're using marketing and inbound or we're doing cold calling, whatever. The absolute right answer comes down to unit economics. And there's a couple different ways to measure unit economics. Let's just say payback period, which is the CAC divided by the ACV. Someone pays us $10,000 a year, then the CAC needs to be $10,000 for us to have a payback period of a year. So if someone pays us $10,000 a year and it costs us $10,000 to acquire them, we get paid back in 12 months. Anything above that, you start to question whether Unit Econx work, anything below that, it's really good. The problem is.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “I would do something like this, Harry. You're a salesperson. Your job's braining customers. I'm going to pay you 3% rate on the first ACB from a customer and 5% on any expansion revenue. So now it's like, oh, sweet. Okay, I get it. So I will make the most money if I sell customers on a very small ACV to start and expand them later. Yes. That's what you do. And then the salesperson's like, wait, wait, wait. Am I a CSM now? No. No, you just go hunt. You go hunt, you sign up customers, and we have a CSM team that onboards them. They expand them. They have their own different compl plan. They have their incentives too. That's just how yours works. If you sign up good, healthy customers with good expectations, you make a lot of money. If you sign up a bunch of crappy customers that don't stick around and don't expand, you're not going to make a lot of money.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “So many, if you're pursuing PLG or Lan and Expand, the sales compensation plan can really F that up because most sales compensation plans put most of the payment, the commission, on the first ACV from the customer and have very little, if any, on expansion. It puts the salesperson at odds with how you want customers to buy your product. Because when you're in PLG or Land and Expand, the buyer wants to start small to test it out and then expand it, whether that's with other functions or departments or whatever. And you as a company, a startup, your strategy is to do the same thing. Make it easy for customers to just like give it a shot and expand it. But if your reps are paid in that way, they want the opposite. They want you to buy everything up front. And you're likely to contract or churn. So that's a huge fuck up that we see a lot.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “Market fit, but we have to make sure that as we scale, we keep customer value and success top of mind. And so I want to make sure that my reps are not just selling customers and revenue. They're selling healthy customers, customers that are in my ICP, they're going to see a lot of value from our product. Most complans don't motivate that, don't incentivize that. But here's an example of what we talk about, like think about your strategy and align it with a complaint. It's like, okay, Harry, when you sell a deal, you're going to make 5% on that deal. I'm going to give you half of the commission when the customer pays and half the commission when they hit their leading industry.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “If we have three design partner customers and we need to get to like 20 to understand product market fit, am I not bringing on a salesperson to help us do that? And that person's making, say, $150, like 75 base, 75 commission. I don't want to put them on a comp plan. I'm going to just say like, listen, I'm going to pay you like 125 flat out no matter what with some equity. That's the right person. Because like we're sitting around and we're pivoting, pivoting, pivoting. We're shoot, we've got it wrong. We have to got to go back to the driving board and it's going to take us three weeks to build this thing. All the engineers are making their salary paying their mortgage and the sales rep is like desperate and sweating. I don't need that. And furthermore, like that's not the rep I'm trying to attract right now. I'm trying to attract a rep that like enjoys that design journey is sitting there shoulder to shoulder with the engineers not sweating making the mortgage payment or thinking short term. But then like once we get into, okay, now we have product market fit, then this is a classic example where it's like now we need to get like go.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “What most people do, which is, I think, a big mistake is they hire a salesperson or leader and sort of delegate it to them because they sort of are the functional expert on it. And then that person uses the sales comp model from their last company. That's really broken. What a lot of founders don't realize is you can get pretty creative here, especially in the early stages. The best way to devise a comp plan is to think about what you need the business to do in the next six to 12 months strategically. Don't even think about sales. Just strategically and holistically. Are any of those reinforceable with sales piercing behavior or action? And if so, that's going to start deciding your compl plan. So I'll give you some really common examples. First off, which is like semi-related to that point. I don't like commission plan salespeople in the journey to product market fit. Like I just want pure equity people. If we're trying to find product market,”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “I don't think it does. To your point, I think it's a red flag for the candidate. But if I have a star and I have to give them a VP of sales title instead of director or a CRO title instead of VP to get them to do the job I see for them for the next 18 months and assess, I don't see it be an issue. Like it's like, okay, I hire someone. They kill it for 18 months. after that we decide we have got to up level them in one case their title is director of sales in another case their title is vp of sales i don't think that's harder”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “Probably a red flag if they're over obsessed with it, a little bit of ego stroking, and that's not going to be great for culture, especially early on when it has to be like, let's roll up our sleeves and do whatever it takes.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “Going up for a week and go down, yeah, we probably need to make a cut. But if they're staying there, this has taken a little while. Let's hang in there. I think we're going to get there. That's the best I can see to get an early signals to where this person's going to make it”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “It takes a while, and I have a lot of situations where I had a rep that was in there for three or four months and we weren't sure and they weren't hitting it, but we gave it a shot and seven months in they were toward the top and they stayed there. So that was perplexing to me, Harry, because like I want a lot of early knowledge and lead indicators, but I've seen that happen quite a bit. It just took them a little while to get there. The only thing I can say early on kind of comes back to that coachability again. If I have a manager come to me and say, oh yeah, Pete's not working out. And I'll say, how do you know? Like, we'll look at their numbers. And I'm like, okay, well, what are you coaching Pete on? And I, well, we're trying to get him to do a little better job on sense of urgency development. And I'll say, okay, how are you coaching him? So now I can assess if the manager's got a good diagnosis and good coaching model. And then I'm like, okay, when you're coaching them, are they staying when you move them up a little bit? Are they staying there or are they there for a week and then they go down?”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “And a piece of need for improvement. So I give it positive, I give a need for improvement. I watch how they take the coaching. And then usually I have them redo the role play. And then if we're going to do another meeting, I'll say we're going to do it again. So let you think about it for two days and then come back. And that's a big part of my assessment.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “I love getting into a role play. That's the most important part this part where it's like, okay, Harry, we're hiring for HubSpot. It's like, let's just pretend you're a small business owner and you downloaded the HubSpot, inbound marketing ebook yesterday and you got the lead. Let's just do the first call. And so we'll do the call and I'm looking at things like really good open-ended questions, follow-on questions to do discovery and qualify need and quantify need. I'm hoping that there's no show up and throw up and they give me like a five minute commercial on HubSpot that I could have just read online. And then I'll stop the interview a couple minutes in. And then I'm going to assess coachability. You know, in most startup contexts, no one's going to come out of the gate hitting their productivity in month one. Like they have to learn the product, the methodology, the customer. So I'm assessing their ability to be coached. And so I'll have you self-assess. And if you're like that, I was awesome. I have no feedback for myself, then that's a red flag. Every interview, I give a piece of positive feedback.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “I have strong conviction that deal size has a higher weight in correlation to success. Let's just say we sell million dollar deals to banks. And I have two candidates. One candidate sells $10,000 deals to banks. And one candidate sells million-dollar deals to hospitals. The skill necessary to get a million dollar deal done, there's so much in there in terms of like, how do I identify and build a good champion? How do I understand the political dynamics? How do I differentiate between an economic buyer, a technical buyer, an end user, a coach, and a champion? How do I like understand medic as a sales process? How do I deal with procurement? How do I deal with legal? My million dollar seller that sells to healthcare has all those skills. Okay. My person that sells to banks, but they sell $10,000 deals has none of those skills. I'll be much easier for me to teach the million dollar seller about banks than...”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “On their own, they might get it to like 70% of the way there. And then a professional seller is going to come in and take it in the final mile and add the details like cold calling, getting the appointment, doing discovery calls, tailoring the pitch, handling the”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “It depends on the aspect of the playbook, Harry. So, in terms of a Sandler level or winning by design, like force management methodology, that's going to take a professional leader to bring in and navigate. Like even things like how do you manage the first meeting and do discovery well? I don't see a lot of product founders coming up with that. But one of the underlying pieces of the sales playbook is a buyer journey. What are the different ways that buyers describe the problem you solve or the opportunity that you create? And how do they look to solve that? And how do they look to make that decision? That's something that a founder should be working on from day one just to start crystallizing that. Another piece is the ideal customer profile. So what are the attributes of like what a home run fit is for us versus not? The other attribute is like just the general value proposition that we're pitching. These are typically areas where founders can make a lot of progress.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “An advisor. Advisors are cheap. They're usually a little bit of equity. Go find someone that's hired a bunch of salespeople, particularly that in this case, it could be okay that it's in your domain.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “Yeah, it's a really hard one and it's a key a lot of founders today are product and engineering oriented and don't have a lot of experience in sales. Every time I ask them, what are you looking for? They always say the same thing. 10 years of experience selling a product like mine to a customer like mine. And there's tremendous research that shows that that mindset doesn't work out. And it's not that it doesn't help. It's just that there's a whole bunch of other things you need to assess, largely around sales skills that are not looked at. And because of that, you end up with the bottom 25% performers in your industry. That's the biggest pothole. Essentially, what that means is a founder needs to learn how to assess a seller on sales skills. And that's like saying to a salesperson challenging them to assess and engineer on how well they write job. It's hard to do. You almost have to go to school for five years. So it's kind of the same thing. It's difficult. I can't just like say a statement in like you learn it in a minute. Go find.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “John Mesh is trying to recruit Brian. And so about a couple months through into my consultancy with Dharmesh, he said, Hey, I was successfully recruited Brian to be my co-founder and BCEO. And so we sat down and Brian's like, I like Mark. Let's keep Mark on. But Mark just do sales if we have you one day a week. So I did that for about six or seven months. And then he took me into a Red Sox game and was like, so at that point now, we've acquired between Brian and I, we've probably acquired like 40 customers. We're probably at like couple hundred thousand in ARR. We brought a Mike Vopius CMO. Brian took me to a Red Sox game and was like, hey, listen, General Catalyst is coming in for our A round. We're going to raise $5 million or something like that. He's like, why don't you come join full time, be our first salesperson?”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “I had sat next to Darmesh in school at MIT in 05 in a class. It was one of those classes where you, there's like 50 students, everybody shows up with a business idea on like one page. That night you read them all, you vote, and 10 people get picked to be CEOs. I got picked to do mine, which is in the social networking space. And Darmesh got picked and his was Hubs bot. So that was like the first time I met HubSpot. And then he and I became friends. We would grab Chinese food once a month or so, talk and got to know each other. And then when I was like, hey, by the way, I'm actually going to do mine and raising money. He's like, I'm in, I'll be an angel. I'm like, great. And then at some point through that journey, he was like, can I pay you as a consultant too to help me with Hubsbot? I'm sure you need money. You have this big loan from MIT and all this stuff. And I'm like, sure. When I first got engaged on that level with HubSpot is it was just Darmash. He was Brian was in venture capital but had been working with Dharmash at MIT on the concept and had”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “We could consult, and I want you to sell. And so that's how I got into sales. Dharamesh hired me for one day a week. You're now the CEO. If you want me to sell, I'll sell. If you want me to write code, I'll write code. Like, it is what it is. So that's how I got into it. And it actually worked out beautifully because I was not only in sales, but I was selling cutting-edge marketing software. So I got to learn all about both, which was completely accidental but awesome.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “Like a lot of the wins in my career, it was completely serendipitous, almost accidental. At 23, I discovered that I wanted to be an entrepreneur. And even to this day, I kind of consider myself more of an entrepreneur than a sales leader. Even though I was a founder, CEO coming out of school, I knew I wanted a functional alignment and I was torn between marketing and sales. I was like, there's not a lot of MBAs that go into sales. So that's weird. But I really love the art of the deal. And I know generally speaking in tech, salespeople make more than marketers. And I had a young family and like I was the financial responsible for that. So like that was important and ingredient. But I felt like the MBA provided you more for marketing. Marketing was going more in a data-driven direction. I was consulting to HubSpot when it was like one or two people and eventually joined the company as the fourth employee. And that's where it sounded kicked in because Halligan was the co-founder and he is a sales guy. And he was like, if we're going to use you one day.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source

  46. “I was consulting to HubSpot when it was like one or two people and eventually joined the company as the fourth employee, the skill necessary to get a million dollar deal done. There's so much in there in terms of like, how do I identify and build a good champion? How do I understand the political dynamics? How do I differentiate between an economic buyer, a technical buyer, an end user, a coach, and a champion? How do I deal with procurement? How do I deal with legal? My million dollar seller has all those skills.”

    2024-07-12 · The Twenty Minute VC · 20Sales: Biggest Lessons Scaling Hubspot from $0-$100M in ARR, The Framework for How Startups Should Scale into the Enterprise, How to do Channel Partnerships Right and How to Construct Sales Comp Plans Early On with Mark Roberge · IDENTIFIED FROM THE TRANSCRIPT · source