YouSaid · the spoken record

Ishan Mukherjee

lines on the record: 90
first: 2025-04-04
most recent: 2025-04-04
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“My time horizon from a recency perspective, like let's call it maybe the five years, I would say MongoDB, Dave, and that whole crew, I see their leaders in every great company, like ex-Mongo people running go to market in AI companies or fostering companies is so common. Like they just build a winning culture and he's completely transformed the business and it's a huge success. I learned a lot from him. The other one would be Ramp, like Eric and those folks, they were kind of second private private beta customer. Now we have the most used products. And there what I've seen is really high horsepower sales folks who've really grown from selling one thing to selling multiple things and now going upmarket, selling to some of these largest large customers. And it's all because of this kind of score talent base that they had, those two things.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Everything Mark Vineo's ever done, like he's this phenomenal visionary, really told the story well. Marketing and sales is obviously like a top-notch from what they've done. They have taken legacy enterprise bars. Think like CIOs and European, Asian, kind of industrial companies to really go on this kind of agent kind of journey where every CIO in the world is buying this year, right? And that is a lot of it is because of him and Agent 4. So painting the vision of what a gentic workforce could look like, he's in a great job. And that's why he's the code, right?”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“If you're running kind of the motion where everybody's hitting or hitting and the company's doing great, the morale hits happen when the company collectively isn't doing great because of something macro or the TAM, if it's the other where there's winners and losers constantly, there's two different things. In general, my view is three things. First is keep cranking. You got to keep working. Second is truth seek. Call your gaps and wins early. Take extreme ownership. Talk about what worked, what didn't work. And the third is in terms of morale, I do believe in the power law. There's going to be those 10 to 15% of the folks who are true believers, who are going to be there for the long term, just double down on them. If they hit great, if they miss, like how do we help them win the next time? And then the middle kind of 40 to 50%. Will they sway to the top 10% or the bottom 10%? And that's what you have to manage. But the only way to manage that is have doubling.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Like 50% of the customer that we work with, this is boring stuff, is private equity on. Like New Relic is yeah, 50% people who come inbound, our portfolio-wide rollouts. So there is definitely an element of efficiency. Can businesses run dramatically more efficient manner when they're not kind of growing at all costs? Yes, there's a huge part to it. Where does the capital go? Hopefully some of it goes to increasing the compensation of your supercharged frontline sellers. The other, I'd hope I'm contradicting. I still do think there's so much more to invest in R&D. I think if your technology business who wants to be a winner or be the number one, I still feel like R&D is severely underinvested in most scale businesses. I'd hope for their kind of frontline quota carrying reps to gain time to make more money so the company is doing well and that capital to be reallocated to R&D because we don't do enough of it.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Change of the quota as humans get more productive, as they are able to support more and more customers, the book size that they support fundamentally changes. If that changes, the complete structure of the organization changes. Instead of having large teams, you need fewer teams who hold more book and management layers kind of compress, and then you need different kinds of leaders. And that completely changes. Like sales and marketing is 40% of your OpEx, right? It could potentially go down to 20%.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Arvin talks about this as well. It's really hard to build what they have built and the talent that they have. At the very minimum, they'll find a massive kind of niche, like a large dowry. Large DAO segment that they will be the best at. If not, they would be like a strong player in the top three for sure”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“They keep the eyeballs and keep shipping the end feature that they are doing. I think there will continue to be a player. Is ChatGPT the default? Yes.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“He did the deal. He did the deal? And he's running the whole show now. It's a pretty large kind of public company. Oh, wow.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“I helped a buyer map out their path to promotion in a large streaming company that had nothing to do with the technology that we're providing. It was about how to deeply understand his career objectives to help him be successful. Nothing political, like he was just looking out for help. I probably spent like two months on it.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely. You're spot on. I think that is the biggest learning getting designers early, people deeply think about experience, getting kind of product engineer.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“And let's centralize our focus on working with them to build an amazing application. So about a month, four, month, five, we learned that, hey, we will hire amazing applied AI engineers who are shipping products. We're not a research company. Obviously, those are the two things.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Between us and every listening, and I think I spend 40 to 16 percent of my time on talent, the team, I underestimated how important and how powerful it is. We built a founding team of mostly all kind of top AI engineering talent, and that team has built the product, the culture. And hindsight, I would have moved faster to build out that team. And then kind of going back after going to San Francisco, I need to spend more time. So the biggest mistake is I would have maybe 5x the value I would put on just hiring. Second is very detail when thinking about AI hiring specifically. The first three months, I wasn't pragmatic enough. I was still looking for, hey, maybe we could do research and let's hire like researchers. No, we're pragmatic. We're building apps here. We're building product. So let's work with the best intelligence providers, opening eyes of the world, entropics of the world.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so like day in, day out, I managed a billion dollar revenue book. I've seen large businesses operate and been part of it. So it requires a lot of experience to being able to manage capital well.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“I think we have, keep me honest, 50 47 in the bank. We put in our own money to the precede. So we have full screen in the game. We're not going anywhere.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't think you're wrong. It's really, really hard. And I've gone back and forth ultimately my framework and our framework is we're building this to the long term. Who do we want around the table who can help us build this long term?”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Central software system that's helping you secure and grow your revenue. So we want to be essential. Just like SAP is or Salesforce was.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“So, if his upper mid-market enterprise we want to be at 45 days from M1 to having that first initial land basically done and signed, after it depends on how we can construct it, there's a one-year contract with a 30-day paid eval period, where 30-day the customer, I know there's a lot of discussions, we're still beta, right? So enterprises are buying beta software, so we give them the right 30 days. If you don't know how the ROI, you can downgrade to our premium product, or we can have a conversation. After that, it kind of converts. So once it's converts, then we're looking to deliver more value and can drive more expansion. So 45 days to get to the first land. And then we have the clock starts. First is we need to prove value in 30 days. After that 30 days, it's about delivering more value, kind of finding an expansion. And I think that's the, we've already at that six-figure range. And how do you kind of really kind of grow from there? Ultimately, we want to be the”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, 100k, like low six figures, and then really prove value. And we're doing that as a no brainer quick clan. We compete on time to value. And is there a path to high six figure, seven figures? And that's what we really care about.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Which means they are irrational Probably the most interesting thing for me to just manage my psyche around, I would say, the way I think about it is you're building something long term and what matters is enduring revenue, high quality revenue from customers who can be with you for the long, long term. And is the unit economics are the numbers looking great for that? Like for us, it's traditional enterprise Land and Expand. Are we landing the right logos? Are we landing them at a decent land ACV? Are we growing?”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“So, my framework is a framework of explainability. The idea is comp and how much money make people make an equity. I'm still old school. It doesn't need to be public. But let us say it did leak and became public. Like everybody's compensation should be explainable. There should be a rational reason as to why somebody is compensated a certain way. So I have guardrails, explainability guardrails that I don't want to kind of breach because if you're giving somebody some irrational package and it leaks and it's going to have like trickle down effects on the team and the company's the team, the team's the most important part. So what I try to do is if somebody's truly outlier and they've kind of went through the thing and they're really like capitalist and thinking about kind of incentives, very aggressive with performance based either compensation or equity grants and 100% like the outlier victories happen when you go you break rules, right?”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I try to founder led, early stage sales, which is what customers and talent, like you need to be able to make deals in the room.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Try to overshare context. Can the Silicon Valley ethos don't hide anything? Just share what you're working on because if somebody beats you on your own game, that's on you. So I just share everything. Like, hey, here's a product strategy, here's where we are, here are customer case studies. That's probably about the first 30 minutes. So when I'm doing it, I'm trying to see the questions that they're asking. They might ask about pricing or case studies, what worked, what didn't work. That could take a lot of time, like 30 to 45 minutes. And I do that for every candidate because I'm trying to understand kind of how they would go about because that's where we want them to abstract it, build a list from there. Their brain should be running. After that, we get into specific scenarios. Okay, now that we want to do a scenario, let's say we're working a strategic deal called a large company in Europe. If I gave it to you, how would you run this deal? And then I flipped, then I ask them questions, right? Like, what if this happened? What did that happen? So first 30 to 45 minutes is me sharing context and them asking. The next 30 minutes is like them.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“My interviews are long. I don't believe in 30 minute interviews. Either I believe in my kind of trust on a network of folks telling me somebody's good or not, or I do hour and a half working sessions. In the working session, by, I would say the half hour mark, I can tell based on the quality of the question they're asking”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, a lot of them, especially in COVID. So I really try to get deep into did you actually hold a number? What did your conversation look like? Where do you want to get to? Because you kind of gets deep to the psyche of a person. The best A's are complete owners. They're owners of their own book, not very different than a CEO or than a founder. And that's kind of the third thing I try to get to. And that's kind of separates a lot of folks who are doing it because it was easy. They also have a real estate portfolio on the side. They're doing a lot of things. And so you're trying to hone in on those kind of three things. Bag has some experience holding a bag, a real enterprise bag. Second is kind of creative. Third is, did you hold a number? Like I go really deep into that.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, should have held the number at that ACV size for two to five years. Not less than two, either not more than five. Within those, they need to show that they've been innovative in the pocket. Within deals, they either built tools on their own or were actually creative in kind of progressing or closing the deal because early stage selling requires a lot of creativity that founders can come in and we can use investors and harass involved, to kind of paper over cracks, but they need to be kind of creative. That's number two thing. The number three is just they need to want to make money. I really kind of deeply think about DD hold. You would be surprised a lot of AI companies, AEs, are not compensated with commissions.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“There's different variations. I back myself to recruit, train, and build the machine with five reps reporting to me directly, and then bring on a sales leader who kind of doubles the team and takes it from there.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm going to walk you through the whole strategy. Here's what's worked. Here's how we messed up. Here are our reference customers. How would you go about producing your list of people to reach out to and how would you actually get to having a high quality first meeting?”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Repeatable sales motion is Are you able to go from a list of potential customers to a high quality first meeting autonomously without the founder helping you? The second one is can you go from a successful first meeting to landing the customer without extreme founder assistance if you can't do both you don't have repeatable sales emotion. So in this early stage where I do have to kind of grow really regressively what I'm looking at is the first part is based on the case studies, reference studies can an enterprise A come in, build their own list of target customers without needing a BDR team, without needing like marketing people and then go from there to the first meeting autonomously can I completely take a step back after M1 we just have to be truth seeking like look we don't have a massive brand we don't have a huge demand engine it's not perfect product market fit we're early Italy founder assisted so that's what we're looking for it's the working session that I do”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Its bundling cycle. With us, we want to be hopefully the default new option of an AI native kind of bundled software provider.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“He's spot on. Benny offs the goat. You respect him a lot. I've learned so much from him. I used to read about his stuff way back in small town, India. Our approach is just time to value. Going back to the New Relic learnings and just kind of being like a product folks founder is incumbent systems have data and distribution. They have massive amounts of both. From our, but it takes quarters, system integrators, to actually implement things to prove ROI for us is how do we leverage our shipping machine to land something that gets started today and gives you ROI in an extremely time-compressed manner. And then we earn the right to connect span from there. So what's going to happen is all the incumbents have obviously repositioned as AI companies now or agent companies. And they're also all bundling. Like as SaaS exploded, there was massing unbundling across sectors. Definitely in the CRM space, right? You have phenomenal businesses like Clarity and Gong and Clean folks. So they're all bundling and they're AI companies.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“So, when we go into a customer, our agents will go enrich contacts, hey, if you have data, zoom in for data in Salesforce or whatever, it's going to go search and kind of verify that information. And internally, we have kind of OEM'd a few data partners and that we waterfall like Clarity just to kind of bootstrap us. So these agents today are enriching the information that you already have versus going and actually gathering it. There's a split company data is free gram. Company data is public. Agents are pretty much at par. Contact data is where the divergence happens. If you look at what the question that you brought up is like LinkedIn information. Like LinkedIn is involved garden, rightfully so. It's an extremely kind of valuable network that Microsoft and LinkedIn have. People who have LinkedIn data as a data product that they sell into is just a different world that we don't see ourselves going into.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“We didn't start rocks, or this amazing company is going to work in the space, kind of deeply thinking about how to source agents, but the agents have gone phenomenally good at scale gathering information that is in the public internet. And now systems like Lean and stuff in the intranet or in the internal systems. So yes, the agents will get more and more capable to just collect information, especially with search APIs and the access of the world. Having said that, the data providers, they provide a kind of source of value where they have 10 to 15 years of back tested data of human contact information, LinkedIn information that they've been verifying through a lot of software, but also a lot of operational rigor. That's really hard to rep.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“So first, hire the right folks who are future proof. They understand the word. So, are they using these tools maybe illegally in their personal lives? If they're not using it, they don't see the alpha in their personal life. They're probably not going to get it. Second is, I might be completely wrong here, but ramp much faster because A, you can just do it faster. B, the consumer expectations are changing too fast that you have to do so. Once you're fully ramped, push the envelope of how many customers that they could support. And those are the three things without obviously losing overall quality and containment levels. Will there be teams which are much dramatically smaller who are pulling the same numbers? I think it has to be proven, but strong kind of intuition that that's where we'll get to.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Why I'm here in London. I think Jason's point is important those folks who are there to build non transactional long-term relationships at a strategic level, so high ACV, deeper conversation, they will be able to do a job a lot more. They'll be able to do two to maybe three times more this year. We're seeing some of the best organizations increase their book size. Hey, you would have supported five customers last year, this year, maybe seven, next year, 12.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, dramatically smaller, just like engineering, just like any other function in any business. It could be 10 to 20% of current kind of orc sizes. And it's just a harsh kind of reality, but that is a probable productivity gain path we're on. And it's tough, it's brutal. And I've seen, like, I've worked on automation systems all my career. I built robots in warehouses before the company that Amazon acquired. We've seen these things happen all the time.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“There's massive amounts of experimental budget. We've made the decision of not tapping into it at all because of the focus on retention, usage adoption, RI. We only work with customers from their operational budget, program, now kind of people budgets. That's a way for us to control, be truth-seeking. But we are in the very early stages of the adoption curve. What I see is small group of outlier operational CEOs, CEOs, CFOs who really understand that there is an existential decision to be made this year to transform the business, to kind of keep their lead. The rest are still figuring things out.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“And if the end user sees something that's not good, it's going to kind of shave away some of their trust. And if it gets to a point where I just can't trust this thing, I'm not going to come back. That is the biggest thing. Is there going to be retention and churn issues from an end user perspective? 100%. We're seeing so many tools come in and out.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“It's like Dane. We've chosen the hard path we want to be on the mao Dow train and build applications where people come in and do important work every day, which is not easy. I think where people are going to die off is in terms of usage is if they just lose trust. What you have to understand is these products are inherently non-deterministic. These are probabilistic systems, right? So the experience, the research output that you get for, say, your Siemens agent could be different, what I get from a Siemens agent because the LLM is trying to figure out what's relevant to me.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“What we did is we decomposed the experience to a part where we have essentially kind of workflows designed for the job at hand. So we went like Bill Belichick style. Like, what are the jobs to be done? How do we actually kind of organize it that way? Like meetings are separate and emails. Emails are separate than account research. And the adoption just completely, it was insane. We go from the few people using us to the whole company using it very, very fast. And again, like, is that a terminal state? I'm not sure.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Because our kind of end users expect the software to do work, so they essentially want workflows, right? So if the agent went out and did in customer research, they just need all the customer researches listed versus them asking, hey, tell me this, tell me that. So we have account reports and org charts created pre-created for them. Similarly for outbound sequences, instead of you going and say, hey, produce an email, we just queue up all of your email tasks. So these are these places where the software does have to lay out its outputs. Like chat is a interface for them to do more introspection and go deeper. So I'll give you a very simple first we start with a chat app with just a blank Google bar. Next is give me pills. Give me suggested things to click on. Then you hit pills like, hey, give me more output panels. And those things work really well in consumer applications like perplexity, which is amazing. Love the product. But in a B2B software where people are coming in to get job done, we have to just do more.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“I think I'm pretty pragmatic because we have to be very iterative on the interface layer. We've already pinned it about the back end and how to manage all the context. But in the front end, we just have to really try to track the consumer expectations. What we learned was chat interfaces are very powerful, but we're very limiting to do daily work.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. So you kind of hit on, you should be our head of product as well. Give us a lot of feedback insights to contact or human level insights, and that's kind of the journey. That's the number one piece. The second thing is it is in net new form factor, net new UI. Like if you look at our product and UI, it kind of looks like a CRM, but it's actually a sort of agents working for you. So there's a new paradigm of UI or UX, which is between a chat interface and a traditional flat SaaS experience, where this kind of more task-oriented. And that's where we're at. So the history of ROX is a pretty experienced team. The first three to four months we built a God mode agent that knows everything about every customer with a chat interface. This does not work.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Three things relevance is our agents, it is an agentic CRM. These agents are trying to do a lot of the work for you. So it collects all the data, finds relevant opportunities to reach out, and then tries to compose all of your outreach because we just got pulled so fast out of us, like Roxy Stellar, beta honestly. It's public, it's open, but it's still pretty early. Finding relevant moments to actually reach out to customers is actually a pretty hard engineering problem. Earnings coming out might be interesting, but it not be compelling enough for you to actually reach out to those customers.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Active, close to the car. Like, we have an iOS app, we have a Slack. We really want to craft the application that people use to do their work. So we index, if people are not using it, you can remove us.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Adoption. Traditionally, the adoption about a lot of these tools, they're abysmal, like the NPS scores until we kind of index ourselves in pretty aggressive. We've hit 75% weekly active usages with more than 50% daily actives. We want to be the daily driver application.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Pipeline progressed because these agents are really good at making sure a human can manage a larger book of customers really effectively. If they have tens or hundreds of customers, because the agents are doing most of the back office work, is doing the research, it's outbounding, it's prepping for meetings, managing our opportunities so that you can actually engage.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Generated or progressed. The second was adoption, third one's activity. The system needs to return all three. If not, you can fire rocks.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“Consolidate more yes, the definition of spend what I am seeing is changing and is changing from program to people. What I mean by that is when you look at traditional SaaS, and I'm saying New Relic and I've been in this space for a while, we're thinking about CC, you're thinking about productivity tooling and kind of basically selling from the IT budget. Now a lot of sophisticated buyers are looking at systems, hopefully like Rocks as well, is, hey, can I just make my humans a lot more productive so that I might not have to hire as many, just kind of brass tacks, right? So it's their view of kind of the ROI is changing from ROI on just software to kind of the people spend. So what we focus on is we want to be the only right now is we only convert if we hit our ROI metrics. We're on a 30 day white glove like Palantir kind of boot camp where we work with the CFO, the CRO and the C suite on three metrics. The first one is dollar normalized outcomes, whether that's Python.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“And yes. So supply is infinite. Yes, it becomes less effective. What our view is, how do we make the communication authentic? So very basic thing. The email needs to come from your email. Second, the email that comes out should be personalized in your voice and tone. And then you should probably review it. And that's the only way to actually rise above the noise floor because noise floor is increasing exponentially. Everything else just will not work. The second thing is you kind of brought up like multi-threading and kind of talking through it. The key thing is the human has to create a human connection and one email is not going to do it. It usually takes 13 to 15 touches. So emails, LinkedIns, meeting them in person, getting on plane, as Jason says. So again, our idea is how this is going to swarm of agents help you produce the content, but you have to really put in the work to have those touchpoints. If people think that you can close enterprise deals, but having one email go out, that's not going to happen.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source
“So we have tons of VCs on the platform. 100%, like, we're pretty maximalist in terms of where systems like these could be helpful. We think deeply about what's going to happen to Knowledge Force across the board. But today we have some of the best VCs, hopefully EU as well, using us, we tune our agents based on the context. So the emails that it drafts, it's not really trying to convince a founder to take a meeting. Those are things that we have to do, but it's completely feasible.”
2025-04-04 · The Twenty Minute VC · 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox · IDENTIFIED FROM THE TRANSCRIPT · source