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

“Absolutely. The second is outbounding. We're the anti AISDR. My mic and a view on automation is the human evolves to become an orchestrator, a quarterback. So we do all the work of composing your sequences, who to reach out to, but the human reviews and sense. This year, we look at this data pretty closely. We're not at a point where a CEO or a CRO can just fire on the hole, kind of fill the pipe with these kind of outbound systems because it's going to dilute your brand. On the outbound, we basically do compose olifer outreach where the human kind of reviews and sense. So that's the second part. So it's called Rock's Outreach. After that, when you do reach out, it does all your meeting work. So it does your pre-meeting research in meeting support, follow-ups. Again, the mindset was, let's just call it Obama or like a precedent before you go into a meeting, usually get a brief, like a folder, which everything lined up. That's kind of what we want to do is what if you had every knowledge worker had a”
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. So today it does all customer research and prioritization. So we're doubling, tripling the customer's books. And now they have 10, some hundreds of customers they're dealing with. So it does all the research and prioritization for 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
“Or these team of analysts working for you so that you have full context and are basically kind of moving the conversation along.”
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
“Let me go back to the origin story a little bit because you kind of brought up New Realik earlier. When I was competing head on with six or seven public companies, the difference what I was seeing in the trenches within customers, in calls where most account customer facing refs were just not proactive enough. They knew a partial view of the customers, but they had no real-time understanding of how much are they using, what are the support tickets look like, what are they looking to buy, how are they growing? Everything was not in the CRM. So the kind of feature of sales is how do you feed in real time context? Hopefully our kind of complete context about the customer so that the human in front of the conversation is extensively supercharged with this kind of batsuit and actually moving the deal along. So what we do is Rox gets installed in parallel to your CRM, HubSpot, Salesforce Dynamics. It runs in your warehouse. It indexes all internal context and brings in public context. And it's trying to do the work for you. So you have a team of proxy.”
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
“Right, so this is the first time I'm seeing what they're doing in their personal lives carry over to their professional lives. In the personal life, they're teaching their kids with chat GPT anthropic. And now they're coming in and they're experiencing totally different. Like if you look at the intent logs of how people are using rocks, they expect software to not just do some work. In some cases, they wanted to do all the work. Humans across the board, including my mom in India, everybody has been obviously sold on the promise of AI and LLMs. When they come into the workforce, they actually want the software to do as much work as humanly possible, specific word as humanly. The software should do anything that the human can at scale. So that they could do more and more in my domain is support more 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
“So there's questions that they ask me or us, and then there's questions I ask of them. And the question is, if they are asking us to deeply understand the psychology of the customer and the buyer, things like, hey, what is their expectation? What do you think of you? Those are really good questions because the thing that you have to really understand is, what is your pain? What is their propensity to buy or sell? But now deeply, every consumer's expectations of software has changed. Where are they in their journey? Do they get it? Are they early? Those questions are important versus any boring discovery question, 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
“This is where I'm not the expert for scale kind of go to market because I kind of lean in early stage my mindset is still the same, which is get them in front of customers with mentorship as fast as possible. So what I do in early stage is after a few weeks, you have to shadow a ramped AE or myself without being in that room, it's just really hard to replicate what's happening in the world. Like the world's just moving too fast. I'll give you an example. We have a capability where you can basically do deep research in your customers. Four weeks back, people were like vowed by what we had. Three weeks later, deep research launched. They were like, oh, no, I now expect PhD level research. And if your training doesn't keep up to tage, if you're not in the front line, you just won't see customer expectations change because they're changing every day. So my general mindset is hire somebody in the first week, I have a sense that if they're based on the questions.”
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
“Data access, these same simple things. I think the words change, just give them access to the tools. Second is when you think about how you train onboard folks, it's very similar to schools versus teaching your kids through YouTube, which is you've got to completely change how you train people by making it more kind of AI enabled and so that you basically get them in front of deals, give them live customers versus having them going through like two to three months of basically old school training because that information stale.”
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 very basic things. Most sales reps in the world use ChatGPT perplexity LMs in their private life, but they can't use in the professional life.”
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, and it implies to most functions in venture, founders, builders. We had it relatively easy the past four to five years, and I want to be morbid, but things are hard. Winning is hard. It's hard work. And if you look at sales specifically, when everybody's spending and everybody's kind of buying, it became pretty easy. You're kind of becoming auto takers. You're, as they say, like shooting fish in a barrel. But when you're selling something new or selling something large, there's no easy way around deeply understanding the customer's pain and how do you actually solve it. I'm seeing that constantly. Like, honestly, candidly, like, we've done really well the last year, but it's taken me maybe two to three months longer to find those outlier sales reps is because it's just, it was pretty easy.”
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
“The best two. So Rock's focuses a lot on enduring enterprises. We work with large legacies, some old school enterprises. When you spend time with 20, 30 year vets who've been selling into automotive or airlands in Europe, they get it because that's the only way to earn the credibility, to even get a conversation, kind of let alone kind of move pieces. What has happened over the last five to seven years is people think this is easy. It's not easy. You have to be kind of a consultative expert in the customer's business and you have to do the research. Just like you all do on founders, and that's the only way.”
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
“Is deep research, understanding kind of pain, and kind of building your own internal frameworks of how to communicate your solution to the pain, which at the nitty gritty of it is the game of sales hasn't changed for a long, long time. Like what people used to do is print out 10Ks, 10 queues, SEC filings, read every CEO transcript. Now you can do that on your phone in a few days. It's just reducing the time to do research and forming your opinion”
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 there's two phases as a salesperson. First, you ramp to the job, you learn up how do you actually do the job, and then while you're doing the job, you're trying to hit or exceed kind of your targets. In the ramp phase, what used to take two, maybe two and a half quarters to run a rep where you're reading everything about the customer, about the product and going through training onboard. If you're a really savvy person, you go to perplexity, you go to ChatGPT, hopefully with rocks, you understand everything about the customer, everything about what you're selling, and really ramp much faster. So you're talking about gaining a quarter, quarter and a half.”
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. And that's where management leadership comes in like the business owner and the leaders have to understand that the distributions getting more and more bimodal. You got people who are falling behind, people who are actually rising. So the opportunity is to completely retrain the workforce. Hey, the job has changed. The way you do your work has changed. And you hope to kind of have them evolve and thrive in the modern kind of economy. If not, it is an existential decision.”
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
“These outlier sellers who can sell without a massive brand, a demand engine, and perfect product market fit. And you're trying to find those outlier humans.”
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
“Now I support some of the best go to market leaders in the world, and honestly, I know like 0.1%, right? So it was GC at OpenAI, and these folks are legends. What I see is two folks. Some CEOs and CROs and CFOs want to run a go-to-market engine where they're really going for high revenue targets, and they want to keep the vibes good. They want more and more people to be attaining 80 to 90 percent of their revenue. The other are more who really want to see a normal or bimodal distribution. The top 10%. So there's actually two different philosophies. So, first philosophy is you set up the comp in a way where everybody's kind of winning. Yes, you have your club killers, but most people are hitting quota. In that, that model works if the whole company is growing, the TAM's large and you're getting there. The rest is the power law, which is now getting more and more extreme. My general view, I'm doing early stage sales at this point. In early stage sales is the most important thing is to find”
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
“The other school of thought was the more traditional thing, where every account has account executives, AMs, CS, customer success, sales engineers is kind of 5 to 6% pod. But there's only one true hunter there. The AE is the one who's actually commissioned. Everybody else is on a fixed salary, right? That's a fine way to go about it. Data doc has a similar model. If you have really good leadership where you can kind of manage the incentives well. But in most companies, like in my case, is really high, as Charlie Munger says, is all about the incentives. It's really hard to set up the incentives across a five to six person team to make sure they're all focused on making the customer happy and for them to actually kind of increase usage or consumption.”
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 there's two kinds of salaries. There's two ways people make money in kind of go to market where you might have a let's call it a 50-50% of your salaries is salary, the 50% you only make if you can bring in revenue commission. The other is 100% is fixed and then you could get a bonus. Two very different things. So the first one is what traditional salespeople, where hey salespeople, the term from eat what you hunt is you only get your full salary if you brought in. So that is holding a number. I have to bring in revenue to actually put in some way food on the table. Like that's how we'll see your thinks about it. That's how a founder thinks. It's kind of this owner's mindset. And I do believe that it is a hard path, but that is where modern businesses will go. You will invest in people who have full skin in the game and have this kind of owner mindset.”
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
“Again, like, just like you and a bunch of founders, the best way to get it is you got to go close to the source. So I just join customer calls. I own managed customers. You can tell how people behave.”
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
“In CS were traditionally designed as a function to onboard the customer, make sure you go through the checklist. It kind of CSAT was their primary metric. Expansion or renewal wasn't their primary metric. AMS are completely whole the number for expansion and renewals, which is manage a large account to make sure there's kind of growth across the organization or depth within our existing teams, and they are comped to a certain degree on the upsell. Again, the philosophical thing kind of I learned again, the hard way is not every human can hold a number.”
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
“Account managers. So if you're a large account, you kind of have this relationship focused but strategic account manager.”
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 Stutman School of Thought days only invest in the bag carriers. Get the AEs, people who can hold a number. You eat what you hunt, like those folks, they should hold both the commit number but also the consumption number. And this intense way to operate, but I actually think that's the right way.”
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're just going to get better. They're not going to stop. This is an information arbitrage game, and they'll get better. So the rest has to adopt AI to fundamentally get better or they risk kind of being irrelevant, i.e. it sales as a power law, the top 10% bring in 90% of the revenue, and it's going to get more acute if you're not using what is now like LMs or the new computer.”
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
“A hundred percent leg across the stack, and that's what I learned the hard way. You talked about New Relic, obviously we had a lot of success in the first part of my time there. The second half, like the backside of COVID, we just realized the game had changed, and specifically what the game changed was there's a boring detail where the way you sell, the revenue models change from commit-based revenue to users or consumption-based revenue. So now you had the dollar values in the contract with just words. You only made money when people actually used the product. When you do that, you have to have the right leader. You have to retrain your entire frontline kind of workforce. And the underlying systems have to fundamentally change, and that's where Kind of Rocks comes from. So that's that core thing, like that has changed. And now with AI, what we're seeing with cursor and cognition on the building side is the best are going to get better. Your President's Club sellers, your best VP sales, your best CEOs like Eric at Ramp,”
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
“Initially at her product when Zen, myself, Eric had benchmarked, we were starting Pixie, we thought, hey, we're just going to build a tennis by the product. But when you actually compete with them, it was consistency and it's specifically consistency in go-to-market execution. So you're in the trenches, you're kind of competing with Datadog and Spunk and these other kind of really established public companies. You realize that Datadog is a machine. Olivia, Amit, and that whole crew, they never change segmentation. They never change comp models. They just ran a dialed-in machine for six to seven years, and they compounded value while everybody else kind of kept thrashing, changed pricing models, change segmentation, change comp, it seems very boring at the surface level, but you're just”
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
“Rocks like, oh man, this is not perfect by any means, but you got to have it out there because at the very least, it reduces friction from a sales motion. At the core is this undeniable confidence that you can ship your way out of holes and also ship your way to the promised land because you're not hiding anything. So my view is paid pilots and paid design partners. And then as product gets better, keep it open. Don't put gates.”
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 don't do any free design partners. Like, we really focus on doing paid customers with a pilot clause. If the customer is not separating with some sort of cash, there's just not enough skin in the game for them to put in the time to work with you for a few weeks, for a few months, for a few quarters to build a product. So I'm very anti, unpaid design partners because the cost for them to just say yes is a lot lower than it is for you to keep kind of making them happy. So my view is kind of first have paid design partners who are on an alpha or a beta. Like we're on an open beta now. In parallel, the product has to be open, especially for competing with incumbents. Incumbent enterprise software is gated by demos and implementation steps. These are just three to six to nine month time to value. If you are a product shipping machine, you have to have it out. Even if you're extremely embarrassed like we are at.”
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
“You're bidding on keywords and topics and kind of subject matters. But if there's money to be made, each keyword or brand name is a market of its own. Like competitors bidding, so it's really hard to figure out kind of signal to noise, but for us at New Relic, we had figured out there was 10 to 20 keywords where we were really good and we could put customers on a stitched path. They could see an ad, get to a landing page, use the product, get to an aha. And these could be very boring things. How do I debug my Kafka key with New Relic? Very specific, those made a lot of sense. We could pour money in and see returns within the quarter, maybe within the month. The rest, I really think I don't buy their ZROI. And that's where kind of SEM's headed is if you can get really good at capturing intent and produce stitch path, keep investing. The rest are acceptable.”
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 SEO is a long term strategy. It takes a lot of time to build credibility, and that will change in form factors with kind of AI answers and search, I guess, perplexity-like systems, but that's not going away. You need a core engine that produces high quality content, that's indexed, and it's kind of discovered in new form factors. For me, it was not an option. I owned a 14-year-old brand. Like the first few blogs still outworked every new blog that you wrote. So what I look for is what's their top 10 to 15 kind of percent blogs or pages that return 90% of your value and then distribute it really well? So I think SEO, you still have to produce a super thoughtful content, but just do fewer but higher quality ones and make sure they're distributed. SEM. All right, E1 has to be proactive. Like, I came in first principles. I think it's a complete cartel. So if you really look at how you invest capital into the SEM game, you're just kind of selling your soul to a pretty messy market.”
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, he's amazing. It's probably the greatest exec I worked with. I worked at Amazon and Apple, he's that good. And these are these operators who build businesses from the ground up who don't look for the fame and glory, but they're really, really good. His kind of point was the dinner after the event around the conference is a lot better than the conference itself. Yeah. Right. So the best thing to do is take your dollars. We still did the events. You just don't do the booth. Don't do the one of 100 sponsors. Just have an amazing ball or dinner right after. Have an authentic conversation. You get two or three kind of deep relationships.”
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. One of my kind of ex-colleagues and a mentor now, Manov, who's the chief product officer, he was early Twilio, early.”
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 am somebody who goes all in on things that are work, and then you bet on finding the next thing. If events are not working for you, if you don't have a dial-in operation, don't do 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
“And then organic content. It's kind of a slower ball, but just do those two things. The rest is distraction. And then you get to the next phase, which is consideration. So you got the eyeballs. How do you get developers to consider your product? The biggest mistake even I did. I made so many mistakes. I made more mistakes than successes is people treat a free tier product as a converted customer. They're not converted customers. Free tier product is just a better website. People come in instead of browsing the website and marketing, they're just tinkering with the product. So just move your freedier customers to, hey, this is consideration. So what that means is now you're investing in converting customers from consideration to converted customers in the product. So those two were the singular things. And then once you do that, then you don't have resources. So you start divesting everything else.”
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. I am not a seasoned go to market exec. I'm a first principal founder. This is what I live for. So when I came in, I just had a simple Jason Lemkin funnel mindset. Let's break out all the channels, let's break it down into awareness, consideration, conversion. Can I break down the funnel? And when you look at it out, most growth organizations or marketing organizations will be stretched too thin. They'll invest in six or different channels at the top of the funnel. So for me, what tactically it meant was if you look at the data, organic content and then performance marketing.”
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
“Ultimately, I do think the largest customers need humans to actually work with, to build non-transactional long-term relationships between a bar and a vendor. And what I look for is customer pull. When the customer's pulling the company along, both in terms of building out the roadmap or coming up with a commercial construct, that's where you have to learn an enterprise sales. Fully believe that you need humans because customers want their problem to be solved. give a f about products or services. They want their pain to be solved. And they want to build a non-transactional relationship with these vendors. So that's where sales comes in. So my view is get the product to do product, yes, get humans who are super strategic to the commercial yes, but they're doing non-transactional commercial yes. They're not just signing an auto form. They're really working with the customers, figuring out what is the multi-year and a roadmap both from a product perspective. And that's how I think about the future of sales. The top 10% who are working with 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
“Absolutely. So, the core idea is you can invest in bits or atoms. Bits is in the product. Atoms is in distribution or sales. Like a person that comes to mind is Amitagarval at Datadoc. Not a lot of people know about him, but he's kind of the brains behind the product-led distribution engine at Data Dog. The core idea is how can you keep investing in the product so that it does most of the product, yes, and then layer in humans to do the commercial yes. So you have to have a singular figure who understands engineering, product, sales, services support to really manage that fun loan on a day in, day out basis. If not, it's going to become like two or three siloed organizations who just don't work effectively.”
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 very hard. It's only possible if you have a dialed in CEO or kind of a C suite who really gets it. If not, do not do it. You need a singular person who understands emotion. If not, I wouldn't do 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
“The central word is like focus. So we centralize the entire go to market engine on a captive audience of developers for whom Neuralic was still the default brand. Neuralic kind of lost its aura, but there was this audience of about 100,000 plus developers who joined the workforce 2008-2014. For them, New Relic was still the hot brand. So we basically shut everything down, reallocated investments to really go after them and earn the right for them to use the product again. And that's what the whole machine was built on. Divest everything else, invest where we are default. So we came in in a position where the company had reduced their investment or shut down the PLG motion. So there was this kind of latent demand that we just had to unlock. We just went back out to the developer community and said, hey, we have this unlimited free offering. You get all of what you need in a pretty kind of cost-effective manner. And then that just was like drilling into an all reserve.”
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, we had it relatively easy the past four to five years, and I want to be morbid, but things are hard. Winning is hard. It's hard 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
“Dramatically smaller. It could be 10 to 20% of current kind of orc sizes, sales as a power law, the top 10% bringing 90% of the revenue”
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