Lenny RAG MCP Server

{ "episode": { "guest": "Jeanne DeWitt Grosser", "expertise_tags": [ "Go-to-Market Strategy", "Sales Leadership", "Product-Market Fit", "AI in Sales", "GTM Engineering", "Sales Organization Building", "Pricing Strategy", "Customer Segmentation", "Enterprise Sales", "PLG Strategy" ], "summary": "Jeanne DeWitt Grosser, COO at Vercel and former CPO at Stripe, shares comprehensive insights on building world-class go-to-market teams in the AI era. She discusses the emerging go-to-market engineer role that leverages AI to automate sales workflows, the importance of thinking about go-to-market as a product, and specific tactics for effective customer acquisition. The conversation covers segmentation frameworks, the balance between PLG and sales-led growth, pricing strategy, and how to build sales organizations that engineers respect. Key themes include customer-centric journey design, using AI for leverage in sales processes, and the critical importance of discovery and listening in sales conversations.", "key_frameworks": [ "Go-to-Market as a Product", "Customer Journey Mapping", "Segmentation Framework (Size, Growth Potential, Business Model, Traffic, Workload Type)", "Sales Role Hierarchy (SDR, AE, Enterprise AE)", "GTM Engineer Workflow Development", "Lead-to-Opportunity Conversion Process", "Value Demonstration Through Insights", "Discovery and Objection Handling", "Build vs Buy for AI Agents", "Sales Compensation Strategy" ] }, "topics": [ { "id": "topic_1", "title": "Introduction and Defining Go-to-Market", "summary": "Lenny introduces Jeanne and her background at Stripe and Vercel, establishing her expertise in building go-to-market teams. The conversation begins with defining what go-to-market actually encompasses beyond just sales and marketing.", "timestamp_start": "00:00:00", "timestamp_end": "00:08:44", "line_start": 1, "line_end": 65 }, { "id": "topic_2", "title": "Changes in Go-to-Market Over Time", "summary": "Jeanne discusses how go-to-market has evolved from transactional sales to consultative approaches, the rise of consumption-based business models, and how AI is reshaping the field. She introduces the concept of forward-deployed engineering and the emerging go-to-market engineer role.", "timestamp_start": "00:08:44", "timestamp_end": "00:11:23", "line_start": 67, "line_end": 79 }, { "id": "topic_3", "title": "The Go-to-Market Engineer Role", "summary": "Deep dive into what go-to-market engineers do, including the story of Project Rosland at Stripe and how it's being reimagined with AI at Vercel. Covers the automation of outbound prospecting, personalized email generation at scale, and the six-week process to reduce SDR headcount from 10 to 1.", "timestamp_start": "00:11:23", "timestamp_end": "00:18:17", "line_start": 81, "line_end": 115 }, { "id": "topic_4", "title": "AI-Powered Email Outreach and Agent Development", "summary": "Jeanne explains how Vercel builds AI agents for outbound prospecting with human-in-the-loop review, maintains conversion rates while reducing touches, and the practical approach to training agents through human feedback.", "timestamp_start": "00:18:17", "timestamp_end": "00:21:56", "line_start": 117, "line_end": 129 }, { "id": "topic_5", "title": "Will AI Replace SDRs and Sales Roles", "summary": "Discussion of whether AI will replace SDRs entirely, Jeanne's perspective that AI will handle repetitive tasks while humans move to higher-value activities, and the opportunity for career advancement in sales beyond entry-level SDR positions.", "timestamp_start": "00:21:56", "timestamp_end": "00:26:05", "line_start": 131, "line_end": 144 }, { "id": "topic_6", "title": "Sales Roles Explained: SDR vs AE vs Enterprise", "summary": "Jeanne provides clear definitions of Sales Development Representatives, Account Executives, and the progression through SMB, mid-market, and enterprise sales complexity, decision-making structures, and selling approaches.", "timestamp_start": "00:24:01", "timestamp_end": "00:26:25", "line_start": 139, "line_end": 147 }, { "id": "topic_7", "title": "Hiring First Salespeople and GTM Engineers", "summary": "Advice on when to hire your first salesperson (around $1M ARR), the importance of repeatable sales processes, founder-led sales transition, and the profile of ideal first go-to-market engineers coming from sales engineering backgrounds.", "timestamp_start": "00:26:25", "timestamp_end": "00:32:28", "line_start": 147, "line_end": 172 }, { "id": "topic_8", "title": "Go-to-Market Tools and Agents", "summary": "Jeanne discusses modern GTM tools, particularly Gong and building internal AI agents. She covers using Gong transcripts with AI to analyze lost deals, the deal-bott agent providing real-time insights, and the approach of building custom agents versus buying off-the-shelf solutions.", "timestamp_start": "00:34:33", "timestamp_end": "00:39:00", "line_start": 184, "line_end": 199 }, { "id": "topic_9", "title": "Build vs Buy for AI Agents", "summary": "Analysis of the economics of building custom AI agents (lead agent cost $1000/year versus $1M+ for SDRs) versus purchasing solutions. Discussion of the emerging agent platform landscape, procurement challenges, and when to build versus buy.", "timestamp_start": "00:40:46", "timestamp_end": "00:44:34", "line_start": 208, "line_end": 231 }, { "id": "topic_10", "title": "Go-to-Market as a Product", "summary": "Jeanne's foundational thesis that the buying experience itself is a differentiator when products are similar. She discusses designing customer journeys like a product manager would, creating unique experiences at every touchpoint, and examples like Stripe's whiteboarding sessions during discovery.", "timestamp_start": "00:46:56", "timestamp_end": "00:52:35", "line_start": 247, "line_end": 272 }, { "id": "topic_11", "title": "Adding Value and Building Trust", "summary": "Tactics for adding value at any touchpoint regardless of immediate sale, sharing insights about customer performance, benchmarking, and building trusted relationships that drive long-term customer lifetime value and repeat purchases.", "timestamp_start": "00:50:43", "timestamp_end": "00:52:57", "line_start": 261, "line_end": 278 }, { "id": "topic_12", "title": "Go-to-Market Tactics and Unique Insights", "summary": "Specific tactics including sharing unique insights about product capabilities, creating well-architected guides and blueprints, and the importance of excellent discovery through questioning rather than pitching. Examples from Stripe and Vercel.", "timestamp_start": "00:52:57", "timestamp_end": "00:55:43", "line_start": 280, "line_end": 288 }, { "id": "topic_13", "title": "Customer Psychology and Buying Motivation", "summary": "Discussion of the insight that 80% of customers buy to avoid pain or reduce risk rather than increase upside, and how this should influence go-to-market messaging and positioning. Difference between founder enthusiasm and enterprise risk mitigation.", "timestamp_start": "00:00:27", "timestamp_end": "01:00:36", "line_start": 10, "line_end": 320 }, { "id": "topic_14", "title": "Customer Segmentation Framework", "summary": "Comprehensive primer on segmentation including X/Y axis approach (size, growth potential, business model, traffic rank, workload type), how to identify attributes that correlate with revenue, and why three attributes are the practical limit for actionability.", "timestamp_start": "01:00:45", "timestamp_end": "01:09:36", "line_start": 325, "line_end": 369 }, { "id": "topic_15", "title": "Building Sales Orgs That Engineers Respect", "summary": "The litmus test of salespeople being indistinguishable from product managers, the importance of product depth, and how sales can function as both revenue driver and R&D extension through customer feedback synthesis and market signal detection.", "timestamp_start": "01:09:59", "timestamp_end": "01:13:01", "line_start": 373, "line_end": 385 }, { "id": "topic_16", "title": "Sales and Product Collaboration", "summary": "Company strategy as intersection of product strategy and go-to-market strategy, sales leadership wearing a GM hat, involvement in pricing strategy, and how go-to-market insights feed product roadmap decisions.", "timestamp_start": "01:13:01", "timestamp_end": "01:14:00", "line_start": 385, "line_end": 387 }, { "id": "topic_17", "title": "PLG vs Sales-Led Growth", "summary": "When PLG makes sense versus sales-led approaches, the ceiling on PLG growth, timing of transitioning to sales, and why almost all companies eventually need a sales org even if they start with PLG.", "timestamp_start": "01:14:28", "timestamp_end": "01:16:30", "line_start": 391, "line_end": 400 }, { "id": "topic_18", "title": "Pricing Strategy and Product Thinking", "summary": "Approach to pricing as a product decision, understanding customer value and cost structures, avoiding default freemium strategies, unbundling overpriced tiers, and using pricing changes to drive growth in specific segments.", "timestamp_start": "01:16:52", "timestamp_end": "01:19:24", "line_start": 403, "line_end": 411 }, { "id": "topic_19", "title": "Sales Compensation and Hiring", "summary": "Hot takes on sales comp structure and flexibility versus fixed plans, hiring diverse profiles mixing sales professionals with consulting and banking backgrounds, and creating learning environments where different sales profiles teach each other.", "timestamp_start": "01:19:41", "timestamp_end": "01:22:22", "line_start": 415, "line_end": 420 }, { "id": "topic_20", "title": "Life Lessons from Diving and Closing Thoughts", "summary": "Lightning round discussion of Jeanne's life mottos, lessons from competitive diving about precision and handling failure, the importance of comfort with 'no' in sales, and obsession with replicability and predictability.", "timestamp_start": "01:22:46", "timestamp_end": "01:25:35", "line_start": 436, "line_end": 464 } ], "insights": [ { "id": "i1", "text": "80% of customers buy to avoid pain or reduce risk as opposed to increase upside, which is critical for startup founders to understand when messaging their products.", "context": "Jeanne contrasts the common founder approach of talking about 'art of the possible' with what actually resonates with enterprise buyers focused on risk mitigation.", "topic_id": "topic_13", "line_start": 11, "line_end": 11 }, { "id": "i2", "text": "The experience of being sold to will increasingly differentiate a company and drive buying decisions if products are only different at the margin.", "context": "Fundamental thesis about why go-to-market design matters as much as product design when technical differentiation narrows.", "topic_id": "topic_10", "line_start": 17, "line_end": 17 }, { "id": "i3", "text": "The litmus test for building a sales org that works with engineers: if you put an AE in front of 10 engineers, it should take them 10 minutes to figure out they aren't a product manager.", "context": "Test of product depth and credibility in sales hiring and team building.", "topic_id": "topic_15", "line_start": 23, "line_end": 23 }, { "id": "i4", "text": "With consumption-based business models, go-to-market shifted to being much more consultative because the first land represents only a small percent of ultimate customer value.", "context": "Explains why modern go-to-market requires deeper customer understanding and longer-term relationship building.", "topic_id": "topic_2", "line_start": 71, "line_end": 71 }, { "id": "i5", "text": "Forward-deployed engineering (deployed engineers embedded with customers) is about getting into the customer environment to understand their needs and help bring technology to life, while feeding learnings back to product.", "context": "Describes emerging role of embedded technical resources in modern go-to-market.", "topic_id": "topic_2", "line_start": 74, "line_end": 74 }, { "id": "i6", "text": "Salespeople spend only 30-40% of their time actually talking to customers; AI agents can handle research and follow-up, ideally getting that to 70% customer interaction time.", "context": "ROI of deploying AI agents in sales is primarily about unlocking human time for high-value customer conversations.", "topic_id": "topic_4", "line_start": 113, "line_end": 113 }, { "id": "i7", "text": "The best go-to-market orgs on the planet are equal parts revenue driving and R&D because a 20-person sales team talking to customers weekly generates valuable signal that should feed product roadmap.", "context": "Reframes role of sales from revenue-only to strategic input on product direction.", "topic_id": "topic_15", "line_start": 374, "line_end": 374 }, { "id": "i8", "text": "No one graduated college wanting to become an SDR; it's a forcing function for entry-level sales. AI is just accelerating their progression to higher-value activities like outbound or closing.", "context": "Humanistic take on AI disrupting entry-level sales roles as a net positive.", "topic_id": "topic_5", "line_start": 134, "line_end": 134 }, { "id": "i9", "text": "You can't apply go-to-market engineering unless you have a documented, replicable sales process with clear best practices and defined playbooks.", "context": "Prerequisite for AI agent development is understanding what humans are doing first.", "topic_id": "topic_7", "line_start": 152, "line_end": 152 }, { "id": "i10", "text": "A single go-to-market engineer spending 25-30% of time built Vercel's lead agent in six weeks, achieving a 90%+ cost reduction compared to 10 SDR salaries while maintaining conversion rates.", "context": "Concrete evidence of AI leverage in go-to-market; $1000/year cost versus $1M+ in salaries.", "topic_id": "topic_3", "line_start": 128, "line_end": 128 }, { "id": "i11", "text": "AI agents revealed that a deal was lost due to never reaching an economic buyer (a conclusion the AE didn't reach), demonstrating AI's ability to surface insights humans miss.", "context": "Lost deal analysis using Gong transcripts showed AI finding root cause invisible to human review.", "topic_id": "topic_8", "line_start": 188, "line_end": 188 }, { "id": "i12", "text": "Excellent salespeople talk less than half the time in conversations; they ask questions, probe, and help customers arrive at their own conclusions rather than immediately problem-solving.", "context": "Core discovery skill often violated by founders eager to talk about their product.", "topic_id": "topic_12", "line_start": 287, "line_end": 287 }, { "id": "i13", "text": "Adding value at every touchpoint regardless of immediate sale builds trust; customers lost in one buying cycle often return three to five years later when ready to buy.", "context": "Long-term customer lifetime value justification for generous, consultative approach.", "topic_id": "topic_11", "line_start": 263, "line_end": 263 }, { "id": "i14", "text": "PLG typically has a ceiling around $1M contract sizes; sustaining growth requires layering in sales and moving to larger deals, which many companies delay too long.", "context": "PLG is not sufficient as a permanent growth strategy; timing of sales transition is critical.", "topic_id": "topic_17", "line_start": 392, "line_end": 392 }, { "id": "i15", "text": "Think about pricing like a product; understand where customers drive value, where you incur costs, and align pricing to incentivize optimal customer behavior.", "context": "Pricing is a strategic lever tied to product strategy, not an afterthought.", "topic_id": "topic_18", "line_start": 404, "line_end": 404 }, { "id": "i16", "text": "Killing freemium when it didn't match strategy (Stripe Billing) and unbundling overpriced tiers (Vercel Enterprise) can immediately unlock growth in specific segments without downside.", "context": "Examples of pricing model changes with measurable revenue impact.", "topic_id": "topic_18", "line_start": 407, "line_end": 407 }, { "id": "i17", "text": "Fixed annual sales compensation plans reduce organizational flexibility; there's tension between motivating salespeople with commission and enabling the company to pivot when product or market changes.", "context": "Challenge of balancing sales motivation with business agility in changing markets.", "topic_id": "topic_19", "line_start": 416, "line_end": 416 }, { "id": "i18", "text": "Mixing sales professionals with consulting/banking backgrounds creates learning environments where consultants learn sales is a skill while salespeople learn P&L thinking and CFO conversations.", "context": "Diversity of profile in sales teams improves collective capability.", "topic_id": "topic_19", "line_start": 419, "line_end": 419 }, { "id": "i19", "text": "Segmentation is a company-wide strategy, not just go-to-market; product teams should understand their target segments when building features to ensure alignment.", "context": "Segmentation should inform product development, not just sales targeting.", "topic_id": "topic_14", "line_start": 368, "line_end": 368 }, { "id": "i20", "text": "Three customer attributes is the practical limit for segmentation reasoning; beyond that, you can't allocate resources meaningfully across segments.", "context": "Simplicity rule for segmentation framework design.", "topic_id": "topic_14", "line_start": 368, "line_end": 368 }, { "id": "i21", "text": "Company strategy is product strategy meeting go-to-market strategy; as a revenue leader, focus on both having a winning product and commercializing it well.", "context": "Integration of product and commercial strategy at executive level.", "topic_id": "topic_16", "line_start": 386, "line_end": 386 }, { "id": "i22", "text": "Observing founders often confuse sales with showing up and talking to people; sales is a skill requiring discovery, objection handling, and value demonstration, not just customer interaction.", "context": "Common misconception that founder sales can be replicated without formalizing the skill.", "topic_id": "topic_7", "line_start": 149, "line_end": 149 }, { "id": "i23", "text": "The build-versus-buy calculus for AI agents is shifting; because the space is nascent, custom agents tuned to your specific context, workflows, and content often outperform generic tools.", "context": "Competitive advantage exists in building internal agents before standardized platforms mature.", "topic_id": "topic_9", "line_start": 224, "line_end": 224 }, { "id": "i24", "text": "Whiteboarding sessions during discovery create unique customer experience where customers learn about their own architecture while you learn about their stack, converting it from boring quiz to collaborative design.", "context": "Example of making first sales interaction memorable and valuable rather than transactional.", "topic_id": "topic_10", "line_start": 254, "line_end": 254 }, { "id": "i25", "text": "Providing unsolicited insights on customer performance metrics (e.g., Core Web Vitals, AEO benchmarking) piques interest and builds trust even if customer doesn't buy immediately.", "context": "Tactical application of value-first approach at outreach stage.", "topic_id": "topic_11", "line_start": 263, "line_end": 263 }, { "id": "i26", "text": "Well-architected guides and blueprints (AWS model) are valuable for larger companies; they want best practices for their specific setup, not generic documentation.", "context": "Content strategy differentiation for enterprise versus self-serve buyers.", "topic_id": "topic_12", "line_start": 281, "line_end": 281 } ], "examples": [ { "id": "ex1", "explicit_text": "I was at Stripe for nine years... we lost and then half a decade later, here they are and they bought.", "inferred_identity": "Stripe", "confidence": 0.95, "tags": [ "Stripe", "Customer Retention", "Long-term LTV", "Payment Processing", "Enterprise Sales", "Multi-year Sales Cycles", "Winning Back Customers" ], "lesson": "Demonstrates the importance of maintaining relationships with customers lost in one buying cycle as they often return when market conditions change; adds value at every touchpoint even for non-buyers.", "topic_id": "topic_11", "line_start": 263, "line_end": 263 }, { "id": "ex2", "explicit_text": "At Stripe, there were two ways we further cut the business... business model. So are you a B2B? Are you B2C? Are you B2B2B, E.G. a platform or B2B2C, E.G. a marketplace", "inferred_identity": "Stripe", "confidence": 0.98, "tags": [ "Stripe", "Segmentation", "Business Models", "Marketplace", "B2B", "B2C", "Sales Strategy", "Product Selection", "Payments" ], "lesson": "Shows how to layer multiple segmentation dimensions (business model on top of company size) to drive different product recommendations and sales approaches; B2B marketplaces need different payment products than B2C consumers.", "topic_id": "topic_14", "line_start": 332, "line_end": 336 }, { "id": "ex3", "explicit_text": "At Stripe, we launched Stripe Billings years ago. It had a freemium strategy because that's what you do. And then we sort of looked at it and we're like, 'actually integrating straight billing takes a little bit of work. So if you do that, you're probably going to stay.' And so we killed that, killed the free trial to zero downside.", "inferred_identity": "Stripe", "confidence": 0.98, "tags": [ "Stripe", "Pricing Strategy", "Freemium Model", "Free Trial", "Billing", "Product-Led Growth", "Pricing Optimization", "SaaS", "Churn Reduction" ], "lesson": "Demonstrates that default freemium strategies don't always work; questioning assumptions and data can reveal that removal of a feature actually increases unit economics and retention because switching costs rise.", "topic_id": "topic_18", "line_start": 404, "line_end": 405 }, { "id": "ex4", "explicit_text": "When I was at Stripe, we went to launch an outbound SDR function... and Stripe always ran lean... most companies out there probably would've had 30 SDRs and I was going to get four.", "inferred_identity": "Stripe", "confidence": 0.98, "tags": [ "Stripe", "SDR Function", "Outbound Prospecting", "Sales Efficiency", "Data-Driven Sales", "Lean Operations", "Pipeline Generation", "Resource Constraint" ], "lesson": "Shows how operational constraints force innovation; being unable to hire many SDRs led to building Project Rosland (database of company attributes) to enable targeted, personalized prospecting at scale.", "topic_id": "topic_3", "line_start": 82, "line_end": 83 }, { "id": "ex5", "explicit_text": "At Stripe an example would be knowing that their business model was a marketplace was super helpful, because that would mean you wanted to sell Stripe Connect versus vanilla payments.", "inferred_identity": "Stripe", "confidence": 0.99, "tags": [ "Stripe", "Marketplace Business Model", "Product Differentiation", "Sales Customization", "Stripe Connect", "Payments", "Segmentation Application", "Targeting" ], "lesson": "Demonstrates how understanding customer business model enables targeted product positioning; same company type needs fundamentally different product solutions.", "topic_id": "topic_3", "line_start": 83, "line_end": 83 }, { "id": "ex6", "explicit_text": "At Stripe was Stripe was excellent at marketplaces. Most, Lyft, Instacart, DoorDash, they were all on Stripe.", "inferred_identity": "Stripe", "confidence": 0.99, "tags": [ "Stripe", "Lyft", "Instacart", "DoorDash", "Marketplace", "Payments", "Product Fit", "Competitive Advantage", "Network Effects" ], "lesson": "Shows how Stripe became the default for marketplaces; deep customer base in a category creates defensible positioning and expertise that becomes a selling point.", "topic_id": "topic_12", "line_start": 281, "line_end": 282 }, { "id": "ex7", "explicit_text": "And so when you then would go and sell a marketplace and say, 'Oh yeah, we've got docs, go check them out.' They didn't like that, because they're like, 'Hey, every marketplace runs on Stripe. I don't want to look at generic docs. I want you to tell me what's the best way to set up payments for a marketplace.'", "inferred_identity": "Stripe", "confidence": 0.98, "tags": [ "Stripe", "Marketplace", "Documentation", "Best Practices", "Sales Positioning", "Enterprise Customer Expectations", "Domain Expertise", "Consultative Selling" ], "lesson": "Customers in categories where you have deep expertise expect you to share that expertise, not point them to generic documentation; this is the basis for creating well-architected guides.", "topic_id": "topic_12", "line_start": 282, "line_end": 284 }, { "id": "ex8", "explicit_text": "My first job out of college was working on Gmail in 2004. So Gmail launched on April 1st, I joined on June 1st. And as I'm sure you'll remember as well, Gmail was this incredible innovation, massive JavaScript application that didn't really exist at the time. And it had this gig of storage.", "inferred_identity": "Google/Gmail", "confidence": 0.99, "tags": [ "Google", "Gmail", "Product Innovation", "Technical Differentiation", "Storage", "Email", "Product-Market Fit", "Early Career" ], "lesson": "Establishes Jeanne's origin story and the fundamental insight that technical differentiation (1GB storage) can eventually narrow as commoditization occurs, forcing companies to compete on other dimensions like buying experience.", "topic_id": "topic_10", "line_start": 248, "line_end": 248 }, { "id": "ex9", "explicit_text": "one of the things we try to do when we reach out is actually give folks insight immediately into how they're performing on an absolute basis, how they're performing relative to peers... So ideally that piques your interest and you want to learn more from us, but even if it doesn't, you still have insights", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "Outreach Strategy", "Performance Metrics", "Benchmarking", "Value-First Selling", "Web Performance", "Core Web Vitals", "Customer Education" ], "lesson": "Demonstrates providing unsolicited value through performance insights at outreach; builds trust and positions company as knowledgeable partner rather than vendor, even if customer doesn't convert immediately.", "topic_id": "topic_11", "line_start": 263, "line_end": 263 }, { "id": "ex10", "explicit_text": "we're talking to a very large airline and that airline obviously gets tons and tons of support queries... But the more interesting conversation was actually with one of the C-level executives who said, we also actually transcribe every single one of those support calls. And so what I really want to know is why are they calling and how do I make it so that fewer people call the next week?", "inferred_identity": "Unnamed Large Airline", "confidence": 0.7, "tags": [ "Airline Industry", "Customer Support", "AI Application", "Root Cause Analysis", "Operational Efficiency", "Call Center Reduction", "Preventive Strategy", "Enterprise Use Case" ], "lesson": "Shows how AI applied to customer support transcripts can shift focus from reactive cost reduction to proactive problem prevention; C-level executive's insight about understanding root causes of support queries.", "topic_id": "topic_8", "line_start": 203, "line_end": 203 }, { "id": "ex11", "explicit_text": "I mentioned the lead agent that was a six-week process with one human, a third of his time, that deal-bott, the lost bot version was two days basically we riffed on it, he had it 40 hours later.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "AI Agents", "Internal Tools", "Development Speed", "GTM Engineering", "Lead Scoring", "Deal Analysis", "Rapid Prototyping" ], "lesson": "Demonstrates that building custom AI agents is fast and doesn't require massive engineering resources; 40 hours of one engineer's time produced tools with massive impact on operational efficiency.", "topic_id": "topic_9", "line_start": 221, "line_end": 221 }, { "id": "ex12", "explicit_text": "And so great example of this would be OpenAI. OpenAI, I forget these days how many employees it has. Let's say it's 3,000, it's probably more than that at this point, but so that's going to put it in the mid-market at most companies, but they're a top 25 traffic site on the internet. So for us, that's going to push them in our enterprise because we need to go lean in with a much more in depth sales process.", "inferred_identity": "OpenAI", "confidence": 0.99, "tags": [ "OpenAI", "Vercel", "Enterprise Segmentation", "Traffic Ranking", "Customer Complexity", "GTM Strategy", "Company Size Mismatch", "Sales Process Customization" ], "lesson": "Shows that company size alone doesn't determine sales complexity; traffic/impact can push a mid-market company into enterprise sales category requiring more resources and customized approach.", "topic_id": "topic_14", "line_start": 338, "line_end": 344 }, { "id": "ex13", "explicit_text": "we have an enterprise at a pro-skew. And if you looked at the enterprise skew, it's called Enterprise for a reason, enter, it's meant to be sold to an enterprise. And actually about half of the folks on the enterprise skew were startups, which suggests that there's stuff in the enterprise skew that a startup really wants. So we kicked a lot of that stuff out of the enterprise skew and made it so you could buy it self-serve online", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "Pricing Tiers", "Product Bundling", "Self-Serve", "PLG Optimization", "Pricing Unbundling", "Startup Segment", "Revenue Growth" ], "lesson": "Shows how data on tier adoption can reveal pricing misalignment; unbundling enterprise features for self-serve drove both startup growth and reduced need for human intermediation.", "topic_id": "topic_18", "line_start": 407, "line_end": 410 }, { "id": "ex14", "explicit_text": "At Vercel in particular, we basically get to be customer zero. So everything that we're building with agents, we're building on Vercel's AI cloud. So these agents now have multiple steps that they go through. So we're using Vercel's workflow SDK and workflow offering.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "AI Cloud", "Dogfooding", "Internal Tools", "GTM Agents", "Customer Zero", "Product Feedback", "Platform Advantage" ], "lesson": "Demonstrates competitive advantage of eating your own dog food; building on your own product uncovers missing features and provides real-world validation before customer release.", "topic_id": "topic_8", "line_start": 176, "line_end": 176 }, { "id": "ex15", "explicit_text": "I managed to do it in college, but that was the extent of that career... diving is a precision sport and it is a repetitive sport. And it is also a sport where when you land flat on your back, and literally as you are swimming to the side of the pool, welts are forming on it, you always 100% of the time will be forced to immediately get back on the diving board and do that exact same dive again.", "inferred_identity": "Jeanne DeWitt Grosser (Personal)", "confidence": 0.95, "tags": [ "Diving", "Precision", "Repetition", "Failure Recovery", "Resilience", "Personal Background", "College Athletics", "Grit" ], "lesson": "Explains Jeanne's obsession with excellence and replicability in sales; diving sport teaches immediate failure recovery and continuous improvement, directly applicable to sales processes and handling rejection.", "topic_id": "topic_20", "line_start": 455, "line_end": 455 }, { "id": "ex16", "explicit_text": "when we wrote the sales plans for this year at Vercel, the AI cloud did not exist. We were selling our front-end cloud and we were selling VZero and introduced the AI cloud halfway through the year.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "AI Cloud", "Product Launch", "Sales Planning", "Mid-Year Launch", "Sales Compensation Misalignment", "Incentive Flexibility" ], "lesson": "Demonstrates challenge of annual sales compensation planning when products launch mid-year; inflexible comp structures can't adapt to new product opportunities, reducing organization agility.", "topic_id": "topic_19", "line_start": 416, "line_end": 416 }, { "id": "ex17", "explicit_text": "So the biggest loss that quarter according to the account executive was lost on price. And when you ran the agent over every Slack interaction, every email, every GONG call, it said actually you lost because you never really got in touch with an economic buyer.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "Deal Analysis", "Gong", "Lost Deal Review", "Root Cause Analysis", "AI Insight", "Economic Buyer", "Sales Process Gap" ], "lesson": "Shows AI agents revealing root causes invisible to human review; AE blamed price, but analysis showed lack of economic buyer contact; demonstrates value of systematic deal review.", "topic_id": "topic_8", "line_start": 188, "line_end": 188 }, { "id": "ex18", "explicit_text": "At some point I think we'll get to a place where we feel like, 'Hey, the human reviewer is saying yes enough of the time that we feel confident that these will be on brand targeted, et cetera,' but right now we're still trying to train the agent and it incorporates feedback on what we choose to reject, edit, et cetera.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "AI Agents", "Human-in-the-Loop", "Quality Assurance", "Agent Training", "Feedback Loop", "Brand Safety", "Continuous Improvement" ], "lesson": "Demonstrates disciplined approach to deploying AI agents with human oversight; feedback from human reviewers trains the model, allowing gradual removal of human in the loop.", "topic_id": "topic_4", "line_start": 122, "line_end": 122 }, { "id": "ex19", "explicit_text": "So we had 10 SDRs doing this inbound workflow and now we just have one that is effectively QA-ing the agent. The other nine we deployed on outbound, so we got to move them up the value chain.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "AI Agents", "SDR Reallocation", "Outbound Prospecting", "Team Leverage", "Career Progression", "Value Chain" ], "lesson": "Demonstrates that AI agent deployment doesn't replace people but redeployed them to higher-value work; nine SDRs moved from inbound (now automated) to outbound (higher-touch, higher-impact).", "topic_id": "topic_4", "line_start": 122, "line_end": 122 }, { "id": "ex20", "explicit_text": "Ben Salzman who went on to go to ZoomInfo and then actually recently just founded a go-to-market startup that is basically sort of productizing that concept of a company universe and then layering AI on it on top of it.", "inferred_identity": "ZoomInfo / GTM Startup Founder", "confidence": 0.85, "tags": [ "ZoomInfo", "Ben Salzman", "GTM Startup", "Company Universe Database", "AI Layering", "Product Commercialization", "Stripe Alumni" ], "lesson": "Shows how individuals inspired by Project Rosland at Stripe went on to commercialize the concept, building AI-native GTM companies; demonstrates how internal innovation creates future entrepreneurs.", "topic_id": "topic_3", "line_start": 101, "line_end": 101 }, { "id": "ex21", "explicit_text": "we had a lot of penetration and e-comm not that surprising actually, given that we drive highly performant sites and e-comm having a superfast performance site really matters. But at the time, if you looked at as an example, an enterprise SaaS companies, we didn't have a lot of penetration, even though you would've thought, okay, front-end cloud, very developer oriented.", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "E-commerce", "Enterprise SaaS", "Segmentation Analysis", "Market Penetration", "Migration Cost", "Target Segment Selection" ], "lesson": "Shows how segmentation analysis revealed Vercel's strength in e-commerce despite seemingly good fit with enterprise SaaS; legacy systems create migration barriers even when product fits.", "topic_id": "topic_14", "line_start": 362, "line_end": 362 }, { "id": "ex22", "explicit_text": "Vercel builds Vercel with Vercel. So you're just always looking for ways to, Hey, how can we use our product to go do what we need to do?", "inferred_identity": "Vercel", "confidence": 0.99, "tags": [ "Vercel", "Dogfooding", "Product Development", "Customer Empathy", "Internal Usage", "Feedback Loop", "Company Culture" ], "lesson": "Cultural practice of using your own product to do internal work forces understanding of customer pain points and reveals product gaps before release to customers.", "topic_id": "topic_8", "line_start": 242, "line_end": 242 } ] }