[Highlight] Grammarly's Evolution into an AI Agent Platform with Shishir Mehrotra

This is an excerpt from our full conversation with Shishir Mehrotra, CEO of Superhuman (formerly Grammarly).Shishir discusses why Grammarly is one of the most underestimated companies in Silicon Valley, how it's transforming from a grammar tool into an open platform for AI agents, and why "assist" AI—which meets you where you work—may be more powerful than chat or autonomous agents.Watch the full episode here: https://www.youtube.com/watch?v=S7UO7AOLgBAThanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is a short excerpt from our full conversation with Shishir Mehrotra, CEO of Superhuman (formerly Grammarly).Shishir discusses the fundamental differences between working at big tech companies versus startups, why skills at large companies are less transferable than you think, and what separates world-class recruiting processes from mediocre ones.Watch the full episode here: https://www.youtube.com/watch?v=S7UO7AOLgBAThanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Henry Shi, founder of Super.com (scaled to $200M+ annual revenue, 50 million users, profitable), joins Village Global GP Anne Dwane to discuss his unconventional path from founder to Anthropic.Henry shares why he stepped back from his company at its peak, what he learned during his gap year building AI resources in public, the patterns he discovered tracking lean AI companies, and why he ultimately chose a frontier lab over VC or starting another company. He also gives a candid look inside Anthropic's culture and shares his predictions for what's coming in 2026. Mentioned in the Episode:Lean AI Leaderboard: https://leanaileaderboard.com/AI Crash Course (GitHub): https://github.com/henrythe9th/AI-Crash-CourseAI 2027 Report: https://ai-2027.com/Super.com: https://www.super.comAnthropic: https://www.anthropic.comHenry on X: https://x.com/henrythe9thsHenry on LinkedIn: https://www.linkedin.com/in/henrythe9th/Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is a short excerpt from our full conversation with Zoom founder and CEO Eric Yuan and LinkedIn co-founder / Village Global Chairman Reid Hoffman.Eric and Reid discuss what separates companies that last from those that flame out, why hypergrowth can hide critical problems, and how founders should think about their "theory of the game" for the next ten years.Listen to the full episode here: https://podcasts.apple.com/us/podcast/the-future-of-work-with-zoom-ceo-eric-yuan-and-reid-hoffman/id1316769266?i=1000744325171Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Magnus Sandstrom and Debbie Wiss are senior partners at Swing Search, specializing in go-to-market roles at director, VP, and head levels for nearly 20 years. They joined Village Global partner Lindsay Pettingill to discuss the mistakes founders make when hiring their first sales and marketing talent, and how to get it right.Takeaways:Don't go too senior too early. Look for someone who can see around corners, not over mountains. Senior hires want teams and foundations. You need someone doing outbound calls and chasing deals.Don't try to solve product-market fit with a go-to-market hire. Talk to customers first. If you're pre-PMF, it's too soon to hire sales.You'll never leave sales. Even $100M+ CEOs are on sales calls. Accept this reality and get good at it rather than trying to hand it off.Strong sellers know their metrics to the decimal. "112.2% quota attainment" reveals discipline and ambition. "Around 100%" is a red flag.Hire two founding AEs, not one. They work in the trenches together while competing. If one doesn't work out, you still have revenue coming in.Marketing is more complex than sales. Define whether you need product marketing, demand gen, or brand. Wanting someone analytical and creative is unicorn territory.You can't delegate what you can't document. Write down your processes before expecting new hires to execute them.Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is a short excerpt from our full conversation with Zoom founder and CEO Eric Yuan and LinkedIn co-founder Reid Hoffman.Eric and Reid discuss where startups can compete against big tech in the AI era, why enterprise adoption of AI tools remains surprisingly slow, and what founders should focus on when selling AI products to enterprise customers.Listen to the full episode here: https://podcasts.apple.com/us/podcast/the-future-of-work-with-zoom-ceo-eric-yuan-and-reid-hoffman/id1316769266?i=1000744325171Thanks for listening — if you like what you hear, please review us on your favorite podcast platform.Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Eric Yuan is the founder and CEO of Zoom. Reid Hoffman is the co-founder of LinkedIn. Both are luminary LPs at Village Global. They joined Village GP Ben Casnocha to discuss the future of AI agents, digital twins in the workplace, selling AI to enterprise, and what it takes to build companies that endure.Takeaways:Digital twins will handle meetings you're unsure about attending. Your AI can join internal meetings, summarize key points, and alert you only when your presence becomes critical. This frees you to focus on what truly matters.External AI interactions are coming too. Eventually, digital twins could negotiate contracts, discuss pricing, and handle preliminary conversations before humans finalize agreements.Enterprise customers want partners, not just products. When selling AI to enterprise, become a trusted guide through anxiety-ridden territory. Trust matters as much as features, especially when customers feel behind.Make customers part of your innovation cycle. Get enterprise customers deploying early, even partially. The unique data they generate becomes your moat that competitors can't replicate.Focus on vertical markets with domain expertise. Generic horizontal AI products are vulnerable to big players who can give similar tools away for free. Build where deep domain knowledge creates defensibility.Hypergrowth hides problems. Rapid revenue growth can mask fundamental issues in your product and operations. The best scenario is growing fast while proactively fixing hidden problems, but that's extremely hard.Theory of the game matters more than current metrics. Companies aren't valuable in a year; they're valuable in ten years and beyond. Have a clear theory for how your initial traction compounds into long-term value.Be honest with yourself about durability. Rapid early success doesn't automatically mean you have a long-term strategy. Understand what's driving growth and whether those factors will last.Thanks for listening — if you like what you hear, please review us on your favorite podcast platform. Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

This is a short excerpt from our full conversation with Airtable founder and CEO Howie Liu. Watch the full episode here: https://www.youtube.com/watch?v=rCR-zFXiXKA&t=2sHowie spent 2.5 years building Airtable before launching – and only talked to about a dozen customers in that time.In this clip, he explains why that approach made sense for a platform company, and how founders can validate ideas without drowning in customer discovery.

Van Jones is a political commentator, author, and former Obama White House advisor. Phaedra Ellis-Lamkins is founder and CEO of Promise, a software company transforming how governments deliver services to people in need. They joined the Village Global team to discuss what founders building in complex sectors need to know about power, narrative, and influence. Takeaways:Political people often operate on emotion and relationships, rather than rationality. When selling to the government, demonstrating genuine care matters more than demonstrating expertise.Relationships precede transactions. Government buyers want to feel like partners in solving a problem, not targets of a sales pitch. Staff them like a colleague, not a customer.Authenticity cannot be manufactured. Know your (and your company’s) deep "why" and let it show. People can always tell when you're running a script on them.Fame and brand are a hack for time. Walking into a room where people already know and trust you changes everything about the conversation that follows.Your founding story is a strategic asset. People want to belong to something meaningful. A compelling origin story turns government contacts into advocates who champion you behind closed doors.Find the sliver of alignment. Working with someone you disagree with on nine out of ten issues can still yield results if you're aligned on the one thing that matters. Principled, narrow partnerships can achieve what ideological purity cannot.For mission-driven companies, revenue is how you measure impact. If your product serves the mission, making more money means helping more people.Choose investors like you'd choose a spouse. Turning down better terms to work with people you trust pays off. When a crisis hits or you need to pivot, those relationships let you make the best decision for the company without panic.Thanks for listening — if you like what you hear, please review us on your favorite podcast platform. Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup

Jennifer Tejada is CEO of PagerDuty, a public company serving 30,000+ customers worldwide. She joined Village Global GP Ben Casnocha for a masterclass on scaling in the AI era, followed by live feedback sessions with four founders building AI-native companies.Takeaways:Enterprise sentiment has shifted from “fear of missing out” to “fear of getting in.” Customers are anxious about security, resilience, and managing the people transition.Know what gets your customer promoted and what gets them fired. Different personas care about different things. A CIO has different anxieties than a developer or CMO.Pricing is a strategic foundation, not a tactical enabler. Start with value realization for the customer, then build pricing metrics that tie back to that value. Consumption-based models are popular, but predictability matters more than novelty.Transparency is becoming an expectation. Customers want instrumentation in your product that makes their consumption and costs visible. Nobody likes surprises when managing margins.The AI transformation is moving faster than any previous shift. Old playbooks don't always apply. The people willing to embrace change and experiment with new ways of operating will win faster.Build your CEO village. Having a trusted network of other CEOs who understand the unique pressures of the role makes all the difference. Invest in that community on a daily basis.Psychology matters in people transitions. Asking employees to use AI to replace themselves won't work. Think differently about how you organize to get work done while helping people transition to where they can add value.Thanks for listening — if you like what you hear, please review us on your favorite podcast platform. Check us out on the web at www.villageglobal.com or get in touch with us on X @villageglobal.Want to get updates from us? Subscribe to get a peek inside the Village. We'll send you reading recommendations, exclusive event invites, and commentary on the latest happenings in Silicon Valley. www.villageglobal.com/signup