Tish Whitcraft

I rarely make predictions, but... No company founded after 2026 will organically grow to more than 10k FTEs. The leverage of rapid iterative decision loops by teams using best-in-class AI has reached escape velocity over traditional economies of scale.

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In hindsight, it was obvious and I was naive to think otherwise. A VP of Marketing recently broke it down for me: "I want to buy your tool. But it will come out of the marketing fund. And if sales are flat, then my marketing fund is flat. So whatever I need to pay for you, I'll have to cut that same amount to make it fit." This is the challenge that best of breed products face. We think about our core problem 24/7 (for us, how to operationalize guest data to drive traffic and frequency), but we also need to: ➡️ show the depth of the problem ➡️ differentiate from others using the same language ➡️ clearly explain what our solution unlocks ➡️ frame the ROI ➡️ demonstrate that it's all deep / urgent enough to change the status quo And even then - it's one thing for us as vendors to speak to it (it's our job!), but no one really tells the story better than a member of the restaurant community. To that end, I'm very excited about my upcoming conversation with Ellie Ovsenik and Jon Greenlee. Ellie is a guest data wizard. 🧙‍♀️ She is building one of the most innovative marketing engines in the business. It's got 1:1 engagement and offers, content that emphasizes dishes that drive repeat visits, and advanced tactics like perfectly timing PR campaigns in the weeks after a new restaurant opening to sustain guest awareness and traffic. Ellie's work - and entire career - speaks to the exceptional ROI you can unlock with best in class solutions. In an environment where consumers are drowning in noise / promotions / discounts / LTOs, she and her team are executing in a way to make every guest interaction feel personal and memorable. The results speak for themselves - the amount Postino guests spend in their first 120 days with the brand exceeds our full service benchmark by double digits. Join us on Wednesday 12/3 at 1pm ET. We'll dive into how Ellie built her tech stack, why she's best of breed for life, how she's actually putting guest data at the center of her marketing decisions, tips to align other stakeholders in the organization around her efforts, and what's in store for 2026. You can register here: https://lnkd.in/esTBtSYn

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In the San Francisco Bay Area, founders are relentless about growing and scaling their companies. They spot opportunity, scale through uncertainty, and create companies that redefine industries. Recently, we gathered a group of founders and tech leaders to discuss the intersection of company growth and long-term personal success. Eric S. Yuan, Founder and CEO of Zoom Communications, shared the inspiring story behind his company’s growth and eventual IPO. Eric reiterated that the founders who create the most impact don’t just plan for an exit – they prepare for what comes after. Too often, personal wealth planning lags company growth, and that gap can become costly at the most pivotal moments. The rest of the evening was focused on closing that gap. Our colleagues in Goldman Sachs Investment Banking, Pawan Tewari and Nick Giovanni, shared a candid outlook for M&A and IPOs in this environment, along with important steps founders should take to prepare for a strategic exit. We ended with a conversation around the key considerations for maximizing founders’ personal outcomes. Pre-transaction planning isn’t defensive - it’s opportunistic. Your company’s exit strategy and your family’s long-term planning work should not be done in isolation. When investment banking and private wealth work in sync, founders can cohesively optimize outcomes on all sides of the equation. To learn more about the practical “do’s and don'ts” for founders, we are happy to share our ‘Goldman guide’ for navigating wealth planning, business exists, and IPOs: https://lnkd.in/ewhEGjV3. Thank you, Eric, and to all the founders who joined us at The Battery in SF. On behalf of Goldman Sachs Private Wealth Management and Investment Banking, we look forward to the next conversation.

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Essential services are under more strain and complexity than ever—but most still operate with limited visibility, reacting to failure instead of anticipating it. At BrightAI, we’re changing that. With $51M in Series A funding co-led by Khosla Ventures and Inspired Capital, we’re scaling Physical AI to bring real-time observability to the physical world—so essential services can act before things go wrong, not after. We’ve spent the past few years proving what’s possible—now it’s time to scale. Thanks to Dina Bass for the thoughtful writeup in @Bloomberg: https://lnkd.in/gisEct4G Grateful to Upfront Ventures—and especially our board member Nick Kim—for being such thoughtful, steady partners in this work, and to BoxGroup, Marlinspike, and Rsquared VC for their participation in this round. Because when the systems that support daily life run with preventative monitoring, everything else grows stronger.

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The best time to sell your successful software company on your terms is when it has strong growth and has serious momentum. That’s when the right buyers want to buy. They see much better odds of continued growth and are willing to pay a premium. Darryl Pahl is the co-founder of DFnet, a Seattle-based company providing clinical trial data management software and services. Along with his wife and co-founder, Lisa Ondrejcek, they started the company more than 20 years ago after careers at Fred Hutchinson Cancer Research Center. The company runs DFdiscover, an enterprise-grade electronic data capture and management platform used in clinical studies worldwide. With offices in the U.S., Canada, and South Africa, DFnet has grown to over 50 employees and is approaching $10 million in revenue. Clients range from the U.S. Department of Veterans Affairs to nonprofits like PATH and major universities. Still independent and bootstrapped, DFnet has made key moves to prepare for the future—like bringing in a growth-focused CEO this year and stepping back to let her run the company. This is a good thing for their precious business, whether they choose to sell the company or not. They know that a growing, healthy company is worth more—to them or to someone else. And they will have much better negotiating power if they can walk away from any offer at any time. Check out this practical interview with Darryl Pahl on the Practical Founders Podcast. https://lnkd.in/gAJ3JtmM

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Seattle VC panels are not exactly known for being spicy, which is why my AMA with Brooke and Rolanda at AI House last night was so refreshing. We got into the questions founders are too embarrassed to ask out loud. How do VCs actually decide behind closed doors? What counts as traction when you have zero revenue? Is enterprise SaaS dead? Do Seattle founders actually have a shot against the Bay Area? A few takeaways that stood out: ✅ Associates can't get to yes without a partner sponsor — but partners often can't reach deals without associate diligence. Arm them with the facts to fight for you internally. ✅ Expect 50-70 investor conversations before a term sheet. Send your deck a day early but assume nobody read it 😎 ✅ Enterprise SaaS isn't dead, but it's shifting from seat-based to usage and outcome-based pricing. Large orgs still need governed software. ✅ Traction isn't just revenue. How excited are your customers? Would they advocate for you? Paying pilots with automatic, KPI-specific conversion > free trials, every time. ✅ Learning slope > starting background. The strongest founders they've backed adapted fast — not started perfect. Brooke and Rolanda WILL take a second meeting even if you whiff the first one! ✅ Seattle has fantastic enterprise buyers and founders with sales relationships into them. But the equity-vs-cash culture gap is real, and hiring against big tech is still hard. What made it different was how candid Brooke and Rolanda were about what actually happens after your pitch ends, aka the internal deal dynamics most founders never see. Shoutout to the room full of 100+ early-stage founders who went against the Seattle grain and asked hard questions live to the VCs. That energy is what makes AI House work. Huge thanks to Brooke B. (FUSE) and Rolanda Fu (Madrona) for keeping it real! More AMAs like this coming. Tag a founder who we should invite for the next one! #AIHouse (photo credit to Jonathan G. Blanco 🛠)

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Innovation today is about more than launching a product. It is about creating ecosystems, enabling value chains, and building solutions that influence markets and communities at scale. What Saritha and her team are working on reflects a shift in how founders think, from ambition to responsibility, from growth to purpose. This kind of mindset will define the next generation of global leaders. . . . #Leadership #InnovationEcosystem #FounderMindset #BuildingForScale #TechForGood #FutureOfBusiness #EntrepreneurialLeadership #GlobalInnovation #PurposeDriven #IndiaStartups #TalentAndImpact https://lnkd.in/ewW9TWz8

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800–1,000 emails per week. Sales, installs, support, scheduling, & follow-ups - all handled by one founder. Ari Laquidara runs Bay Area Tech Hero, a 5-star WiFi & smart home installation company. He handles every customer touchpoint himself. No ops team, inbox delegation, or bloated CRM workflow. For five years, Polymail has been the control layer for his entire business. Ari follows a strict Inbox Zero system. His inbox functions as his to-do list. One monitor stays dedicated to Polymail all day. If something needs action, it lives there. The system works because it removes guesswork:  → Auto follow-up reminders resurface emails automatically when a reply doesn’t come back, eliminating manual chasing → Read receipts show whether a message was seen, so Ari knows when to wait vs. act → Templates move routine decisions instantly once consensus lands → Inbox Zero discipline keeps every commitment visible & tracked For Ari, Polymail replaces most of what a CRM is supposed to do. The CRM stays secondary. The inbox is where velocity lives. “I genuinely couldn’t operate without it,” he told us. “Polymail is the most important productivity platform in my company.” Ari's tried nearly every email client on the market. He always comes back to Polymail. Watch how Ari runs a high-trust business with precision, directly from the inbox. 👇 #Founders #SmallBusiness #InboxZero #Operations #Productivity #Polymail

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MIT’s recent report found that 95% of enterprise AI pilots fail to deliver ROI, with value trapped in workflows, slow scaling, and misplaced bets in sales and marketing instead of back-office and integration wins. But these are symptoms, not the root cause. The real issue is strategic misalignment, as oftentimes organizations don’t clearly define the kind of bet they’re making. At the core, every pilot is a capital allocation and risk management decision. Pilots fail without clarity on the business angle, hypotheses, and go/no-go criteria. To address this, I’ve developed The Pilot Strategy Framework™, a structured approach to categorizing AI pilots based on their strategic intent and business impact. 1️⃣ Validation pilots - validate feasibility before scaling and committing further resources. 2️⃣ Internal adoption pilots - phased rollout of AI within departments, inside existing workflows, to see if it can unlock ROI. This can often signal market readiness to customers, competitors, investors, and the industry overall. 3️⃣ Customer-facing pilots - test whether existing customers will adopt new AI capabilities and whether it’s commercially safe to scale. 4️⃣ Legacy integration pilots - answer if AI can unlock value in legacy systems. 5️⃣ New product pilots - test whether additional AI offerings can be introduced; offerings that are core or adjacent to our current products and generate new ROI. Each pilot is a bet: upfront decide how much capital to risk, what value it’s meant to unlock, tradeoffs to consider, and the conditions under which you’ll scale or stop. Ultimately, it's about prioritizing the one(s) that provide the most enterprise value. Which pilot types is your organization running, and how are they moving the needle on your business outcomes? I am currently talking to leadership teams to apply this framework to drive clarity and ROI; if your organization is navigating similar questions, I'd be happy to connect. #productstrategy #aistrategy #aitransformation

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Love it or hate it, being in the SF Bay Area is still one of the biggest hacks for First Builders to discover huge opportunities before anyone else. But what can you do if you’re not here? Cecilia for example moved here in 2001 and instantly joined Yahoo after feeling the palpable energy around early internet. And it’s been nonstop ever since as she later joined Amazon, Cruise, Replit, and her own breakout company GC AI. She credits a lot to the emerging tech density and optimism in the Bay Area. But she also mentions additional ways people can identify these opportunities early on: - Follow intuition around big waves - Follow your envy - Never lose curiosity - Watch the teen hackers - Talk to peers early and often (builds long term networks/insights)

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Today, I’m thrilled to share that the Glass team is officially launching the City of Santa Monica’s next-generation government e-commerce platform for public procurement. Powered by our G-Commerce technology, this cutting-edge marketplace is designed exclusively for the public sector—bringing the speed and simplicity of modern e-commerce to government purchasing. Read the press release: https://lnkd.in/g9N3Gmcm

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AI Is Rewriting the Rules of Go-to-Market (GTM) As someone who’s spent years aligning strategy, systems, and outcomes across product, engineering, and GTM teams — this article by Dave Birckhead really hits home. In his latest Full-Stack Growth post, “Why AI Requires a New Kind of GTM Role and Org Structure,” Birckhead explains why traditional functional silos — marketing ops, sales ops, customer success ops — can’t keep pace in the AI era. AI doesn’t thrive in isolation. It thrives on shared context, unified data, and connected workflows. Most enterprise AI projects fail not because the models are weak, but because the systems they live in are fragmented. The takeaway: AI value is created when organizations reimagine entire workflows that span the customer journey — using AI as connective tissue, not as point solutions. Birckhead makes a compelling case for a new leadership role: Head of GTM Systems — the orchestrator of data, tools, and AI workflows across marketing, sales, and customer success. The payoff? ✅ Faster innovation ✅ Higher ROI on AI investments ✅ Seamless customer experience ✅ Shared measurement across the funnel Just as SaaS created Marketing Ops and RevOps, the rise of AI now demands GTM Systems Leadership — a discipline that connects, aligns, and scales the way growth truly happens. 📖 Full article here: https://lnkd.in/gU2fa5Jn By Dave Birckhead, Full-Stack Growth (Oct 14, 2025) #AI #GoToMarket #ProductOperations #GTMSystems #RevOps #DigitalTransformation #Leadership #Strategy #Innovation #FutureOfWork #OperationalExcellence #ProductManagement #SalesOps #MarketingOps #CustomerSuccess #B2BLeadership

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💫 We’re proud to welcome Tenzo AI as our newest Warden Assured platform, and one of the early adopters of our California FEHA bias audit solution. Tenzo’s AI improves candidate experience through faster response times, reducing recruiting costs by automating initial candidate screening. Now, they’re going a step further: aligning with California’s Fair Employment and Housing Act (FEHA) amendments to ensure fairness and transparency in AI-driven recruitment. Tenzo’s AI Recruiting Co-Pilot now undergoes: ✅ Monthly auditing ✅ Bias testing across 12 protected characteristics ✅ Audit record-keeping 🔗 Explore their AI Assurance Dashboard: https://lnkd.in/g-DsSJdg

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🔥 𝗙𝗶𝗿𝗲𝘀𝗶𝗱𝗲 𝗖𝗵𝗮𝘁 𝗼𝗻 “𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝘄𝗶𝘁𝗵 𝗔𝗜 𝗔𝗴𝗲𝗻𝘁𝘀” Had an incredible evening hosting a fireside chat with Matt Kraning (𝗙𝗼𝘂𝗻𝗱𝗲𝗿 & 𝗖𝗧𝗢 𝗼𝗳 𝗘𝘅𝗽𝗮𝗻𝘀𝗲, 𝗲𝘅 𝗖𝗧𝗢 𝗣𝗮𝗹𝗼 𝗔𝗹𝘁𝗼 𝗡𝗲𝘁𝘄𝗼𝗿𝗸𝘀) and a group of technology and product leaders from some of the world’s biggest 𝗰𝗼𝗻𝘀𝘂𝗺𝗲𝗿 𝗯𝗿𝗮𝗻𝗱𝘀, 𝗵𝗲𝗮𝗹𝘁𝗵𝗰𝗮𝗿𝗲 𝗰𝗼𝗺𝗽𝗮𝗻𝗶𝗲𝘀, 𝗮𝗻𝗱 𝗳𝗶𝗻𝗮𝗻𝗰𝗶𝗮𝗹 𝗶𝗻𝘀𝘁𝗶𝘁𝘂𝘁𝗶𝗼𝗻𝘀 in the Bay Area. We discussed one of the most urgent questions facing every product and engineering organization today: building 𝗔𝗜 𝗮𝗴𝗲𝗻𝘁𝘀 𝗳𝗼𝗿 𝘆𝗼𝘂𝗿 𝘂𝘀𝗲𝗿𝘀, and 𝗹𝗲𝘃𝗲𝗿𝗮𝗴𝗶𝗻𝗴 𝗔𝗜 𝗮𝗴𝗲𝗻𝘁𝘀 𝘁𝗼 𝘁𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺 𝗵𝗼�� 𝘆𝗼𝘂𝗿 𝘁𝗲𝗮𝗺𝘀 𝗼𝗽𝗲𝗿𝗮𝘁𝗲, 𝘀𝗵𝗶𝗽, 𝗮𝗻𝗱 𝘀𝗰𝗮𝗹𝗲. 𝗔𝘁 𝘁𝗵𝗶𝘀 𝗽𝗼𝗶𝗻𝘁, 𝘁𝗵𝗲𝗿𝗲 𝗶𝘀 𝗻𝗼 𝗽𝗹𝗮𝘆𝗯𝗼𝗼𝗸. The companies that win won’t be the ones waiting for others to define it - they’ll be the ones learning, experimenting, evolving, and writing it themselves. Because the reality is: Your competition is already re-architecting their business around AI agents - driving higher efficiency, faster iteration, and reinvesting those gains to build better products. The next era of product leadership isn’t about adopting AI. It’s about adopting an 𝗔𝗜-𝗮𝗴𝗲𝗻𝘁 𝗺𝗶𝗻𝗱𝘀𝗲𝘁. Grateful to everyone who joined and contributed such sharp perspectives and open conversations. Deepak Kumar P Vache Moroyan DB Banerjee

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Founders like John Kennedy build community into the company from day one. At Actual AI, that belief shows up in how they hire, how they invest in culture, and why they built Seattle’s largest dev tools meetup. So when the team decided to grow, they focused on conversations first (which led to a hire that started at a MeeBoss Hiring Festival 🚀) When conversations are real, hiring tends to take care of itself.

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Powerful work here. The 18-month CRO tenure stat is eye-opening and is surely a strategic misalignment problem. The shift from "which AI tool" to "what should be human-led vs. AI-led" is the exact reframe revenue leaders need right now. That's a strategy question that separates operators from order-takers. Excited to dig into the Six Traits framework. If GTM Operating Partners across top-tier funds are converging on common patterns, that's a signal worth heeding.

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To make enterprise agents work reliably, what do you need? semantic contracts, explicit rules? Both, but it’s only half the picture. The other half is the layer that runs enterprises but rarely shows up cleanly or coherently in systems of record: decision traces. These are the exceptions, overrides, precedents, and cross-system context that live in Slack threads, deal-desk conversations, escalation calls, and, most often, in people’s heads. You can’t reliably reconstruct them from your CRM or ERP. Rules tell an agent what should happen in general (“use official ARR for reporting”), but they fall apart on edge cases (“a VP approves a discount on a Zoom call”) where the action is logged but the reasoning is lost. When that happens, agents don’t know what they’re allowed to do next, or why. Systems-of-agents startups have a structural advantage because, when they sit in the execution path, they can see what inputs were gathered, what policy was evaluated, what exception route was invoked, who approved, and what state was written. If you persist and link those traces, you get what my partners Jaya and Ashu call a “context graph”: a living, queryable record of decision traces that links decision events to the why behind them. Our bet is that context graphs will power a new generation of startups and become the core asset behind the next trillion-dollar platforms, especially in workflows where “the AI decided” is not an acceptable answer.

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