Building Radical Empathy at Scale with Vanessa Thompson of Twilio

The Three Roles Every Lean Marketing Team Needs to Hire First with Scott Holden of Vanta

In this episode of Future of Marketing, hosts Mada Seghete and Ethan Smith sit down with Scott Holden, CMO at Vanta, to unpack how marketing changes when AI accelerates output, weakens old playbooks, and makes authenticity harder to fake. Scott shares why he believes “expertise is dead,” how Vanta is moving upmarket from SOC 2 into broader compliance, risk, trust centers, vendor questionnaires, and privacy, and why the company’s “compliance” campaign used buyer pain, humor, AEO, LinkedIn, and AI-mined Gong insights to reach senior CISOs. He also explains why brand can act like performance spend, how AEO requires repeated message consensus across trusted sources, and why the modern marketing team needs product marketers, systems architects, and creator-style operators. We discuss: * Why Scott believes marketing is moving toward human authenticity as AI-generated content floods every channel * Why relying on old CMO playbooks is no longer enough, and why reinvention now needs to happen weekly or daily * Why category creation is less effective when competitors can copy category language quickly * How Vanta balances technical category language with emotionally resonant messaging around audit stress and compliance fatigue * How Vanta is using humor, risk messaging, thought leadership, social, out-of-home, and executive content to keep a theme fresh * Why brand spend can behave like performance spend when the product solves an urgent, transactional pain * What Scott learned at Brex when pausing out-of-home and top-of-funnel brand activity caused search, SEO, LinkedIn, and other metrics to drop * How Vanta used AI to mine hundreds of Gong calls and identify “audit hell” as the emotional insight behind its enterprise compliance campaign * How Scott thinks about AEO as a strategic discipline, especially when AI tools understate enterprise capabilities or product differentiation * Why AI can help draft executive content, but human editing is still required to preserve personality, taste, and credibility * Why Scott would build a 10-person marketing team around three profiles: product marketer, systems architect, and influencer-style creator * How messy GTM systems become even messier with AI, and why shared workflows, company-level memory, and systems thinking are the next advantage Where to find Scott Holden: LinkedIn: https://www.linkedin.com/in/scottiholden/ [https://www.linkedin.com/in/scottiholden/] Future of Marketing is brought to you buy the Upside AI Revenue Intelligence and Attribution platform [https://upside.tech/], Graphite Growth Research-Driven SEO & AEO Agency [https://graphite.io/] and XYZ Venture Capital [https://www.xyz.vc/] and is handcrafted by our friends over at: fame.so [https://www.fame.so/?utm_medium=podcast&utm_source=bcast&utm_campaign=masters-of-community-with-david-spinks?utm_medium=podcast&utm_source=bcast&utm_campaign=fame-client] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thefutureofmarketing.substack.com [https://thefutureofmarketing.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

The AI Native CMO Playbook with Morgane Palomares of Braintrust

In this episode of Future of Marketing, hosts Camille Ricketts and Mada Seghete sit down with Morgane Palomares, VP of Marketing at Braintrust, to unpack how marketing leaders can build credibility, speed, and leverage inside technical companies. Morgane shares how she used Reddit scraping, Gong calls, AI transcript analysis, and monthly executive readouts to shape her first 90 days at Braintrust. She also breaks down why Braintrust prioritized brand before education, how AI agents are changing PMM and field marketing workflows, and why developer marketing teams should move fast without lowering the quality bar. We discuss: * Why the first 90 days as a marketing leader should start during the interview process * How Morgane used Reddit feedback, Gong calls, and AI transcript analysis to diagnose Braintrust’s market and customer reality faster * Why monthly executive readouts helped build trust by making observations, gaps, and tradeoffs explicit * How to decide whether a technical company needs education, brand visibility, demand creation, or executive-level messaging first * How San Francisco transit shelters, bus wraps, posters, a 500-person user conference, a Series B announcement, a new brand, and a new website worked together as one market signal * Why product marketing may become one of the highest-leverage AI-enabled functions in technical B2B companies * How to earn credibility with engineering teams by shaping technical insight without slowing down product launches * Why dev tool companies may not need marketing early if users cannot already experience product value on their own * How senior marketing leaders can use AI to move faster without outsourcing their judgment, taste, or point of view Where to find Morgane Palomares: Linkedin: https://www.linkedin.com/in/morganepalomares/https://www.linkedin.com/in/morganepalomares/ Future of Marketing is brought to you by the Upside AI Revenue Intelligence and Attribution platform [https://upside.tech/], Graphite Growth Research-Driven SEO & AEO Agency [https://graphite.io/] and XYZ Venture Capital [https://www.xyz.vc/] and is handcrafted by our friends over at: fame.so [https://www.fame.so/?utm_medium=podcast&utm_source=bcast&utm_campaign=masters-of-community-with-david-spinks?utm_medium=podcast&utm_source=bcast&utm_campaign=fame-client] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thefutureofmarketing.substack.com [https://thefutureofmarketing.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Building Radical Empathy at Scale with Vanessa Thompson of Twilio

In this episode of Future of Marketing, hosts Mada Seghete and Ethan Smith sit down with Vanessa Thompson, a senior marketing leader who helped scale Twilio from a developer tool into a $5B revenue company, to unpack how AI changes the operating model for marketing. Vanessa argues that the future of marketing is radical empathy at scale: using data, AI agents, and customer signals to help buyers succeed in the moments where they are actually stuck. She shares how Twilio runs PLG and sales-assisted motions in parallel, why brand has to serve developers, solopreneurs, and enterprise CEOs at once, and how experimentation, usage data, LLM visibility, Reddit, video, and AI-powered workflows are reshaping modern GTM. We discuss: * Why Vanessa believes the future of marketing is “radical empathy at scale” * How AI can remove the repetitive work that makes marketers less human and create more room for creativity, taste, discernment, and customer understanding * Why the old model of forms, nurtures, lifecycle emails, and one-size-fits-all journeys is giving way to more personalized buyer support * How marketers can use customer signals, usage data, product errors, search behavior, and drop-off points to improve the experience * Why Twilio runs PLG and sales-assisted motions in parallel with one marketing team * How brand has to do more work when the same company serves enterprise CEOs, solopreneurs, developers, and API-driven teams * How Twilio built a test-and-learn culture where teams own budgets, run two-week experiments, and reallocate spend based on what works * How Twilio uses AI agents across 100% of signups and inbound sales requests to help prospects get started, qualify intent, and route the right people to sales * Why gated thought leadership is no longer the high-performing lead engine it used to be * How Twilio approaches LLM visibility through structured developer documentation, video, Reddit, AMAs, and community participation * How internal hackathons, team-built tools, and experimentation OKRs help create the cultural conditions for AI adoption Where to find Vanessa Thompson: LinkedIn: https://www.linkedin.com/in/vanessathomps/ [https://www.linkedin.com/in/vanessathomps/] Future of Marketing is brought to you by the Upside AI Revenue Intelligence and Attribution platform [https://upside.tech/], Graphite Growth Research-Driven SEO & AEO Agency [https://graphite.io/] and XYZ Venture Capital [https://www.xyz.vc/] and is handcrafted by our friends over at: fame.so [https://www.fame.so/?utm_medium=podcast&utm_source=bcast&utm_campaign=masters-of-community-with-david-spinks?utm_medium=podcast&utm_source=bcast&utm_campaign=fame-client] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thefutureofmarketing.substack.com [https://thefutureofmarketing.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

How to Build a Brand That Stands Out in the Age of AI with Anthony Kennada of Goldenhour

In this episode of Future of Marketing, hosts Camille Ricketts and Mada Seghete sit down with Anthony Kennada, Founder and CEO of Goldenhour to examine what happens when AI automates the mechanics of marketing. Anthony argues that the old B2B playbook, gated content, nurture sequences, demo requests, and attribution fights, is breaking down because buyers have learned to avoid it. He shares why distribution is now the central challenge for AI-era companies, how Gainsight built the Customer Success category around audience pain instead of product features, and why the “human last mile” of brand strategy still depends on taste, judgment, and wisdom. We discuss: * Why the marketing automation era trained teams to optimize for traffic, forms, nurture, and attribution instead of buyer experience * How AI exposes existing weaknesses in B2B marketing rather than creating them from scratch * Why distribution becomes the harder problem when products are easier to build with AI * How brands can stand out through authenticity, emotion, founder presence, community, events, and belonging * Why Anthony believes people will still shape enterprise buying decisions, even as agents influence shortlists and recommendations * How CMOs should rethink paid distribution and consider more direct, experiential, event-led motions * How the 95-5 rule changes audience strategy by forcing marketers to serve people who are watching but not ready to buy * Why over-engineering measurement can reduce the creative impact of brand campaigns * How GTM engineering requires both technical orchestration and real understanding of revenue, sales, and pipeline * Why owned media is powerful but difficult for small B2B teams without strong content, distribution, conversion, and audience-building capability * How Goldenhour uses AI-enabled brand systems and activation agents while keeping human operators at the center * Why the final 10% of brand work still requires human judgment: asking better questions, knowing what to cut, and reading the room Key Takeaways → AI is not killing marketing. It is exposing the parts of marketing that were already broken: gated content loops, lead spam, attribution fights, and metrics that optimized activity over buyer experience. → As products become easier to build with AI, distribution becomes the harder problem. Anthony’s view: marketing is now responsible for helping companies stand out when features are easier to copy and categories are more crowded. → The work that becomes more valuable is the work AI cannot fully own: authenticity, emotional storytelling, founder presence, community, events, and brand trust. The End of the Old Playbook → Anthony argues that the marketing automation era trained B2B teams to send traffic to owned properties, convert it with an offer, then email people until they booked a demo or unsubscribed. → That system is breaking because buyers understand the exchange. They know what happens after they fill out the form. → AI may automate parts of that machinery, but the strategic opportunity is not more volume. It is creating stronger human experiences. Brand and Distribution → In an AI-shaped market, the existential question is not just “Can we build the product?” It is “How do we get seen?” → Anthony believes the best brands will be built around trust, familiarity, emotion, community, and belonging. → That is why events and experiential strategies matter more, not less. In-person connection is becoming a counterweight to digital noise and AI-generated sameness. Positioning and Category Creation → At Gainsight, Anthony learned that positioning around customer pain can be more powerful than positioning around platform capability. → Instead of leading with features, Gainsight built around the customer success manager: a persona with limited budget, support, technology, and internal recognition. → The lesson for founders and CMOs: move upstream from product functionality and tell the story of the customer, the problem, and the market shift. Audience-First Marketing → Anthony pushes past the narrow definition of ICP. The 5% of buyers in the market today matter, but the other 95% are still watching, learning, and forming opinions. → Audience-first marketing means leading a conversation before buyers are ready to buy. → That conversation could be a manifesto, a strategic narrative, a category point of view, or a content system that helps the market understand what is changing. The Human Last Mile → AI can accelerate brand and positioning work by gathering context, synthesizing inputs, and producing drafts. → But Anthony believes the final 10% remains human: asking sharper questions, knowing what to cut, reading the room, and applying wisdom built from experience. Where to find Anthony Kennada: LinkedIn: https://www.linkedin.com/in/akennada/ [https://www.linkedin.com/in/akennada/] Future of Marketing is brought to you by the Upside AI Revenue Intelligence and Attribution platform [https://upside.tech/], Graphite Growth Research-Driven SEO & AEO Agency [https://graphite.io/] and XYZ Venture Capital [https://www.xyz.vc/] and is handcrafted by our friends over at: fame.so [https://www.fame.so/?utm_medium=podcast&utm_source=bcast&utm_campaign=masters-of-community-with-david-spinks?utm_medium=podcast&utm_source=bcast&utm_campaign=fame-client] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thefutureofmarketing.substack.com [https://thefutureofmarketing.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

From 22 Marketers to 2: Automating 80% of Marketing at Chili Piper with Alina Vandenberghe

Alina Vandenberghe is the Co-Founder and Co-CEO of Chili Piper, a demand conversion platform used by companies like ClickUp, Gong, Cursor, Verizon, and Upside that turns inbound leads into booked meetings via agentic workflows. She founded the company in 2016 with her husband Nicolas and bootstrapped past $3M ARR before raising funding. With a background in computer science, she previously built mobile products used by millions at Thomson Reuters, Bloomberg, and Pearson, some featured on stage by Steve Jobs. Alina grew up in Romania, started working at age eight, held three jobs to pay for school, and moved to the US in 2007. She took over as acting CMO at Chili Piper in 2023 and led the company’s shift toward agentic marketing operations. We discuss: * How Alina built a 65-task automation backlog scored by revenue impact and engineering effort * Why almost 80% of routine marketing work at Chili Piper was automatable through internal agents * How invisible operational fixes like a spam email checker prevented 195,000 junk meetings from cluttering sales calendars * Why Qualified Held Meetings, not opportunities, became the intermediary metric for measuring automation outcomes * How chaining agents together enables full-funnel measurement from pipeline to NRR * Why qualified booked meetings alone can hide churn risk and a leaky bucket * How analyzing 3,000 account characteristics rebuilt ICP and dropped CAC dramatically * Why Chili Piper documents every major decision asynchronously and uses the log as a proprietary LLM input * Why LLMs average creative output and where sharp opinions and storytelling still win * How a return-to-office parody campaign drove 800,000 impressions for the corporate account * Why 50% of Chili Piper’s open pipeline overlapped with engagement on Alina’s LinkedIn posts * How Alina spends only three hours a week on LinkedIn, posts three times a week, and writes everything on her phone * What a lean marketing team actually requires: one deeply technical operator and one creative generalist * Why the durable advantage in an AI-first world is human taste and contrarian creative judgment * Advice on co-founding and co-leading a company with a spouse Where to find Alina Vandenberghe: * LinkedIn [https://www.linkedin.com/in/alinav/] Future of Marketing is brought to you by the Upside AI Revenue Intelligence and Attribution platform [https://upside.tech/], Graphite Growth Research-Driven SEO & AEO Agency [https://graphite.io/] and XYZ Venture Capital [https://www.xyz.vc/] and is handcrafted by our friends over at: fame.so [https://www.fame.so/?utm_medium=podcast&utm_source=bcast&utm_campaign=masters-of-community-with-david-spinks?utm_medium=podcast&utm_source=bcast&utm_campaign=fame-client] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thefutureofmarketing.substack.com [https://thefutureofmarketing.substack.com?utm_medium=podcast&utm_campaign=CTA_1]