What Fractional CMOs Actually Do for SaaS Companies ft. Geraldina Olson

How Sean Malone Built an 8-Figure DM Empire

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-drjay-01https://tinyurl.com/revyops-sean-malone [https://tinyurl.com/revyops-sean-malone] Episode Summary: In this episode, Ben Reed sits down with Sean Malone, co-founder and CMO of Flowchat, to break down the future of social DM prospecting, LinkedIn automation, and AI-powered sales outreach. Sean shares his incredible entrepreneurial journey from struggling with cold calls and sales rejection to building multiple eight-figure businesses through direct messaging systems and scalable outbound frameworks. The conversation dives deep into LinkedIn automation safety, storytelling in sales, personal branding, AI-driven outreach, and the lessons Sean learned working alongside Russell Brunson. If you're looking to scale outbound sales, protect your LinkedIn account, and build predictable lead generation systems through social DMs, this episode is packed with actionable insights. What you'll learn: * Why LinkedIn DMs outperform traditional cold outreach channels * How Flowchat protects users from LinkedIn bans and account restrictions * The safest way to scale LinkedIn automation without triggering algorithms * Why personal branding is critical for successful outbound prospecting * Sean’s DM outreach benchmarks for scalable lead generation * How storytelling and the “hero’s journey” improve sales and marketing * The role of AI in modern sales outreach and personal DMs * What Sean learned inside Russell Brunson’s mastermind ecosystem Featured Guest: Sean Malone, Co-Founder & CMO of Flowchat Host: Ben Reed, host of the Next Gen Sales Leaders Podcast Episode Highlights: [00:01:00] Intro [00:03:00] LinkedIn automation tools and account safety [00:07:00] Understanding LinkedIn algorithms and outreach limits [00:10:00] Sean’s LinkedIn connection and response benchmarks [00:13:00] Sean’s journey into sales and early struggles [00:15:00] Growing businesses from millions to eight figures [00:17:00] Learning paid ads and discovering DM outreach [00:18:00] Working with Russell Brunson and building software companies [00:19:00] Building a high-ticket sales agency through DMs [00:23:00] Storytelling frameworks and the hero’s journey in sales Connect with Sean: LinkedIn: https://www.linkedin.com/in/seanmalone/https://www.linkedin.com/in/theseanmalone/ [https://www.linkedin.com/in/theseanmalone/] Flowchat: https://flowchat.com/https://flowchat.com [https://flowchat.com] Follow Ben on Social: LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/ [https://www.linkedin.com/in/benjamin-aaron-reed/] Join our B2B GTM & RevOps Entrepreneur Community: https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600 [https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600] Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-drjay-01https://tinyurl.com/revyops-sean-malone [https://tinyurl.com/revyops-sean-malone]

Enterprise Sales Secrets from a $50M ARR Operator ft Barry Flanagan

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-barry-flanagan [https://tinyurl.com/revyops-barry-flanagan] Episode Summary: In this episode, Ben Reed sits down with Barry Flanagan, CEO and founder of AI IQ Systems, to discuss scaling B2B sales teams, startup go-to-market strategy, and using AI to better understand buyers. Barry shares lessons from helping scale companies like Citrix, VMware, and ControlUp, including how to hire effectively, structure sales teams, and build trust-driven sales processes. They also dive into product-led growth, outbound sales, buyer psychology, and how AI is changing modern B2B marketing and sales. What you'll learn: 1) How Barry helped scale a startup from $2M to $50M ARR 2) The biggest hiring mistakes founders make in sales 3) Differences between product-led, sales-led, and marketing-led growth 4) How SDRs, AEs, and Sales Engineers work together 5) Why deep ICP and persona research improves sales performance 6) How AI can help with messaging, content, and buyer research 7) Why trust-building is critical in enterprise sales 8) The psychology behind objection handling and buyer decisions Featured Guest: Barry Flanagan, Founder/CEO of GetBuyerIntel.ai [http://GetBuyerIntel.ai] Host: Ben Reed, host of the Next Gen Sales Leaders Podcast Episode Highlights: [00:03:00] Scaling ControlUp from $2M to $50M ARR [00:08:00] Sales team roles explained: SDRs, AEs, and SEs [00:12:00] Founder-led sales and outbound strategy [00:17:00] Product-led growth and SaaS go-to-market [00:27:00] AI-powered buyer personas and messaging [00:38:00] Trust-building and sales psychology [00:45:00] Final advice for founders and sales leaders Connect with Barry: LinkedIn: https://www.linkedin.com/in/barryflanagan/ [https://www.linkedin.com/in/barryflanagan/] Follow Ben on Social: LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/ [https://www.linkedin.com/in/benjamin-aaron-reed/] Join our B2B GTM & RevOps Entrepreneur Community: https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600 [https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600] Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-barry-flanagan [https://tinyurl.com/revyops-barry-flanagan]

What Fractional CMOs Actually Do for SaaS Companies ft. Geraldina Olson

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-geraldina-olson [https://tinyurl.com/revyops-geraldina-olson] Episode Summary: In this episode, Ben Reed sits down with Geraldina Scarascia Olson, fractional CMO and B2B SaaS growth strategist, to discuss how companies scale beyond founder-led growth. Geraldina breaks down how she helps SaaS companies build structured growth systems, align marketing with product and sales, and avoid common scaling mistakes. They also dive into AI overload, product-market fit, customer experience, and why great marketing can never compensate for a weak product. What you'll learn: * How founders become the bottleneck in scaling * Why structured KPIs improve marketing execution * The biggest AI and automation mistakes companies make * Why product and marketing must work together * Why great marketing can’t fix a weak product Featured Guest: Geraldina Scarascia Olson, Fractional CMO and B2B SaaS Growth Strategist Host: Ben Reed, host of the Next Gen Sales Leaders Podcast Episode Highlights: [00:03:00] Founder-led growth challenges [00:08:00] AI tools and automation mistakes [00:11:00] KPI frameworks and accountability [00:16:00] Best-performing B2B growth channels [00:24:00] Why great products outperform great marketing Connect with Geraldina: LinkedIn: https://www.linkedin.com/in/geraldinascarasciaolson/https://www.linkedin.com/in/geraldinascarascia/ [https://www.linkedin.com/in/geraldinascarascia/] Website: https://geraldinaolson.com/ [https://geraldinaolson.com/] Follow Ben on Social: LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/ [https://www.linkedin.com/in/benjamin-aaron-reed/] Love this episode? Subscribe to the Next Gen Sales Leaders Podcast for insights on B2B sales, RevOps, AI, and leadership. If you found value in today’s conversation, please leave a review. Join our B2B GTM & RevOps Entrepreneur Community: https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600 [https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600] Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-drjay-01https://tinyurl.com/revyops-geraldina-olson [https://tinyurl.com/revyops-geraldina-olson]

From Doctor to Inc. 5000 Founder: Jay Feldman’s Lead Gen Secrets

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-drjay [https://tinyurl.com/revyops-drjay] Episode Summary: In this episode, Ben Reed sits down with Jay Feldman, founder of Otter PR and the creator of "Lead Gen Jay," to break down the realities of B2B lead generation, cold email, and scaling a high-growth agency. Jay shares his journey from medical school to entrepreneurship, how he built a multi-Inc. 5000 company, and why cold email remains one of the most powerful low-cost acquisition channels. They also dive into copywriting, AI's role in modern outreach, and what it really takes to build and scale a business in today's competitive landscape. What you'll learn: * How Jay transitioned from medical school to building a successful PR agency * Why cold email is still one of the most effective lead generation channels * The three key components of successful cold email (open, read, reply) * How to approach copywriting as both an art and a psychological system * Why giving away free value accelerates brand growth and authority * How long-form YouTube content builds trust and drives inbound demand * How AI can be used as a co-pilot for copywriting and lead generation * Why beginners should avoid ads and focus on direct outreach first * The difference between demand-side and supply-side constraints in scaling * Why templates fail and real subject matter expertise wins Featured Guest: Jay Feldman, Founder of Otter PR and B2B Lead Generation Expert Host: Ben Reed, host of the Next Gen Sales Leaders Podcast Episode Highlights: [00:01:00] Jay's journey from doctor to entrepreneur [00:03:00] Building Otter PR and early lead generation challenges [00:06:00] Why cold email became the primary acquisition channel [00:10:00] The power of personal branding and "Lead Gen Jay" [00:14:00] Long-form YouTube content as a growth strategy [00:18:00] Cold email fundamentals: open, read, reply [00:22:00] Copywriting frameworks and psychology [00:30:00] Using AI to improve outreach and campaigns [00:40:00] Scaling challenges: hiring, ops, and systems [00:50:00] Final advice for beginners in lead generation Connect with Jay: LinkedIn: https://www.linkedin.com/in/dr-jay-feldman/ [https://www.linkedin.com/in/dr-jay-feldman/] YouTube: https://www.youtube.com/@leadgenjay [https://www.youtube.com/@leadgenjay] Follow Ben on Social: LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/ [https://www.linkedin.com/in/benjamin-aaron-reed/] Join our B2B GTM & RevOps Entrepreneur Community: [https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600](https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600) [https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600](https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600)] Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-drjay [https://tinyurl.com/revyops-drjay]

Clay vs Claude Code: Why DIY GTM Systems Break ft. Jay Bhandari | Clay

Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-jay-clay-bhandari [https://tinyurl.com/revyops-jay-clay-bhandari] Episode Summary: In this episode, Ben Reed sits down with Jay Bhandari, GTM Engineer at Clay, to unpack how one of the fastest-growing companies in sales tech helped create an entirely new category: GTM Engineering. Jay shares his journey from private equity and startups into the world of Clay, while Ben and Jay explore the rise of AI-powered revenue systems, the RevOps vs GTM Engineer debate, Clay’s explosive growth strategy, and the future of SaaS in an agentic AI world. They also discuss Claude Code, vibe coding, product complexity, and why having fun may be the most important career lesson of all. What you'll learn: * How Jay transitioned from Wall Street and private equity into GTM Engineering * What a GTM Engineer actually does and why the role is growing rapidly * The differences and similarities between GTM Engineers and RevOps professionals * How Clay built a category-defining brand and product-led community * Why orchestration and enrichment are transforming modern pipeline generation * The truth about Claude Code, vibe coding, and AI software hype cycles * Why building scalable software is harder than most people think * How AI should augment sales teams instead of replacing core systems * Why creativity is a competitive advantage in go-to-market strategy * Jay’s personal philosophy on career growth, fulfillment, and having fun Featured Guest: Jay Bhandari, GTM Engineer at Clay Host: Ben Reed, host of the Next Gen Sales Leaders Podcast Episode Highlights: [00:01:00] Jay’s path from private equity to startups [00:03:00] Discovering Clay and joining as a GTM Engineer [00:06:00] How Clay built a category around GTM Engineering [00:10:00] GTM Engineer vs RevOps explained [00:18:00] Clay’s branding, creativity, and community strategy [00:25:00] Advanced Clay workflows and real customer use cases [00:27:00] Claude Code vs Clay: build vs buy debate [00:35:00] Why vibe coding has limits at scale [00:43:00] Where AI fits in modern GTM systems [00:46:30] Jay’s life advice: fun, fulfillment, and enjoying the journey Connect with Jay: LinkedIn: https://www.linkedin.com/in/jay-bhandari-profile/ [https://www.linkedin.com/in/jay-bhandari-profile/] Follow Ben on Social: LinkedIn: https://www.linkedin.com/in/benjamin-aaron-reed/ [https://www.linkedin.com/in/benjamin-aaron-reed/] Join our B2B GTM & RevOps Entrepreneur Community: https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600 [https://www.skool.com/outbound-b2b-sales/about?ref=07a56393b2d2435d9366f2e6151e2600] Sponsored By RevyOps (The #1 GTM Data Management Platform): https://tinyurl.com/revyops-jay-clay-bhandari [https://tinyurl.com/revyops-jay-clay-bhandari]