B2B Go-To-Market Leaders

Hosted by Vijay Damojipurapu

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May 2026

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Behind the scenes with top go-to-market practitioners from the B2B tech industry to understand their mindset and tactics: how they define go-to-market, their journey to the top role, team size, top of mind challenges and goals. Learn how product, sales, marketing and customer success leaders create internal alignment, achieve desired outcomes and help their teams perceive their customer in a human way. Hosted by Vijay Damojipurapu. Presented by Stratyve

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May 28, 2026Episode 9758 min

From CEO Operator to PE Advisor: PV Boccasam on Why Enterprise Buyers Buy Certainty, Not Software

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with PV Bóccasam, advisor to private equity firms and veteran operator across enterprise software, venture-backed startups, and category-defining companies, to explore a radically different way of thinking about go-to-market.PV argues that go-to-market is not about sales motions, pipeline generation, or even positioning frameworks—it’s about one thing: reducing buyer anxiety and lowering the perceived risk of change.Drawing from decades of experience building and scaling enterprise software companies across identity governance, GRC, enterprise risk management, and private equity-backed transformations, PV shares how the best GTM leaders think less about “selling” and more about helping customers justify, adopt, and communicate measurable value internally.They dive into:Why GTM should focus on reducing customer risk, not maximizing seller activity.The difference between customer convictions and customer incentives—and why both matter.Why measurable proof is the only reliable way to break buyer inertia.How enterprise software companies should rethink value delivery in the AI era.Why AI should reduce operational uncertainty—not create more chaos.The evolution from product-led to sales-led to partner-led GTM motions.Why “platform” messaging fails for most enterprise SaaS companies.How modern AI-native SaaS products are becoming systems of orchestration, not systems of record.The importance of helping customers retell your value proposition internally.Why enterprise GTM leaders must become the clearest thinkers during periods of uncertainty.How private equity firms should approach AI adoption through organizational redesign, not just cost-cutting.And why long-term impact matters more than short-term velocity in building a career and a company.PV’s central insight is simple but powerful:Customers don’t buy software—they buy reduced uncertainty, measurable outcomes, and confidence in the future state.This episode is a deep philosophical and operational masterclass on enterprise go-to-market strategy, AI adoption, organizational design, and what it truly means to build trust at scale.Connect with Vijay Damojipurapu on LinkedInConnect with PV Boccasam on LinkedInBrought to you by: stratyve.com

April 23, 2026Episode 9648 min

From Oracle and SAP to Founder to Stanford: Holly Roland on Building GTM That Compounds with AI

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Holly Roland, former executive at SAP and Oracle and founder of Rebel GTM, to break down what go-to-market really means in today’s AI-driven world.Holly introduces a simple but powerful framework: go-to-market is an infinity loop of discovery and value, where buyers move from awareness to purchase, and then into expansion, cross-sell, and advocacy. Yet most B2B companies still over-index on acquisition while underinvesting in the value loop.Drawing from decades of experience across enterprise tech and startups, Holly shares how she evolved from product management into go-to-market leadership, and why she ultimately built Rebel GTM to help companies align product, marketing, sales, and customer success into one unified system.They dive into:Why go-to-market should be viewed as a discovery loop + value loop, not just a funnel.The common mistake B2B companies make by prioritizing new logos over expansion.How marketing alone can’t fix growth if upstream and downstream functions are misaligned.Career lessons on moving from IC roles to leadership through collaboration and influence.Why storytelling and positioning are as important as the product itself.The rise of Generative Engine Optimization (GEO) and how it’s reshaping digital presence.A real-world GEO case study that improved readiness from ~30% to nearly 80% in weeks.Why LLM-driven traffic produces higher-intent, higher-conversion buyers than traditional SEO.The importance of reframing your product to match how customers think (not how you describe it).Practical ways to approach AI in GTM; starting with workflows, not tools.Holly’s core message is clear:Great go-to-market isn’t about isolated tactics. It’s about aligning the entire company around how customers discover, buy, and realize value.This episode is a deep dive into modern GTM strategy, combining foundational principles with emerging trends like AI and GEO that are redefining how companies reach and convert buyers.Connect with Vijay Damojipurapu on LinkedInConnect with Holly Roland on LinkedInBrought to you by: stratyve.com

March 19, 2026Episode 9549 min

How GTM Teams Win More by Moving Faster with Kris Rudeegraap, Sendoso CEO

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Kris Rudeegraap, co-CEO of Sendoso, to explore how modern go-to-market teams are evolving beyond traditional sales and marketing and why agility, creativity, and customer experience are now the real drivers of revenue.Kris shares his journey from early entrepreneurial hustles and sales roles to founding Sendoso, a category-defining platform that transformed direct mail and gifting into a scalable GTM channel. Along the way, he reveals how identifying untapped channels became his competitive advantage and how that mindset shaped Sendoso’s growth.The conversation dives deep into how GTM has shifted from a top-of-funnel obsession to a full lifecycle strategy, where post-sale expansion, customer engagement, and advocacy play a critical role in driving sustainable growth.They dive into:Why go-to-market should include post-sale expansion, not just top-of-funnel acquisition.How the “growth at all costs” era led teams to ignore retention—and why that’s changing.The origin story of Sendoso and how direct mail and gifting became a breakout GTM channel.Why finding unsaturated channels creates unfair advantages in outbound.The three core GTM levers behind Sendoso’s growth: outbound, events, and content.How community and advocacy became a powerful, compounding growth engine.A real GTM success story behind Sendoso’s Clay integration launch, generating millions in pipeline.The shift from large SDR teams to AI-enabled outbound systems that produce more with fewer resources.How to think about AI agents, org design, and system redesign in modern GTM teams.Why agility—launching fast, killing what doesn’t work, and pivoting quickly—is the defining advantage today.Kris’s core message is clear:The future of go-to-market belongs to teams that can adapt faster than the market itself.This episode is a masterclass in building a modern, adaptive GTM engine, combining creativity, systems thinking, and AI to stay ahead in an increasingly noisy world.Connect with Vijay Damojipurapu on LinkedInConnect with Kris Rudeegraap on LinkedInBrought to you by: stratyve.com

February 19, 2026Episode 9449 min

Inside the Mind of a Chief Growth Officer: Building a Bowtie GTM Engine with AJ Gandhi

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with AJ Gandhi, Chief Growth Officer and Go-To-Market Operating Partner, to unpack what it really takes to build a high-performing, holistic GTM engine.With a career spanning Bain, McKinsey, venture-backed startups, Salesforce, RingCentral, and private equity, AJ brings a rare 360-degree perspective on strategy, sales, marketing, partner ecosystems, and post-sales execution.AJ defines go-to-market as the entire lifecycle journey of a customer — not just sales — and explains why most companies underperform because they fail to integrate product, marketing, sales, partners, and customer success into a unified system.They dive into:Why GTM must be holistic across the full “bow tie,” from acquisition to expansion and advocacy.The diagnostic framework AJ uses to assess strategy, talent, execution, and performance in portfolio companies.How to identify waste in sales coverage, geography expansion, marketing spend, and organizational design.Why partner ecosystems follow the 80/20 rule — and how doubling down on top partners drives disproportionate returns.The importance of measuring value realization, not just selling ROI promises.How to elevate mid-level business problems to CFO-level strategic priorities through economic impact framing.Lessons from scaling enterprise and mid-market GTM motions — and the danger of straying from your ICP.Why pricing optimization and expansion within existing customers often deliver faster impact than new logo acquisition.The leadership discipline required in the first 100 days of a transformation.And AJ’s advice to rising GTM professionals: master the fundamentals, focus on the 80/20, and develop influence without authority.This episode is a masterclass in combining strategic rigor with execution discipline — and a reminder that sustainable growth comes from fundamentals done exceptionally well.Connect with Vijay Damojipurapu on LinkedInBrought to you by: stratyve.com

January 27, 2026Episode 9355 min

From Hyperscalers to Startup: GTM Lessons from a Former Microsoft & Amazon AI Executive

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Joseph Sirosh, Founder & CEO of CreatorsAGI, to explore how go-to-market strategy fundamentally changes in the age of AI, and why trust, differentiation, and customer clarity matter more than ever.With nearly three decades of experience leading AI initiatives at FICO, Amazon, Microsoft Azure, Compass, and Alexa Shopping, Joseph shares rare behind-the-scenes insights into how AI products actually make it to market, from early neural networks and fraud detection to today’s agentic AI systems.The conversation spans founder-led sales, product-led vs. sales-led growth, and why AI forces companies to rethink how customers discover, evaluate, and trust complex products.They dive into:How Joseph defines GTM as ICP clarity plus differentiated value, not tactics or channels.Why GTM is never static and must evolve alongside product and customer maturity.The role of trust in B2B buying, and why buyers are betting their careers on your product.Lessons from selling AI at hyperscale versus starting from zero as a founder.Why product-led growth resembles DevOps for go-to-market.When sales-led growth is unavoidable and why complex products demand partnership selling.The early pivot from creator-focused AI to B2B agentic AI at Creators AGI.A real GTM success story showing how AI agents cut sales cycles in half.Why customers can’t always tell you what AI product to build, and what founders should do instead.Practical advice for founders building GTM motions around emerging, fast-moving technology.This episode is a masterclass in AI-native go-to-market strategy, blending deep technical insight with real-world GTM execution from one of the industry’s most experienced AI leaders.Connect with Vijay Damojipurapu on LinkedInConnect with Joseph Sirosh on LinkedInBrought to you by: stratyve.com

December 25, 2025Episode 9249 min

From SDR to SVP of Sales: The Go-To-Market Thinking Behind Akshay Doshi’s Rise

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu speaks with Akshay Doshi, SVP of Sales at SpotDraft, about building repeatable value in B2B SaaS—and why great go-to-market is ultimately about elevating customers, not just closing deals.Akshay shares his journey from SDR to sales leader, including formative lessons from customer success, enterprise account management, and scaling sales teams during uncertainty—most notably, building SpotDraft’s GTM engine just as the pandemic reshaped buying behavior worldwide.The conversation explores how modern GTM leaders can design sales motions that mirror the customer experience, create trust through expectation-setting, and build systems that scale culture—not just revenue.They dive into:Why Akshay defines GTM as go-to-repeatable value, not just pipeline or quota.How experience in customer success makes sales leaders more credible and effective.Designing sales processes that reflect the onboarding and delivery experience customers will actually receive.Building trust by saying “no” to the wrong customers—and why it pays off years later.Scaling a sales culture through values, micro-wins, and cultural carriers.How sales and marketing must operate as a single orchestration layer, not separate functions.Lessons from scaling SpotDraft through outbound, word-of-mouth, and customer love during COVID.Why AI in legal tech requires careful expectation-setting, not hype-driven positioning.Advice for aspiring GTM leaders: learn adjacent functions early and think like an operator, not just a seller.This episode is a deep, practical look at how modern sales leaders can build durable GTM systems by aligning value, culture, and customer outcomes.Connect with Vijay Damojipurapu on LinkedInConnect with Akshay Doshi on LinkedInBrought to you by: stratyve.com

November 13, 2025Episode 9153 min

GTM In The AI Era: 30 Years of Lessons with Mayfield’s Gamiel Gran

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Gamiel Gran, Partner at Mayfield, to explore how decades of GTM experience—from IBM and Oracle to BEA Software and now venture capital—have shaped his philosophy on customer-centric growth and founder leadership.Gamiel shares timeless lessons from building sales teams, scaling enterprise software in the early internet era, and coaching today’s AI-first founders through the next great technology shift. His message is simple but profound: it’s not about you—it’s about them.They dive into:How curiosity and empathy separate great salespeople from quota chasers.Lessons from IBM’s legendary consultative sales training and Oracle’s “win at all costs” culture.The importance of founder clarity—why every word you say shapes how your team sells.How defining who not to sell to creates stronger product-market fit.The discipline of persona mapping: knowing your buyer so well you could do their job.Why AI isn’t just another wave—but a complete redesign of the IT and GTM stack.How agentic workflows will change selling, buying, and business process itself.Why founders must balance open-mindedness with focus—clarity is leadership.And the advice Gamiel gives every entrepreneur: Be your own North Star.From fax-era product-led growth to AI-native go-to-market design, this conversation is a masterclass in how technology, empathy, and leadership evolve together.Connect with Gamiel Gran on LinkedInConnect with Vijay Damojipurapu on LinkedInBrought to you by: stratyve.com

October 15, 2025Episode 9051 min

The Hybrid GTM Playbook: Turning Customer Success into a Growth Engine

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Alon Ahronberg, VP of Customer Success at Atera, to explore how customer success drives sustainable revenue and long-term retention in modern B2B companies.From his early career in engineering and BI consulting to leading customer success at global SaaS startups, Alon shares lessons from scaling teams, building onboarding frameworks, and transforming a PLG motion into a hybrid sales-led growth (SLG) strategy.Together, they unpack:How to define go-to-market holistically across product, sales, marketing, and customer success.The critical role of onboarding and re-onboarding in improving renewal rates and product adoption.Why internal collaboration between CSMs, marketing, and sales determines customer lifetime value.The cultural shift needed to elevate customer success from “call center” to strategic growth partner.How AI will reshape customer success, bridging high-touch strategy with scalable automation.Whether you’re a founder, go-to-market leader, or customer success professional, this episode offers a masterclass on aligning post-sale execution with growth.Connect with Alon Ahronberg on LinkedInConnect with Vijay Damojipurapu on LinkedInBrought to you by: stratyve.com

September 29, 2025Episode 8956 min

Curiosity-Driven GTM: 3x Founder Cy Khormaee on Building AegisAI

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay Damojipurapu sits down with Cy Khormaee, co-founder of AegisAI, to explore his journey from computer science research and early Microsoft days to entrepreneurship, Google, and eventually building AegisAI. Cy shares insights into curiosity-driven sales, the challenges of scaling security solutions, lessons from pivots like reCAPTCHA, and how entrepreneurs can stay ahead of technological and market shifts while remaining grounded in customer problems.They dive into:How curiosity and problem-solving shaped Cy’s GTM approach from Microsoft through startups.Lessons from Contastic and Google that informed AegisAI’s AI-native solutions.Why focusing on real customer pain is the foundation of entrepreneurship.The role of referrals, trust, and customer success in scaling GTM motions.Practical advice for young professionals entering sales and go-to-market career.Connect with Cy Khormaee on LinkedInConnect with Vijay Damojipurapu on LinkedInBrought to you by: stratyve.com

August 28, 2025Episode 8843 min

From Cold Calls to Customer-First GTM: Max Gartner’s Playbook to Scaling Revenue

Send us Fan MailIn this episode of the B2B Go-To-Market Leaders Podcast, Vijay sits down with Maximilian Gartner, Head of Go-To-Market at Brightwave, to explore how GTM leaders can balance sustainable growth with predictable revenue, while staying rooted in authentic, founder-led perspectives.Max shares his journey from inside sales “boiler rooms” to leading GTM teams at high-growth companies, and how lessons from cold-calling, enterprise deal cycles, and sales leadership shaped his philosophy on customer-first GTM.They dive deep into:Why founder-led POVs are powerful in early stage, and how they must evolve as companies scale.The critical difference between predictable and sustainable revenue, and why ignoring sustainability leads to churn.Lessons from inside sales: why clarity and credibility in the first 10 seconds of a call are everything.A Brightwave GTM pivot that front-loaded product experience, shortened feedback loops, and tripled adoption.Why “knowing your customer” (KYC) at every level: user, manager, executive, is the ultimate GTM advantage.How doubt and imposter syndrome can be reframed as signals of growth.If you’re leading sales, marketing, CS, or product, or simply curious about how GTM leaders scale customer-first strategies, this episode is packed with tactical insights and leadership lessons.Connect with Max Gartner on LinkedIn:https://www.linkedin.com/in/maximiliangartner/Connect with Vijay Damojipurapu on LinkedIn:https://www.linkedin.com/in/vijdam/Brought to you by: stratyve.com