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In 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.

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In 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.

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In 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.

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In 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.

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In 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.

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In 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.

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In 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.

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In 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.

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In 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/

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Use cases, not just features.

That’s how Simon Ooley, co-founder of Veles,  a YC-backed startup reshaping how enterprise sales teams engage buyers, and former sales leader at Procore and Builder, reframes the future of enterprise sales. Instead of selling products, he helps teams sell outcomes—anchored in urgency, ROI, and the real problems customers are trying to solve.

In this episode of the B2B Go-To-Market Leaders podcast, Simon joins Vijay to unpack his journey from BDR to founder and YC-backed entrepreneur. 

They dive deep into:

• Why traditional sales roles are merging under the GTM umbrella.
• How can large teams eliminate inefficiencies in quoting and deal desk processes?
• The power of use case-based selling to drive urgency, personalization, and long-term customer success

Simon breaks down why founder-led sales isn’t just about hustle, but about curiosity, experimentation, and relentless clarity on what your buyers actually care about. You’ll learn how Velus is shifting sales conversations from product features to business cases—and why that shift might be the most important evolution in GTM strategy today.

Whether you’re scaling a sales team or starting from zero, this conversation is packed with tactical insight and a whole lot of heart.

Connect with Simon Ooley on LinkedIn:
https://www.linkedin.com/in/simonooley/

Connect with Vijay Damojipurapu on LinkedIn:
https://www.linkedin.com/in/vijdam/

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