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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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Connect with Holly Roland on LinkedIn

Brought to you by: stratyve.com

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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.

Connect with Vijay Damojipurapu on LinkedIn

Connect with Kris Rudeegraap on LinkedIn

Brought to you by: stratyve.com

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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.

Connect with Vijay Damojipurapu on LinkedIn

Brought to you by: stratyve.com