Shows
The New GTM Playbook: Winning in the Margins for B2B TechEverything’s Back on the Table: Why AI is Revolutionizing GTM with Craig RosenbergIn this game-changing episode, Craig Rosenberg, Chief Platform Officer at Scale Venture Partners, explains why we’re experiencing the most revolutionary period in go-to-market history. With 25 years of experience and a front-row seat to GTM innovation through Scale’s 60+ portfolio companies, Craig reveals how AI has forced even the most experienced executives to completely rethink their approach.Craig shares incredible stories of founders like David Boscovich who rebuilt their entire sales process from scratch, using AI to generate 30-page prospect research reports and hiring unconventional profiles like theater actors for demo specialists. He explains why the traditional disc...2025-08-0141 minThe New GTM Playbook: Winning in the Margins for B2B TechThe AI Revolution in Solutions Engineering with Stephen MorseStephen Morse, founder of the Sales Engineering Leadership Institute, brings three decades of experience to this discussion about AI’s impact on go-to-market strategies. Having lived through the client-server, cloud, and now AI paradigms at companies like Siebel and Salesforce, Stephen offers unique perspectives on how this transformation differs from previous technology shifts.The conversation explores why AI feels more disruptive than past innovations, automating human functions rather than just enhancing productivity. Stephen and James dive deep into the convergence of pre-sales and post-sales roles, discussing how solutions engineers are increasingly taking on full customer lifecycle responsibilities an...2025-08-0139 minThe New GTM Playbook: Winning in the Margins for B2B TechThe Death of the Traditional GTM Playbook with Brett QueenerThe traditional go-to-market playbook is dead. Brett Queener, who literally wrote the original SaaS playbook at Salesforce, explains why everything we’ve learned about GTM over the past 20 years is becoming obsolete in the age of AI agents. As Managing Director at Bonfire Ventures, Brett invests in the seed-stage companies that are building the future of software — products that actually do work for you instead of making you hunt and peck across databases. He reveals why Solutions Engineers are perfectly positioned to become the dominant sales role, how AI is eliminating the need for traditional sales hierarchies, and w...2025-08-0137 minThe New GTM Playbook: Winning in the Margins for B2B TechFrom Rep to CEO: How Gal Aga Created a Growth Engine with Buyer-Centric GTM and LinkedInThe go-to-market playbook has fundamentally changed, and Gal Aga, CEO of Aligned, is helping to lead the charge. In this episode, Gal shares his journey from 17 years in sales to building a digital sales room platform that’s revolutionizing buyer enablement.Discover how a single 440K AAR deal revealed the secret to top sales performance, why the traditional “closer” mentality is dead, and how buyer-centric approaches are the future. Gal breaks down his LinkedIn strategy that generates 700K-1M weekly impressions and drives 65% of Aligned’s leads, proving that founder branding isn’t vanity — it’s a growth engine...2025-08-0142 minThe New GTM Playbook: Winning in the Margins for B2B TechAI-Native Selling: From Consumption Pricing to Agent-Powered GTM with Zach LawrykIn this episode of The New GTM Playbook, host James Kaikis sits down with Zach Lawryk, Solutions Leader at OpenAI, for a deep dive into AI-native selling and the future of go-to-market strategies.With 25 years of experience spanning Salesforce, Box, Rippling, and now OpenAI, Zach provides unique insights into how AI is fundamentally changing the way companies approach sales, pricing, and customer success. Unlike previous technological shifts that simply improved productivity, AI requires a complete mental model transformation in how we interact with technology and approach work. Zach reveals how OpenAI operates as “AI-native sellers,” using...2025-08-0141 minThe New GTM Playbook: Winning in the Margins for B2B TechBack to Basics: Why Go-To-Market Fundamentals Beat the Latest Trends with Bart FanelliBart Fanelli has lived through multiple hyperscale journeys, including Splunk’s incredible growth from $60M to $1.5B revenue in seven years. In this episode, he reveals why go-to-market fundamentals consistently outperform the latest trends and tactical experiments.The conversation dives deep into operational discipline, realistic capacity planning, and cross-functional alignment as the foundation for sustainable growth. Bart shares tactical examples from Splunk’s success model with virtually no quota over-assignment and how full lifecycle teams with aligned compensation transformed customer experience.This isn’t about avoiding innovation; it’s about building the proper infrastructure first. Bart emp...2025-08-0141 minThe New GTM Playbook: Winning in the Margins for B2B TechGo-to-Market Engineering: Building Data Moats in the AI Era with Jordan CrawfordIn this episode, Jordan Crawford breaks down go-to-market engineering — a role that’s becoming critical as companies need data moats in the AI era. Unlike RevOps professionals who consume business strategy, GTM engineers drive strategy by connecting bespoke data insights to execution channels. Jordan shares his framework for moving beyond spray-and-pray outbound tactics toward segment-specific targeting with what he calls “permissionless value propositions:” messages that deliver independent value before asking for anything. He explains why horizontal companies must verticalize their motions and introduces his systems of intelligence model that will reshape how CROs operate.The conversati...2025-08-0139 min
Go-to-market MavericksTestBox’s James Kaikis on winning land and expand with intentionalityIn this edition of GTM mavericks, we welcomed James Kaikis, Chief Revenue and Experience Officer at TestBox.
James shared his thoughts on winning land and expand with intentionality and a whole lot more.
We explored why:
- Acquisition starts at home
- Homework speeds up sales cycles
- Customer success isn’t a department Dive deeper into GTM mavericks here: https://www.commonroom.io/podcast/ Follow Common Room on LinkedIn here: https://www.linkedin.com/company/common-room-hq/
Follow James on LinkedIn here: https://www.linkedin.com/in/jameskaikis/
Join Uncommon, the Common Room community, here: https://www.commonroom.io/community/2025-03-207h 00
GTM News DeskYour Go-To-Market Playbook Is Broken with James KaikisHow is go-to-market strategy evolving in a world of shifting buyer expectations?What role does AI play in reshaping sales, solutions engineering, and customer success?Why are traditional sales playbooks breaking down, and what comes next?Those are the three big topics we’re covering in this episode of GTM News Desk. We’re joined by James Kaikis, CRXO at TestBox, who shares insights on the convergence of trends reshaping B2B sales, the rise of solutions engineering, and how companies can move beyond transactional selling to become true strategic partners.Jump...2025-02-1131 min
The New GTM Playbook: Winning in the Margins for B2B TechLessons in Scaling with Kyle NortonIn this episode James Kaikis, Chief Revenue and Experience Officer at TestBox, sits down with Kyle Norton, CRO at Owner.com, to uncover how modern revenue leaders are driving transformative growth. Drawing from his experiences at Shopify and Owner.com, Kyle shares tactical insights on scaling SaaS businesses, fostering customer-centric growth, and building efficient, innovative teams.
Kyle opens up about leading Owner.com to a 10x revenue growth in just two years, leveraging unconventional strategies like centralizing lead research for BDRs and designing compensation plans tied to customer outcomes. He reflects on the critical importance of enablement...2025-02-0742 min
The New GTM Playbook: Winning in the Margins for B2B TechAligning Solutions with Business Outcomes with Josh AranoffIn this episode James Kaikis sits down with Josh Aranoff, VP of Global Solutions Engineering at Procore Technologies, to discuss the evolution of the solutions role in SaaS. Drawing from his extensive experience at Salesforce and Procore, Josh shares insights on how solutions professionals are becoming essential strategic partners in driving revenue growth and predictability.
James and Josh delve into how the solutions role has expanded from technical demos to influencing business strategy, bridging gaps between sales, customer success, and product teams. Josh shares his innovative approach to forecasting, including implementing deal scoring and creating alignment between...2024-12-0443 min
The New GTM Playbook: Winning in the Margins for B2B TechThe Power of Alignment: How GTM Teams Can Deliver More Value Together with Jesse DaileyIn this episode James Kaikis sits down with Jesse Dailey, SVP of Solution Engineering and Field CTO at People.ai, to talk about the critical importance of aligning go-to-market (GTM) functions to drive customer value and business growth. Drawing from his extensive career at Salesforce, Mixpanel, Talkdesk, and People.ai, Jesse shares insights on breaking down silos between sales, solution engineering, and customer success teams.
Jesse also shares his innovative approach to team collaboration, where pre-sales and post-sales functions work together as part of a unified account team. He also highlights the importance of staying engaged with...2024-12-0441 min
The New GTM Playbook: Winning in the Margins for B2B TechNavigating the Evolving B2B SaaS Landscape with Godard AbelIn this episode James Kaikis speaks with Godard Abel, CEO of G2, about navigating the shifting B2B SaaS landscape. Drawing from his experience founding Big Machines, SteelBrick, and G2, Godard shares lessons on staying ahead of industry trends and building enduring companies.
The conversation highlights key shifts in SaaS, including the trend toward consolidation, the rise of AI-powered agents, and evolving buyer expectations. Godard explains how AI is transforming software discovery and buyer-seller interactions by improving qualification, personalization, and efficiency.
Hear Godard reflect on lessons learned from decades in SaaS, including navigating downturns and s...2024-12-0334 min
The New GTM Playbook: Winning in the Margins for B2B TechWhy Solutions Leaders Make Exceptional GTM Executives with Thomas BieserIn this episode James Kaikis sits down with Thomas Bieser, Chief Customer Officer at Cerby, to discuss how solutions leaders are redefining go-to-market (GTM) leadership by putting customers at the center. Drawing from his experiences at Opsware, Okta, and Cerby, Thomas shares how his journey from solutions engineering to overseeing all GTM functions has been shaped by a customer-first approach.
Thomas highlights how solutions leaders bring unique value to GTM organizations by fostering alignment across sales, marketing, and customer success teams. He shares how building trust throughout the customer lifecycle, including “transitioning trust” from sales to post-sales team...2024-12-0339 min
The New GTM Playbook: Winning in the Margins for B2B TechDesigning Customer-Centric GTM Strategies with Lexi BohonnonIn this episode James Kaikis sits down with Lexi Bohonnon, Managing Director at Roam, to explore how a solutions mindset in leadership can drive business impact. With a career spanning IBM, Yext, and now Roam, Lexi shares her unique journey from solutions engineering to senior leadership, revealing how solutions-oriented professionals are redefining traditional roles.
Lexi and James highlight the value of putting solutions-minded individuals in leadership positions and the impact it has on GTM strategies. Lexi explains how solutions thinking helps leaders break down silos, align teams, and focus on delivering consistent customer value. She also shares r...2024-12-0330 min
The New GTM Playbook: Winning in the Margins for B2B TechDemo Automation Demystified with David YockelsonIn this episode, James Kaikis, Chief Revenue and Experience Officer at TestBox, sits down with David Yockelson, Distinguished VP and Gartner Fellow, to break down the complexities of demo automation and its evolving impact on GTM strategies in B2B SaaS.
With extensive experience advising tech companies on go-to-market strategies, David shares his insights on why demo automation has become an essential tool for aligning sales and marketing and driving efficient pipeline growth. The conversation dives into the nuances of demo technology, exploring the differences between interactive demos, live demos, and product tours, and why these distinctions...2024-12-0335 min
The New GTM Playbook: Winning in the Margins for B2B TechPersonalization at Scale: The Future of SaaS Buyer Journeys with Elaine ZelbyJames Kaikis sits down with Elaine Zelby, CRO of Tofu, to discuss how buyer behavior is evolving and how SaaS GTM teams need to adapt. With insights from her dynamic career, Elaine offers a fresh perspective on aligning with today’s buyers.
She explores how changes in buyer expectations—like the demand for self-education and validation—are forcing GTM teams to evolve and shares Tofu’s approach to personalization at scale, using AI to create tailored buyer journeys that resonate at every touchpoint.
James and Elaine dive into aligning sales, marketing, and CS teams for a seamles...2024-12-0334 minThe New GTM Playbook: Winning in the Margins for B2B TechThe New GTM Playbook with James Kaikis Coming 12.3Winning in the Margins for B2B Tech. The traditional GTM Playbook is under attack as new, innovative motions emerge in B2B tech. Join James Kaikis, Chief Revenue & Experience Officer at TestBox, as he interviews B2B operating experts redefining the playbook by ‘winning in the margins’—tactics that focus on incremental innovation and leveraging non-obvious advantages. Tune in to stay ahead in the ever-changing world of go-to-market strategies in B2B tech.
2024-11-2700 min
Revenue Mavericks PodcastHow to Build a Truly Customer-Centric GTM Strategy with James Kaikis, Head of GTM at TestBoxJames Kaikis is the head of GTM and Chief Solutions Officer at TestBox. He has over 14 years of experience working across various industries ranging from hospitality to B2B SaaS and Venture Capital. His expertise lies in sales strategy and execution, customer relationship management, social selling, SaaS and technology solutions, team leadership and management, PreSales operations, and business development.
In this Revenue Mavericks episode, he shares his journey of transforming TestBox’s GTM strategy to be more customer-centric. He talks about how he challenged the norms and workflows of traditional B2B SaaS businesses and how he managed to pu...2024-08-1926 min
B2B Pipeline PioneersHow to Create Predictable Excellence and Repeatable ResultsJames Kaikis, Chief Solutions Officer at TestBox, realized the necessity of a well-defined ICP and accurate data to guide data-backed decisions. This year, TestBox is overhauling its GTM approach by purging bad data to improve accuracy. James is investing in a variety of growth strategies to ensure predictability and repeatability for his GTM team.About the Pioneer > 00:46Biggest Challenge > 04:04Looking Forward > 06:42100 Pennies > 10:16Final Thoughts > 13:15View the 100 Pennies Game: Click Here!Follow James Kaikis on LinkedInFollow Manoj Ramnani on LinkedInAbout...2024-08-1414 min
The GTMnow PodcastGTM 90: The GTM Playbook Under Attack and Bootstrapping a Community to Multi-Million Dollar Revenue with James KaikisJames Kaikis currently serves as the Head of Go-To-Market and Chief Solutions Officer at TestBox, an innovative company revolutionizing the way buyers interact with product demos. Before his tenure at TestBox, James co-founded the PreSales Collective with Yuji Higashi. Under their leadership, the community became a pivotal resource in the presales domain until its successful acquisition in November 2021. James also has a rich history in solution-oriented leadership roles at prominent companies including Salesforce and Showpad.Discussed in this Episode:The power of presales in driving revenue growth and customer successStrategies for scaling a community-based...2024-04-1651 min
The GTM Pack ShowEpisode 72: This B2B SaaS executive talks GTM, customer experience, & demo automation strategiesIn this episode of #TheGTMPack podcast, we interview James Kaikis, Head of Go-To-Market at TestBox based in Chicago, IL.
In this conversation, we dig into:
💡 His learnings from being the successful founder of the now exited PreSales Collective
💡 How GTM professionals should approach pipeline creation in 2024
💡 How has the presales function has evolved & where it's trending towards
& more!
#b2b #gtm #demoautomation #sales2024-04-0137 min
Presales Podcast by Presales CollectiveBuilding a Complex GTM Organization w/Peter PolizziOn the PreSales Podcast, James Kaikis and Peter Polizzi connect on the topic "Building a Complex GoToMarket (GTM) Organization. Peter, Senior Vice President of Market Strategies and Technical Sales, talks about his new role at Splunk and how it could be the future of PreSales. Peter’s new role unifies five different departments under one roof to have a unified go to market message.2021-05-0338 min