The New GTM Playbook: Winning in the Margins for B2B Tech

The GTM Playbook by James Kaikis
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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.

Episodes

  1. Lessons in Scaling with Kyle Norton

    FEB 7

    Lessons in Scaling with Kyle Norton

    In 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, rev ops, and continuous learning in creating a high-performing revenue organization. James and Kyle dive into the evolving role of CROs, why transitioning trust post-sale is essential for long-term success, and how businesses can avoid the pitfalls of “spreadsheet scaling.”  Key Takeaways: Why investing in enablement and rev ops early is a growth multiplier. How to align sales, customer success, and onboarding for customer-first scaling. Practical ways to incorporate AI to streamline operations and boost efficiency. Jump into the conversation: (02:00) Kyle’s Background in GTM (07:30) The Case for Early Investments in Enablement (15:45) Building a Customer-Centered Sales Team (27:15) Transitioning Trust and Long-Term Success Follow Kyle on LinkedIn: https://www.linkedin.com/in/kylecnorton/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    42 min
  2. Aligning Solutions with Business Outcomes with Josh Aranoff

    12/04/2024

    Aligning Solutions with Business Outcomes with Josh Aranoff

    In 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 solutions and sales teams to improve predictability and customer outcomes. Josh also explores the integration of presales and post-sales functions, highlighting the rise of hybrid roles and the need for solutions engineers to balance technical expertise with business acumen. He shares the importance of enabling teams with the right training, tools, and incentives to align with evolving customer expectations. Key Takeaways: How solutions professionals can shape revenue predictability and de-risk deals. The shift toward hybrid roles and their impact on GTM alignment. Why customer expectations are reshaping presales and post-sales collaboration. Tune in to hear Josh’s take on:  (07:30) Expanding the solutions role (21:15) Bridging presales and post-sales (29:40) The importance of enabling solutions teams with tools and training Follow Josh on LinkedIn: https://www.linkedin.com/in/josharanoff/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    44 min
  3. The Power of Alignment: How GTM Teams Can Deliver More Value Together with Jesse Dailey

    12/04/2024

    The Power of Alignment: How GTM Teams Can Deliver More Value Together with Jesse Dailey

    In 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 customers beyond the sales process and creating a seamless journey through value checkpoints, ensuring customer goals are consistently met. He explains how aligning GTM teams improves efficiency, increases customer retention, and fosters long-term growth. Key Takeaways: Why aligned GTM teams are critical for delivering consistent customer value. How to implement value checkpoints across the customer journey to drive retention. Practical strategies for leveraging AI to improve team efficiency and customer outcomes. Tune in to discover how to foster collaboration, scale success, and build a GTM strategy for the future.(06:45) Why aligning GTM teams is critical for customer value(12:30) Breaking silos: Sales, solution engineering, and customer success(19:20) The role of value checkpoints in improving retention(32:50) Lessons on risk-taking, team-building, and scaling efficiently Follow Jesse on LinkedIn: https://www.linkedin.com/in/dailey/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    42 min
  4. Navigating the Evolving B2B SaaS Landscape with Godard Abel

    12/03/2024

    Navigating the Evolving B2B SaaS Landscape with Godard Abel

    In 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 scaling during growth cycles. He offers practical advice for GTM leaders on adapting to buyer demands and leveraging AI to streamline workflows while preserving human connection. Key Takeaways: How consolidation and integration are reshaping the SaaS ecosystem. How AI agents are driving efficiency in software buying and selling. The importance of clean data and personalization in today’s SaaS environment. You don’t want to miss Godard’s insights on: (08:45) Key SaaS trends: Consolidation and evolving buyer expectations (15:20) How AI-powered agents are transforming software discovery (22:30) Lessons learned from navigating SaaS downturns and growth cycles Follow Godard on LinkedIn: https://www.linkedin.com/in/godardabel/ More from The New GTM Playbook Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    34 min
  5. Demo Automation Demystified with David Yockelson

    12/03/2024

    Demo Automation Demystified with David Yockelson

    In 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 matter for GTM leaders striving to deliver a frictionless buying experience. Key takeaways include tactical insights on: How to choose the right demo solution for each stage of the funnel and audience type The influence of product-led growth (PLG) on modern sales, and where/when it makes most sense Why signal-based selling and precise account targeting are critical to maximizing resources and boosting conversion rates Get practical advice on building a streamlined GTM strategy with demo automation, plus tips on avoiding common pitfalls when adopting this technology.  Tune in to hear from the leading demo automation analyst : (01:12) Meeting David Yockelson (08:27) Understanding Demo Automation in Sales & Marketing Alignment (18:45) Choosing Between Interactive Demos, Live Demos, and Product Tours (33:10) Signal-Based Selling and Its Growing Role in SaaS Follow David on LinkedIn: https://www.linkedin.com/in/david-yockelson-452324/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    35 min
  6. Designing Customer-Centric GTM Strategies with Lexi Bohonnon

    12/03/2024

    Designing Customer-Centric GTM Strategies with Lexi Bohonnon

    In 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 real-life examples, including how integrating SEs into customer success roles helped turn around a difficult client relationship and foster long-term advocacy. Lexi delves into her role at Roam, where she’s challenging traditional go-to-market approaches with a focus on customer empowerment through frictionless buying experiences.  Key Takeaways: Why solutions-oriented leadership drives alignment and customer value. How to integrate solutions thinking into GTM strategies for better results. The impact of self-guided buying experiences on customer satisfaction and conversion. Tune in to hear Lexi share her lessons learned:  (07:20) The power of a solutions mindset in leadership (21:45) Aligning teams and breaking silos with solutions thinking (28:00) Redefining go-to-market with self-guided buying experiences Follow Lexi on LinkedIn: https://www.linkedin.com/in/lexi-bohonnon-818b4418/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    31 min
  7. Personalization at Scale: The Future of SaaS Buyer Journeys with Elaine Zelby

    12/03/2024

    Personalization at Scale: The Future of SaaS Buyer Journeys with Elaine Zelby

    James 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 seamless customer experience, how to break down silos between GTM functions, incentivizing teams on shared revenue goals, and leveraging AI for both automation and meaningful connections.  Key Takeaways: Why personalization at scale is the future of SaaS buyer journeys. How fewer tools and better data can improve GTM alignment. The power of collaborative incentives in driving shared success. Tune in to hear Elaine’s take on the future of B2B buying and how GTM teams can adapt: (15:20) Personalization at scale: Using AI to tailor buyer journeys (22:50) Breaking down the silos: Aligning sales, marketing, and CS teams (29:15) Collaborative incentives: Tying revenue goals to GTM alignment (35:40) The future of SaaS GTM: Fewer tools, better data, and leaner teams Follow Elaine on LinkedIn: https://www.linkedin.com/in/elainezelby/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe

    35 min
  8. Why Solutions Leaders Make Exceptional GTM Executives with Thomas Bieser

    12/03/2024

    Why Solutions Leaders Make Exceptional GTM Executives with Thomas Bieser

    In 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 teams, ensures long-term success.  Thomas also offers tactical advice for solutions leaders looking to break through perceived career ceilings. From leveraging curiosity to partnering with cross-functional teams, he emphasizes the importance of broadening expertise to build scalable and impactful leadership. Key Takeaways: Why solutions leaders excel in GTM roles by aligning customer and business goals. How transitioning trust ensures continuity and customer satisfaction. Actionable steps for solutions leaders to expand their remit and influence. Learn how solutions thinking can align customer and business goals, build trust, and drive impactful leadership in SaaS. (06:35) How solutions leaders foster alignment across GTM teams (13:20) The role of transitioning trust in the customer lifecycle (27:50) Tactical advice for solutions leaders to expand their careers (34:10) Thoughts on customer-first GTM leadership Follow Thomas on LinkedIn: https://www.linkedin.com/in/tbieser/ More from The New GTM Playbook:  Watch more episodes at: https://www.testbox.com/gtm Subscribe to the newsletter: https://www.testbox.com/subscribe Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    39 min

  9. 11/27/2024

    The New GTM Playbook with James Kaikis Coming 12.3

    Winning 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.

    1 min

Trailer

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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.

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