The GTMshift

James Kaikis
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Execution > Theory. GTMshift is the no-fluff GotoMarket interview series for B2B SaaS operators looking to win in today's competitive market. Host James Kaikis interviews leaders on the plays that are cutting through the noise. Expect specific tactics on GTM experimentation, org design, AI-driven workflows, and everything in between.

  1. Lessons in Scaling with Kyle Norton

    12/11/2025

    Lessons in Scaling with Kyle Norton

    James Kaikis interviews Kyle Norton, CRO at Owner.com, about driving transformative SaaS growth. Kyle shares how Owner.com achieved 10x revenue growth in two years through strategies like centralized lead research and customer-focused comp plans. They discuss the evolving CRO role, the importance of enablement and rev ops, and actionable AI applications. Learn how to scale smartly, foster customer-centric growth, and build high-performing teams. Tune in for tactical insights to create your SaaS success playbook. Jump into the conversation: (00:00) Welcome to the Episode (04:30) Kyle’s Journey (09:15) Scaling Through Customer-Centricity (15:45) Investing in Enablement and RevOps (21:30) Hiring for Growth Mindset and Curiosity (28:40) Transitioning Trust Post-Sale (34:50) Leveraging AI for Internal Efficiency (42:15) The Future of Sales Roles in SaaS (50:00) Unconventional GTM Strategies for the Future This episode is sponsored by TestBox. Please visit www.testbox.com to learn more! This episode originally premiered on The New GTM Playbook. Watch the original: www.testbox.com/gtm Watch This Episode on YouTube: https://youtu.be/BNr6iIqWDZ8 Follow Kyle on LinkedIn: https://www.linkedin.com/in/kylecnorton/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

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

    12/04/2025

    Aligning Solutions with Business Outcomes with Josh Aranoff

    James Kaikis sits down with Josh Aranoff, VP of Sales and Solutions at Trimble, to explore the evolving role of solutions professionals in SaaS. Josh shares insights from his time at Salesforce and Procore, highlighting how solutions engineers are moving beyond demos to become strategic partners in revenue growth. He discusses deal scoring, hybrid roles, and the integration of presales and post-sales functions. Learn how customer expectations are reshaping GTM strategies and how enabling solutions teams with training, tools, and incentives creates better business outcomes. Jump into the conversation: (01:05) Introduction to Josh Aranoff and his career journey (07:30) Expanding the solutions role: From demos to strategic impact (14:50) How deal scoring improves forecasting and alignment (21:15) Bridging presales and post-sales: Hybrid roles and GTM alignment (29:40) The importance of enabling solutions teams with tools and training (36:20) How evolving customer expectations reshape SaaS strategies This episode is sponsored by TestBox. Please visit www.testbox.com to learn more! This episode originally premiered on The New GTM Playbook. Watch the original: www.testbox.com/gtm Watch This Episode on YouTube: https://youtu.be/IAQ0AMnNtqU Follow Josh on LinkedIn: https://www.linkedin.com/in/josharanoff/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    44 min
  3. Leading Change through an AI Revolution with Diana Cappello

    11/27/2025

    Leading Change through an AI Revolution with Diana Cappello

    Diana Cappello, Director of Solutions Consulting, US & Demo Engineering at Eightfold, reveals how AI is revolutionizing hiring from entry-level to executive roles—and why every professional needs to prepare for bot interviews. She shares battle-tested strategies that cut onboarding from 12 months to 4 months, her "Demo Dojo" training methodology, and how managed sessions using real customer data consistently beat competitors. Learn why she hires performers over techies, how AI will augment rather than replace human roles, and why solutions engineers must choose their evolution: deeper into customer success or broader into sales. Jump into the conversation: (00:00) Welcome to the Episode (4:20) - Hiring for potential: The gregarious performers who succeed in solutions (10:47) - Managed sessions: The demo strategy that beats competitors every time (13:54) - Enabling AEs to demo: Movie trailers that earn discovery calls (18:14) - Eightfold's AI interviewer: Revolutionary hiring at scale (26:04) - Removing bias: How AI creates equal playing fields in hiring (29:45) - The future of solutions: Picking sides between sales and customer success Watch This Episode on YouTube: https://youtu.be/ArViri73Rek Follow Diana on LinkedIn: https://www.linkedin.com/in/dianacappello/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    35 min
  4. The AI Revolution in Solutions Engineering with Stephen Morse

    11/20/2025

    The AI Revolution in Solutions Engineering with Stephen Morse

    Solutions engineering veteran Stephen Morse discusses how AI is transforming go-to-market strategies and reshaping the SE profession. From the convergence of pre- and post-sales to outcome-based pricing trends, this episode explores what the future holds for technical sales professionals. Jump into the conversation: (00:00) Welcome to the Episode (03:15) Stephen’s 30-year journey through tech paradigms (12:30) Why AI feels different from previous disruptions (18:45) The consolidation of pre-sales and post-sales functions (28:20) Solutions engineers transitioning to AE roles (35:40) The rise of outcome-based pricing (42:15) What sales engineering will look like in five years This episode is sponsored by TestBox. Please visit www.testbox.com to learn more! Watch This Episode: https://youtu.be/P8edj0rJ0L0 Follow Stephen on LinkedIn: https://www.linkedin.com/in/morsestephen/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    40 min
  5. Building World Class Solutions Orgs within a Private Equity-backed Business with Sharon Martin

    11/13/2025

    Building World Class Solutions Orgs within a Private Equity-backed Business with Sharon Martin

    Sharon Martin, SVP of Global Sales Engineering at Alteryx, breaks down how to position solutions teams as the strategic drivers of organizational AI adoption. She explains why solutions engineers are uniquely equipped to bridge technical capabilities with business outcomes during periods of massive change. Jump into the conversation: (00:00) Welcome to the Episode (3:28) - Thriving in private equity: Career-building years, not career-ending (10:51) - Building AI specialist teams organically through volunteer hand-raisers (18:03) - Monthly C-suite operational reviews: Elevating solutions engineering strategy (19:56) - Individual revenue goals for every solutions engineer: The controversial shift (24:06) - The death of traditional UIs: Conversational data and agentic AI (35:20) - Channel strategy as foundation: Getting scale through partners right from day Watch This Episode on YouTube: https://youtu.be/_7rL9OTvprA Follow Sharon on LinkedIn: https://www.linkedin.com/in/shamarti/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    40 min
  6. The Solution Exec Guide to Navigating the Great AI Shift with Jeff Margolese

    11/06/2025

    The Solution Exec Guide to Navigating the Great AI Shift with Jeff Margolese

    Jeff Margolese, SVP of Global Solution Consulting at ServiceNow and 20+ year industry veteran, explores how AI is fundamentally transforming enterprise sales and the solutions engineering profession. Having guided ServiceNow's SE organization through explosive growth from $300M to over $10B in revenue, Jeff shares insights on navigating massive technological shifts while building trust with enterprise customers who now demand "show me my data in your product" rather than traditional demos. Jump into the conversation: (0:00) - Welcome to the Episode (7:05) - From coding to solutions: Jeff's journey through the tech evolution (10:02) - The "hook demo" era and why it doesn't work anymore (16:03) - ServiceNow's billion-dollar AI revenue and dual LLM strategy (28:28) - Leaning into POCs: Using Miro, Obsidian, and Cursor to build live solutions (32:05) - Forward Deployed Engineers: The new competitive advantage (38:02) - The future of solutions engineering: Will AI replace or enhance the role? Watch This Episode on YouTube: https://youtu.be/YIZVPWNK4tY Follow Jeff on LinkedIn: https://www.linkedin.com/in/jeff-margolese-816478/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

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

    10/30/2025

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

    James Kaikis sits down with Elaine Zelby, Co-Founder & CRO of Tofu, to explore how evolving buyer behaviors are reshaping SaaS go-to-market strategies. Elaine discusses the demand for self-education, validation, and hyper-personalized experiences, sharing Tofu’s approach to using AI for scalable buyer journeys. Together, they unpack aligning sales, marketing, and CS for seamless customer experiences, breaking down silos across GTM functions, and incentivizing teams on shared revenue goals. This episode is packed with actionable insights for SaaS leaders to meet buyer demands, foster alignment, and thrive in today’s competitive market. Jump into the conversation: (00:00) Welcome to the Episode (01:01) Elaine’s journey from mechanical engineering to VC to Tofu’s CRO (08:45) Evolving buyer behaviors (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 This episode is sponsored by TestBox. Please visit www.testbox.com to learn more! This episode originally premiered on The New GTM Playbook. Watch the original: www.testbox.com/gtm Watch This Episode on YouTube: https://youtu.be/xZZ5nJLF8zA Follow Elaine on LinkedIn: https://www.linkedin.com/in/elainezelby/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    37 min
  8. AI-Native Selling: From Consumption Pricing to Agent-Powered GTM with Zach Lawryk

    10/23/2025

    AI-Native Selling: From Consumption Pricing to Agent-Powered GTM with Zach Lawryk

    OpenAI’s Zach Lawryk reveals how AI is fundamentally transforming go-to-market strategies, from AI-native selling methodologies to the future of consumption pricing. Learn why intelligence has become a commodity and how agent-powered workflows will reshape sales teams. Jump into the conversation: (00:00) Welcome to the episode (05:16) The AI “aha moment” at Rippling (12:19) OpenAI’s AI-native selling approach (20:04) Evolution of sales roles in AI era (28:54) Consumption vs. outcome-based pricing (39:00) Future: 10-person billion-dollar companies This episode is sponsored by TestBox. Please visit www.testbox.com to learn more! Watch This Episode: https://youtu.be/KGHnF3vzV6A Follow Zach on LinkedIn: https://www.linkedin.com/in/zlawryk/ More from The GTMshift: www.gtmshift.com Subscribe to the newsletter: https://gtmshift.substack.com/ Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

    42 min
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About

Execution > Theory. GTMshift is the no-fluff GotoMarket interview series for B2B SaaS operators looking to win in today's competitive market. Host James Kaikis interviews leaders on the plays that are cutting through the noise. Expect specific tactics on GTM experimentation, org design, AI-driven workflows, and everything in between.

Information

  • Creator
    James Kaikis
  • Years Active
    2K
  • Episodes
    14
  • Rating
    Clean
  • Copyright
    © Copyright 2025 James Kaikis
  • Show Website
    The GTMshift