The GTMshift

Lessons in Scaling with Kyle Norton

Thu, 11 Dec 2025 06:00:00 -0600

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/

Aligning Solutions with Business Outcomes with Josh Aranoff

Thu, 04 Dec 2025 06:00:00 -0600

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/

Leading Change through an AI Revolution with Diana Cappello

Thu, 27 Nov 2025 06:00:00 -0600

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/

The AI Revolution in Solutions Engineering with Stephen Morse

Thu, 20 Nov 2025 06:00:00 -0600

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/

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

Thu, 13 Nov 2025 06:00:00 -0600

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/

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

Thu, 06 Nov 2025 06:00:00 -0600

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/

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

Thu, 30 Oct 2025 06:00:00 -0600

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/

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

Thu, 23 Oct 2025 06:00:00 -0600

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/

Creating a Growth Engine via Buyer-Centric GTM and LinkedIn with Gal Aga

Thu, 16 Oct 2025 06:00:00 -0600

Aligned CEO Gal Aga reveals how buyer-centric sales and LinkedIn founder branding drove 4X growth. Learn why transactional sales is dead and how to build authentic content that generates real business results.

Jump into the conversation:

(00:00) Welcome to the Episode

(02:47) From sales rep to founder journey

(06:12) The 440K deal that changed everything

(14:09) Why transactional sales doesn’t work

(20:13) Building a founder brand on LinkedIn

(32:54) LinkedIn impressions and business impact

(38:56) Advice for getting started on LinkedIn

This episode is sponsored by TestBox. Please visit www.testbox.com to learn more!

Watch This Episode: https://youtu.be/CVd5Ud0oS0k

Follow Gal on LinkedIn: https://www.linkedin.com/in/gal-aga/

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/

Designing Customer-Centric GTM Strategies with Lexi Bohonnon

Thu, 09 Oct 2025 06:00:00 -0600

James Kaikis speaks with Lexi Bohonnon, Chief Revenue Officer at Roam, about how a solutions mindset in leadership drives business impact. Lexi shares her journey from solutions engineering to senior leadership, emphasizing how solutions-oriented professionals are reshaping GTM strategies. She discusses the value of aligning teams, breaking silos, and focusing on consistent customer value. Lexi also highlights her work at Roam, where frictionless, self-guided buying experiences redefine customer empowerment and satisfaction

Jump into the conversation:

(00:00) Welcome to the Episode

(01:00) Lexi’s career journey: From IBM to Yext and Roam

(07:20) The power of a solutions mindset in leadership

(15:30) Real-life example: Turning around a difficult client relationship

(21:45) Aligning teams and breaking silos with solutions thinking

(28:00) Redefining go-to-market with self-guided buying experiences

(35:10) The impact of monthly value models on customer engagement

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/Irlw-fE3iJE

Follow Lexi on LinkedIn: https://www.linkedin.com/in/lexi-bohonnon-818b4418/

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/

Everything’s Back on the Table: Why AI is Revolutionizing GTM with Craig Rosenberg

Thu, 02 Oct 2025 06:00:00 -0600

Craig Rosenberg from Scale Venture Partners reveals why AI is forcing a complete reinvention of go-to-market strategies. Learn how founders are rebuilding sales processes from scratch and why traditional GTM playbooks are now obsolete. Discover the revolutionary changes happening in buyer behavior, sales roles, and revenue efficiency.

Jump into the conversation:

(00:00) Welcome to the Episode

(05:32) Why this GTM revolution is different

(08:17) The Scale Summit “midlife crisis” moment

(11:07) David Boskovic's complete sales process rebuild

(26:09) The speed of AI implementation

(28:35) How hands-on should executives be?

(33:00) Revenue per employee revolution

(38:53) What will still be true in five years?

This episode is sponsored by TestBox. Please visit www.testbox.com to learn more!

Watch This Episode: https://youtu.be/E_qgfUZgwgU

Follow Craig on LinkedIn: https://www.linkedin.com/in/craigrosenberg/

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/

Back to Basics: Why GTM Fundamentals Beat the Latest Trends with Bart Fanelli

Thu, 25 Sep 2025 06:00:00 -0600

Bart Fanelli shares how operational discipline and Go-To-Market fundamentals drove hyperscale at Splunk and OutSystems. Learn why going back to basics beats chasing the latest trends in this engaging conversation about sustainable go-to-market strategies.

Jump into the conversation:

(00:00) Welcome to the Episode

(02:19) Hyperscale journey: Growth at Splunk and OutSystems

(05:05) Why companies avoid fundamentals

(13:51) Full lifecycle teams at Splunk

(25:13) The board-to-ground level disconnect

(32:07) AI and the future of go-to-market

This episode is sponsored by TestBox. Please visit www.testbox.com to learn more!

Watch This Episode: https://youtu.be/keM9YTDkoeI

Follow Bart on LinkedIn: https://www.linkedin.com/in/bartfanelli/

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/

GTM Engineering, RevOps, and the AI-Savvy Chief Revenue Officer with Jordan Crawford

Thu, 18 Sep 2025 06:00:00 -0600

Jordan Crawford explains go-to-market engineering and why it’s different from RevOps. Learn how to build data moats, create permissionless value propositions, and prepare for the future of CRO roles in the AI era.

Jump into the conversation:

(00:00) Welcome to the Episode

(06:16) What is go-to-market engineering?

(10:29) GTM engineering vs. RevOps

(20:39) Permissionless value propositions

(26:12) Systems of intelligence framework

(29:59) The future Jedi CRO

This episode is sponsored by TestBox. Please visit www.testbox.com to learn more!

Watch This Episode: https://youtu.be/DXxBT2AHbBc

Follow Jordan on LinkedIn: https://www.linkedin.com/in/jordancrawford/

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/

The Death of the Traditional GTM Playbook with Brett Queener

Tue, 05 Aug 2025 07:00:00 -0600

Brett Queener, architect of the original Salesforce GTM playbook, explains why traditional go-to-market strategies are dead and how AI agents are creating the biggest opportunity for solutions professionals in decades. As Managing Director at Bonfire Ventures, Brett shares insights from both building the first SaaS playbook and now investing in the companies that will replace it.

Jump into the conversation:

(00:00) Welcome to the Episode

(00:55) Brett’s journey from Salesforce to AI-first investing

(08:25) The moment Brett realized the old playbook was obsolete

(16:28) Why user interfaces are disappearing

(19:28) Why Solutions Engineers will become the new Account Executives

(31:30) How Bonfire Ventures is betting on vertical AI solutions

This episode is sponsored by TestBox. Please visit www.testbox.com to learn more!