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/

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Watch more episodes at: https://www.testbox.com/gtm

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Follow James on LinkedIn: https://www.linkedin.com/in/jameskaikis/

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/

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/