AI in the Wild - What Top GTM Teams Are Getting Right About AI Adoption

AI in the Wild - What Top GTM Teams Are Getting Right About AI Adoption

In this episode, SBI’s Ray Makela sits down with Craig Riley and Jamie Halpin, to explore what separates successful AI-driven go-to-market organizations from those still struggling to realize measurable ROI. Together, they unpack the growing divide between “AI haves” and “have-nots,” and why leading companies are using AI not just to improve productivity, but to make smarter revenue decisions across the customer lifecycle.Craig shares fresh research on AI adoption across sales organizations, highlighting how top-performing teams are leveraging AI for everything from intelligent lead routing and conversational intelligence to predictive churn modeling and customer expansion strategies. The discussion also explores why many organizations fail to see results despite significant investment in AI tools.Jamie breaks down the foundational elements required for successful AI adoption, including strategy, governance, clean data, workflow design, talent readiness, and change management. The conversation also dives into real-world use cases transforming sales and customer success, including AI-powered coaching, inbound SDR automation, and customer signal engines that help teams proactively identify churn risks and expansion opportunities.Whether you’re leading sales, enablement, RevOps, or customer success, this episode delivers practical insights on how modern GTM organizations are operationalizing AI—and how to move from experimentation to real business impact.

Client Success Training That Drives Revenue - From Handoffs to Expansion Strategy

In this episode, SBI’s Ray Makela sits down with Annie Stefano, Senior Training Consultant for Client Success, to unpack what it really takes to turn client success teams into revenue drivers. Annie shares how organizations can shift from a transactional “buyer” mindset to a long-term customer growth strategy—starting with one of the most critical moments in the journey: the sales-to-CS handoff. Together, they explore how leading organizations are building high-impact client success programs by focusing on strategic thinking, proactive engagement, and time mastery. Annie breaks down the skills modern CSMs need most—from running efficient, outcome-driven meetings to anticipating customer needs before they surface—and why many teams struggle to balance client-facing and behind-the-scenes priorities. They also dive into practical ways to align sales and client success through shared journey mapping, internal kickoff calls, and better cross-functional collaboration—turning friction into a competitive advantage. Plus, Annie shares how to measure the real impact of training using metrics like time-to-value, net revenue retention (NRR), and NPS, while setting realistic expectations for behavior change. Looking ahead, the conversation explores how AI and automation are reshaping the role of client success—freeing teams from manual work so they can focus on what matters most: building human-centered relationships and acting as true strategic partners. Whether you’re building a client success function or scaling an existing one, this episode offers actionable insights on how to drive retention, expansion, and long-term customer value.

Customer Success 2.0: How AI & Education Are Redefining Growth | Sales Readiness Podcast

In this Gainsight Pulse debrief, SBI’s Ray Makela and Annie Stefano explore the dual forces transforming customer success: AI as a strategic partner and customer education as a growth engine. Learn how leading CS teams operationalize tools, build outcomes-based journeys, and upskill talent to deliver measurable, value-driven results.

Activating Sales Playbooks – Turning Strategy into Daily Manager Impact

In this episode of the Sales Readiness Podcast, SBI’s Ray Makela sits down with Charlie Dorrier, leader of SBI’s enablement activation team, to unpack why most sales playbooks fail to drive performance — and what high-performing organizations do differently. Drawing on joint research with the Revenue Enablement Society, Ray and Charlie explore a surprising finding: simply having a manager playbook does not directly correlate with improved performance. They break down why playbooks often fall flat — from lack of executive sponsorship and overbuilt content to poor integration into managers’ daily workflows. Charlie shares what “best-in-class” activation actually looks like: leadership-led initiatives, bite-sized content shaped by influential sales leaders, and a structured 6–10 week enablement rollout designed to embed behaviors, not just distribute documents. Together, they discuss how to eliminate low-value manager tasks, define a clear operating cadence, and make the playbook a living, evolving system rather than a static manual. The conversation also dives into the future of playbooks — including AI-driven coaching prompts, CRM-integrated nudges, conversational intelligence triggers, and real-time digital access that transforms the traditional “owner’s manual” into an on-demand performance engine. If your organization has invested in playbooks but hasn’t seen the expected uplift, this episode offers a practical roadmap for turning strategy into sustained manager impact — and measurable performance gains.

Selling Change, Not Products – How to Overcome Buyer Friction and Win Against No Decision

In this episode of the SBI Sales Enablement Podcast, SBI’s Ray Makela sits down with Steve Shorey, a 20-year sales enablement leader, to explore how applying change management principles can help sales teams navigate today’s complex buying environment and reduce losses to indecision. Steve shares why most deals stall—not because of competition, but because organizations default to status quo—and how sellers can create true urgency before a crisis forces change. Together, they unpack how to build a guiding coalition across up to 30 stakeholders, define a shared strategic vision, generate quick wins during the sales process, and align around what success actually looks like. They also discuss why discovery is where deals are truly won or lost, how to enable champions internally, and why high-integrity selling—including walking away when you’re not the right fit—builds long-term trust. Steve highlights a real-world case where applying these principles reduced deals lost to indecision by over 40%. If your team is struggling with stalled deals, buyer friction, or “no decision” outcomes, this episode offers a practical blueprint for turning sales into a collaborative change journey—and winning the right way.