In this episode of CRO Spotlight, host Warren Zenna sits down with Lindsay Guzowski, CEO at The Crucible, to explore the power of targeted competency assessments for chief revenue officers. They trace the origins of a bespoke CRO test built for private equity–backed companies, showing how tailored assessments can pinpoint the strengths and gaps that drive high-impact revenue leadership.

Many off-the-shelf tests fall short when evaluating executive readiness. Lindsay and Warren unpack pitfalls such as misaligned reference sets, cultural mismatches, and predictable question phrasing that candidates can game. They explain why tracking correlation coefficients and grounding assessments in rigorous validity studies is key to ensuring predictive accuracy.

Beyond individual metrics, they highlight the strategic value of team assessments for mapping leadership dynamics. Lindsay describes measuring urgency, resilience, pattern recognition and adaptability against a frozen reference cohort. She shows how private equity firms can configure custom CRO profiles and use nuanced data to optimize hiring, onboarding and development roadmaps.

In real-world case studies, they reveal how Crucible insights steer tough hiring choices and fuel candid candidate conversations. By also testing for “contaminants” like fragility or arrogance under pressure, organizations can align roles to specific growth stages. This episode delivers actionable guidance for current and aspiring CROs—and for CEOs seeking to elevate their revenue leadership team.

In this episode of CRO Spotlight, Warren Zenna sits down with Bobby Morrison, Chief Revenue Officer at Shopify, to explore how the CRO role has evolved beyond traditional sales leadership. Bobby shares his approach to unifying marketing, sales, customer success, and support under a single revenue organization focused on the complete customer journey rather than siloed handoffs.

Bobby reveals his philosophy of building revenue flywheels through aligned incentives and systems-first thinking, explaining how he restructured Shopify's go-to-market approach to eliminate friction. He discusses the importance of creating pods that bring together account executives, solution engineers, and customer success managers with shared objectives and territories to deliver better customer outcomes.

The conversation shifts to how AI is transforming revenue operations, with Bobby predicting that traditional CRMs will be replaced by AI-enabled systems within months. He emphasizes that tomorrow's successful CROs must become more technically proficient, understanding data structures and AI capabilities to build competitive advantages through technology while maintaining the human relationships that drive trust.

Warren and Bobby conclude by discussing the future of customer engagement, with Bobby sharing his belief that despite automation, human interaction remains essential in building trust. He emphasizes Shopify's commitment to helping customers navigate uncertain times through an anti-fragile platform that enables businesses to adapt quickly to changing market conditions.

On this episode of CRO Spotlight, host Warren Zenna sits down with lighting-rod revenue leader Jessica Robertson, Chief Revenue Officer at Orbb. After first connecting at a lively CRO roundtable, they unpack a conversation that could have lasted hours—touching on business philosophy, sales innovation, and the evolving role of relationships in growth. Tune in to discover why Jessica’s intelligence and empathy make her a standout leader in today’s noisy market.

Jessica traces her rise from a teenage sales development representative to spearheading revenue as Orbb’s CRO, reflecting on a decade spent mastering sales leadership across multiple industries. From navigating complex enterprise cycles to running thousands of monthly transactions, she explains how a puzzle-shaped mind fueled her creativity before sharpening it with data-driven rigor. Learn how empathetic listening, agile experimentation, and strategic analytics blended in her approach to drive authentic growth.

They dive into the nuts and bolts of designing scalable revenue operations: defining an ideal customer profile, segmenting ICP tiers, mapping clear funnel stages, and choosing a flexible CRM that grows with you. Jessica emphasizes starting with precise targeting over mass outreach, building functional pipelines grounded in relationship intelligence, and iterating relentlessly by capturing first-party email and calendar data to combat peak noise, maintain data hygiene, and prioritize real connections.

In the final segment, they explore the future of outbound outreach: leveraging email and calendar metadata to surface genuine champions and establish a relationship funnel that complements traditional channels. Jessica unpacks Orbb’s smart career overlap technology—how it uncovers verified networks to fuel warm introductions, reduce wasted touches, and unlock untapped pipelines. Host Warren Zenna closes with actionable insights to help current and aspiring CROs stay ahead in revenue intelligence.