Building Scalable Revenue Operations from the Ground Up with Jessica Robertson

The CRO Spotlight Podcast

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.