CRO Stories: Building a Relationship-Led GTM Engine with Jessica Robertson

Jessica Robertson is 11 months into her first CRO role and she's building a go-to-market engine around something most revenue leaders talk about but never operationalize: relationships. After scaling Accessibly from under $10M to $50M as VP of Sales, she watched the outbound playbook she'd relied on for years stop working. The 1:1 capacity math that used to be predictable fell apart, and no amount of headcount fixed it. So she made the jump to CRO at an early-stage startup to build a GTM motion from scratch that treats existing relationships as a real revenue channel. In this episode of CRO Stories, Rachael Bueckert sits down with Jessica Robertson, CRO of Orb, for a conversation on what it looks like to build a relationship-led GTM engine from zero, the culture shock of going from a scaled org back to startup basics, how she uses network mapping to turn existing customers into new pipeline, why her curated dinner events convert when most events don't, and what she's learned about navigating sales and CS misalignment as the person who owns both. Resources Mentioned in This Episode: USC Frameworks 00:36 - Intro to Jessica Robertson and Orb06:06 - From SDR to VP of Sales to first-time CRO07:26 - Why she left a $50M org for a startup12:09 - The culture shock of going back to ICP basics17:05 - How relationship mapping actually works in practice23:48 - Using your own product to build pipeline29:14 - The GTM motions driving Orb's growth31:19 - Why their curated events convert when most don't36:09 - Tripling revenue as a year-two goal42:41 - Advisors: Warren Zena and Bridget Winston47:41 - Navigating sales and CS misalignment as the CRO _______________________________________________________________GTM STRATEGY & AI ENGINEERING FOR B2B TECH● Website● LinkedIn● TikTok