Outbound Squad How to crush the Director of SDR role with Rippling’s Sr SDR Director
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Mar 17, 2026 Bert Brokaw, Senior SDR Director at Rippling who builds and scales large outbound SDR teams. He discusses Rippling’s shift to outbound and rapid scaling. He talks hiring fit when moving inbound reps to outbound. He covers enablement, ops and marketing specialization. He outlines leadership transition, manager development, and a practical weekly rhythm.
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Specialized Ops Teams Scale SDR Leadership Faster
- Cross-functional specialization (rev ops, enablement, territory ops, growth marketing) can prop up less-experienced SDR leaders and enable rapid outbound scale.
- Bert credits Rippling's dedicated ops and enablement roles for turning a novice second-line leader into an effective director.
Prepare For Higher Outbound Friction Today
- Expect more resistance today: lower deliverability, AI blockers, and automated competitors require tighter cross-functional tactics to reach prospects.
- Use marketers and deliverability experts to warm domains, optimize copy, and reduce bounce rates before scaling sequences.
CEO Sent A Lesson That Changed How Bert Leads
- Early in his career Bert fought CFO-driven quota increases to protect his reps' morale and pay, which led to a CEO-sent article about first and second teams.
- That article shifted his mindset from protecting his direct reports to prioritizing what's best for the broader business.
