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How this SDR Director 3x pipeline (same 4 reps)

Fix your team the way he did, step by step.

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Will Rohleder is the SDR director at TeachTown, special education software for school districts, where he took over a four-person SDR team sitting on $200K of pipeline and, in about a month, had the same four reps building roughly $600K a week. Today he runs 14 SDRs at a 92% show rate and 88% conversion to opportunity. He hires almost only former teachers, and he pays his SDRs to move deals forward, not just book the meeting.

We discuss

  • How he rebuilt a four-person SDR team and 10x’d weekly pipeline in about a month

  • The territory design and SDR-to-AE alignment behind the numbers

  • His show-rate playbook: the calendar-accept trick, layered reminders, and letting the prospect talk 70% of the time

  • Why half of SDR comp is tied to the opportunity reaching stage 3, not just booking the meeting

  • Who owns moving a deal forward, and the six-point qualification gate

  • Why he almost only hires former teachers, and the one interview question he swears by

  • Where he uses AI, and the inbound AI SDR that emailed a lawyer

Referenced


My biggest takeaways from this conversation

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