Will Rohleder is the SDR director at TeachTown, special education software for school districts, where he took over a 4-person SDR team with $200K in pipeline and, within about a month, had the same four reps building roughly $600K a week. Today he leads 14 SDRs at a 92% show rate and 88% conversion to opportunity. He previously built and led SDR teams across fintech and HR software. He hires almost only former teachers and 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 blank-calendar-invite 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
Chapters:(00:00) Smile and Dial Fails(01:04) Meet Will Rohleder(02:35) Career Lessons SDR(04:42) Teachtown Turnaround(06:27) Territory Strategy(07:35) SDR AE Pairing(08:41) Show Rate Playbook(13:04) Handoff and Discovery(15:46) Research Led Outreach(18:02) BANT and Conversion(19:24) Comp Plan Incentives(23:33) Quota Quality Focus(24:55) Quota and Payout Tweaks(25:32) SDR AE Collaboration Systems(28:13) Multi Threading District Deals(29:04) Hiring Former Teachers(30:46) Interview for Curiosity(33:30) First 30 Days Ramp Plan(38:56) AI for Research Only(44:44) Cold Call Openers That Work(46:52) Research Driven Outreach Mindset
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