Harry Sims

Pipe Gen Operations @ Glean | Fish in puddles, not the ocean.

Nashville Metropolitan Area

About

I’m one of those weird people who’s obsessed with outbound. I love the part of sales that most hate—real deep love. Chasing strangers for meetings is a fun game for me. I’ve been doing it for well over a decade and built 4 teams from $0 to $MMs while prospecting daily and failing over and over again to figure it out. I'm good at two things: 1)Running experiments to find high-conversion (10-30%) outbound plays. 2)Coaching others to do the same and love outbound like I do. Personally, I'm a girl, dad, and husband. We live in Nashville via San Diego, LA, and London. When I'm not on dad duty, I watch Arsenal, dream of being a DJ, work out, and collect mostly vintage Air Max, AF1s, and J1s.

Experience

  • Glean ()
    • Field Ops & GTM Engineering - Pipeline Generation
      Mar 2026 - Present · 5 mos

      - On a mission to make outbound our most efficient revenue driver. - I’m in Field Operations for everything PG - basically an old SDR who’s job is to lift up pipeline per rep, top of funnel conversion rates, and drive down the effort and activities needed to generate pipeline over time. - We’re doing it through AI, automation, education and systems design across SDRs and AEs.

    • Field Operations - Sales Development
      Jan 2026 - Mar 2026 · 3 mos

  • Chief Outbound Officer at Outbound Works LLC
    Jan 2024 - Present · 2 yrs 7 mos

    If outbound starts to feel like milking a bull - no matter how hard you squeeze, nothing comes out - then DM me. Advised Apollo, Cisco, Hockeystack, HerculesAI, Jed Mahrle, Aneesh Lal and dozens of others on better outbound. I'm currently not accepting any clients but will try to help if I can.

  • Strategic SDR at Common Room
    Jan 2025 - Jan 2026 · 1 yr 1 mo

    #1 SDR FY26 all metrics - Sourced $1.8M Closed Won Revenue (7x next best, 8x FY25 record). 14 new logos. - Generated $11M Qualified Pipe (4x next best, 5x FY25 record) - 195 Qualified Meetings Booked (+65% next best, +75% FY25 record) - Averaged 16% Account Conversion. 70% SQO%. 84 touches per Meeting Booked.

  • Apollo.io ()
    • Outbound Expert - Community, Marketing, Product
      Mar 2024 - Sep 2024 · 7 mos

      6 month contract: - Advisor to H o Product on AI research (Power Ups) and AI email. - Sourced and sold $160K worth of events sponsorships in 3ish months for VP Community. - Worked with 100+ community members and customers to improve outbound plays. - Advisor to VP Demand Gen on high-conversion outbound plays for T1/2 accounts.

    • Advisor
      Jun 2023 - Sep 2024 · 1 yr 4 mos

  • Scratchpad ()
    • Advisor
      Mar 2024 - Aug 2024 · 6 mos

      Advisor to CEO on all things outbound.

    • SDR Leader
      Mar 2023 - Mar 2024 · 1 yr 1 mo

      Ran first outbound experiments to turn PLG data/signals into pipeline. Fun - I know. - Q2 2023 (Ramp). 49 ATL Meetings Booked (163%) at an average of 82 sales activities per meeting and in 9% of‬ accounts targeted.‬ ‭- Q3 2023. 44 ATL Meetings Booked (99%) at an average of 48 sales activities per meeting in 8% of accounts‬ targeted.‬ ‭- Q4 2023. Hired + ramped first 1.5 SDRs. 46 ATL Meetings Booked (101%) at an average of 91 sales activities per meeting and in 12% of‬ accounts targeted.‬ ‭Scratchpad makes Salesforce bearable for Reps so Sales and Ops Leaders get the data‬ ‭they need to coach, inspect, and forecast less fictionally.