In this episode of The Orita Podcast, Aaron sits down with two operators who’ve seen (and fixed) just about everything in e-commerce: Charles Cushing (Founder, StartOps) and Joe Gullo (SVP, Thursday Boot Company; ex-Glossier). We get into why ops is the quiet growth engine, and how the best brands turn constraints into velocity.

They tackle:

• Automation that actually ships: where AI + Sheets beat shiny SaaS for real ROI.

• Own your data: why trusting a 3PL’s portal is like letting someone grade their own test.

• Team design in 2025: fewer hires, more IC-style leaders, and the rise of fractional talent.

• Tool stack sanity: when spreadsheets win, when to try new software, and how to make switching painless.

• Ops x Retention: “get people what they ordered when you said you would” as the ultimate LTV unlock. • Community leverage: how StartOps crowdsources answers to the same hard problems across brands. Stick around for war stories (Jet.com hyperscale, packaging that shouldn’t pop like biscuit dough), practical tips you can steal this week, and a candid look at what’s next for ops-led growth.

👥 Meet the guests Charles Cushing: Founder, StartOps (community of 250+ senior ops leaders) Joe Gullo: SVP, Thursday Boot Company; Advisor, StartOps; former Head of Ops, Glossier

🎙 Hosted by Aaron Schwartz, Co-founder, Orita.ai

🎧 Chapters [00:00] How three operators met and why ops still matter. [03:00] StartOps Origins, building a no-vendors, operators-only community. [05:30] Jet.com hyperscale and the 500-Friend Warehouse [10:20] From Logistics to LTV, Aaron’s pivot from shipping chaos to smarter segmentation. [15:00] “It’s Not BS Anymore” Joe explains why automation finally works for ops. [18:20] Google Sheets to SaaS, How AI and scripts beat shiny platforms every time. [22:20] Death by Dim-Weight, The box-size problem that’s secretly eating your margins. [26:40] Speak CFO or Get Air-Freighted, Turning ops pain into financial fluency that CEOs hear. [36:40] Ops × Marketing: The Truce, Why packaging, forecasting, and timing decide customer joy. [44:40] Forecast or Ruin Christmas, Joe’s BFCM survival advice and what innovation really means in ops.

🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when.

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