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Orlando Diggs

Orlando Diggs

Startup operator

Chicago, IL

Ops lead turned advisor—helps founders avoid the chaos he lived through twice.

Role
Operators
On StartCoLink since
Feb 2020

Exploring Operations, fintech and marketplace mechanics, and fundraising readiness.

Runway isn't just cash. It's how many decisions your team can make without breaking.

Orlando ran operations at two Chicago seed startups—one fintech, one marketplace—before moving into advisory work. Founders call him when hiring plans outpace how decisions actually get made.

He keeps playbooks short: hiring rubrics, weekly operating rhythms, and fundraising prep that doesn't eat the whole quarter. He'd rather fix one broken process than install a suite of tools.

On StartCoLink he answers ops questions in threads and occasionally reviews cap tables and vendor stacks for pre-seed teams—always with the caveat that context matters.

Path so far

A short arc—not a résumé dump. Dates are approximate where early work overlapped.

  1. 2020 – present

    Startup operator & advisor

    Ops, fundraising prep, and team systems for seed-stage companies.

  2. 2016 – 2020

    Head of operations, fintech & marketplace startups

    First ops hire at both companies; built finance, people, and vendor ops from scratch.