Startup hiring improves fast when you stop hiring for titles and start hiring for the work that actually needs to get done. In this episode, Sarah Sheikh (Chief of Staff at Loop Financial) shares how she loves a generalist for her task-forward hiring plan, and why we shouldn’t be dazzled by big company names.
This episode’s all about finding the right fit. Here’s a quick breakdown of what we’re chatting about this week on Looks Good on Paper:
🏦 About Our Guest
Sarah Sheikh is Chief of Staff at Loop Financial, a cross-border banking platform for Canadian businesses. Working closely with the CEO, Sarah supports scaling operations and execution, team growth, and complex product or system migrations in a fast-moving fintech environment—bringing hard-won lessons from seeing a startup lifecycle end-to-end.
📄 About Looks Good on Paper
Looks Good on Paper is powered by Willo, the platform that's on a mission to restore trust in hiring at scale through candidate verification, employer proof, and actionable hiring insights.
Chapters
00:48 From Moves Financial to Loop: seeing the full startup cycle
01:54 The truth about early-stage work (and why it’s “trial by fire”)
02:57 What Loop Financial does + what a Chief of Staff actually owns
05:19 Biggest hiring mistake: planning by titles vs tasks
06:24 Quarterly “task audit”: automate, cut, or rebalance work
07:16 The case for hiring generalists (and letting people specialize)
09:43 Hidden bias: “ex-[big company]” and what it really signals
10:55 Why Sarah asks tough interview questions (and why it saves pain)
13:59 “Get rid of CVs”: what she’d do instead
14:51 Why LinkedIn often beats a resume for understanding candidates
16:53 The Catch-22: hundreds of applicants and limited time
17:45 AI in hiring: “death by tool” vs what’s actually useful
18:12 AI application fails (and why obvious copy/paste gets rejected)
19:20 AI for applicants + the sourcing tool Sarah wishes still existed
20:47 Practical sourcing: target companies + find proven generalists
21:35 Wrap-up
Show Resources
