Looks Good on Paper
Looks Good on Paper flips hiring on its head. Hosted by Andrew Wood and Anita Chauhan, we dive into why CVs and "perfect fits" are overrated. Through fun, insightful conversations with industry experts, we explore how skills, potential, and real experience should be the focus of hiring... not what looks good on paper.
Quick, candid, and packed with actionable insights, we’re here to rewrite the rules of hiring, one episode at a time.
Looks Good on Paper
Stop Hiring for Titles: What Startup Hiring Actually Requires
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Startups don't need the person with the best title. They need the person who can do the work that exists right now — and probably three other things that don't have titles yet.
Most early-stage hiring fails because founders write job descriptions for the company they want to be, not the company they actually are. They hire for structure that doesn't exist yet and miss the generalists who could build it.
Sarah Sheikh, Chief of Staff at Loop Financial, has built and scaled teams inside the pressure of early-stage growth. In this episode of Looks Good on Paper, she shares why generalists consistently outperform specialists in startup environments, how task-forward hiring beats role-based hiring, and what most founders get catastrophically wrong when they're making their first critical hires.
What you'll learn:
→ Why generalists outperform specialists in early-stage environments
→ How to write a job description based on actual work, not imagined structure
→ The hiring mistakes that compound fastest in the first 10 hires
GUEST
Sarah Sheikh — Chief of Staff, Loop Financial
LinkedIn → https://www.linkedin.com/in/sarahsheikh/
YOUR HOST
Anita Chauhan — Fractional CMO, host
LinkedIn → https://www.linkedin.com/in/anitachauhan/
Chapters
00:00 Intro + Sarah’s role at Loop Financial
00:48 From fintech shutdown to startup “trial by fire”
01:54 Why startup life is glamorized (and what it’s really like)
02:57 What Loop does + how Chief of Staff connects to hiring
05:19 The biggest hiring mistake: planning by titles vs tasks
06:24 Quarterly “task audit”: automate, cut, or reassign work
07:16 The case for hiring generalists (and letting them specialize)
09:43 Hidden bias: “ex-[big company]” signal vs real work done
10:55 Tough interview questions + upfront expectations (hours, ambiguity)
12:20 Why fintech is hard in Canada (and why that matters for hiring)
13:59 “Get rid of CVs”: what Sarah would replace them with
14:51 Why LinkedIn tells you more than a resume
16:18 Why traditional screening breaks—and what video enables
16:53 The Catch-22: 279 applicants, limited time, and resume triage
17:45 “Death by tool” + what AI should actually do in hiring
18:12 AI mistakes: obvious copy/paste applications (and why they get rejected)
19:20 AI for applicants: searching roles faster + reducing busywork
19:50 AI for recruiters: smart sourcing tools (and what Sarah misses)
20:47 Practical sourcing: target companies + find proven generalists
21:35 Wrap-up + why Chief of Staff perspectives matter
LISTEN & FOLLOW
Spotify → https://open.spotify.com/show/0dbfz6y0tMq3crViHQD66H
Apple Podcasts → https://podcasts.apple.com/podcast/id1625835562
All episodes → https://looksgoodonpaper.buzzsprout.com
WATCH ON YOUTUBE - https://youtu.be/3b08JzpBEzg
POWERED BY WILLO
Hire humans, not resumes → https://www.willo.video/looks-good-on-paper
CONNECT WITH US
LinkedIn → https://www.linkedin.com/company/10170893
If this episode changed how you think about hiring, share it with one person who needs to hear it. And subscribe — we're rewriting the rules of
Show Resources
- Willo: willo.video - The most cost-effective way to screen candidates at scale. Interview candidates anywhere & at any time
- CV Free Toolkit: cvfree.me/join - Break up with the CV and get everything you need to modernize your hiring approach with skills-based assessments
- Anita Chauhan: linkedin.com/in/anitachauhan - Connect with the host
