Startups love being scrappy. They love the hustle. And they keep making the same mistake with that energy: hiring three or four junior people when they should have hired one senior person. Not because junior talent isn’t valuable but because without someone who has the reps, the strategy side falls apart and the execution side has nobody steering it.

Jen Paxton is VP of People and Talent at Roofr, where she took the company from around 125 to 260 people. Roofr is her ninth startup. Before that, she co-founded Jamyr (acquired by Recruitics) and built people functions at Smile.io, Privy, LevelUp (acquired by GrubHub), TrueMotion, and more across the Boston tech ecosystem. She holds a master’s in vocal performance from Boston Conservatory at Berklee. In this episode, she breaks down the seniority mistake startups keep making, the pedigree bias that drives comp decisions, a big-company horror story involving managers doing their own payroll onboarding, why her team still reviews every resume by hand, and the five-word question Boston TA leaders are using to catch ghost candidates.

GUEST
Jen Paxton, VP of People and Talent, Roofr
https://www.linkedin.com/in/jenpaxton/

YOUR HOST
Anita Chauhan, Host, Looks Good on Paper https://www.linkedin.com/in/anitachauhan/

LISTEN & FOLLOW
Apple Podcasts → https://podcasts.apple.com/us/podcast/looks-good-on-paper/id1625835562
All episodes → https://looksgoodonpaper.buzzsprout.com

WATCH ON YOUTUBE
→ https://youtu.be/KEKYr6m32Yg

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If this episode made you think, share it with one person who hires people.

Startups frequently under-hire on seniority, bringing in multiple junior employees to fill a role that requires senior-level judgment and strategic capacity. The cost extends beyond salary: without experienced leadership, teams lack the ability to balance execution and strategy, context switching overwhelms less experienced hires, and retention suffers when people are placed in roles they are not yet equipped to succeed in. Companies continue to overpay for candidates from well-known brands while undervaluing proven capability from lesser-known organizations. As AI-generated applications flood hiring pipelines, talent acquisition teams face a verification crisis, with structured verification methods, referral networks, and manual review processes emerging as critical defenses against a system producing more noise than signal.

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