Why do creatives assume stakeholders don't care about good work, while stakeholders assume creatives are precious artists who can't handle feedback? That fundamental misunderstanding damages relationships, undermines creative quality, and keeps teams stuck in reactive, order-taking mode.

In this episode, Jen Perry, Executive Creative Director at Vagrants, shares what she learned by doing something most creatives never do: going in-house, then returning to the agency world. That dual perspective gave her rare insight into the pressures both sides face. She explains how to build genuine empathy with stakeholders, why information sharing is a core leadership responsibility, and what it takes to position creative teams as business partners instead of service providers.

About the Guest

Jen Perry is the Executive Creative Director at Vagrants, a creative studio in Boston. She spent 15 years at traditional network agencies including BBDO, Deutsch, and Hill Holiday before moving in-house to build and lead a creative team at a tech company. Unlike most creatives who go in-house and never return, Jen went back to agency life with a fundamentally different understanding of stakeholder pressures, business constraints, and what it takes to connect creative work to business outcomes.

Key Topics Discussed

• Why traditional agencies separate creatives from clients and how that stunts professional growth, especially when creatives go in-house
• The empathy gap: what creatives misunderstand about stakeholders and what stakeholders misunderstand about creatives
• Practical ways to build empathy
• Why information-sharing is a core part of creative leaders’ jobs

Connect with Jesse

• Take the free Creative Ops Assessment at www.infocusconsulting.net/creative-ops-assessment
• Connect with Jesse on LinkedIn: https://www.linkedin.com/in/jessekrinsky
• Have a creative ops challenge you're facing? Want to be a guest on the show? Reach out at jesse@infocusconsulting.net

Subscribe & Review

If you found value in this episode, please subscribe to Creative Ops Compass and leave a review. Your feedback helps other creative leaders find the show and shapes future episode topics.