• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
C-Suitesuccess

Exec on the worst advice he ever received: ‘Don’t rock the boat’

By
Erin Cabrey
Erin Cabrey
and
Retail Brew
Retail Brew
Down Arrow Button Icon
By
Erin Cabrey
Erin Cabrey
and
Retail Brew
Retail Brew
Down Arrow Button Icon
October 30, 2025, 2:38 PM ET
The worst piece of advice I ever received was “Don’t rock the boat," said Jason Jacobs, VP of programmatic media and partnerships at digital advertising company Captivate.
The worst piece of advice I ever received was “Don’t rock the boat," said Jason Jacobs, VP of programmatic media and partnerships at digital advertising company Captivate.Getty Images

On Wednesdays, we wear pink spotlight Retail Brew’s readers. Want to be featured in an upcoming edition? Click here to introduce yourself.

Jason Jacobs is VP of programmatic media and partnerships at digital advertising company Captivate.

How would you describe your job to someone who doesn’t work in retail? I work in the digital out-of-home (DOOH) space, which means any digital screens you see in public that are not your phone, computer, or TV. Within DOOH, the retail media side is growing quickly. At Captivate, we help influence shoppers’ buying decisions by showing brand and product messages on screens in places like office buildings and residential complexes. My role is to help brands and agencies connect with these consumers in the right place at the right time.

One thing we can’t guess about your job from your LinkedIn profile? One thing you can’t guess from my LinkedIn profile is how much time I spend troubleshooting campaigns and resolving client issues. I also create new collateral that helps tell our story and showcase our capabilities.

What’s your favorite project you’ve worked on? One of my favorite projects was developing a cross-venue retail media package that combined office, residential, and other high-traffic environments into a single offering. It required collaboration across multiple teams, creative problem solving to align inventory and targeting, and gave brands a way to reach consumers throughout their daily routines.

Which emerging retail trend are you most excited about right now, and why? I am most excited about the growth of retail media beyond traditional e-commerce channels and into real world environments like digital out-of-home. Retailers are finding new ways to reach shoppers during their daily routines, not just when they are browsing online. This opens the door for more targeted, contextually relevant messaging that can influence buying decisions in the moment, and I think this blend of digital precision with physical presence is where the biggest opportunities lie.

What’s your go-to coffee order? Iced coffee, heavy on the flavored creamer!

Worst piece of advice you’ve received? The worst piece of advice I ever received was “Don’t rock the boat.” I believe that asking questions, challenging the status quo, and pushing for better solutions is how progress happens, both for businesses and for personal growth.

What was your favorite retail product when you were 15, and what’s your favorite retail product now? When I was 15, my favorite retail products were definitely clothing and sneakers. Now, it’s probably my smartwatch. I love tech gadgets and I use it to track my activity as I try to hit 10,000 steps a day.

This report was originally published by Retail Brew.

At the invitation-only Fortune COO Summit, taking place June 1–2 in Arizona, COOs from the nation’s largest companies will come together to examine how AI and emerging technologies are reshaping operating models, strengthening resilience, and enabling faster and smarter decision-making. Register now.
About the Authors
By Erin Cabrey
See full bioRight Arrow Button Icon
By Retail Brew
See full bioRight Arrow Button Icon

Latest in C-Suite

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in C-Suite

jamie dimon
Workplace Culturereturn to office
Jamie Dimon, office-work champion, vows his anti-remote culture ‘would crush you.’ The economy’s top talent begs to differ
By Jake AngeloApril 1, 2026
9 hours ago
Ayesha and Stephen Curry
C-Suitephilanthropy
Warren Buffett revives his legendary charity lunch auction—this time with Stephen Curry. His last one raised $19 million
By Jacqueline MunisApril 1, 2026
10 hours ago
How AI will make your Shake Shack order even faster
NewslettersCIO Intelligence
How AI will make your Shake Shack order even faster
By John KellApril 1, 2026
11 hours ago
Chief human resource officer salaries have surged 30% at S&P 500 companies. Here’s why boards are opening the checkbook
C-SuiteHuman resources
Chief human resource officer salaries have surged 30% at S&P 500 companies. Here’s why boards are opening the checkbook
By Courtney Vinopal and HR BrewApril 1, 2026
12 hours ago
Nvidia CEO Jensen Huang
SuccessJobs
Nvidia CEO Jensen Huang’s advice to workers scared of AI: You’re just confusing your job with the tools you use to do it
By Emma BurleighApril 1, 2026
13 hours ago
Adobe faces an AI-era test of whether the creative economy still needs it
C-SuiteNext to Lead
Adobe faces an AI-era test of whether the creative economy still needs it
By Ruth UmohApril 1, 2026
16 hours ago

Most Popular

Jerome Powell says the $39 trillion national debt is ‘not unsustainable,’ but warns the trajectory ‘will not end well’
Economy
Jerome Powell says the $39 trillion national debt is ‘not unsustainable,’ but warns the trajectory ‘will not end well’
By Fortune EditorsMarch 30, 2026
2 days ago
Two-thirds of parents say their adult Gen Z kids still rely on them financially  for support—even though it's putting them under strain
Success
Two-thirds of parents say their adult Gen Z kids still rely on them financially  for support—even though it's putting them under strain
By Fortune EditorsMarch 31, 2026
2 days ago
A man used AI to call 3,000 Irish bartenders to track the cost of Guinness. Now pubs are lowering their prices to compete
AI
A man used AI to call 3,000 Irish bartenders to track the cost of Guinness. Now pubs are lowering their prices to compete
By Fortune EditorsMarch 30, 2026
2 days ago
Current price of gold as of April 1, 2026
Personal Finance
Current price of gold as of April 1, 2026
By Fortune EditorsApril 1, 2026
15 hours ago
Current price of oil as of April 1, 2026
Personal Finance
Current price of oil as of April 1, 2026
By Fortune EditorsApril 1, 2026
16 hours ago
Kevin O'Leary says if you earn $68,000 a year and follow this rule, you'll retire a millionaire
Personal Finance
Kevin O'Leary says if you earn $68,000 a year and follow this rule, you'll retire a millionaire
By Fortune EditorsMarch 31, 2026
2 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.