About Us         Our Values         Team         Careers

Get to Know What If Media Group

Formed through the merger of the media and ad-serving experts at What If Holdings and the messaging and data gurus at All-Inbox in 2019, our technology, platform, and extensive proprietary media assets make us one of the only performance marketing platforms that enable customers to take multiple “bites of the apple” across multiple channels in order to drive consumer acquisition.

In other words, we get your offers in front of valuable potential new consumers where they are and get them to take your desired actions. Whether they’re surfing the web, checking their phones, or perusing their inboxes, we’re uniquely able to meet them at their precise moment of need.

The combination of our customer-obsessed approach (our customer retention rate is 95%), deep investment in technological innovation, and our ability to utilize multiple marketing channels on your behalf, means that when you work with What If Media Group, you’re working with a partner who’s uniquely qualified to achieve your strategic business outcomes.

Our reputation has led us to become one of Crain’s NY Fast 50 for the past three consecutive years, and featured on the Inc 5000 list of the fastest-growing private companies in America for four consecutive years (one of only 7% of companies to accomplish this feat since the inception of the award).

But while awards and numbers may offer proof points of the power of our platform and our people, for us, working at What If Media Group goes deeper.


Inclusion & Diversity Advisory Group


In 2020 we created the IDAG to assist and advise us in providing a workplace and organizational culture that values diverse thoughts and perspectives.

Working closely with HR staff, the IDAG seeks to expand our vision of matters related to diversity, equity and inclusion (DE&I), provides ideas and suggestions of how What If Media Group promotes an inclusive workplace and culture, and collaborates in the planning and support of DE&I initiatives we pursue.

From challenging conversations and increased diversity targets in hiring practices to bias training, employee surveys, direct volunteering, philanthropic donations and partnerships, we’re investing time and resources to be a leader in inclusion in order to create an organization where everyone feels seen, heard and valued.

People at a Crosswalk

Our Core Values



We are constantly asking ourselves “What If…?” We believe the question makes us challenge the status quo, sparks the creativity that drives innovation, and ultimately inspires us to find better solutions that affect value.



We stay flexible so we can adapt with speed and agility when circumstances change. When we need to change course, we do it.



 We use effective collaboration to deliver solutions that are the sum of our collective skills. We are driven by mutual respect, communication, and compassion.



We ensure our clients and colleagues can always count on us to fulfill the promises we make because we are professionals. We take ownership of our actions, and use our successes and failures as an opportunity to learn and grow together.



We prioritize our efforts to achieve maximum productivity with minimal waste.  We are efficient with our time & energy.

Meet Our Team

We’re a group of seasoned Internet professionals who enjoy the discipline of creating, analyzing, and innovating web-based media. Each member of our team is hard working, talented and humble — and they love what they do. Just ask them.

  • Partners
  • Seth Gottlieb
    President & CVO
  • Josh Gillon
    Chief Executive Officer
  • Kat Herskovits
    Chief Experience Officer
  • Ben Zitter
    Chief Compliance Officer
  • Danny Regenstein
    Chief Marketing Officer
  • Ryan Day
    Chief Strategy Officer
  • Brian Schwartz
    Chief Operating Officer
  • Holden Collick
    Chief Optimization Officer
  • Nick Abad
    COO, GlassRoots
  • Rob Schwartz
    Chief Revenue Officer
  • Andrew Klayman
    Chief Sales Officer
  • Senior
  • Gregg Pluta
    COO, Message
  • John Pershing
    Chief Technology Officer
  • Risa Schwartz
    Chief Accounting Officer
  • John Cuccinello
    Chief Financial Officer
  • Hannah Kearney
    Chief Integration Officer
  • Beth Grinter
    Chief Solutions Officer
  • Admin
  • Spencer Elg
    General Counsel
  • Mindy Thompson
    SVP of Human Resources
  • Engineering
  • David Foucher
    VP of Product Management
  • Yuni Moon-Kim
    VP of User Experience
  • Operations
  • Charlie Morgan
    SVP, Voice Monetization
  • David Vogel
    SVP of Direct Mail
  • Dave Pearlman
    VP of Product Strategy
  • Eric Shaeffer
    VP of Business Intelligence
  • Jacob Zitter
    VP of Email Operations
  • Sales &
  • Domenic Caravello
    VP, Political & Advocacy
  • Gary Smith
    SVP, Publisher Dev
  • Mike Kelly
    SVP, Data Sales
  • Jason Jacobs
    VP of Sales Ops, Message
  • Rachel Miller
    VP of Sales Operations

Join Our Team

With our physical headquarters in Fort Lee, NJ, complemented by a distributed workforce across the country, we have the best talent in the world on our team —

wherever they may be — and stay connected through our annual team outings at inspiring locales and weekly virtual events. And while we stay on top of business 24/7, we also find time to stay healthy, let our hair down, and have fun at work.

What If You Got These Perks:

  • Work around your schedule (or your kids, pets, parents…) We trust each other to get the job done, always

  • Philanthropic participation (dedicated time and company matching to causes you care about)

  • Annual Full Team Outings at incredible places

  • After hours entertainment: poker, trivia, craftwork, yoga, barre class, cooking classes, fitness challenges 

  • Comprehensive benefits: Paid maternity and paternity leave, healthcare, 401k match, salary bonus, development groups/ERGs, conference attendance, trainings
If you’re interested in working at What If Media Group and you don’t see the role that is right for you, please feel free to reach out to
[email protected]

What Can We Help You Achieve?

Let us show you how leveraging our proprietary media, AI, data science and our highly custom campaigns are redefining performance marketing and generating outstanding customer acquisition for brands.

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