Creative leaderPerformance creativeProduct builder

Hi, I’m Jason.

I make creative that moves the number. Then I build the system that keeps it moving.

For more than a decade I’ve worked where brand and performance meet. I led creative behind $70M+ a year in ROI-positive ad spend at Calm, ran growth creative across five product lines at Lemonade, and rebuilt Sprout Social’s brand creative studio. On my own time, I ship products.

Now: Head of Creative & Brand at Thesis
Calm · performance creative
Jason Benjamin
Jason BenjaminLos Angeles
Where the work happened
CalmLemonadeSprout SocialUberApple TV+NBC 5 Chicago
$70M+Annual ad spend I led creative strategy for, ROI positiveCalm
1,500Ad assets a year from an in-house teamCalm
5Product lines on one creative systemLemonade
9Creatives in the studio I rebuiltSprout Social
EmmyRegional, for art direction and motion designNBC 5 · 2013
Selected work

Brand and performance
are one discipline.

Most companies split them into different teams with different budgets speaking different languages. I’ve spent my career proving they’re the same job.

012019–2021

Performance data
that shaped TV.

Calm · Associate Creative Director, User Acquisition

I led creative strategy behind $70M+ in annual ad spend, ROI positive. My team made most of the ads that drove that return, on a testing system that turned emotional storytelling into structured hypotheses across Meta, YouTube and display.

The winners didn’t stay on social. They shaped two years of Calm’s partnership with Uninterrupted, LeBron James’s media company, and the TV that came out of it.

Emotionally resonant creative and measurable outcomes aren’t in tension. They’re the same thing done honestly.

LeBron × Calm · Year 1
LeBron × Calm · Year 2
022021–2022

Five products.
One standard.

Lemonade · Growth Creative Director

Five insurance products, five growth teams, thirty-plus stakeholders. Hundreds of ad variations a month across video, static, UGC and animation, each one true to its product and accountable to CAC, CTR and ROAS.

I led a team of nine plus agency partners and freelancers, and built the system that made volume and quality the same job.

Lemonade Pet: pet insurance for top dogs
Lemonade Life: help protect your family in minutes
Lemonade Pet: saved Kona's parents $4,619
Lemonade Home: five-star customer review
Lemonade Home: Best Home Insurance, three years running
2022 · National TV

Protect A Lot, For Not A Lot

I was part of the team that made Lemonade’s first in-house produced national TV campaign, then carried the platform into paid social and digital.

2022 · Co-brand partnership

Apple TV+ × Lemonade: Luck

For the launch of Apple TV+’s first feature film, we worked with Skydance Animation on bespoke ads and a dedicated landing page, all tied to the Protect A Lot platform. More than a dozen variations ran across a six-week promo.

See the Luck landing page ↗
032023–2026

Recruited back
to rebuild the studio.

Sprout Social · Director, Creative Studio

Three years after I left, Sprout brought me back to rebuild the Brand Creative Studio: design, video and motion under one roof. Nine creatives who needed a shared identity, clear expectations and rituals that made the work feel like ours.

This is what the team shipped once we had a standard.

It’s not magic, it’s Sprout Social
Product story
Campaign
See the brand story: All Business Is Social ↗
2015–2018 · First chapter

There was no video team. I was it.

As Lead Video Producer on the brand team I concepted, scripted and produced everything: live action, animation, explainers, launches and campaigns. I grew the function from one person to five, and it kept shipping after I left.

042018–2019

Modular creative
at global scale.

Smartly.io × Uber · Performance Art Director

Uber across every vertical: Rider, Driver, Eats and Freight. Ad systems designed to swap language, market and product feature without breaking the design.

052012–2014

Where I learned
to design for time.

NBC 5 Chicago · Producer and Senior Designer

I started in broadcast and won a Regional Emmy for art direction and motion design. Broadcast taught me how motion and sound create feeling before the conscious mind catches up.

It also taught me that a deadline that won’t move sharpens everything it touches.

Jason on stage accepting a Regional Emmy
Regional Emmy · 2013
How I think

Nobody opens a feed
looking for your product.

They open it for novelty, stimulation or escape. Good creative honors that first, then earns the right to sell.

Every ad is a mirror and a key.

The work has two jobs, and it has to do both in the first second.

MirrorThe person sees themselves in it, instantly. Miss this and they scroll.
KeyIt unlocks what they came looking for, and the product is how. Miss this and you buy cheap clicks that leak.

The ego spectrum.

All creative lives on one line. Brand films sit at one end, platform-native ads at the other. The through line isn’t a logo. It’s the emotional truth that connects every touchpoint to the person on the other end.

High egoWho we want to be
Emotional truthThe through line
Low egoMeet them where they are

The performance creative engine.

Not a theory. The operating system I’ve used to manage $70M+ in creative spend.

People

Come, grow,
and go.

That’s the culture I build.

People do their best creative work when they know where they stand, trust that the system is fair, and believe their growth matters to the person leading them.

I don’t believe in ambiguity about expectations. It’s the least kind thing a manager can do. My job is to help people outgrow the team, and to build something strong enough that it keeps getting better when they do.

The Sprout Social creative studio team on a video call, 2024
The Sprout Social creative studio · 2024
Calm

Agency to in-house

Flipped the agency-to-internal ratio from 80/20 to majority in-house in two years.

Lemonade

Nine plus partners

Nine creatives, agency partners and freelancers across five product lines and thirty-plus stakeholders.

Sprout Social

Built it twice

Grew video from one to five. Came back years later to rebuild a nine-person studio.

Studio sessions

Cross-team critiques, inspiration shares and craft deep dives. Not a meeting. A practice.

Performance infrastructure

Role scorecards and project-level reviews instead of hallway opinions. I built the system. Then I built the product.

Inclusive by design

Led Sprout’s DEI Council and built the BIPOC Development Framework for mentorship, manager support and peer advocacy.

AI fluent, every seat

Every hire I make needs real AI fluency in their own discipline. Rhythm produces outcomes more than new tools do.

Builds

I build what
I wish existed.

A broken workflow, a people gap, a personal need. Every product I’ve made started with noticing something broken and not being able to leave it alone. Building keeps me close to the tools my teams use, and honest about how hard shipping is.

pannall · Live

What if the work could speak for itself?

In a meeting I overheard two directors talking about someone on my team. Not a first impression. Confirmation of a story they’d already formed, one neither of us knew existed. That’s a systems problem.

So I built a scorecard that fired at project close inside our Asana workflow and took under two minutes. People could finally see their own growth as it happened, and they recognized the picture as true.

590Reviews collected
353Projects
23Reviewers, 5 roles
The pannall dashboard showing a team's scores
Pop In app icon
Pop In · Live in the App Store

Bring back the drop-by.

Texting “you around?” felt like being a burden. Pop In lets the people you’d actually want over see when you’re home. The first real test was a Sunday afternoon. Two friends got the notification, forgot about it, then rang the doorbell.

Within

A personal problem that became a product.

A self-talk audio journal with an anonymous community. Speak what you feel, name it, sit with it, and if you want, let someone know they’re not alone. No likes. No comments. Just being heard.

LoveLab Studio insights view
LoveLab Studio

One workspace for creative and media.

Designers don’t often speak data. Media buyers don’t often speak creative. LoveLab turns a pattern in the numbers into a brief waiting to be built: opportunity, insight, hypothesis, greenlight.

Match My LogicFunded by 267 backers
Match My Logic

Oh, and I made a card game.

Fully funded on Kickstarter. Concept, design, manufacturing and fulfillment. How you think is the game.

How I work

A point of view
worth arguing with.

I walk into every room with a position on the strategy, the creative, the audience and the platform. Not because I think I’m right, but because the work deserves a real starting point. Being wrong in the first test means being right by the third. The worst thing a creative leader can do is protect their taste at the expense of the truth.

Jason Benjamin · Los Angeleshimeetjason.com