March, 2026.- In the saturated digital ecosystem of 2026, attention is no longer something you can buy; it is something you must earn. Based on this premise, Saylor has solidified a vision where advertising ceases to be an interruption and becomes programming. Leading this evolution are Harris Sherman, Head of Production, and Brian Freia, Creative Director, who spearhead a workflow architecture designed to solve the great modern paradox: delivering studio-quality polish with the agility and authenticity of a content creator. For this duo, the “Screen War” is not won with massive media budgets, but with a “Give before you ask” philosophy, ensuring that every piece of content offers real value—be it a laugh, an emotion, or a moment of awe—before introducing the brand message.
In this exclusive interview with Roastbrief, Sherman and Freia reveal how they have re-architected the agency’s workflow to eliminate industrial-era bottlenecks, allowing production and creative to walk hand-in-hand from minute one. While Harris focuses on building a shared operational language and retention metrics that would make any TV showrunner envious, Brian dedicates himself to fostering a culture of “strategic bravery” where experimentation is the rule rather than the exception. Together, they analyze why, in 2026, ads that look like ads are destined for oblivion, and how Saylor is helping brands navigate unexplored spaces to become cultural pioneers. Discover why the true metric of success today is not reach, but the ability of an idea to be sought out, shared, and remembered in a world that has learned to ignore the conventional.
For Both:
1. The “Entertainment-Led” Definition: Saylor’s evolved mission is to help brands “stop chasing attention and start earning it” through entertainment-led advertising. Beyond just making ads that look like TV shows, what are the three core principles that define an “entertainment-led” creative and production philosophy? How does this fundamentally change the relationship between brand, agency, and audience?
HARRIS: To me, being ‘entertainment-led’ isn’t just a buzzword; it’s about respecting the audience enough to offer them a fair exchange. It comes down to three principles:
First, you have to Give Before You Ask. Traditional ads demand a transaction immediately. We believe you have to earn the right to that message by providing value first—whether that’s a laugh, an emotional beat, or just a moment of awe. If the viewer feels shortchanged on the entertainment, they won’t stick around for the brand.
Second is Format Fluidity. We respect the media buy, but the creative has to thrive in the container it’s bought for. Whether it’s a Super Bowl spot or a 6-second social asset, the ‘entertainment’ standard applies equally. We don’t view time limits as barriers; we view them as the parameters to build the best possible story for that specific moment.
Third, we focus on Winning the ‘Screen War.’ We remind our clients that placement doesn’t equal attention. When you buy a slot, you aren’t just competing with other brands in your category; you’re competing with text notifications, news alerts, and the entire internet. To make the media investment pay off, the creative has to be compelling enough to beat everything else fighting for that screen.
Ultimately, this shifts the dynamic. We stop being just a service provider filling ad slots and become a programming partner. We help brands act less like interruptive advertisers and more like creators—ensuring that the money they spend on media actually buys them real attention.
2. The Creator vs. Studio Paradox: Harris, you describe needing “the polish of a studio and the pace of a creator.” Brian, you’re tasked with developing work that performs across platforms. How do you, as a creative-production partnership, resolve the inherent tension between high-production-value craft and the relentless speed and volume demands of social-first content? Where do you compromise, and where do you hold the line?
Brian: Gonna verge a bit into eye-roll territory, but that tension—the “pressure makes a diamond” mindset—is a really necessary part of the formula. “High production value” is somewhat subjective and can be tailored for the expectations of our audience. The question for me is always ‘what makes sense?’ not ‘what made sense last time?’ Almost everything is a compromise of some sort, but we never let clarity or ownability suffer in that process.
3. The “Content People Seek Out” Brief: Harris mentioned creating “content people seek out, rather than ads they scroll past.” Brian, how does that ambition change the way you write a creative brief or evaluate an idea at concept stage? What specific questions do you ask to determine if an idea has that magnetic, pull-based quality versus push-based advertising?
Brian: First and foremost, we, as the creative team, need to be excited and intrigued. As creatives deep in the weeds of our feeds, we get to be that first tough audience to ask ‘is this special?’ I like to ask myself ‘Is this idea familiar or frightening?’ I’d much rather we embrace and solve the idea that pulls us in even if it’s tricky, than rely on the idea we have seen work already.
We also really think about shareability. We always ask ‘what would make you share this?’ knowing it’s not just about the single viewer experience but how those viewers act as our key advocates for the rest of the world.
4. Scaling the Creator Muscle: Harris, you’ve scaled teams and infrastructure at Wildcatter and React Media. What is the single most critical operational investment you’re making at Saylor to expand the “creator team’s capabilities” at scale? Is it about technology, talent pipelines, workflow architecture, or something else entirely?
Harris: The single most critical investment isn’t just a piece of software; it’s building a shared operational language. If you want to scale smart for the long term, you can’t just throw bodies at the problem. We are fundamentally shifting how our teams communicate—moving away from top-down permission bottlenecks and toward proactive, empowered problem-solving. Once you establish that unified vocabulary, then you layer in the right tech stack and automation to eliminate the busywork. The goal is to build a workflow architecture that is sturdy enough to last, but agile enough to constantly improve as the industry shifts.
5. Campaigns vs. Always-On: Brian, your title is “Creative Director, Campaigns.” In an era of always-on content and real-time cultural responsiveness, how do you define a “campaign” today? Is the distinction between campaign work and continuous content still useful, or are you reimagining that framework entirely at Saylor?
Brian: Reimagination is one of Saylor’s strengths for sure. Leadership is always paying close attention to the ask at hand and pushing for more bespoke ways to show up.
I still view campaign work as foundational where we have a larger objective and voice to establish, especially when we partner with brands hoping for a refresh or young brands really making their first big imprints. Campaign work really lets the world know what to expect long-term from a brand or entertainment title. Always-on and real-time reactive are hugely important and sometimes lets brands experiment with risks and new thinking without completely building a campaign around an anomaly or a trend. Campaign work at Saylor doesn’t seek to distance itself from responsiveness rather than to layer it in to bolster the larger scope of work.
6. Talent Mix & Mentorship: Brian, you noted a “rare mix of ambitious young talent and experienced leadership” at Saylor. How do you structure creative teams and mentorship to ensure that emerging creatives absorb entertainment-thinking and craft standards, rather than just learning how to execute briefs quickly?
Brian: When developing strategic campaign-level creative, speed is an asset but it should never be the standard. There is so much to learn on both ends of the spectrum, so I try to foster collaboration and a true quality-over-quantity approach. We mix teams with brand or title fanatics, senior creative and strategic voices and young team members. I love the experience and obstacle-avoidant thinking of veteran minds and the “why not?” challenger mentality of this emerging generation of creatives.
There is an acknowledgement that in order to bend or break the standards, you must first understand them, so we aim to build a very strong foundation of the timeless—and current—marketing basics, and then invite the teams to chip away and carve out the creative that works for the brief.
7. The Multi-Platform Production Pipeline: Harris, you’re building a production engine for “studio-quality content at the speed of social.” Can you walk us through a hypothetical production workflow—from receiving a brief to final delivery—that demonstrates how you’ve re-architected the process to achieve both speed and polish? Where are the bottlenecks you’ve eliminated?
Harris: The biggest bottleneck we’ve eliminated is the rigid, industrial-era assembly line where creative just tosses a script over the fence. Instead, we task our producers to be the operational engine of the work. We give them holistic project ownership from the moment a brief comes in—they are the ones building the teams, managing the budgets, and designing the workflows required to translate creative standards into delivered reality. Because we build frameworks that empower teams rather than restrict them, our producers can run varying setups on the fly. That end-to-end ownership is what strips out the friction, allowing us to bypass traditional handoffs and move straight into a parallel post-production process without missing a beat.
8. Measuring What You Can’t Count: Both of you are tasked with creating work that is “impactful and memorable” rather than just performant. How do you, as a leadership team, defend and measure brand-building, cultural resonance, and entertainment value in an analytics-obsessed market? What metrics do you prioritize that aren’t standard in the typical agency dashboard?
Harris: Typical agency dashboards are built to measure interruption, which is why they prioritize reach and views. But because Saylor is an entertainment-led agency, we have to look at our metrics the way a showrunner would. A view is just someone turning on the TV. We care if they stayed to watch the whole episode and then told their friends about it. That’s why we index heavily on retention and engagement—like shares and saves. Views can be bought, but retention has to be earned through craft, pacing, and storytelling. If the retention curve drops off at second three, we didn’t make a piece of entertainment; we just made an ad.
Brian: Agree wholeheartedly with Harris. Numbers are important of course, but not always reliable. As Creative Director, I like to keep the conversation and emotional impact the work will provide top of mind. Audiences are very smart and we want to give them an experience that is worthy of their time, not just a five second blip. Our strategy team does a great job of looking beyond metrics and diving into the comments and reactions to help us shape future work.
9. The “This Could Work” Philosophy: Saylor recently launched a podcast titled This Could Work. Brian, how does that experimental, “let’s test it” mindset inform your creative development process? How do you create psychological safety for your teams to propose ideas that might fail, while still delivering reliably for clients?
Brian: For me, experimentation equals joy. Very simply, our job is two-fold: satisfy a client brief while evolving the advertising landscape. The greatest perk of social and digital marketing is that it embraces risk more than any other vertical.
Our process welcomes thought starters, unexpected insights and “Hear me out” thinking. You don’t come to Saylor for the table-stakes ideas, you come and hopefully stay, because we are partners that can bring you one-of-a-kind concepts as well as entertain and help build your one-of-a-kind concepts. Let’s be first and set the bar together. Nothing feels better than moving from “this could work” to “it worked!”
10. The 2026 Attention Mandate: Will Trowbridge stated that 2026’s focus is clear: help brands earn attention, not chase it. As the two new leaders charged with executing that vision, what is the one industry convention or agency norm you are each most determined to break or leave behind in 2026?
Harris: The convention I want to break is defaulting to the standard ‘advertising aesthetic.’ When you follow the traditional commercial playbook—the standard lighting, pacing, and sound design—you immediately signal to the audience that they are being sold to, and the barrier to earning their attention goes up. It’s not that people dislike brands; they just have a very high bar for what deserves their time. I want to leave that predictable format behind. In 2026, our production engine is built entirely around the aesthetic of entertainment—equipping our teams to produce cultural moments instead of just ads.
Brian: Building off of the last question, I’d love to change the constant need for airtight proof of concept. Some think that the only way to confidently invest in an idea is to see that it has already been done successfully by others. Our model is designed to explore the spaces that haven’t been tapped, helping brands pioneer not just participate.
