The debate between brand marketing and performance marketing is over: they are the same thing. Or at least, they should be.

Brent Bowles, Senior Director of Growth at Upwork, joins the show to dismantle the idea that brand is just "vibes." For Brent, brand is the operating system that makes every performance dollar work harder. If your brand spend isn't lowering your CAC or improving win rates, it is just expensive noise.

In this episode, Brent takes us inside Upwork's sophisticated growth engine. He reveals how they used Times Square billboards not for mass awareness, but as a "strategic weapon" to target a specific group of 200 investors. He also shares an unexpected lesson in consistency from a Detroit personal injury law firm that became a cultural icon.

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Guest Bio

Brent Bowles is the Senior Director of Growth at Upwork, the world’s leading work marketplace. Based in the San Francisco Bay Area, Brent oversees the paid acquisition and growth teams that drive Upwork’s client acquisition engine. His remit covers a massive portfolio of channels, including paid search, social, podcasts, CTV, and affiliates.

Before joining Upwork, Brent served as VP of Digital Marketing at Wells Fargo. There, he helped transform the bank's performance marketing from early experiments into a nine-figure annual operation. He specializes in scaling complex marketing ecosystems in regulated and competitive industries, balancing strict compliance with aggressive growth targets.

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Key Takeaways

Brand Is Not Vibes, It’s Math: Brent rejects the notion that brand marketing is unmeasurable. He views brand as the "operating system for demand." It must account for itself through Media Mix Modeling (MMM) and its ability to improve the efficiency of lower-funnel performance channels.

OOH as a "Strategic Weapon": For Upwork’s Investor Day, the goal wasn't broad reach. They bought expensive media on the NASDAQ building to target a specific room of 200 analysts and investors. It was a precision strike designed to create a "spectacle" and control the narrative for a single day.

The Sam Bernstein Lesson: Brent breaks down his favorite example of Out-of-Home (OOH) effectiveness: The Sam Bernstein Law Firm in Detroit. By blanketing the city for decades, they turned a succession plan (father to children) into a public storyline. The lesson: absolute consistency creates cultural trust.

The Integrated Portfolio: Upwork allocates 10-15% of its budget to experimental bets. The rest funds a core set of channels that feed off each other. When brand and performance are siloed, you lose the portfolio effect where one channel lowers the cost of another.

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Quote of the Episode

"I think it's disingenuous to think of brand as something separate from performance. It's all linked. Think of brand as the operating system that drives demand. When it works, it should boost performance. And when it doesn't work, it's just expensive noise... It's not vibes, it's math."

- Brent Bowles

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Key Moments

1. The Upwork Engine: How Brent manages growth across paid search, social, and CTV.
2. The "Strategic Weapon":...

Most people think of billboards as the first introduction to out-of-home advertising—“but there’s so much more to that.” Hosts Charlie Riley and Greg Wise talk with Brian Donohoe about place-based marketing: “leveraging signage, within a specific location,” literally inside the location, to “serve advertising at scale.” Brian shares the moment at a show in Chicago—during that “set break time”—when it felt “kind of crazy that there’s just zero brand presence here whatsoever,” and why indie venues and festivals can be a “captive” environment without “plastering ads all over the place.” The conversation covers independent music venues and festivals, live music fans, brand affinity and cultural relevance, and why marketers can’t “over index in mediums that they can easily attach a number to.”

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Brian Donohoe is a media veteran for “almost 20 years,” with time on the agency side and “10 years at Google.” He’s the co-founder and chief commercial officer of Venue Ad Network, “an ad and sponsorship platform built exclusively with independent music venues and festivals,” giving brands opportunities to be “in some of the most iconic rooms, in the country.” He also talks about independent comedy venues as part of the network.

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1. Why “Beyond the Billboard” exists: most people think “billboards,” but “there’s so much more to that” in out-of-home advertising
2. Place-based marketing as “leveraging signage, within a specific location,” and using screens that are “pre-wired as an out-of-home network”
3. The “set break time” insight: “really good energy in the room,” people “kind of milling around,” and “zero brand presence” (without “plastering ads all over the place”)
4. How venues already use screens for “band artwork” and “upcoming shows,” and how ads can be “slot[ted]” in between that content
5. Positioning the audience: “music fans, live music fans,” “they bought a ticket,” they’re “captive,” and how festivals can be more “genre specific” (folk country, hip hop, EDM)
6. The pitch for indie: “a third of shows are happening in indie rooms and festivals,” and why it’s an “untapped, uncluttered space” versus bigger partners
7. Who says yes: brands that already see “live music is a strategic pillar,” and what “street cred,” “brand affinity,” and “cultural relevance” look like in this environment
8. Measurement + expectations: moving away from treating every tactic like “one step removed from search,” attaching “awareness metrics,” and the idea that “just because you can attach some metric to a channel doesn’t necessarily mean that you should”
9. Experimentation: carving out budget to “experiment and try new stuff,” having a plan to evaluate, and “at some point you’re gonna have to roll the...

Out-of-home is on fire in B2B, and it’s not just the big legacy brands. Host Nick Bennet sits down with Greg Wise and Charlie Riley from Onescreen to go through original research with 101 senior marketers on how out-of-home fits into today’s mix. They talk about 46% adoption in the past two years, mid-market SaaS and growth-stage brands leading the way, and why so many marketers still call out-of-home “boring” or “outdated” even while they see it everywhere.

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Greg Wise and Charlie Riley walk through real examples from Dreamforce, airports, roadside bulletins, bus shelters, digital billboards, wrapped vehicles, and street teams, and connect it all to A BM, field marketing, and brand campaigns. They break down how modern data, mobile devices, and telco aggregation power targeting and measurement, why creative is at least half the battle, and how out-of-home gives events, PR, and paid digital an extra layer of air cover that helps everything else hit harder.

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• Current state of B2B out-of-home adoption: 46% of marketers in the report used out-of-home in the past two years, with mid-market and growth-stage SaaS companies, series A and above, often leading the way instead of only Fortune 100 or legacy enterprise brands.
• The perception gap: “boring and outdated” vs everywhere and memorable: Marketers describe out-of-home as boring or outdated while also recalling roadside bulletins, airport ads, transit ads, LED trucks, billboards, and city activations around Dreamforce, Moscone, and other venues.
• Art and science: data, placements, and creative on the same canvas: Greg Wise and Charlie Riley explain how one screen subscribes to hundreds of data sources, combines demographic, psychographic, and consumer data, and then pairs that with creative that is simple, bold, fast to read, and tied to the brand instead of just blowing up a Facebook ad.
• Why mid-market and venture-backed brands are leaning in: Series A and above companies with 15–30 million raised, fast growth, and well-known VCs are feeling the squeeze on digital, seeing CAC and other numbers slide, and turning to out-of-home for physical brand presence and a real moat as AI levels the playing field.
• Targeting in modern out-of-home: How aggregation of telco data and 250–260 million unique devices per day enables targeting by audience attributes, movement patterns, zip codes, and inventory that index highest for specific groups, from job-related profiles to Whole Foods shoppers and fitness enthusiasts.
• Measurement that goes beyond guessing: Ways marketers are measuring brand lift, organic and direct search, web traffic in exposed vs non-exposed markets, target account list activity, meetings, event or demo requests, and recall, especially when out-of-home runs alongside A BM and other campaigns.
• Events, trade shows, and swarm tactics: Why “swarm events” are such a strong use case: wrapped cars and buses, street teams handing out coffee or hot chocolate, experiential executions,...