Attribution is broken. Email gets too much credit. And fake out-of-home ads? They're everywhere.

On this episode of Beyond the Billboard, host Charlie Riley and co-host Greg Wise sit down with Jay Schwedelson for an unfiltered look at what's working (and what's not) across marketing channels today. Jay, known for his email marketing expertise and outspoken industry takes, doesn't hold back.

They explore how internal infighting over marketing attribution has led to budget brawls, why email only closes the deal because brand already did the work, and how brands are misusing performance metrics. From holdout testing to skydiving stunts at virtual events, Jay makes the case that trust—not tracking—is the real metric to watch.

Plus, they get into how out-of-home has evolved beyond Times Square, and why modern marketers need to stop playing safe and start thinking creatively—even when budgets get tight.

Jay Schwedelson is the founder of SubjectLine.com and leads Outcome Media, a 100-person demand gen agency in South Florida. He also runs GURU Media Hub, which produces large-scale virtual events and podcasts in the marketing space. Known for causing “some trouble” in the email world, Jay's insights and bold takes make him one of the most visible voices in the industry.

• Why Jay says attribution is “total garbage” and how internal budget politics drive flawed thinking
• How holdout groups can expose false performance signals in email marketing
• The performance marketing trap: chasing dashboards instead of building trust
• Out-of-home as a powerful tool for account-based marketing and B2B sales
• Jay's reaction to Times Square bias and what out-of-home really looks like today
• Using audience data to map campaigns around office HQs and event venues
• The rise of fake out-of-home ads and why IRL still wins
• Creative formats—from street teams to mobile trucks to skydiving at virtual events
• Why uncertainty is killing marketing experimentation—and what smart brands should do instead
• The hidden opportunity as loyalty drops and switching behavior spikes

• SubjectLine.com
• GuruConference.com
• Nudge by Richard Thaler
• SampleABox.com

Low-Tech, High-Impact Account-Based Marketing

If you’re ready to trade expensive, tech-heavy account-based marketing for a repeatable, revenue-driving...

Feeling the pressure to deliver short-term results, while knowing brand matters more than ever? Join hosts Charlie Riley and Greg Wise as they talk with Kathleen Booth, who brings the perspective of a startup marketer and agency founder turned SVP of Marketing and Growth at Pavilion. Kathleen shares her journey from international development to leading growth in B2B tech and describes the constant tension between brand and demand generation. She reveals why marketers are “crying out for understanding and help,” how AI and generative search are making brand investments more crucial, and how creative out-of-home and “ambush marketing” tactics can punch above their weight—even with a scrappy budget. Listeners hear candid takes on why marketers feel underappreciated, why brand is both a long- and short-term investment, and how the smartest brands are zigging while others zag, from urinal screens to subway takeovers.

Kathleen Booth is the Senior Vice President of Marketing and Growth at Pavilion. Her path started in international development consulting with USAID and the World Bank before shifting to marketing through agency ownership and startup leadership. Kathleen was an early HubSpot partner, built and sold a national agency, and has held in-house roles in B2B tech. She joined Pavilion as a member in 2019 and now leads its marketing, bringing both founder experience and a customer’s perspective to the role. Kathleen Booth on LinkedIn

• The real meaning of “earning the right” to invest in brand (and why that’s reality for most marketers)
• Marketers “crying out for understanding and help”—anxiety, burnout, and the divide between brand and demand
• Why AI and generative search optimization are making brand investment more important (brand as a proxy for trustworthiness)
• Classic marketers vs. “heads of sales who are now heads of marketing” and how that changes company focus
• Data and “proof in the pudding” as the way to earn internal buy-in for brand
• Case study: How Six Sense built loyalty and differentiated in a crowded market through community, events, and brand
• “Ambush marketing” with urinal screens at Inbound—turning a $300 stunt into major buzz
• Scrappy out-of-home tactics: sidewalk graffiti, projection art, branded petty cabs, and subway takeovers
• Out-of-home isn’t just for big companies—how B2B marketers can use small budgets to stand out
• The power of cross-pollination—how B2C, D2C, and nonprofit experience drives creativity in B2B

• Pavilion
• Six Sense (referenced as a brand case study)
• HubSpot (referenced, no URL stated)
• Scrappy ABM
• CXL (referenced via Pep Laya, no URL stated)
• Kathleen Booth on LinkedIn

Low-Tech, High-Impact Account-Based Marketing

If you’re ready to trade expensive, tech-heavy account-based marketing for a repeatable, revenue-driving ABM program, check out Scrappy ABM. Led by a team of Scrappy ABM experts, they specialize in low-budget plays and programs that deliver high impact—no shiny tools required. Scrappy ABM has built account-based programs that have delivered millions in revenue, and you can build your first...

Welcome to episode 14 of Beyond the Billboard, hosted by Greg Wise and Charlie Riley. In this episode, Greg and Charlie are joined by Elaine Zelby, who describes her background as “extremely random and non-linear,” sharing insights from her journey through engineering, enterprise software, Slack, venture capital, and now co-founding Tofu. Elaine opens up about why titles are “dumb,” how brand means “planting a stake in the ground,” and what it really takes for marketers to define their identity in a crowded landscape. The conversation explores how marketing roles have shifted, why performance marketing alone no longer works, and what brand means in a time when “everyone is coping with change.” Elaine’s hands-on stories cover narrowing your target audience, building a platform versus a point solution, and the importance of integrated campaigns, omnichannel experiences, and company-wide consistency. This episode is filled with real-world examples, from DocuSign’s beginnings in commercial real estate to HubSpot’s jeans-and-t-shirt energy, plus tactical advice on sales incentives and brand alignment that you can hear directly from the transcript.

Elaine Zelby is the co-founder and CRO of Tofu. Previously, she worked in enterprise software, led enterprise marketing at Slack, and spent five years as a partner at Signal Fire, a venture capital firm focused on artificial intelligence and software. Elaine shares that she once listed her LinkedIn title as “Chief Spear Fisher Woman” because, as she says, “titles are dumb,” and describes her approach as non-linear and defined by “no North Star.” Connect with Elaine on LinkedIn.

• Why “brand is intentional” and the importance of defining what you want to be known for
• The pitfalls of skipping the “who” and how to narrow your ICP over time
• Real stories: Tofu’s journey, DocuSign’s path from commercial real estate to horizontal software
• How brand shows up in consistent employee experience and customer touchpoints
• Why not every company should focus on brand marketing—and which personas care most
• Incentives and comp structures that actually align sales, marketing, and SDR teams with the buyer
• The role of integrated campaigns, omnichannel tactics, and out-of-home in brand building
• How negative buyer experiences become “negative deposits” in your brand bank
• Concrete airport out-of-home ideas for targeting high-frequency travelers and company events

• Tofu HQ
• Elaine Zelby on LinkedIn
• Scrappy ABM
• Mention of companies and platforms: DocuSign, Slack, HubSpot, Salesforce, Signal Fire, McKesson, Fannie Mae, Colliers, Gong, McKinsey, Deloitte, Accenture, Wipro, Aptio, OpenAI

Low-Tech, High-Impact Account-Based Marketing

If you’re ready to trade expensive, tech-heavy account-based marketing for a repeatable, revenue-driving ABM program, check out Scrappy ABM. Led by a team of Scrappy ABM experts, they specialize in low-budget plays and programs that deliver high impact—no shiny tools required. Scrappy ABM has built account-based programs that...