Is your brand ready for the holiday season—or stuck in the same old cycle?

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In this episode, Charlie Riley and Greg Wise sit down with Jennie Kaylie, CEO of Rock the Brands, to explore the shifting dynamics of DTC branding, where even the most performance-driven marketers are now investing in sonic logos, creator partnerships, and emotional value.

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Jennie breaks down why today’s consumers expect authenticity over polish, what makes creators more trusted than brands, and how long-term loyalty—not short-term ROAS—defines success. The conversation covers how out-of-home can seed digital campaigns, why most brands live in a bubble, and why your team might need to hit autopilot just to make Q4 count.

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If your marketing still thinks like it’s 2019, this episode will challenge your entire playbook.

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Jennie Kaylie is the CEO of Rock the Brands, a branding agency focused on helping DTC brands grow through strategy, marketing, customer experience, and innovation. A self-described brand “Swiss Army knife,” Jennie has worked with companies including Wayfair, PwC, Suntory, and Edelman. She brings deep expertise in brand strategy, creative direction, and building emotional value in a crowded market.

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• Why performance marketers are embracing brand-building tools like creator partnerships and sonic logos
• How Gen Z and millennials trust creators more than brands—and what that means for strategy
• The difference between polished vs. native content in modern brand storytelling
• Out-of-home as a driver for digital retargeting and campaign amplification
• Why emotional marketing and functional marketing must be balanced
• The “magic brandformance formula” that blends awareness with action
• Planning for Q4: earlier timelines, limited inventory, and smarter holiday messaging
• Why brand marketing needs to prioritize LTV over short-term performance metrics
• What most brands get wrong about awareness, and how to avoid “Blockbuster syndrome”
• How creative testing, speed, and cultural timing win in the modern DTC landscape

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• Rock the Brands
• Jennie Kaylie on LinkedIn
• Glossier subway campaign with digital retargeting
• Spotify Wrapped outdoor campaign
• Brand measurement platforms: Yuca, Google Brand Lift, Meta Brand Lift

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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 successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.

Charlie Riley and Greg Wise sit down with Jonathan Gandolf, co-founder of The Juice and CEO of AudiencePlus, to rethink how B2B marketers allocate their chips. They challenge the “publish five blog posts or else” mindset and argue for “one really good blog post” paired with a laser-focused distribution strategy. From blending digital content with out-of-home tactics to measuring investments in terms of leads and pipeline, Jonathan calls on marketers to earn internal trust—and trust their own instincts—while shifting resources to winning plays.

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👤 Guest Bio

Jonathan Gandolf is Co-Founder & CEO of AudiencePlus, a B2B content platform that helps brands publish content, distribute content, and convert from the content their teams are already creating. Formerly The Juice, AudiencePlus bridges creative storytelling with data-driven distribution. Connect with Jonathan on LinkedIn.

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📌 What We Cover

• Why “promotion versus production” matters more than pumping out volume
• How “one really good blog post and distribute it really well” trumps five average posts
• The untapped value of out-of-home advertising for B2B buyers “still driving home from work”
• Shifting your “chips” to marketing bets that deliver increasing returns
• Translating website traffic and dwell time into leads, pipeline, and spend
• Earning trust internally—sales, executive team, even the board—by speaking in their language
• Balancing brand creativity with measurable ROI without over-indexing on every metric
• Trusting your gut instincts when lived experience “doesn’t fit in a spreadsheet”

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🔗 Resources Mentioned

• AudiencePlus – B2B content platform: publish, distribute, convert
• The Juice – Co-founded by Jonathan Gandolf
• One Screen – Out-of-home partner, powering this podcast
• Jonathan Gandolf, LinkedIn: https://www.linkedin.com/in/jonathan-gandolf/

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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 successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.

Charlie Riley welcomes Matthew Sciannella, Senior Director of Demand Gen at Refine Labs, for a refreshingly sharp conversation on why out-of-home advertising is making a serious comeback.

They explore why now is the time to zag instead of zig, how SaaS brands often miss the mark by being too clever, and what B2B marketers can learn from law firms and jewellers. Matt shares what he sees while driving from Sacramento to San Francisco—billboards that hit, and ones that absolutely don’t.

He also breaks down why performance marketing can’t replace brand marketing, what makes a campaign stick, and how creative consistency can quietly outperform cleverness. This one is packed with real talk, real-world examples, and a no-fluff perspective on what actually works today.

Matthew Sciannella is the Senior Director of Demand Generation at Refine Labs, where he helps B2B SaaS brands elevate their paid media strategy beyond just digital. With a strong focus on demand, content, and product, Matt brings a fresh lens to traditional marketing channels like out-of-home, CTV, and podcasts—especially when the rest of the market zigs.

• Why out-of-home is “the ultimate zag” when everyone else is zigging
• The “single image ad” advantage that billboards still own
• How brand consistency between creative, website, and placements builds trust
• A candid critique of SaaS billboards vs. standout law firm ads
• The problem with AI messaging that sounds like everyone else
• Lessons from Incident.io’s OOH campaign and how it sparked brand lift
• Why performance marketing is transactional—and brand is durable
• The difference between clever and clear messaging in outdoor creative
• Why measuring out-of-home is like brand: a long-term play
• How agencies can advise clients beyond the Google + LinkedIn duopoly

• Incident.io
• “I Hate Steven Singer” billboards
• Drake the Lawyer
• Monday.com
• HeyGen
• n8n
• Clay
• Ro

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 successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.

What happens when high-growth startups hit the ceiling with digital? They turn to the physical world. In this episode, Greg Wise and Charlie Riley sit down with Mike Gunderson, founder of Gundir and PostReminder, to explore why more marketers are rediscovering direct mail.

Mike shares how he grew his agency from solo consultancy to a 30-person team working with some of the biggest consumer and B2B brands in the U.S. He explains how offline tactics like direct mail and out-of-home aren't legacy channels—they’re precision tools for real engagement. With a focus on targeting, testing, and marrying physical formats with digital follow-ups, Mike lays out a clear path for making these so-called “old school” tactics work smarter, not louder.

👤 Guest Bio

• Mike Gunderson is the founder of Gundir (formerly Gunderson Direct), a direct marketing agency that helps B2B and consumer brands scale through targeted direct mail. He also founded PostReminder, a tool that connects physical advertising moments—like mail and billboards—to digital reminders that drive action when the time is right.

📌 What We Cover

• Why high-growth startups are turning to real-world marketing when digital plateaus
• How direct mail builds brand awareness—even if it’s tossed
• The targeting capabilities that make modern mail campaigns precise and measurable
• Lessons from working with brands like Square and SoFi on direct mail
• Why scale matters: 5,000 pieces won’t cut it—think 150,000 to 500,000
• How direct mail and out-of-home can work together in an ABM strategy
• Mike’s advice for dipping your toe in direct mail with retargeting postcards
• How attribution works—and doesn’t work—when it comes to physical media
• Why the physical world isn’t going anywhere, and why that's a good thing

🔗 Resources Mentioned

• Gundir.com – Download the 2025 Direct Mail Best Practices Book
• PostReminder.com – Set digital reminders from physical ads
• Companies mentioned: Square, SoFi, Meta
• Scrappy ABM Podcast

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 successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.

Marketing leaders today are facing rising CAC, shrinking budgets, and pressure to prove short-term results. In this episode, host Charlie Riley and co-host Greg Wise sit down with Jonathan Bland, co-founder of Omni Lab Consulting, to break down what’s keeping B2B SaaS marketers up at night. From the dangers of short-termism to why only 5% of your buyers are actually in-market, Jonathan shares how paid media strategies must evolve — and why performance-only mindsets are no longer enough. You’ll also hear candid takes on internal marketing, the role of trust, and what brand really means when budgets are tight.

Jonathan Bland is the co-founder of Omni Lab Consulting, a demand gen agency focused exclusively on paid media for B2B SaaS brands. For the past four years, Jonathan and his team have specialized in acquisition, acceleration, and awareness campaigns across channels like Google Ads, LinkedIn, and YouTube. Based in DC, Jonathan is also a regular presence at events and on LinkedIn, where he shares honest takes on what’s working — and what’s not — in SaaS marketing today.

• The rising pressure on marketers to prove short-term pipeline at the expense of brand
• Why third-party intent data is expensive and often misses the majority of out-of-market buyers
• How the 95/5 heuristic helps frame long-term thinking and buyer timing
• The return of brand marketing and why performance fatigue is setting in
• CAC trends, attribution bias, and the challenge of proving untrackable influence
• Internal marketing: assessing how your board, product, and sales team define “brand”
• Why trust-building content outperforms demo CTAs — even in performance channels
• Tactical brand plays from Omni Lab, including a new actor-led campaign filmed in Toronto
• Thoughts on out-of-home, LinkedIn, Google, and understanding the intent of the channel

• Berg-Bass Institute (referenced: 95/5 rule)
• Winter (research on brand consideration)
• Luminous (brand campaign example)
• Turtle (interactive PDF campaign)
• Storylane and Exit Five (OOH example)

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 successful ABM program with their help.

Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.

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...