What happens when a creative leader builds a system that powers 30,000 web pages—without a single developer? Charlie Riley welcomes Dmitry Shamis, former global head of brand and creative at HubSpot and now co-founder of the brand agency OhSnap! They unpack why creative is making a comeback, why brand shouldn’t be a bottleneck, and how to build systems that scale with your team.

Dmitry shares how his team at HubSpot introduced modular brand tools, expanded Canva use across global teams, and used out of home to make bold, visible statements. He also explains why AI won’t replace creativity—it’s creativity’s best friend. If you’re navigating brand execution across channels or wondering how to think differently about your creative process, this conversation is a must.

Dmitry Shamis is the co-founder of OhSnap!, a brand agency focused on scalable brand systems. Previously the global head of creative and brand at HubSpot, Dmitry helped marketing teams navigate challenges around execution, scale, and visual identity. He started his career as an engineer and now brings systems thinking to brand development. Find him on LinkedIn at linkedin.com/in/dmitryshamis.

• Why OhSnap! focuses on brand systems, not just rebrands
• What it means for brand to enable rather than bottleneck creative teams
• The importance of adapting design to medium—transit ads vs. billboards vs. digital
• Lessons from launching HubSpot’s first out of home campaign in San Francisco
• Anecdotal signals that out of home is working (hint: text messages from friends)
• Why “brand is back” and what that means for modern marketing teams
• How AI supports, but never replaces, true creative work
• Why bad habits in digital advertising are holding teams back
• Creating time and space for creatives to do their best work
• Building scalable brand systems early to avoid downstream chaos

• OhSnap! — Dmitry's brand agency
• The Brief Creative — Dmitry’s weekly newsletter
• What's Your Process podcast — hosted by Dmitry Shamis
• LinkedIn – Dmitry Shamis
• Capsule (video tool)
• Air (digital asset management platform)
• Scrappy ABM Podcast

What happens when you blend creativity, strategy, and relentless execution? Greg Wise welcomes Melissa Rosenthal, Co-Founder of Outlever, to explore the real-world meaning of brand and how media and marketing collide. Melissa shares her journey from shaping BuzzFeed and Cheddar to leading marketing at ClickUp, where bold out-of-home (OOH) campaigns turned heads and drove measurable results. Listeners will hear how she negotiated prime Times Square placements, why buses became her secret weapon, and why testing, measurement, and audience context are everything. Melissa also opens up about launching Outlever, the exhaustion and exhilaration of entrepreneurship, and why her LinkedIn strategy is her own “personal billboard.”

Melissa Rosenthal is the Co-Founder of Outlever, a company transforming brands into the number one news source in their industries. Previously, Melissa served as Chief Creative Officer at ClickUp, CMO at Insight Timer, CRO at Cheddar, and VP of Creative at BuzzFeed. Named to Forbes 30 Under 30 and Business Insider’s 30 Most Creative People Under 30, Melissa has shaped some of the most recognized and fastest-growing brands.

LinkedIn

• Melissa’s early days at BuzzFeed and Cheddar and the leap to B2B SaaS
• What “brand” really means across company stages — from reputation to perception
• How out-of-home campaigns became ClickUp’s competitive advantage
• Strategic buying: negotiating Times Square ads and selecting high-visibility placements
• Measurement tactics: from aided/unaided awareness to sales team feedback
• Navigating leadership buy-in and scaling investment in brand
• The journey from ClickUp to launching Outlever — and why timing matters
• How Melissa uses LinkedIn as her personal “billboard” and inspiration from OOH in digital strategies

• Scrappy ABM Podcast
• Momentum AI
• SurveyMonkey
• ClickUp
• Outlever
• Brex
• BuzzFeed
• Cheddar
• Insight Timer

Brand isn’t just a logo or a marketing line item—it’s the foundation of your business. In this episode of Beyond the Billboard, host Greg Wise sits down with Bill Kenney, CEO and partner at Focus Lab, to unpack what it really means to build a brand that sticks. Drawing from 15+ years leading a B2B branding agency, Bill explains why brand is not a marketing expense, but a business pillar. He outlines how performance-only thinking creates a short-term hamster wheel, and how companies can break free by investing in identity, culture, and long-term affinity. From Series B tech startups to M&A transformations, Bill shares what signals show a company is ready for a rebrand—and what red flags say otherwise. For marketers trying to earn executive trust, this conversation is a roadmap to internal alignment and sustainable growth.

👤 Guest Bio

Bill Kenney is the CEO and partner at Focus Lab, a B2B brand agency helping high-growth startups and venture-backed companies define and express their boldest, most original selves. He brings more than 15 years of experience evolving businesses from generic design shops into strategic branding partners. Bill is also the author of Conquer Your Rebrand, which outlines Focus Lab’s full branding process for CMOs and CEOs.

👉 Connect with Bill on LinkedIn

📌 What We Cover

• Why performance marketing alone creates a rat race of short-term returns
• The evolution from creative-led marketing to finance-driven metrics—and back again
• How brand drives recruitment, internal alignment, and long-term customer affinity
• What brand really means beyond the website—"it's literally everything"
• Focus Lab’s analogy of branding as building a house, not just decorating one
• Key pain points that signal it’s time for a rebrand (e.g., M&A, growth-stage gaps)
• What happens when internal teams don’t have the time or alignment for brand work
• Real client stories from Totango, TrustedSec, and Marketo
• Why Bill thinks of LinkedIn as his own out-of-home billboard

🔗 Resources Mentioned

• Scrappy ABM Podcast
• Conquer Your Rebrand by Bill Kenney
• Focus Lab

Independent agencies are thriving in a tough economy—but not for the reasons you might expect. Hosts Charlie Riley and Greg Wise sit down with Daniel Weiner from "You Should Talk To" to explore why nimbleness and speed give smaller agencies a real edge. Daniel shares sharp insights into what brands often misunderstand about agency relationships and the specific challenges marketers face when trying to communicate value to executives. This episode dives into the tension between full-service solutions and specialization, the return to brand storytelling, and why not every marketing effort needs to be a win to be worth it.

Daniel Weiner is the founder of "You Should Talk To," a service helping brands pair with agencies that match their specific needs. He focuses on connecting marketers with independent agencies based on relationship quality and expertise, not just reputation or size. Daniel brings deep knowledge from both the agency and brand sides, giving him a unique lens into what makes these partnerships work. LinkedIn

• The current landscape for independent agencies in today’s economy
• Why nimbleness and speed are key advantages of independents
• The tension between specialization and full-service offerings
• Common misconceptions brands have about agencies
• What challenges brands face in today’s marketing landscape
• The shift back toward brand marketing and storytelling
• Accepting that not all agency work will succeed, and why that’s normal
• How marketers struggle to explain marketing realities to executives

In this episode of Beyond the Billboard, hosts Charlie Riley and Greg Wise welcome Chantelle Rapport, CMO and EVP of Growth at Upstart, to discuss the evolving landscape of brand and performance marketing. They explore how brand extends beyond marketing campaigns to encompass every customer touchpoint, why the separation between brand and performance is artificial, and strategies for measuring long-term brand investments.

Best Moments:

• (00:50) Introduction to Upstart, an AI marketplace connecting borrowers with lenders
• (02:28) Chantelle’s belief that brand and performance marketing are interrelated, not separate
• (04:50) Internal marketing’s role in brand building across the entire organization
• (07:44) Navigating conversations with CFOs about investing in brand marketing
• (12:48) The scrutiny marketers face compared to other business functions
• (16:42) How consumer behavior is changing, leading to digital marketing fatigue
• (20:40) The impact of AI on search and consumer research behaviors
• (23:44) The resurgence of creativity in marketing and its importance in brand building
• (25:09) How AI and data will enhance traditional creative marketing approaches

Guest Bio

Chantelle Rapport is the Chief Marketing Officer and EVP of Growth at Upstart, an AI-powered lending platform that uses over 1,500 variables in its underwriting process to expand access to credit. With a self-described “nontraditional” marketing background that gives her a more analytical perspective, Chantelle oversees brand marketing, performance marketing, creative, and growth product at Upstart. She believes in taking a holistic approach to brand building that spans every customer touchpoint and experience.

“Mobile ads with real-world measurement.” That’s the core of what James Heller created with Wrapify, the out-of-home platform that wraps rideshare and delivery vehicles in brand messaging — and makes it measurable.

In this episode of Beyond The Billboard, Greg Wise, Co-founder of OneScreen.ai, and Charlie Riley, OneScreen’s Head of Marketing, talk with James about turning everyday drivers into moving billboards, Wrapify’s evolution from an idea to a nationwide platform, and how it’s challenging traditional perceptions of OOH.

James shares how he went from running global digital marketing for a cloud division of a Fortune 50 company to cashing out his 401(k) to make the Wrapify vision real. He breaks down why Wrapify’s success isn’t just about the cars — it’s about attribution, media measurement, and the ability to retarget based on physical ad exposure. If you’ve ever wondered what happens when creative marketing meets hard data, this one’s for you.

James Heller is the CEO and Founder of Wrapify, the nation's leading rideshare and mobility advertising platform. He’s a digitally native marketer who previously led global digital marketing for a cloud division of a Fortune 50 company. With Wrapify, he built a way for brands to scale out-of-home across rideshare and gig delivery vehicles, paired with data visualization, attribution, and retargeting capabilities.

LinkedIn Profile

• How Wrapify turns Uber, Lyft, DoorDash, and Instacart vehicles into mobile ad platforms
• Why brands use Wrapify not just for the cars but also for measurement and attribution
• The origins of Wrapify and why James left a Fortune 50 job to build it
• Challenges in traditional out-of-home: “great for top-of-funnel, hard to measure”
• The rise of the gig economy and the gap James saw in OOH advertising
• Using real-world exposure to trigger retargeting

James Heller

Wrapify

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Brand is not simply a logo.

It’s the irrational reason people choose you over your competition. That’s the mindset Preston Rutherford brings to Beyond the Billboard in this informative conversation with hosts Greg Wise, Co-founder of OneScreen.ai, and Charlie Riley, OneScreen’s Head of Marketing.

Preston—widely followed on LinkedIn for his brand-building insights—breaks down how Chubbies disrupted men’s apparel and why the obsession with performance marketing has led many brands astray.

This episode is a CFO-friendly argument for why brand marketing is a smart investment. Preston shares how branded search, contribution margin, and organic revenue serve as real business metrics—not soft ideas. He challenges marketers to master their P&L, think in terms of incremental revenue, and measure what really drives long-term, resilient growth, not just immediate revenue.

If you’ve ever struggled to explain brand marketing value to a CEO or CFO, this episode is the blueprint.

This episode is brought to you by OneScreen.ai

Preston Rutherford is a co-founder of the breakout brand Chubbies, a company built around the idea of weekend apparel that flipped the script on men’s fashion. From startup roots to a nine-figure exit, his journey blends brand-first intuition with performance-era insights. Today, he creates educational content for marketers on LinkedIn and is building Marathon—a measurement tool designed to quantify the real value of brand.

LinkedIn: https://www.linkedin.com/in/prestonr/

• Why “brand marketing” is actually the irrational reason people make buying decisions
• How Chubbies built a cult favorite by challenging the serious, cargo-shorts norm
• Why marketers must understand every line of their company’s P&L
• How branded organic search and direct traffic signal a strong brand
• Why contribution margin—not ROAS—is the CFO-approved way to measure success
• How digital ads have turned into "wacky, wavy inflatable tube men" and what to do about it
• The myth of a short-term drop when investing in brand—and what’s really happening
• How investing in brand reduces discounting and increases resilience in a crowded market

• Preston Rutherford’s LinkedIn
• Marathon

Did you enjoy today’s episode? Make sure to hit the subscribe button so you never miss an update! If you found this conversation insightful, share it with a fellow marketer who should think more about out-of-home advertising. For more insights and tips, connect with us on LinkedIn!

In this episode of Beyond the Billboard, Charlie Riley from OneScreen.ai dives deep into brand marketing and the often-overlooked potential of out-of-home (OOH) advertising. Joined by Mandy Thompson, CEO of Digital Reach and the Nonprofit TechShop, they dissect marketers' common misconceptions about brand marketing, discuss the crucial role of awareness in the customer journey, and share real-world use cases that exemplify OOH's effectiveness.

Main Topics Discussed:

1. The value of brand marketing
2. Common misperceptions about out-of-home advertising
3. Effective strategies for using OOH to target hard-to-reach audiences
4. The integration of creativity and data in crafting successful marketing campaigns

Chapters

• 00:01:13 - Discussion on the misconceptions surrounding brand marketing
• 00:03:22 - Insights on targeting with out-of-home advertising
• 00:07:35 - Exploring creative execution in OOH campaigns
• 00:12:23 - Advice for incorporating OOH into marketing strategies
• 00:15:06 - Conclusion and where to find more information

Relevant Resources:

• Digital Reach: digitalreachos.com
• Nonprofit TechShop: nonprofittechshop.com
• OneScreen: onescreen.ai

Call to Action:

Did you enjoy today’s episode? Make sure to hit the subscribe button so you never miss an update! If you found this conversation insightful, share it with a fellow marketer who should be thinking bigger about out-of-home advertising. For more insights and tips, connect with us on LinkedIn!