AI is rapidly changing billboard sales, but technology alone isn't enough. In this conversation, Kevin Gephart shares why successful out-of-home advertising starts with better sales thinking, stronger client relationships, and selling ideas instead of inventory.

Whether you're an independent billboard operator, sales manager, media executive, or advertising professional, this episode explores practical strategies for improving sales performance, leveraging AI, building better compensation plans, and helping advertisers achieve stronger marketing results.

Kevin also explains why local advertising remains one of the biggest untapped opportunities in out-of-home advertising and why operators should focus on growing the overall advertising pie—not just competing with other billboard companies.

Guest: Kevin Gephart - https://oohsalesfaster.com/

Sponsors:

Stark Capital - https://starkcapitalsolutions.com/

Selective - https://www.selective.com/

Time Stamps / Chapters:

00:00 AI Is Changing Billboard Sales

01:00 Kevin Gephart's Background

05:14 Selling Ideas Instead of Billboard Space

10:20 Why Cold Calling Still Works

11:47 Using AI as a Sales Assistant

14:08 Why Short Advertising Campaigns Fail

18:19 Winning in Smaller Local Markets

23:22 Vendor Partnerships & Digital Opportunities

27:30 Stop Competing Only With Other Billboards

37:35 Sales Compensation & Incentives

46:06 Explaining Digital Billboards to Advertisers

53:17 Working With Advertising Agencies

01:00:08 What Has Become Harder About Selling Advertising

01:05:05 The One Mindset Shift Every Billboard Operator Needs

YouTube Tags:

billboard advertising, billboard sales, out of home advertising, OOH advertising, billboard marketing, AI in sales, AI for advertising, digital billboards, advertising sales, sales training, Kevin Gephart, OOH Sales Faster, local advertising, media sales, billboard operator, advertising strategy, cold calling, sales management

Hashtags:

#BillboardAdvertising #OutOfHome #SalesTraining

Keywords:

billboard sales strategy

out of home advertising

OOH advertising sales

AI for sales teams

billboard sales training

digital billboard marketing

local advertising strategy

media sales coaching

cold calling techniques

advertising sales management

billboard operator tips

creative billboard advertising

sales compensation plans

AI for prospecting

Kevin Gephart interview

What happens after the billboard sale is often where the real work begins. In this episode, we sit down with Behind The Board founder Becky Smith, a billboard operations specialist who helps independent operators streamline their businesses and reclaim their time. Becky has spent years managing the day-to-day operations of multi-market billboard companies, working directly with advertisers, installers, printers, and owners to keep campaigns running smoothly.

We discuss the operational challenges that can slow growth, including campaign scheduling, advertiser communication, proof-of-performance reporting, billing, documentation, and digital billboard management. Becky shares why many operators don't need more sales—they need better systems and support behind the scenes to handle everything that happens after a contract is signed.

The conversation also explores delegation, scaling an out-of-home advertising business, building efficient workflows, and creating processes that allow owners to focus on growth rather than getting buried in daily administrative tasks.

Whether you're an independent billboard operator, out-of-home advertising professional, or entrepreneur looking to build a more efficient business, this episode is packed with practical insights on operations, organization, and sustainable growth.

Learn more about Becky and Behind The Board:
behindtheboard.io

00:14:32 IBO Growth and Bigger Industry Events

00:18:29 Why Panels Deliver the Most Value

00:20:53 Learning Through Industry Networking

00:23:05 What Successful Billboard Operators Do Well

00:26:16 Bootstrapping vs Private Equity in Billboard Advertising

00:28:20 Why Billboard Businesses Aren't Traditional Real Estate

00:30:08 Growth Challenges and Delegation

00:35:27 Digital Billboards and Industry Change

00:37:13 Consolidation and the Future of Independent Operators

00:40:19 Attribution, Metrics and Advertiser Expectations

00:42:21 The Challenge of Measuring Out-of-Home Advertising

00:45:15 Launching a New Business Venture

00:48:20 Helping Billboard Operators Scale

00:53:02 Entrepreneurial Advice and Taking the Leap

Tags:

billboard advertising, billboard business, out of home advertising, OOH advertising, digital billboards, independent billboard operators, billboard industry, outdoor advertising, billboard sales, business growth, entrepreneurship, private equity, attribution marketing, advertising metrics, billboard conferences, IBO, out of home media

Hashtags:

#BillboardAdvertising

#OutOfHomeAdvertising

#Entrepreneurship

Time Stamps / Chapters:

Want to build a billboard business? In this episode, Justin of Vital Outdoor shares what he's learned after more than two decades in the out-of-home advertising industry, including finding billboard locations, financing growth, digital billboard adoption, and navigating legal battles.

From launching one of Oklahoma's first digital billboards to fighting a four-year lawsuit over a permit, this conversation is packed with real-world lessons for billboard operators, entrepreneurs, and anyone interested in out-of-home advertising.

Whether you're new to the billboard industry or already own signs, you'll hear practical insights on site selection, sales, permitting, financing, and the realities of growing an outdoor advertising company.

Time Stamps / Chapters:

00:00 Introduction & Sponsor Message (Stark Capital)
00:02:55 Meet Justin of Vital Outdoor
00:03:38 From Sign Company to Billboard Operator
00:05:37 Building the First Billboards in 2004
00:09:02 Launching One of Oklahoma's First Digital Billboards
00:16:28 Extreme Sports, Paragliding & Skydiving
00:19:45 Running a Family Billboard Business
00:23:16 Sponsor Message (Selective Structures)
00:26:08 The Four-Year Billboard Lawsuit
00:35:33 The Billboard Construction Disaster Story
00:40:52 Growing to 15 Digital Billboards
00:44:34 Lightning Strikes a Digital Billboard
00:49:25 Why Some Billboard Locations Surprise You
00:53:03 The Value of the IBO Community
01:00:23 Advice for Young Billboard Entrepreneurs

YouTube Tags:

billboard business, billboard advertising, out of home advertising, OOH advertising, digital billboards, billboard investing, billboard permits, billboard financing, outdoor advertising, billboard entrepreneur, Vital Outdoor, Justin Vital Outdoor, IBO, independent billboard operators, digital billboard business, billboard site selection, billboard sales, out of home media

Hashtags:

#BillboardBusiness
#OutOfHomeAdvertising
#Entrepreneurship

Keywords:

billboard business

digital billboard advertising

out of home advertising

outdoor advertising company

billboard investing

billboard permits

billboard financing

billboard site selection

digital billboard business

billboard entrepreneur

billboard sales strategies

independent billboard operators

billboard legal challenges

billboard acquisition strategy

outdoor advertising industry