What is a good time of year to do this?
This is highly industry-dependent. If we look at the year:
Q1: Reset and Re-Acceleration
Teams return from holidays energized, focused on executing annual plans and budgets. It’s prime time for B2B: decision-makers are back, budgets are open, and industry kickoffs like CES drive high audience concentration. Finance and accounting tools benefit from tax season, while consumer brands face the post-holiday “slump” except in fitness and self-improvement. Cold, wet weather means more drive-time and delivery ad exposure, less walking traffic.
Q2: Spring Surge
Conference season peaks (RSA, SaaStr, Collision), boosting opportunities for geo-targeted OOH near airports and venues. Warmer weather brings foot traffic back and hybrid work stabilizes. As teams race to close H1 targets, quick-win B2B products perform well. College graduations fuel hiring and employer-brand campaigns.
Q3: Summer Slowdown → Autumn Gold
Mid-summer is quiet: decision-makers and investors vacation, buying stalls, and morale-driven campaigns see lower engagement. Exceptions: travel, beverage, and leisure brands. We chose early September through early November as the strongest OOH window of the year where B2B spending restarts, the weather’s ideal, and major conferences (Dreamforce, Inbound, Disrupt, etc.) cluster. It’s the moment to drive pipeline and capture leftover budgets before holiday freezes.
Q4: Holiday Wind-Down
After mid-November, corporate attention shifts to holidays and fiscal wrap-ups; B2B conversions dip. Consumer and retail campaigns thrive between Black Friday and Christmas, while enterprise deals largely pause until January.
Who are the major operators of OOH media?
Across the United States, there’s about a set of major operators that run all of OOH media. The 3 most important are:
- Clear Channel Outdoor (CCO)
- Across the US, CCO owns about 40,000 billboards. In San Francisco, Clear Channel owns the transit shelters, a lot of very high quality premiere panels/billboards in the city and along the Skyway/US 101, and Muni platforms.
- Outfront
- Outfront similarly owns about 40,000 billboard across the US. In San Francisco, Outfront owns the BART, CalTrain, and MUNI stations (Embarcadero, Montgomery, Powell, etc.) as well as many excellent billboards on the highways and in the cities. They also own the NYC city subway cars, the stations, and many incredible placements all over the New York.
- Lamar
- Lamar is by far the largest operator, owning over 116,000 billboard faces all over the US. They have a good selection across many metros, but we did not contract with Lamar as most of their high-profile units were taken.
Collectively, these three own about ~250,000 of the estimated 400,000 billboard faces in the US, or about 62%.
Additional notable vendors include:
- Intersection
- In San Francisco, they own the entire SFMTA - so all types of bus advertising goes through them. Full bus wraps, bus headliners or kongs, or even half-wraps.
- JC Decaux
- Most of San Francisco’s street furniture is owned by JCD. This includes information kiosks/pillars that create an impact directly on the passerby. Units are usually sold in packages - for example JCD’s Moscone center street furniture package has 10 information kiosks that directly target the Moscone center.
Capital Outdoors, Reagan Outdoors, Silvercast, and a few others make up the rest of the landscape of out-of-home.
What are the different types of media? What should I get?
1. Bulletins/Billboards
These are the classic large-format displays you see along highways, rooftops, or major city arteries.
- Use for: Big brand moments, awareness plays, or category leadership statements.
- Strengths: Huge reach, high prestige, long dwell time on highways.
- Weaknesses: Expensive in Tier 1 cities; limited flexibility once installed.
(Examples: US-101 and I-280 corridors in SF, the Sunset Strip in LA, Times Square in NYC.)
Crown jewel pieces in a campaign - any major bulletin on the way up or down from SFO will generate the highest quality impressions and capture everyone. Anchor pieces like these really tie campaigns together.
2. Premiere Panels & Wallscapes
High-impact, high-traffic urban billboards placed at major intersections, bridges, or downtown walls.
- Use for: Company launches, investor signaling, or head-turning creative campaigns.
- Strengths: Prime city visibility, often photographed and shared on social media.
- Weaknesses: Limited inventory; typically booked months in advance.
(Examples: City-32 premiere panel network,SoMa wall murals, NYC SoHo wallscapes.)
Workhorse units. These target your ICP when they are out for dinner, going to watch a game, picking up their kids from school. Pick them carefully.
3. Street Furniture
Includes transit shelters, bus stops, benches, and public kiosks. Managed by JC Decaux, ClearChannel, others.
- Use for: City-wide brand saturation and repetition.
- Strengths: High pedestrian frequency, affordable packages, consistent daily visibility.
- Weaknesses: Smaller format means your creative must be ultra-simple and bold.
(Example: JC Decaux’s Moscone Center package with 10 information kiosks, CCO’s 3rd St Triptychs targeting YC.)
Great for specific targeting of particular accounts or geographies and for creating a consistent sense of your brand on the streets.
4. Transit Advertising
Bus wraps, train station takeovers, subway car interiors, and airport displays.
- Use for: Targeting commuters and travelers, especially in major metros.
- Strengths: Excellent for frequency and brand recall; high engagement for mobile users.
- Weaknesses: Creative must adapt to motion and varying environments.
(Examples: Station dominations via Outfront; full-bus wraps via Intersection, bus shelters via CCO.)
This make sense when some set of your ICP commutes in from suburbs or uses the subway regularly - like enterprise middle management. If you’ve coordinated during conferences, you’ll get some additional exposure from public transit enthusiasts.
5. Digital OOH (DOOH)
LED or LCD billboards that can rotate creatives dynamically or be updated programmatically.
- Use for: Time-sensitive campaigns, A/B testing, or creative experimentation.
- Strengths: Flexible, measurable (via impression tracking), and visually striking.
- Weaknesses: Limited premium placements; shorter dwell time than static boards.
(Examples: Subway station liveboards via CCO/Outfront that play your ad in a fixed set )
Digital boards are usually cherry-on-top for a larger static campaign and then used in subsequent campaigns when people are mildly aware of your brand and you’re looking for consistent performance. Since your Share of Voice is already >10% in this media, you’re not yielding as much value.
Your ideal campaign should bring all these media types together under one package to create the sense of omnipresence in the city.
How should I start putting my campaign together?
When thinking about putting a campaign together, you first want to nail down your goals. Ask yourself these questions in an exercise:
- Why exactly are you doing this?
- What do you really care about? Are you viewing this as a pure brand play?
- Who are you selling to? Who is the exact ICP? Who are the stakeholders?
- Don’t try to sell to too many people in one campaign. Be very specific
- What are we trying to convey about our brand?
- What are we selling? Can we convey it simply and distinctly? Can we avoid becoming beige?
Once you’ve asked yourself these hard questions - and they can change - you’re ready to go to the whiteboard and start figuring out what you want. Research your audience’s physical world habits. Unlike online ads, OOH success depends on placing messages in the real locations your targets frequent. Map out where they live, work, commute, and congregate. If you’re aiming at, say, startup founders in the Bay Area, concentrate on high-density tech corridors (e.g. SOMA, Market Street, Caltrain routes) and highways like the 101 that they drive on. Stych famously did exactly this, plotting out commuting routes and conference venues in SF, then selecting billboard and transit ad locations near those hotspots to maximize impressions among their audience
Delve did something very similar when starting our campaign. We pulled all of our customer addresses from Docusign contracts and plotted them into a map. We also aggregated in data from larger partners to figure out where prospective customers from our Dream 100 (top 100 clients we’d like to sign) are as well. We’d recently run a massive physical marketing campaign, so we had some other address data on hand. We plugged all that into kepler.gl to figure out exactly where we wanted to focus our efforts:
Who else is involved in an OOH Campaign?
Running an OOH campaign is a team effort that involves both external partners and your internal team. Key players include:
- Media Operators: These are the companies who own the billboards, transit ads, bus benches, etc., such as Lamar, Outfront Media, Clear Channel, and local vendors. They provide the inventory and handle installation. You can work with them directly if you’re experienced, but if it’s your first time - find a broker that can take care of this for you. The operator’s job is to lease you the ad space and ensure your creative goes up on schedule.
- Media Buying Agency/Broker: As mentioned earlier, a specialized OOH agency or media broker can plan and negotiate the buy on your behalf They interface with all the operators (so you don’t have to individually call Lamar, Outfront, etc.), get quotes, and secure the best locations within your budget. They also handle a lot of logistics. For a first campaign, having an experienced media buyer is a huge help – they know the landscape and can advise on format mix, flight duration, and fair pricing. Their fee or commission is usually baked into the buy (often a percentage), but a good broker often pays for themselves by stretching your dollars further.
- For our campaign, we worked with Kasper Koczab, Head of OOH Media at Brex. His understanding of OOH all over the country is unmatched and he was able to help us navigate the complexities of media and secure a really solid package.
- Creative Designers/Agency: You’ll need someone to design the actual ads – the visuals and copy that go on the billboard or poster. This could be your in-house design team if you have one (as many startups do), or an external creative agency or freelancer. Some brands use their general creative agency; others hire specialists who understand OOH design principles.
- If you’re doing multiple formats (billboards, bus wraps, etc.), designers will need to adapt the creative to various specs and formats
- Pro tip: There’s so many moving parts to a large campaign, that having an experienced team that knows the ad format, the production specs, and can keep you on top of all the details can make life way easier and potentially save $10,000’s in lost media.
- We worked with Josh and the team at Division of Labor to put our campaign together. They helped us run through multiple design reviews, settle on our brand and visual identity, and caution us through many potential pitfalls.
- Marketing/Growth Team (Internal): Within your startup, your marketing and growth team will quarterback the campaign and work with everyone above. Be prepared for some cross-functional input, for instance, leadership might want to review the billboard messaging, or sales might chime in with an opinion. Align stakeholders early so you can move quickly on execution.
How do you think about copy?
All of marketing is about standing out. How can you be really different? Billboards offer you the opportunity to be among the top 1% of companies that make it off the incessantly bombarded screen and get into the real world. Don’t think that gives you the freedom to finally spew product and feature copy all over. Your campaign is won or lost by the words you put on the billboard. Here’s how to approach it:
Be someone. Thousands of companies come out with stock, harmless, slogans cooked up in a boardroom that won’t elicit any response. Larger enterprises care too much about brand integrity to try anything out-of-the-box and already have enough recall. How can you be truly different?
You need out-of-the-box, contextualized ideas that tap into societal and cultural cues. Think about how you can use your brand, your industry keywords to devise copy that makes someone think “Ha! That’s clever.” That’s how you’ll win. It will take time, revision, and work - but it’s the only way to really win.
If your leadership is willing, make your copy or graphics a little controversial. Bland’s “Still hiring humans?” campaign famously generated incredible engagement. Recently, Friend.com took over social media with ads being defaced all over the subway. It’s your prerogative on how far you want to go, but creating an identity is much better than being invisible.
Simplicity is king. The best billboard messages are extremely short, clear, and instantly graspable – think 7 words or fewer as a rule of thumb. Drivers or pedestrians only glance for a few seconds, so you have to communicate one idea fast. This means one simple message or tagline, with text in a huge, high-contrast font so it’s legible from a distance. An industry saying goes “short copy sticks”– and it’s especially true for billboards.
Beyond brevity, out-of-home is all about sparking emotion. If you can elicit a chuckle, an intrigued eyebrow raise, or an “aha” recognition, your ad will be memorable. No one looks at billboards in pursuit of a mathematical challenge. Frankly, they’re pretty annoyed that they're being marketed to all the time. It's your job to make it as funny, as evocative, and as emotion-inducing as possible.
Now, few practical tips and hygiene for copy/design:
- Contrast and readability: Use large, blocky fonts and strong color contrast (light text on dark background or vice versa). No one should squint to read your ad. Test by printing your design small and see if you can read it from across the room. Product designers often design for small screens, so it’s a conscious adjustment.
- One theme, one idea, one CTA: Memorable campaigns come together around one unifying theme. You’ll have hundreds of pieces of creative, and you want them all to come together and tell a story, not fight for attention. When someone looks at your media, they should subconsciously feel familiarity with it because it matches the tone and theme. Think about “Just do it” or “Think differently”. Delve’s take on this was “Compliance is done in Delve” - and all the creative came back to this idea.
- Let visuals help: A striking image or bold and creative graphic breaks up text and makes it fun to look at. Think about motifs and symbols around your brand that you can incorporate. For example, if you’re building something that makes a process faster - create a leaderboard graphic!
- Test for the “5-second rule”: Imagine a person seeing your ad for 5 seconds or less. Will they get the gist? If not, simplify it. Cut unnecessary words and elements. Many experts literally suggest 7 words, 1 image max for a standard billboard.
In summary: short, bold, and resonant. Your copy should be punchy and easy-to-digest, with a design that grabs attention at a glance. Marry that clarity with a spark, whether humor, emotion, or intrigue that makes people remember it.
Great creative connects on an emotional level, not a rational one. You’re talking to humans — make them laugh, make them excited, make them curious.
Kasper Koczab - Head of OOH Media, Brex