Selling At Events in 2026

๐Ÿ‘‹ Today, weโ€™re following up on the previous email about follows up with more about follow-ups.

Multi-word sentence puns aside, letโ€™s dive in! ๐Ÿš€

๐Ÿ“ฐ Newsletter News

Ad Sales & Media Spend

Newsletters

Creators

Media

 ICYMI

๐Ÿ•ต๐Ÿปโ€โ™‚๏ธ How to close $50k+ deals

IRL Events FTW

Most media companies typically treat events like brand-building exercises. Show up, hand out business cards, post some LinkedIn content, hope for the best.

That's leaving money on the table.

But youโ€™re a savvy content entrepreneur, so you donโ€™t do that. You use them to sell (and hopefully not induce 4-day hangovers).

The economics are simple: brands spending $50k-$150k on a booth are actively hunting for ways to reach your exact audience.

๐ŸŽช Two Types of Events Worth Your Time

Industry conferences aligned with your niche are gold. Every sponsor with paid presence is your perfect prospect. They're already spending big to reach your audience.

Marketing events (think AdWeek, Content Marketing World) offer more volume but less precision. You'll meet more potential prospects, but they're not all relevant. Higher quantity, lower conversion.

Pick based on your industry, location and budget.

๐ŸŽฏ Target the Right People

Your ideal contact at industry events: the marketing contact who booked the booth. They control the budget and understand ROI pain points.

Sales reps manning the booth? Get the marketing contact's name and move on. You can ask if theyโ€™ll be back, and try catch them then.

๐Ÿ’ฌ Conversation Starters That Actually Work

Skip small talk. Start with:

  • "How's the event going for you?"

  • "What are you hoping to get out of being here?"

Most booth sponsors will admit they're not sure if events work. That's your opening.

Follow with:

  • "How do you tie in digital alongside the event?"

  • "What does success look like for this booth?"

Now you're in sales territory without pitching.

For attendees at marketing events, the same applies. Marketersโ€™ goals for EVERYTHING are to grow. So, these types of open questions will lead to the right kind of topics for you.

๐Ÿ”„ The Transition to Pipeline

Once you've identified alignment (i.e. expensive booth/unclear ROI, audience fit, steep 2026 growth goals, they liked your shoes, etc.), position your media property as the solution.

The math: a booth reaches 5-10k people for $100k+. Your newsletter reaches the same audience with better tracking for a fraction of the cost.

Don't try close at the event. Connect on LinkedIn immediately.

For follow-up timing: if the event is Wednesday, wait until the following Tuesday/Wednesday. Let them clear their inbox and deal with other post-event noise first.

๐Ÿ“‹ Pre-Event Prep That Pays Off

This is the most important section.

  1. Pull the sponsor/exhibitor list and research key companies

  2. Look up recent news, acquisitions, or contracts

  3. Check LinkedIn for who's attending and where they'll be

When you congratulate someone on a recent contract win, you signal you're plugged into their industry.

Reach out to LOADS of people before you go, try to:

  • Arrange 1-2-1 meets

  • Group meets (we did this in Austin for the Newsletter Marketing Conference)

  • (Worst case) Generally say hello and gives a good excuse to say hi IRL

๐Ÿ”‘ Getting Contact Details

Never leave the ball in their court. At events, or any other format of sales for that matter.

Business cards still exist in traditional B2B. Digital cards are catching on too. No card? Add them on LinkedIn immediately. Don't trust conference-day memory.

๐Ÿ’ฐ The ROI Question

Events cost $1.5k-$5k to attend. If your average deal is $20k+, you only need one conversion for gross ROI.

This works best when:

  • You're B2B

  • Your average deal size is $10k+

  • or, your industry values in-person relationships

Bootstrapped? Limit yourself to the 1-2 biggest annual events and extract maximum value.

If you're a scaling B2B media company, industry events aren't optional. At minimum, you're building brand credibility. At best, you're filling your pipeline with high-value deals that took 15 minutes of conversation to initiate.

Yes, theyโ€™re time-consuming and expensive. But, if you prep well, so worth it.

P.S. Need help selling more sponsorships? My agency Ad Sales as a Service helps you do just that.