Crafting an Exceptional Event Marketing Strategy with Amy Holtzman - Ep 56

Plus, How is Paid Search holding up In the AI Age?

The Transaction

May 26, 2025

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What Craig’s Reading
Recent Insights from Past Guests
Craig Sightings: Upcoming Speaking Engagements in NYC
Latest Episode: Crafting an Exceptional Event Marketing Strategy with Amy Holtzman - Ep 56
Movie Poster Mockup: The Blues Brothers

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Recent Insight from a Past Guest: (Craig)

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Craig Sightings: Upcoming Speaking Engagements in NYC

A16Z Tech Week - June 3rd

RevFest - June 10th at the House of Yes in Brooklyn

Latest Episode: Crafting an Exceptional Event Marketing Strategy with Amy Holtzman - Ep 56

B2B marketers keep making the same mistakes when it comes to events, only to end up asking why they didn’t see any ROI. Thankfully, we knew just the right person to help you improve your field marketing game…

Amy Holtzman is the Chief Marketing Officer of CHEQ, the leader in go-to-market security, and one of the best B2B marketing leaders in SaaS, especially when it comes to creating unforgettable experiences. Amy joins co-hosts Craig Rosenberg and Matt Amundson to explore how to plan an event marketing strategy that doesn’t suck, why you need to think beyond the vendor booth at a conference to see real ROI, and even how traditional paid search is holding up amidst the onslaught of AI advancements.

Also, Craig says something he immediately regrets, Matt makes an unsettling insinuation, and Producer Sam calls someone a naughty word.

Critical Takeaways

Events are still alive, if you are willing to put in the work to make them stand out. You can’t just “show up and hope.” Great booths need real strategy, creative hooks, and a human-first approach that makes people actually want to engage.
Whether selling B2B or B2C, even strong demand dies in broken systems. Want revenue? Get your backend in order first so you can deliver remarkably good customer experiences
Prospects are already using ChatGPT to build vendor shortlists. If your GTM doesn’t account for AI-powered discovery, you’re already behind.
Despite the hype around AI, traditional paid search drove record enterprise deals for CHEQ in Q1 of this year, especially long-tail keywords. Don’t ditch the old toolbox just yet.

Chapters

00:00 - Episode Teaser
00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater
10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ
13:46 - Lessons to Learn from the Worst Sales Experience Ever
25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals
30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists
35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid
39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands
44:44 - Thinking Beyond the Booth When Planning out Your Event Strategy

Epic Quotes

“ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman
“If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman
“I rub the thing.” - Craig Rosenberg

Connect with Amy

LinkedIn: https://www.linkedin.com/in/aholtzman/
Website: https://cheq.ai/

Shoutouts

Every Little Step I Take by Bobby Brown:

Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/
Jessica Lin: https://www.linkedin.com/in/jessicalin8/
Amy’s Episode on The Drafting Table: https://www.thedraftingtablepodcast.com/content/conferences-arent-a-vibe-theyre-a-sales-channel-how-to-actually-make-them-worth-it-with-amy-holtzman-cmo-at-cheq
Maria Pergolino: https://www.linkedin.com/in/mariapergolino/
G2 Buying Behavior Report: https://learn.g2.com/2025-g2-buyer-behavior-report
Sydney Sloan: https://www.linkedin.com/in/sydsloan/
Scott Albro: https://www.linkedin.com/in/scottalbro/
The Tonga Room: https://www.fairmont-san-francisco.com/dine/tonga-room-hurricane-bar/

Movie Poster Mockup: The Blues Brothers

Just to avoid any confusion, yes, the finger tattoos in *this* image were photoshopped.

A classic, if not somewhat disjointed in parts, comedy from when SNL had characters worth making movies about and when crashing hundreds of police cars in a movie had to be done practically.

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Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/
Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/

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