Do This, NOT That: Marketing Tips with Jay Schwedelson
Do This, NOT That: Marketing Tips with Jay Schwedelson

SPECIAL GUEST!! HUBSPOT's Courtney Dagher 🎤 Why Your Speaker Pitch Keeps Getting Rejected | Ep. 577

October 16, 2026

AI Summary

5 min read

Courtney Dagher, HubSpot’s director of global events revenue marketing and content programming, says the most common reason speaker pitches get rejected is not lack of charisma—it is stale content. She reviews hundreds of session submissions each year for Unbound (HubSpot’s flagship event, which drew over 13,000 in-person attendees in 2024) and sees the same mistake repeatedly: people submit a talk track they have been using for years with minor tweaks. “It just doesn’t land,” she says. “It’s not fresh. It’s not what we’re interested in.”

What event programmers actually look for

Dagher’s team prioritizes speakers who are still active practitioners—people who are “in the weeds, running tests, and able to share real results.” The magic combination, she says, is someone who can both execute the work and communicate it compellingly on stage. If you are a strong speaker but your submissions keep getting rejected, her advice is to go back to basics: “Are you still doing the thing? Are you actually working in a role where you’re seeing these results?” Audiences want practical, how-to guidance grounded in current experiments, not a polished talk that has been recycled across conferences for years. She suggests asking yourself one honest question before submitting: “Would I want to attend my own session?” If the answer is no, go back to the drawing board.

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What you'll learn

  • 1 (02:20) **Courtney’s Unconventional Path to Events** - Courtney explains how a degree in British Victorian history and literature led her to a career in event marketing at HubSpot.
  • 2 (05:22) **The Secret to Creating “Must-Attend” Energy** - How Courtney generates a sense of belonging and excitement for a massive corporate event like Unbound.
  • 3 (07:55) **Rebranding a Legacy Event: From Inbound to Unbound** - Behind-the-scenes on the year-and-a-half-long process of changing a beloved event name.
  • 4 (10:38) **Can an Event Planner Actually Enjoy Their Own Event?** - Courtney reveals how she stays present and calm during a massive live event.
  • 5 (12:59) **Why Your Speaker Pitch Keeps Getting Rejected** - Courtney shares the red flags and green lights she looks for when reviewing speaker submissions.
  • 6 (15:36) **How HubSpot Uses AI in Events (and Where They Draw the Line)** - Courtney explains AI’s role in event operations and content programming.
  • 7 (18:00) **Courtney’s Personal AI Habits** - How she uses AI in her personal life for productivity and planning.

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Show Notes

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Follow Courtney Dagher on LinkedIn, and secure your budget now for UNBOUND 2027, with tickets going on sale Cyber Monday at unbound.hubspot.com.

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Nobody graduates with a degree in British Victorian history and literature planning to run one of the biggest marketing events in the world, but that's exactly where Courtney Dagher landed. She and Jay Schwedelson get into what makes someone feel like they genuinely can't miss an event, and why the answer has less to do with the agenda than you'd think. It's an honest, funny look behind the curtain from someone who still gets a rush from thousands of people and zero sleep.

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Best Moments:

(02:23) How a Harvard history grad with no tech bac

Do This, NOT That: Marketing Tips with Jay Schwedelson