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How Do I Get Enterprise Buyers to Watch My Videos? | Tyler Lessard - 2050

The Sales Evangelist

34m
Transcript

Original podcast

Summary

Written by a model from the transcript; not yet reviewed.

In this episode of The Sales Evangelist, host Donald C. Kelly interviews Tyler Lessard, VP of Marketing and Chief Video Strategist at Vidyard, to discuss how sales professionals can successfully use video to engage hard-to-reach enterprise buyers and executives. They break down common misconceptions about video prospecting, debunking the idea that videos require professional studio production, and explain that webcam recordings and screen shares are fundamentally tools for human connection rather than perfection. The conversation covers practical strategies such as creating curiosity-driven subject lines, leveraging context like a prospect's LinkedIn profile in the background, and offering low-friction calls to action.

Furthermore, Lessard and Kelly explore how video can be integrated into the entire sales cycle beyond initial prospecting, including pre-meeting reminders, post-meeting recaps, and custom feature demos. Listeners learn that adopting a movie-trailer approach and showing rather than telling can significantly accelerate deal cycles and build trust with decision-makers. The episode offers actionable frameworks for both seasoned enterprise sellers and those new to digital communication.

  • Treat video as a communication medium for connection rather than a polished advertisement. 7:05
  • Use curiosity-driven subject lines like a quick video for you to boost open rates. 13:52
  • Incorporate your prospect's LinkedIn profile in the video background for instant relevance. 25:51
  • Send short video recaps after meetings to keep deal cycles moving and reach stakeholders who missed the call. 28:47

Chapters

  1. 0:00
    Podcast Intro and Sponsor Highlights

    The episode opens with sponsor messages and a brief introduction to the show.

  2. 2:14
    Host Introduction and Guest Teaser

    Donald Kelly welcomes Tyler Lessard and previews the video sales topic.

  3. 3:47
    Tyler Lessard’s Background and Book Overview

    Tyler explains his roles at Vidyard and introduces his book, The Visual Sale.

  4. 6:58
    Common Video Mistakes in Enterprise Sales

    Tyler discusses the misconception that video must be high‑production and stresses authenticity over perfection.

  5. 13:06
    Crafting Subject Lines and Call‑to‑Actions

    Tyler shares tactics for enticing opens and effective CTAs in video emails.

  6. 25:07
    Creative Simplicity and Personalization Techniques

    Tyler shows how simple, personalized videos can spark curiosity and build credibility.

  7. 28:05
    Beyond Prospecting: Pre‑ and Post‑Meeting Video Use

    Tyler outlines how short videos can boost meeting attendance and post‑meeting engagement.

  8. 30:34
    Practical Tips for Enterprise Video Adoption

    Tyler offers final advice on starting video use, focusing on connection over perfection.

Highlights

  • 5:35

    Embracing a Digital First Worldstory

    The guest shares how co-authoring the book The Visual Sale coincided with the pandemic, forcing sales teams to integrate video into everyday communication.

  • 7:05

    Redefining Video in Salesinsight

    The guest explains that the biggest mistake people make is thinking videos need high professional production, when sales success actually comes from simple webcam and screen-share communication.

  • 13:52

    Curiosity-Driven Subject Linesstrategy

    Simple subject lines mentioning a short video made just for the recipient create a curiosity gap that increases email open rates.

  • 21:11

    The Trustpilot Video Examplestory

    The guest shares an anecdote of a seller who recorded a video with the prospect's ad on screen, immediately showing expertise and generating trust.

  • 25:51

    Using LinkedIn as a Visualstrategy

    A repeatable template involves recording a webcam video with the prospect's LinkedIn profile on the screen behind you to spark immediate interest.

  • 28:47

    Post Meeting Video Recapsstrategy

    Sending quick video recaps after a meeting helps champions share the message with others who did not attend the live call.

Quotes

  • “A video is just a new, more impactful, more effective way for me to communicate my ideas, to answer a question, to explain something, to walk through something.”
    Unnamed speaker · 7:38
  • “And I think a lot of biggest mistake a lot of people make is not really embracing that and thinking just, hey, wait a minute.”
    Unnamed speaker · 7:32
  • “If you can do it, it might work, but you don't need to do those kinds of things.”
    Unnamed speaker · 25:21
  • “And I would love to share a couple more tips with you, let me know what you think, right?”
    Unnamed speaker · 17:25

About this episode

Your video outreach can look great and still get ignored by the exact executives you're trying to reach. This one is pulled from the archive, and it earned that spot because the problem it solves hasn't gone anywhere. Tyler Lessard https://www.linkedin.com/in/tylerlessard/, VP of Marketing and Chief Video Strategist at Vidyard and co-author of The Visual Sale, joined me to break down what actually gets enterprise buyers to open, watch, and reply to a prospecting video. Rethink What Actually Counts as a Video A lot of people still picture video as a polished, one-to-many production with drone footage and professional editing, and that assumption alone keeps plenty of reps from ever hitting record. A simple webcam recording or quick screen share works fine, because the goal is communicating an idea clearly, not producing something that looks like a commercial. The real shift is seeing video as a faster, more effective way to answer a question or explain something, not as a special project that needs a production budget. Treat Video as Part of the Rhythm, Not a Silver Bullet Sending ten prospecting videos and expecting five replies sets the video up to fail. It's one piece of an outreach sequence, not a standalone bet that has to prove itself in isolation. Video doesn't replace phone calls, social touches, or written emails; it adds a layer of familiarity that makes the rest of that sequence land better. Once a video sits inside the regular rhythm instead of being judged on its own, the fear of it "not working" stops being a reason to skip it altogether. Write a Subject Line That Creates Curiosity A subject line like "Donald, a quick video for you" works because it creates a curiosity gap, and the brain doesn't sit well with an unanswered question without clicking to resolve it. Naming the word "video" directly in the subject line raises open rates on its own, since it stands out against a sea of plain, text-only subject lines. This curiosity effect holds across seniority levels, from an entry-level buyer to a C-suite executive, because it taps into basic human psychology rather than a specific title. End With a Low-Lift Call to Action Asking for thirty minutes of someone's time on a first video is the same awkward ask reps already overuse in cold emails, and it falls just as flat on video. Offering to send a second, slightly more detailed video is a much easier yes, since anyone who already watched the first one has shown they're open to watching another. A low-lift CTA like that opens the door to more face time with a prospect without asking for a meeting before any real trust has been built. Make the Visual Do the Talking Recording with a prospect's own LinkedIn profile visible on screen behind you turns the video thumbnail into something personal enough to earn a click on sight. One memorable example involved a rep showing his own search results next to a competitor's ad, with five-star reviews stacked underneath it, proving a point visually instead of describing it in a sentence. Showing something instead of explaining it saves the viewer the work of looking it up themselves, and that shortcut builds trust faster than a written pitch ever could. Use Video Beyond the First Cold Outreach A short video attached to a meeting reminder lift shows rates, because it puts a real, energetic person in front of the invite instead of another plain calendar notification. A quick recap video after a meeting can travel further than expected. If a champion forwards it internally, it introduces you to decision-makers who were never on the original call. Recording a short answer to a question you get often, once, and reusing it saves real time on every future deal that runs into the same question. "It's about connection, not perfection." — Tyler Lessard Leadership Advice, Books, and Quotes Tyler's core message throughout this episode is that video works because it's human, not because it's polished. Every tactic here, the subject line, the low-lift CTA, the visual proof on screen, is really just a way of making a message feel like it came from a real person rather than a template. His book, The Visual Sale, co-written with Marcus Sheridan, goes deeper into how to build that kind of visual communication into a full marketing and sales process. Resources Connect with Tyler Lessard on LinkedIn to ask about video strategy for your own enterprise outreach. Check out Vidyard https://www.vidyard.com/ for video tools built for sales and marketing teams. Pick up The Visual Sale https://www.simonandschuster.com/books/The-Visual-Sale/Marcus-Sheridan/9781646870189 by Tyler Lessard and Marcus Sheridan for the full framework. Tell me how you're using video in your outreach on LinkedIn https://www.linkedin.com/in/donaldckelly. Connect with Tyler onLinkedIn https://www.linkedin.com/in/tylerlessard/ Sponsorship Offers This episode is brought to you in part by Hubspot. With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales https://www.hubspot.com/products/sales. This episode is brought to you in part by LinkedIn. Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse https://business.linkedin.com/sales-solutions/cx/20/09/sales-navigator-podcast?src=re-pod&trk=tse&veh=tse&mcid=6897323946090332160. This episode is brought to you in part by the TSE Sales Foundation. Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin https://tsesales.typeform.com/to/UCMfjZbX. Credits As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey http://thesalesevangelist.com/survey. https://tsesales.typeform.com/to/lc5yAa8P We’d love for you to join us for our next episodes by tuning in on Apple Podcast https://podcasts.apple.com/us/podcast/the-sales-evangelist/id788738885, Google Podcast https://podcasts.google.com/feed/aHR0cDovL3RoZXNhbGVzZXZhbmdlbGlzdC5saWJzeW4uY29tL3Jzcw?sa=X&ved=2ahUKEwj5kaXI3Pj2AhVKcjABHW5PDVwQ9sEGegQIARAC, Stitcher https://www.stitcher.com/show/the-sales-evangelist-sales-trainingspeakingbusiness-marketingdonald, or Spotify https://open.spotify.com/show/1NjzsFjQwVrgboUfDvbzd5?si=LdQOJDc1T-WBPMxr1h3RsA. Audio provided by Free SFX, https://freesfx.co.uk/ Soundstripe https://soundstripe.com/, and Bensound http://www.bensound.com/. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.

Transcript

0:00
34:20

7,237 words · 2 speakers

Topics

  • LinkedIn
  • Vidyard
  • LinkedIn Sales Navigator
  • The Visual Sale
  • Angel City Football Club
  • Sales Evangelist Sales Training Organization
  • TSE Studios
  • AI-powered recommendations
  • real-time account insight
  • video technology

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