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Customer Corner: The Dos and Don’ts of Running a CI Session at Sales Kickoff from Talkdesk’s Holly Jackson

In this edition of Customer Corner, we caught up with Holly Jackson, Director of Competitive Intelligence at Talkdesk. Below she gives her best advice for any CI practitioner trying to make a splash at their upcoming sales kickoff. Enjoy!

So you want to host a Competitive Intelligence session (or, better yet, multiple shorter sessions) at sales kickoff (SKO). How do you make sure that your CI content is timely, relevant, and going to stay with Sellers long after they leave SKO? And how can you use your session at SKO to reinforce the value of your CI program throughout the rest of the year?

SKO is a great place to lay the CI groundwork among Sellers for the upcoming year. Not only because their use of competitive insights helps tie your work to revenue, but also because the richest competitive insights come from their conversations with customers.

To help you knock your SKO session out of the park, I’ve compiled the ultimate list of SKO dos and don’ts for Competitive Intelligence practitioners:

  • DON’T: Try to boil the ocean
  • DO: Align with sales leadership
  • DON’T: Lose sight of who you’re talking to
  • DO: Make it fun
  • DO: Reserve time at the end for live Q&A

Let’s walk through each of these.


DON’T: Try to boil the ocean

Your Sellers don't have the capacity to learn & retain information about every competitor in your competitive landscape, along with everything else they’re learning at SKO—so get focused. Use this precious time you’ve been given to focus on the key competitive topics that your Sellers need to really know.

Win/Loss data is your friend here. Who’s showing up more frequently in deals over time? Who’s keeping your Sellers awake at night? Who's a new entrant that your Sellers need to know about? Answer these questions and you’ll have no problem identifying which competitors are worthy of your SKO session.

DO: Align with sales leadership

Got your shortlist of competitors who you think are SKO-worthy? Great—now take that list to your sales leaders and make sure you’re aligned. If you’re using Win/Loss data to identify the key competitors, chances are you will be. But you also want to take this opportunity to make sure you're coordinating with sales leadership's top priorities that the rest of SKO is focused on. If they’re talking about Apples, you don’t want to be talking about Oranges. Alignment with sales leadership ensures that the content you’re presenting at SKO is relevant and timely.

DON’T: Lose sight of who you’re talking to

Getting the opportunity to talk to a large Sales audience about Competitive Intelligence is always exciting, especially if it’s your first time. The excitement you’re feeling is awesome—but you need to make sure you don’t get carried away. SKO is not the time to overcomplicate things or cram every single thing you know about a competitor into a 30-minute session.

Your Sellers need tactics to help them win, that’s it. Nothing more, nothing less. Sellers should walk away from your CI session being able to articulate to their customer why your solution is the best solution. 

This is a great reason to get fresh eyes on the content of your session before SKO. I recommend floating your content by both a tenured Seller and a more junior Seller. The experienced Seller will tell you if the content makes sense with what they’re seeing in the market. The junior Seller will tell you if the content is too “in the weeds” to help them compete. If the content of your session goes over the heads of your junior Sellers, you’ll leave a ton of value on the table.

DO: Make it fun

Studies have shown that a mere 24 hours after a presentation ends, only 25% of the audience will remember what was said. You can help increase that retention by making your sessions fun and engaging! Creating a theme is one of my favorite ways to ensure the session is engaging from beginning to end.

Themes we’ve used at Talkdesk include The Price Is Right (pricing session), Jurassic Park (focused on legacy competitors), and Game of Thrones Seats (we sell our software licenses by the “seat”). Associating a competitor with a character in a movie or game is an easy way to increase retention among your audience.

Remember however: the theme, activities, and prizes are just vehicles for delivering the content. Content is the first priority, the theme is secondary. And please make sure that the theme you select is as universal as possible—the last thing you want is people to feel confused or excluded. If a big chunk of your sales team is based in Southeast Asia, don’t make your session all about American football!

DO: Reserve time for live Q&A

What better way to build rapport than to answer your Sellers’ burning questions on the fly? Being able to answer questions in-the-moment positions you as a competitive expert who Sellers can trust when they need help post-SKO.

The Q&A session also helps reinforce the habit of sharing field intelligence back to the CI team so that your function can serve as the central repository for all things competitive. In my experience, the live Q&A at the end of an SKO session is often where the BEST field intelligence gets shared. Sellers often hear about competitors’ new programs, motions, and incentives (through the customer / partner grapevine) before they make their way to the CI team—so make sure you’re ready with pen and paper!

Check out my appearance on Into the Fray: The Competitive Intelligence Podcast

I hope these dos and don’ts help you run an extraordinary SKO session. Remember: As long as your Sellers walk away feeling excited to both consume and contribute competitive insights, you’ve done your job.

If you enjoyed this blog post and you want to learn more about my career in and perspective on CI, check out my appearance on Into the Fray: The Competitive Intelligence Podcast.

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Holly Jackson
Holly Jackson is the Director of Competitive Intelligence at Talkdesk, a leader in cloud-based contact center solutions.