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New Webinar: Uncovering the Best Tactical Insights of 2023

December 14, 2023 at 10 a.m. CST

Phew, what a year. Are we right?

But before you activate that OOO and start practicing “Auld Lang Syne,” let’s reflect on the insights that changed how we sold in 2023:

  • How to sell in a sideways economy
  • Understanding today’s B2B buyer
  • The power of teaching, not pitching, in your sales conversations
  • Why you need a healthy, high-performing sales culture
  • …and much more

Next up on the Leading The Challenger Sale webinar series, Challenger’s Maggie Knauff and Ian Goddard will parse the lessons we learned this long year and think about how sales leaders can bring them forward into 2024.

Join us on Dec. 14, 2023, at 10 a.m. CST for “Uncovering the Best Tactical Insights of 2023,” our final event of the year!

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On-Demand Webinar: A Fight to the Finish

Struggling to bring your stalled opportunities out of limbo and into closed-won status?  

Geoff Hendricks, key account executive at Challenger, joins CEO Andee Harris to discuss how to overcome common obstacles buyers face, the cost of customer inaction, and how a mutual action plan brings both buyer and seller together to complete the buying process. 

Tune in for a practical guide to closing your pipeline, with tactics and strategies that work, even in an uncertain economy. 

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Expert Tips for Planning Your Next Sales Kickoff

In our September webinar, nearly half of the attendees said the started planning their yearly sales kickoff in Q3. Another quarter won’t start until the middle of Q4. Whether it’s a matter of procrastination or prioritization, we hear that sales leaders tend to put off planning their biggest sales gathering of the year, starting well beyond the point they should.

The truth is that to achieve the SKO of your dreams, you can’t afford to wait. If you’re struggling to start, try this step-by-step, repeatable process used by SailPoint’s enablement leaders, Global Revenue Enablement Associate Manager Robin Barde, and Global Revenue Enablement Manager Meredith Linze. For more, watch the full on-demand episode of Leading The Challenger Sale.

What makes a great kickoff?

Maybe your first reaction is “really great swag and a 1:2 person-to-happy-hour ratio.” You might not be wrong, but a truly functional sales kickoff must also achieve several goals. 

  • First, it needs to set the tone for the year. Sellers need inspiration after a tough quarter closing their pipelines, especially following a year of economic uncertainty. Identify how your team needs to feel when they leave the SKO and use it to guide your planning. 
  • Second, think about how you’ll align sellers and revenue teams with the organization's goals and values. Your organization must speak with one voice at your SKO, emphasizing what's important at an organizational level as well as what’s at stake. 
  • Next, recognize that while the SKO energizes sellers, that energy needs to be pointed in the right direction. Sellers should leave the event able to clearly articulate their focus for the year to come. 
  • Finally, yes — it should be fun!

Choose Your Theme

What ideas are you kicking around for your SKO theme? Since you’ll build the rest of your event (ahem—swag! Workshops! Breakout sessions!) around this idea, conversations about the theme should start early and can begin as soon as the end of your previous SKO. Grab a whiteboard, block an hour on your calendar, and make a list of stakeholders whose input you’ll need. 


  • Feedback from your planning team
  • Insights from leadership
  • Insights from your previous SKO’s attendees 

Once you've aligned on an overall theme, consider a tagline. SailPoint’s 2023 SKO, “Sail Forward,” featured the tagline “Faster. Tougher. Together.” Executive speakers and keynote presenters drew this thread through their presentations and even included it in company meetings throughout the year.

Define Your Goals

With a solid theme in place, it’s time to outline your SKO goals. If the theme drives the overall feel of and messaging around your event, then goals help dictate the content. 

Remember that different teams might have different goals. Your enablement team and sales leaders might want to emphasize certain tactical skills or revisit your recent sales training program. Leadership might want to lay out their strategic vision for the year. Encouraging all your stakeholders to articulate their vision can help you settle on the right goals for your event. Each SKO session should map back to those strategic goals. Your follow-ups — training, sales meetings, even your company’s all-hands — in the year ahead should do the same.

It’s all about giving reps what they need to walk away from the SKO feeling confident and excited about meeting their objectives. 

Drive Interactivity

You know that your kickoff will be exciting, that your theme will serve as a rallying cry, and that your speakers will reinforce your goals. But how can you keep your sellers engaged, especially with a full schedule and so many things pulling at their attention? 

Our guests recommended tapping into interactivity, particularly through gamification. That might be as simple as asking them to participate in a photo competition. For our SailPoint guests, selecting an adorable mascot with layers of meaning helped give sellers a focal point. The SailPoint team also used an app to get real-time feedback from sellers. Those tuning in remotely could connect with a live broadcast feed between sessions.  

Plan to incorporate activities that unlock your sellers’ competitive instincts. Adding fun competitions and building opportunities for engagement will keep their attention and increase stickiness, too. 

Plan for Reinforcement

On that note, our SailPoint guests’ final suggestion was this: the SKO is just the beginning of a year-long enablement journey. If you don’t follow up with reinforcement, you risk sellers losing nearly three-quarters of everything they learned within days

To make sure your SKO efforts aren’t wasted, you’ll want to create a reinforcement plan that pulls your theme and goals through to next December. This might look like: 

  • Equipping frontline managers with a “meeting in a box” to help them revisit SKO learnings with their direct reports
  • Planning to add any materials to your learning management or sales enablement platform after the event
  • Creating a feedback loop for participants to submit questions and identify areas where further training is needed 

Effective SKO Planning Starts Now

We hope these steps from expert SKO planners jumpstart your planning journey. No matter where you are in the process, the time to start is now. For more inspiration, including SailPoint’s speaker preparation process and a template you can use to prep your speakers, watch the on-demand webinar “Practical Tips for an Unforgettable SKO.” 

Want to watch the next Leading the Challenger Sale webinar live? Sign up for the series here.

On-Demand Webinar: A Challenger’s Guide to Account Growth

Q4 is here and your account managers’ focus has turned to making quota by end of year.  

Your product delivers.   

Your service couldn’t be better. 

Yet your existing account growth is flat.  

Watch A Challenger’s Guide to Account Growth to find out why your accounts aren’t growing — and what you can do to shift the conventional wisdom at your organization and unlock serious growth potential before year-end. 

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On-Demand Webinar: Practical Tips for an Unforgettable SKO

Your sales kickoff (SKO) is THE opportunity to energize your sales team for the year ahead.  

A well-executed SKO propels your team forward with purpose and clarity — and maybe even a little fun. On this webinar Kate Feldt, senior director of global key accounts at Challenger, welcomes Robin Barde and Meredith Linze, the dream team behind SailPoint’s legendary SKOs. They discuss the nuts and bolts of planning to create the right balance of education and celebration, along with practical tips for speaker selection and prep, gamification, and creating effective networking.  

Watch the recording for everything you need to know to build an SKO that ignites your sellers and gets everyone ready to crush their goals.

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On-Demand Webinar: Create a Healthy, High-Performing Sales Culture

When most people think of sales culture, they likely think “cutthroat.” Historically, the pressure to meet revenue goals has overshadowed the importance of cultivating a positive team culture. But it’s time to break free from the old norms.

In this webinar, we debunk the myth that revenue is the sole key to success. By shifting the focus onto the right skills and behaviors, rather than just meetings booked and revenue generated, we discuss you how to cultivate a sales culture that not only thrives but hits quota.

Download the webinar to unlock the secret to creating a harmonious and high-achieving sales team.

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On-Demand Webinar: Align your sales tech stack to the buyer journey (not the sales process)

Sales tech has been having a moment. For a few years now.  

Set in motion by the pandemic, companies started rapidly adopting new technologies, tactics, and engagement strategies as a crisis response, all to support a digital-first purchase experience. 

And they were right to do so—recent studies have confirmed that buyers now prefer to be sold to virtually instead of face-to-face.  

However, in the haste, many investments were made in sales tech point solutions to solve a specific problem for a specific stage in the sales process. Basic file-sharing for content storage. Company and contact intelligence for prospecting. Sales engagement tools for outreach. Call intelligence for deal acceleration.  And herein lies the fatal flaw. 

What is described above is a sales tech stack aligned with how sellers sell… not how buyers buy. We know that the buying journey is far less linear than the sales process. 

It’s time to revisit how we use sales and enablement tech to empower sellers to provide a better buying experience.  

In this on-demand webinar, host of Leading The Challenger Sale and Challenger CEO, Andee Harris, is joined by Hendrik Isebaert, CEO of Showpad. They discuss how building a sales tech stack that works for you, not against you, is the key to a differentiated and loyalty-driving buying experience. You’ll hear the Challenger perspective on sales productivity in the new work environment and reducing seller burden, complemented with Showpad’s research and approach on how to align sales and marketing to create exceptional buyer experiences. 

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On-Demand Webinar: The Anatomy of a Great Pitch Deck

Take a look at the first 3-5 slides of your standard sales pitch deck. 

Does it start with facts about your company like years in business and number of customers? Is there a map of your office locations? A slide with your mission, vision, and values? 

If you answered yes to any of these questions, then this webinar is for you. 

Challenger has helped hundreds of companies, like Chevron, reconstruct their approach to the “sales pitch” and shift to having insight-led conversations with potential buyers. This is done through a concept known as Commercial Teaching. 

To learn how to stop pitching and start teaching, watch this on-demand webinar for a breakdown of the anatomy of a great pitch deck. Host and CEO of Challenger, Andee Harris is joined by Christine Cox, Sales Methodology Specialist for North America at Chevron, who shares her real-world experience building up the “teaching pitch” and helping her sales reps successfully execute the teaching conversation.

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On-Demand Webinar: Who is Today's B2B Buyer?

Challenger has tracked the evolution of B2B buying and selling since 2008 with our most recent large-scale study in July 2020. A lot has changed since then… and likely will continue to change faster than our research can keep up. 

So, this year, we decided to do a mid-year reprise of our B2B Buyer Study before our next large-scale study this fall. The results are in, and they are fascinating. Read more

On-Demand Webinar: Social Selling & Employee Advocacy with Ryan Barretto, President of Sprout Social

Social selling is a channel with untapped revenue potential in many organizations, but how can sales leaders build a program in their organization that fosters consistency, efficiency, and scalability?Read more