11 Tips for an Effective 2020 Sales Kickoff from Top Sales Enablement Pros

By Allison Sword

The new year is just around the corner, and that means sales kickoff (SKO) season will be here before we know it. If you’re like most sales enablement professionals, you’ve probably already started planning your organization’s 2020 event. 

A sales kickoff can be a great opportunity for a company to gather its teams together to celebrate the successes of the past year and get everyone energized and motivated for the next 12 months. But there are good sales kickoffs — and then there are the not-so-good ones. The good ones leave attendees engaged, inspired, and informed. They walk away understanding the company’s goals for the coming year, the role they play, and the tools and resources they have at their disposal to be successful. The ineffective ones leave reps bored by hours of PowerPoint presentations — and overwhelmed by the sheer volume of information being thrown at them.

How can you take your 2020 SKO from mediocre to exceptional? We asked 11 sales enablement pros to share their top tips for planning an outstanding sales kickoff that sets your teams up for success in the year ahead.


Pick a Great Location 

“Make the SKO memorable by selecting an “out of the norm” location. Build interest ahead of the kick off with teasers about what to expect. Get sales managers involved with presenting success stories, and include the voice of the customer with live customer interviews. Make it as “hands on” and experiential as possible.”

-Terry Mitchell

Director of Sales Enablement 

Fujifilm Graphic Systems Division 


Start with the Why

“Start by identifying the “expected outcome.” Is the goal of the SKO to celebrate the company’s (specifically sales’) achievements or to train salespeople on a particular skill, message or strategy? When salespeople buy in to the end goal, they are more likely to be present and engaged throughout. And I 100% agree with Terry Mitchell’s points about including the VOC and making it “hands on” — give participants opportunities to apply concepts to their day-to-day, practice, give feedback, and receive feedback.” 

-Arielle Rosati

Sales Enablement, Marketing and Growth Initiatives Department 

Lytz, Inc. 


Make it Interactive

“Don’t fly them somewhere fancy just to spend the first day looking at slides! Make the event actionable and give them time and opportunities to build relationships and solve their problems collaboratively.”

-Aaron Howerton 

Global Channel Operations Manager 

M-Files Corporation 


Celebrate Successes

“Your sellers and sales support teams have worked hard all year—it’s crucial that you celebrate and reward those efforts in order to cultivate a rewarding company culture.”

-Stephanie Middaugh 

Senior Sales Enablement Manager 



Determine the Top Three Takeaways

“Before planning, ask ‘What are the three things every rep needs to know coming out of this event?’ Make sure those are consistent and make sure 100% know them when they leave. They will learn a LOT more than three things, but what are the three they must ALL know?”

Todd Caponi

Author of The Transparency Sale


Focus on Content Rather than Fireworks and Pageantry 

“I feel like the most important takeaways for an attendee are to a) clearly understand the role they play in this year’s strategy, b) believe the goals are achievable with a clear path to the target, and c) have a full grasp of the tools at their disposal that will enable them to succeed and monitor their progress.

Most of this may be addressed in breakouts by region and/or specialty, but they are, in my opinion, more important than the fireworks and pageantry.”

-Sean Husick 

Sales Enablement Professional 


Define Guiding Principles — and Get Everyone Energized 

“Wake everyone up on the first morning session with a rocking soundtrack! 

Define some guiding principles – the objective/desired outcomes, the theme, the overarching messages. 

Ensure every message delivered is on theme and as inspirational as it can be, without becoming unrealistic. Script a story that forms the basis of the SKO, that you tell from start to finish, weaving each session into the story and ultimately an eye opening ending. 

Start every session with the ‘Why?’. 

Finally, ensure there is enough downtime — some of the most memorable moments at SKO come during the evenings — make it memorable.”

-Kunal Pandya

Senior Director, Business Operations, Sales & Partner Enablement 



Start Planning Early

“Start your planning early. Get senior leadership involved ASAP and keep them focused on the main goals for the year. As you plan, frequently ask yourself — and your planning team — ‘When this is over, what do I want them to know or be able to do?’  Keep things focused and limited.”

-Bill Parry

Director of Enablement 

Redwood Software 


Develop a Thoughtful SKO Brief

“Taking your sales team off the floor for an internal kick-off is expensive. Having a thoughtful SKO brief in place will ensure that you are utilizing that time effectively so that sellers can feel the time away from their markets was worthwhile.”

-Carly Lehner

Senior Manager, Sales Enablement

Axiom Law


Understand What Motivates Your Teams

“Sales people love cash and recognition. Cold hard folding is a big motivator. Dish it out from the stage. Watch the reaction to gauge the impact.”

-Andrew Moore 

Commercial Management Specialist

Causeway Technologies 


Focus on Reinforcement and Follow Up

“People forget 80% of what they have learned within the first 90 days, so it’s important to reinforce the topics discussed during the kickoff and map out a strategy to ensure continuous improvement and learning.”

-Taryn Rosada 

Head of Global Learning & Development 


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