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Sales Development, Sales Process

Sales Kickoffs Have Evolved. Has Yours?

Jacco van der Kooij

Written by Jacco van der Kooij

Founder, Winning by Design


It is becoming quite common across industries, especially in SaaS, to host bi-annual sales Kickoffs (SKOs). If you browse through the photos on LinkedIn in late January and again in the early summer, you will notice the events are either held at the companies headquarters, or even in a vacation destination.

These Kickoff events are one of the very few moments in the year when the entire GTM team is present and available.

If you look closely, you see that these events are getting bigger, and their production values are going up. Many of you already know that the Sales Kickoff has become a bit of a spectacle.

But there is something missing . . . the teams walk away from their event in London, Singapore, or Vegas with a lot of excitement and motivation to work hard when they return to the office. And yet, 30 days after the kickoff, the sales leaders are not seeing much (if any) impact from the kick-off. We are seeing these SKOs become larger productions with lots of excitement, but often with mediocre results when company leaders measure the resulting revenue impact against the production cost of the SKO. So, what is missing? Why are companies not getting the return on these events that they need?

We?ve seen high growth companies make similar mistakes with how they approach their annual Sales Kickoffs; here are some ways that you can turn those missteps into opportunities.


Opportunity #1. Reset the goal of the event, to avoid the “checkbox mentality”

The checkbox mentality is when we say to ourselves: Let’s organize the SKO, let’s get a trainer, let’s get a keynote speaker – check.? And then attendees say, ?Let?s attend the conference, make sure our manager knows we?re there – check. The trainer/keynote speaker goes: Let’s do the training – check. Everyone can check their own boxes, but nothing was really accomplished.

The real goal is to make it a MESS. Mess stands for:

  • Motivate. Teams look to events like these to be invigorated, to find their shared goal, to feel purpose in what they are doing. If you don?t land the message of that higher purpose, even the best keynote speech will fall flat.
  • Educate. All the attendees must learn three key areas: understanding of the market you operate in, the products and services you offer, and the innovative sales skills that they need to perform.
  • Share. Your entire sales team is present, all in one place. This is the time to spread tribal knowledge, share insights, and share best practices.
  • Socialize. Get to know each other! Eliminate the artificial barriers of who is on what team. That guy on the Product team who sometimes seems to have different goals than Sales – he?s actually quite a funny guy! Crack some jokes and connect with him.


Figure 1. Key pillars of an SKO: Motivate, Educate, Share and Socialize


Opportunity #2. Turn the ‘S in ‘SKO’ from Sales to Shared

If Sales is the only GTM org at the kickoff, then how can you expect Sales, Marketing, and Customer Success to move in lock step toward shared goals? Make it a Shared Kickoff. Include all GTM teams so that everyone actually learns how to work toward the same goal; this is how the magic of connected teams and true enablement for success begins. Your Marketing, Sales & Customer Success teams should all be at the event; some companies find benefit from bringing their Product team as well.


Figure 2. Graphic showing Sales, Marketing, and Customer Success all together

Figure 2. The Shared Kickoff should include all GTM functions for maximum impact.


Opportunity #3. Embed workshop elements into the education.

Sales might walk away from the event having been motivated by speakers who made some very smart remarks, but they will likely spend several days at this event without having practiced any new skills.

Figure 3. The Ebbinghaus forgetting curve depicts how 75% of the knowledge is lost within a week.


Too often we see long agendas that are full of one-way presentations from management or outside speakers. While the content may be interesting in the moment, the lack of practice means that much of that content will not be retained or put into use. Instead, create interactive sessions throughout the day where your teams learn a new sales play, skill, or concept, and then actually role play it out with their peers.


Opportunity #4. Make it engaging!

SKO agendas are often jam packed, so that leadership feels that they are fitting in all of the topics that need to be covered. But this comes at the expense of reps actually retaining all of that knowledge. It?s much more effective to focus on fewer topics that have the most impact, and to make those topics interactive and engaging. Use music and video to provide real life examples. Provide space. Natural light. Whiteboard. Require taking notes. Role-play. Use break-outs. Motivational speakers are of course entertaining and drive a strong message, but often do not tie their message directly back to what reps needs to be learning or improving.


Figure 4. How we often get the concept of motivational speakers wrong

Figure 4. How we often get the concept of motivational speakers wrong

Opportunity #5. Prepare the presenters.

We have seen it all before: the company picked boring presenters, everyone runs over time – often at the cost of the break – and the dense slide decks keep coming. We recommend first training ALL of your presenters to be certified for presenting at kickoffs. Set a maximum number of slides per deck. Set a minimum for the number of practical examples. All of this should start during the planning period, at least 90 days before the event.

An amateur practices until (s)he gets it right;
a professional practices until he can?t get it wrong

– Unknown


Opportunity #6. Use unstructured time purposefully in your SKO agenda.

Right when people are having meaningful conversations which are critical to retaining knowledge, we regroup them into a sit and listen environment with more presentations. Instead, you should build in unstructured time where people can connect across teams and get to know each other more than just passing each other by while getting snacks in the office kitchenette.


Opportunity #7. Spend more on enablement and less on fashion.

We witnessed an event where a company easily spent $100 per person on a gift bag with a $60 branded hoodie, notebook, pen, and cap, all of course with the company logo. Meanwhile, the company felt that it had no money to commit to investing $20 per person for training materials such as work books that would help to reinforce concepts that reps badly needed to learn.


Figure 5. Examples of Handouts & Enablement

Figure 5. Examples of handouts and enablement that help to reinforce the concepts that reps need to learn.


Opportunity #8. Your reps, not your keynote speakers, should be the heroes of this story.

One of the best ways that reps can learn is from their peers and direct managers. This can include storytelling from the front-line customer success managers, highlights of reps or GTM pods who have been successful with a new customer outreach initiative, or managers who have led their teams to a great quarter. Don?t let your company miss the opportunity to achieve alignment across GTMs, motivate your team, and make a real impact on revenue and growth.

Figure 6. Whiteboard & Workshop Together

Figure 6. Whiteboard and workshop together, where reps share their stories and teach each other how they have been successful.


Opportunity #9. Make this an integral part of your year, not just a one-time event.

The SKO shouldn?t be a point in time. It?s part of an entire year-long program. You will see far bigger impact if you think of this event as part of a broader system with what happens before, during, and after.


#10 Oppty. Do what you are good at.

Ask yourself, is this where you excel? Or is there someone who is an expert who can help? We?ve helped drive engaging content, agendas, and event experiences at Kickoffs for over 200+ events and counting . . . we have seen how those companies that adopt these principles drive team alignment, hit their stretch goals, and build unstoppable cultures.


Figure 8. From DIY to Outsourced

Figure 7.? From DIY to Outsourced


If you?d like Winning by Design to run your next Shared Kickoff, here?s what that would look like:??

#1 Before the Shared Kickoff:
We work with you and your leadership team to align on shared goals, bring groups together, coach you on how to prepare, create integrated workshops for each training session, reduce volume of slides, and increase quality.

#2 During the Shared Kickoff:
The key elements of the experience are: high energy educational motivational keynote, followed by a series of breakout sessions with whiteboard, call analysis, and lots of role play.

#3 Post the SKO (2 weeks later):
Follow through includes a 4-week program – repetitive training moments through role play videos, key new lessons that build on the Kickoff topics, and weekly skill training / call reviews.

If you are interested in learning more about how Winning by Design can help design a Shared Kickoff for your GTM team, get more information here. We would love to hear from you and help bring you success.