Whether you’re planning your first sales kickoff (SKO) or it’s your 20th, there’s always pressure to make it memorable and see a return on your investment. To that end, we rounded up 7 ways to ensure an ROI on your sales kickoff.

There is no one-size-fits-all plan for sales teams. Variables like size, experience, team dynamic, past year’s performance, and your big goals for the coming year need to be factored in.

That said, we gathered the 7 top tips and ideas to share with you. These were contributed by Shawn Fowler (SalesLoft’s Director of Sales Engagement) and Richard Harris (Founder of The Harris Consulting Group) in the Modern Sales Pros (MSP) forum.

7 Ways to Ensure an ROI on Your Sales Kickoff (SKO)

1. Make It Emotional

Think about the graduation speeches or TED Talks that go viral on YouTube. They catch on because people feel inspired by them; those videos evoke a desire to be better.

When you’re planning a kickoff, Shawn Fowler suggests asking yourself three things:

  1. How do I want them to feel when it’s over?
  2. What do I want them to do when it’s over
  3. What do I want them to know it’s over?

Too many companies make the mistake of approaching SKO as a chance to train their reps. It’s OK to do some training at the event, but they’ll forget most of it (if they pay attention in the first place), and more importantly, you will have missed a great opportunity to motivate your team.

A great SKO creates an environment in which your reps can come together and reaffirm their membership in your team as part of their identity. It should excite them and make them feel connected. If you do this well, they’ll be energized and motivated to act when they leave.

2. Recognize Your Rockstars

Everyone loves recognition. Especially everyone in sales. Do this on day 1! Celebrating wins with awards on the first night of the kickoff builds the momentum from start.

Each winner should be honored with a plaque they can display on their desk (because bragging rights).

Sales Superlatives: Always Be Closing

Here are some ideas for award categories:

  • Rookie of the Year
  • Top Account Executive
  • Top Sales Development Rep
  • Leadership Impact Award
  • Biggest Deal Won
  • Team Player Award
  • Customer Hero Award

3. Plan the Energy

As you put the agenda together, plan for the emotional/energetic flow throughout the day (are you seeing a theme?). Start and end each day with either high energy or high emotion (or both).

Don’t forget the midday slump. Plan something interactive after lunch or people will be in a food coma. Did you know that exercise helps memory and thinking? A spontaneous flash mob gets people moving and laughing.

Too corny? Organize smaller groups of people from different teams at roundtables and encourage them to discuss a specific topic. To encourage interaction, let a couple of them present their recommendation at the end of the allotted time. Discussion wakes people up and creates an opportunity for people to talk with others they normally wouldn’t.

4. Keep it Short and Lively

Sessions should be no longer than 60 minutes. Most people completely check out after 90 minutes; play it safe. Even better – keep it to 30 minutes. The brain is like a sponge; neither one can absorb a typhoon.

Make sure your stage presentations are interspersed with smaller sessions that have participants engaged in activities and competitions (again with the energy). No one wants to sit and be talked at all day.

The added bonus of breaking up sessions is that it gives people time to grab a cup of coffee and chat. What happens between sessions is often more important than what happens onstage.

5. Get Buy-In and Delegate

Get executive buy-in early and often. Bring leadership in on the theme, goals, and agenda. Establish regular meetings to discuss these things as they develop. If you don’t, everything will be sent sideways at the last minute.

A good way to align everyone is to ask some basic questions surrounding goals. The answers provide great visibility and consensus related to sales, priority improvement areas, reality vs. perception. Here are a few to consider:

  1. After the SKO, we expect the team to be aware of/receive basic information about _____, ______, and ______.
  2. The answers given in Question 1 are informed by the following company objectives: ____, _____, and _____.
  3. True or False: We have an idea of what success looks like at the end of the SKO.
    a. If true, then great.
    b. If false, we must run through 2 sales cycles to get baseline metrics from which we can start to improve
  4. Our team will dedicate _____ and _____ time/resources to spend with sales after the SKO to ensure they are well trained.

Save your time (and sanity) by delegating sessions and activities. Break up tracks and assign owners to each. Include your helpers in status meetings; they can help. It may also be interesting to get their input on a few of the above questions.

Delegating can be a hard one, but if you’re having a large kickoff, it’s unavoidable.

6. Be Realistic with Your Expectations

This is a sales meeting. People will be hungover. As Richard Harris so eloquently (and accurately) put it, “Rare is the human that can do two full days of training and drinking and truly be experts in anything other than the drinking.”

Fighting it is a fruitless effort. Instead, plan for it. There are some easy things you can do to keep people functioning.

  • Don’t skimp on the coffee and the chicken biscuits in the morning. Or water and caffeine throughout the day.
  • Build excitement for the morning sessions with special guests or prizes.
  • Put “welcome bags” in everyone’s room. The bags should include bottles of water, some form of hangover cure/hydration powder, RedBull, Mortin, granola bars, and gum.
  • Understand that people are still working. Give them time to respond to their customers – don’t start too early or end too late.
  • Close the open bar on time and place water bottles at the exits.

7. Follow-Up Is Key

You’re kidding yourself if you think 2-3 days of information (and alcohol) is going to stick with your entire sales organization. If you don’t follow up on the information and momentum you provide at the SKO, you’ve just wasted a lot of time and money.

Shawn Fowler advises the following:

“If you plant the emotional seed at SKO, you need to nurture it for the following couple of months. If you rolled out new messaging at SKO, certify the team in the following weeks. Did you announce a new go-to-market? You need to provide additional details and quiz the team over the following weeks. It might feel excessive, but you can’t talk about this stuff too much.”

Richard Harris agrees. Think about the amount of time you devote to each topic at the SKO. Harris suggests devoting the equivalent of that time reinforcing the message in the following 8 weeks. For instance, if you spent 2 hours on new messaging, spend 2 hours over the next 2 months reinforcing it.

Don’t rely on managers to do this in weekly meetings or 1:1s. The follow up should be a concerted, consistent effort, separate from regular coaching activities.

It takes a persistent cadence to drive organizational change. Get the big bang for your buck.


Want to learn more from the best minds in sales? Join us in Atlanta from March 11-13, 2019 at Rainmaker 2019!Rainmaker 2019