Insight Partners
7 min readMar 5, 2020


10 Steps to Crush Your Sales Kickoff (SKO) Event

Written by Travis Kassay

It’s 2020. If you are a Sales leader, you likely spent the last few weeks of 2019 scrambling to close deals before the year end, and as a result, you’re probably starting January by finalizing your compensation plans and quotas, and planning two of your most important events of the year: Sales Kickoff (SKO) and President’s Club.

Designed well, these two events should excite the sales team for the year ahead, help you set and sell a strategy that inspires everyone to roll up their sleeves (again), and also celebrate the team’s 2019 accomplishments. If you put in the effort and attention to detail, you’ll put yourself in the driver’s seat as you ScaleUp your business in 2020.

Let’s start with the Sales Kickoff.

SKOs may have a bad reputation amongst sales reps, largely due to a history of poorly planned events filled with boring presentations delivered to hundreds of people simultaneously with minimal interaction. Nobody wants to sit through that. To top it all off, the events are costly, and reps are out of the field for 2–3 days, meaning that there isn’t any revenue being generated.

Executed well, SKOs should energize the organization, inform and excite everyone about the company’s strategy for the year, and can get the whole sales team heading in the same direction. If you adhere to the following criteria, you’ll deliver a sales kickoff that will align your team and make them productive in 2020, and beyond.

  1. Have a well-defined 2020 strategy. This is your chance to explain the strategy to the entire sales organization and rally them around a common aspiration. Make sure that the message is clear and that all the presentations delivered during SKO align to that strategy. Ensure your reps know their role in executing the strategy by giving them clear marching orders, as well as collateral to that supports their key talking points with prospects and customers.
  2. Make the content interactive: Two days of presentations is boring for anyone, so refrain from a parade of presenters, and instead create a series of workshops or rotational sessions. The best kickoffs combine amazing presenters (who present for 60 minutes in the main room) with round-robin sessions and workshops for 30–45 minutes. The best workshops, (i) impact how the sales team engages their prospects and clients and/or, (ii) leverage and explain the tools and techniques that help them to do their jobs. The movement and change in pace will keep the sales reps’ attention and, the interactivity helps ensure that all reps are participating. If there are new products or features being launched, this is the opportunity to ensure that everyone is aligned on the messaging and sales pitch. Marketing, Product & Tech leaders, along with the CEO should describe their strategies and how their activities will support the sales team.
  3. Celebrate successes from the past year. Firstly, SKO provides the opportunity to have a formal lookback on 2019 (what worked, what didn’t) and secondly, to applaud your superstars from 2019. Take some time to talk through what happened — both good and bad — and then highlight anyone who achieved plan or showed exceptional effort to help another rep or the overall team. Small award plaques are a great way to present top performers with something that acknowledges the value they have contributed to the company. Bring them up on stage while their peers applaud them, have someone read a sentence of why they’re being recognized (e.g. Sally Jones 145% of plan and $750k in sales) and take a picture with the CRO and CEO. By proactively building a culture of success and recognition in your business you will make your team excited and proud to be recognized in front of their peers.
  4. Leverage themes and imagery. We’ve all sat through dozens of kickoffs where we are going to “Race for 2020” or “Ignite Sales 2020” or something similar. Those themes sound corny and can fall flat if they’re not woven through the entire meeting. Likewise, these types of themes can have a major impact if they’re integrated into all communications, internal branding, and contests for the remainder of the year. So, if you’re Racing for 2020, that theme should show up in your contests (i.e., Q1 — Start your Engines, Q4 — the Final Lap). Pick a theme and stick with it — and make sure it’s different from themes used in the last two years. Work with marketing to be creative. Sales themes can become tired and overused.
  5. Be prepared for the meeting. If possible, you should communicate sales territories, compensation plans, and quotas in advance of SKO. Clarity in segmentation, compensation and territories will help to ensure your sales teams apply the material presented to their specific situation. Plans don’t have to be 100% complete but the closer to final design you can be, the better the outcome of your kickoff. If the sales reps go into the sales meeting blind, the best they’ll be able to do is apply it to last year’s activities. More likely, they’ll just listen without being able to truly connect the material with the activities expected of them. This is one reason that SKOs are often in late January or early February. The timing enables management to finalize strategy and plans before presenting to the team.
  6. Get new hires off to a great start. If you’re going to hire new sales reps, try make sure that they’re onboarded in time to join the kickoff sessions. There is no better way to indoctrinate them into your team’s culture than surrounding them with their teammates and sharing stories. One of the best parts about a SKO is the networking that your teams can do, especially if you have a global team. Having your new hires meet the top reps from each region will help accelerate their onboarding process. For those that join after the kickoff, you can repurpose some of the material for your onboarding training.
  7. Keep logistics simple. Pick a location that is near (the majority of) your team or easy to get to. You don’t want to have people waste an entire day getting to the location or getting home. Also, plan dinners at the hotel or nearby restaurants. This ensures that you can continue to build a solid networking experience for your sales teams and that they don’t waste too much time going to a new location after sitting in sessions all day. Finally, don’t forget to provide enough time for breaks. Your teams will still need to engage with customers, so give them sufficient time to catch up on email and calls in between sessions.
  8. Stick to a reasonable budget. Because you’re celebrating success and kicking off the new year, you want a venue and event that reflects the company. We’re not suggesting that you host your kickoff at the Ritz Carlton, but make sure that the venue is designed for corporate events, and then invest in the key items that will make the event memorable. Make certain that you have an Audio/Visual team, lapel microphones, large projector screens and the ability to play music over the A/V (which is essential to fill the time as presenters walk to the stage). Invest in a few small gifts for attendees (notebooks with the company logo, clothes with the company logo, or similar), a little something for them to take the experience away with them. These should preferably reflect the theme for the year (e.g., Racing to win). Expect to spend around $2,000 per attendee for a professional event (which varies based on the location, duration of the event, distance traveled etc.).
  9. Require attendance. 100% of your reps should be there to hear the company’s strategy and to network with their peers. If you’ve announced a save-the-date well in advance, you should require 100% attendance; sales reps should be expected to modify customer meetings or other plans if you’ve given enough notice. The best SKOs also have 100% attendance from the executive team — that’s right, even your CIO and General Counsel should be there; this is the chance to show the sales organization that the entire company is behind them and supports their efforts. Given the investment in SKO, you should maximize the ROI through full attendance.
  10. Assign an Owner and Rehearse. Successful SKOs are most successful because someone has been orchestrating the event, and sales leaders are engaged early in planning the agenda and cadence of the content. Someone in your company should be managing the SKO, whether this is Sales Ops, Sales Enablement, Marketing, or if you have a larger organization, an Event Manager. This person or team will ensure that presenters practice their speeches (and stay on time) and ensure smooth handoff between presenters. Even if you are doing an SKO for the first time and you don’t have a dedicated team working on your SKO, you can still make this work with some basic project planning.

These are just a few ideas to help you plan out an amazing and impactful sales kickoff. One of our partners, Sales Benchmark Index, recently published a white paper on this topic entitled, Sales Kickoff is Dead. How Market Leaders Use Acceleration Summits to Make the 2020 Number. Their blog aligns with the suggestions that we’ve outlined to make the Kickoff engaging, impactful, and fun.

So, this is your chance to start the year strong and get your team motivated and excited about the new year. Remember, align the team on a single strategy with a few big bets. Celebrate 2019 but focus attention on what needs to be done in 2020. Make your kickoff the jumpstart that your organization needs to ensure that 2020 is your most successful year yet.

This article was originally published on January 6th, 2020 to Insight Partners.



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