If you are planning your first annual sales kickoff meeting, chances are your company is young and your team is small. It can be tempting to just put your head down, keep forging through the day to day and put the whole thing off.
In a small team, a sales kickoff can feel like, “What’s the point? We all talk and meet every day anyway, there won’t be anything to do in a sales kickoff, and we’re all too busy to take time away.”
And yet, no matter your size, nothing could be more important than coming together at the start of the year (and really the start of each quarter too) to review, plan and collaborate. Once you have a few salespeople you should begin the regular cadence of kicking off the year and quarters together in a slightly formalized way. It’s an important part of forming your culture, it’s
So if this is your first annual sales kickoff event, and you aren’t quite sure where to start, or how much time and money you should invest, here’s everything you need to know.
What: A 1-2 day offsite meeting. Ideally followed by a 1/2 day at the start of each quarter.
Who: Everyone in sales. Also consider guest appearances by leaders from marketing, product, operations and customer success.
When: The first week of January (and the first week of each quarter).
Why: To set the tone and goals for the year, review department and individual plans and progress, and help provide fuel to propel you toward hitting your numbers. You may also want to do some skill development and training during this time together.
Where: An annual sales kickoff should be held somewhere offsite that’s free from distraction, with everyone in attendance. Quarterly kickoffs can be held in a conference room at HQ, or virtually via video meetings if you are a remote team.
Your sales kickoff checklist
Keep it simple.
You don’t need paid speakers, an over-the-top exotic location or bells and whistles. Keep your first sales kick off pretty simple.
Have a theme.
Every great sales team has an annual sales theme. I don’t know if that is actually true, but I have never met a high performing team that didn’t have a guiding theme for the year. Rallying around symbols is an important cultural aspect for sales and your annual theme is a mantra to keep everyone focused on what matters most. Pick a theme that crystalizes what the point of the year is. To give you an idea, I’ve recently seen themes like:
- Best year ever
- Work smarter
- Won’t stop
- Just sell
- Sell right
- Land and expand
- We win together
- We learn, we grow, we win
As you can see, sales themes
Have a point.
Similar to your theme, you need a point to bring everyone together. As a leader, know what to accomplish and why you are doing the offsite. Is it to boost morale? Update staff on the corporate strategy for the year? Align goals? Shift focus? Have your reps present their territory plans? Train and develop skills? You can’t do it all in a kickoff, so choose what’s most important to the team right now. Know what you want to accomplish and keep your content and presentation focused on that.
Even the best sales leaders sometimes aren’t prepared for a Monday morning meeting and have to wing it. But you can’t wing a sales kickoff. Prepare well in advance, and give yourself plenty of time to create your agenda, schedule and content. This is one case where almost every minute needs to be well orchestrated—including scheduling a little downtime for mental breaks and walks around the block.
Use a comfortable venue.
You don’t need a fancy hotel conference room (but that’s nice!). If your team is very small you can hold the offsite at your home, or a meeting room tucked in the back of a local restaurant. Flex workspaces usually have conference rooms you can rent by the day. What’s most important is that people are comfortable enough to settle in for a long day.
Provide lots of food, drinks
Offsites work well when refreshments are plenty. Provide breakfast, lunch, and dinner plus lots of healthy snack options, coffee by the truckload and some beer and wine for the end of the day.
Give away swag, money and praise.
Praise team and individual accomplishments, calling out special achievements, deals
Keep it positive.
A sales kickoff is no time to review the negative aspects of the past year—instead, think of it as a pep rally. Even if you have to review some of the lowlights, don’t dwell. Cover the material with a quick look in the rearview mirror and then switch to a positive outlook for the year ahead. You want everyone leaving the kickoff energized, positive and feeling capable and ready to hit quota.
Keep it short.
As your team grows there will be more to cover. A two-day annual sales kickoff is common. But your first annual sales kickoff can be a half day or single day. Something is better than nothing and you don’t need to overextend yourself. The sample agenda below can be compressed into a half day or extended over two days.
Sample annual sales kickoff agenda.
Just a sample of how you may want to structure your first sales kickoff meeting:
- A look back. Provide a look back at key metrics from the previous year. Include total contract value closed, average sales cycle, average contract value, source of deals by category, leaderboard data, win rates by opportunity stage, etc. This is the time to take a comprehensive look at sales metrics and share that information with your team.
- Congratulations! Time for special awards and praise. Consider a bonus or special incentive for the rep who closed the most deals, the rep who closed the highest contract value, the SDR who booked the most qualified opportunities, etc.
- A look ahead. Company goals, team goals and quotas. Review what has to be accomplished in the year ahead, and why.
- What to expect. To support your look ahead, cover what your reps can expect from you, and the company. New major feature releases planned? More leads from marketing? Increased trade show participation? Revamped sales enablement? A new outbound program? If appropriate, bring in leaders from other departments to share news and updates that are relevant to sales. Likewise, share where you need sales to step up (and increase in sales-generated outbound opportunities, for example). Also share key staffing plans if you will be expanding your team significantly in the coming year.
- What’s new. Share new processes, guidelines, territory updates, etc. Even if you have shared these things over the past couple of weeks or months leading into the new year, recap it when you are all together to reinforce new habits and expectations.
- Sales rep presentations. Salespeople should present their plan for the year. How they will build pipeline and hit quota. What they will work on. A review of their past year—what worked, what didn’t. Planning is an important part of being a sales profession and is a skill you want to develop and nurture. Sharing plans with their peers is an important part of that. Provide a presentation template so it is clear what you want each salesperson to cover.
- Key discussions. If there are any topics that warrant group discussion, you can consider including that in your agenda, time allowing. Only include this if there are areas you want to seek rep input, and know that it could take the whole kickoff off course, so carefully consider what discussion topics to include and how to time box those discussions to keep them on track.
- Summary and wrap up. Provide a summary presentation, reinforcing key content covered in the kick off. End on a positive note, with a toast or small celebration where everyone can relax together for drinks or dinner while they wind down and prepare to hit the ground running in the new year.
Now, get planning!
As of this writing, the first week of January has already passed. If you haven’t already planned your event, now is the time to make it happen and pull something off before the end of the month. It’s possible. And it’s important, so get to it!