Sales kickoffs: How to plan an effective SKO event

Have you been tasked with planning your company's next big sales kickoff event? If so, you're in good company. As the Senior Director of Revenue Enablement at Meltwater, I've had my fair share of experience with this overwhelming - yet incredibly rewarding - process.

Over the years, I've learned that pulling off a successful sales kickoff (SKO) isn't easy - it requires meticulous planning, laser-focused stakeholder management, and the ability to sweat every last detail.

But when you see it all come together and witness the energy and excitement, it's all worth it.

That’s why I'm here to share some of the key lessons I've learned to help you ensure your event is a huge success. From setting the right foundation to managing the countless moving parts, I'll walk you through the proven strategies that have worked for me time and time again.

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Teams that actively share best practices hit roughly 82% of quota, while those that don't manage just 32% (AI and Sales eBook, 2023). So let's get you in the first camp.

So let’s get started!

Watch the full conversation with Lisa. For a more comprehensive overview, check out Your guide to Sales Kickoffs (SKOs) video.

What is a sales kickoff?

First, let's clarify what we're talking about. A sales kickoff (SKO) is typically a one or two-day event held at the beginning of a fiscal year or quarter. It's where your entire sales team comes together to align on strategy, learn about new products and initiatives, and get energized for the challenges ahead. Think of it as your annual opportunity to unite the troops, share the vision, and equip everyone with the tools they need to succeed.

Why a strong SKO matters

Sales kick-offs are more than just annual get-togethers - they set the tone, pace, and direction for the entire year. For sales enablement, this is our opportunity to rally the team, align on strategy, and equip our reps with the knowledge and skills they need to succeed.

But beyond strategy, SKOs are all about connection – bringing people together, inspiring them, and making sure everyone leaves with renewed energy and clarity about the year ahead. A well-run SKO does more than pump up the room—it aligns the whole team around the year’s mission. After Google rolled out a focused coaching and alignment program, meeting effectiveness and partner CSAT jumped by three to nine points (5 Key Shifts Workbook, 2022). That’s the kind of lift you can create when everyone pulls in the same direction.

The real magic of an SKO lies in creating an experience that resonates. Every rep should walk away feeling inspired, more capable, and excited to tackle their targets.

So, let’s dive into the planning process that makes all of this possible.

1. Start with clear goals and a cohesive theme

The first step in planning a great sales kickoff is to get really clear on your goals and the overarching theme or narrative you want to weave through the entire event. This has to be your North Star from the very beginning.

For me, it always starts with defining the key outcomes I want our sales team to walk away with - what do I want them to know, feel, and be able to do differently as a result of being at kickoff?

This could be anything from introducing new products and features to aligning on go-to-market strategy, highlighting customer success stories, reinforcing critical selling skills, or simply reigniting their excitement about the year ahead.

Once I have those clear goals in mind, I work closely with sales leadership to land on a unifying theme that will tie all the content and activities together in a cohesive way. This theme becomes the foundation for everything - from the event branding and the visuals, to the storyline that each presenter weaves through their session.

I've found that choosing the right theme is crucial. It needs to be engaging, on-brand, and something that your reps will genuinely connect with. One of my favorite examples was a kickoff we did that had a musical theme - we framed the whole event around the idea that we were all different instruments in an orchestra, each playing a unique role, but coming together to create something magical.

2. Building the agenda

With the goals and theme locked in, I then started to build out the agenda. This is where I lean on a pretty consistent formula that I've developed over the years, making tweaks as needed based on the specific business priorities.

The non-negotiables for me are as follows:

Some (actually) fun activities to get the room engaged
Opening remarks from the CEO and/or CRO to set the strategic vision
Updates from product on new capabilities and roadmaps
Guidance from marketing on how they'll be supporting the sales team
Customer success stories and testimonials
Opportunities for reps to share their own best practices

Let's dive into each of these...

Team building activities

You can't expect your sales team to collaborate effectively if they don't know each other. I always kick things off with icebreakers or team challenges that tie into our theme. For virtual events, this becomes even more critical - consider digital scavenger hunts or breakout room competitions that get people interacting beyond their usual circles.

For more specific guidance, explore these tips for your next virtual SKO.

Executive and leadership presentations

The non-negotiables for me are opening remarks from the CEO and/or CRO to set the strategic vision. But don't just default to standard presentations. I try to mix up the formats - maybe a fireside chat with the CEO, or a panel discussion where sales reps can ask leadership direct questions. Your team needs to understand where the company's headed and how their efforts contribute to the bigger picture.

Product training and updates

Your sales team can't sell what they don't understand. Dedicate substantial time to updates from product on new capabilities and roadmaps. I bring in product managers to showcase new features, but more importantly, to explain the customer problems these features solve. Include hands-on workshops where reps can practice positioning these updates in real selling scenarios.

Sales skills development

Beyond product knowledge, your team needs sharp selling skills. I incorporate role-playing sessions, objection handling workshops, and negotiation training. The key is making these interactive - nobody wants to sit through another PowerPoint on sales methodology. Get reps practicing with each other and sharing what's worked in the field.

Recognition and celebration

Never underestimate the power of recognition. I always build in time to celebrate wins from the previous year - not just quota achievements, but creative problem-solving, teamwork, and growth. Feature customer success stories and testimonials that showcase your team's impact. When reps see their peers recognized, it motivates everyone to aim higher.

Of course, I also always make sure to build in some fun, high-energy moments to keep the team engaged and energized.

One of the keys to success here is making sure to have a diverse array of speakers from different backgrounds, regions, and levels of experience, so consider these 7 qualities of an exceptional SKO speaker to guide your selection. I want our sales reps to see themselves represented on that stage, and guidance from marketing on how they'll be supporting the sales team helps create that unified front your kickoff agenda needs.

3. Establishing your timeline

I learned early on that SKO planning takes time, and a lot more than you think! My first big SKO happened just eight weeks after I joined the team at SurveyMonkey. I don’t recommend planning an SKO in such a tight timeframe, but now I know it can be done!

However, when possible, I start planning in August for a January event. This allows me to focus on big-picture goals and themes without feeling overwhelmed by the day-to-day details.

That first SKO at SurveyMonkey taught me how to streamline processes and prioritize under a tight deadline. I didn’t know many people in the company, so I took every bit of help I could get - project management skills were essential here.

Those eight weeks taught me that while last-minute planning is doable, it’s not ideal. Giving yourself and your team three to four months leads to a much smoother experience.

4. Collaborating with stakeholders

As you can probably imagine, there are a lot of moving parts when it comes to planning an SKO, and keeping all the stakeholders aligned is absolutely critical. This is an area where I've really had to hone my skills over the years.

The first step is getting buy-in and alignment from sales leadership since they're going to be such a big part of making the event a success. This can be tricky, because as you know, Q4 is an absolute beast - sales leaders are laser-focused on closing business, and the last thing they want to think about is kickoff planning.

So I've learned to get really proactive about stakeholder management, especially with the sales leadership team. I block time on their calendars months in advance, and I make sure to keep them updated on progress regularly, even if it's just a quick email. I find that the more I can do upfront to get them onboard and excited about the vision, the more engaged they'll be when I need their input and participation.

Beyond sales leadership, there's a whole host of other stakeholders I have to wrangle - product, marketing, customer success, and so on.

My approach here is to really understand what each team needs to get out of this SKO, and then figure out how I can tailor the content and experience to serve their specific needs. I'm constantly communicating with these teams, sharing my plans, and taking on board their feedback.

The other key is using that overarching theme I mentioned earlier to keep everyone on the same page. I coach all the presenters on how their piece fits into the bigger picture, providing them with a customized briefing document that outlines the goals, audience, theme, and message.

5. Sweat the small stuff - but not too much!

I know how important it is to sweat the small stuff when it comes to a high-profile event like a sales kickoff. There are just so many moving pieces, and any little hiccup can derail the whole experience.

That's why I always start building out a super detailed project plan, with nothing left to chance. I map out every single task, assign owners, and build in generous buffers for things inevitably slipping.

I'm a firm believer that no detail is too small to include - everything from coordinating with the venue, to finalizing the run of the show, to ordering swag.

I also make sure to overcommunicate with all the stakeholders, even the ones who just want periodic updates. I find that the more visibility I can provide into the planning process, the fewer surprises (and headaches) we'll encounter down the line.

And of course, taking care of myself throughout the process is absolutely crucial. Planning a sales kickoff is incredibly intense, and it's easy to get so caught up in the work that you forget to step away and recharge. I've learned the hard way that if I don't prioritize self-care, I'll burn out way before the event even happens.

6. Creating a memorable experience

Lastly - and maybe most importantly - have fun! SKOs are so special because they bring everyone together with a shared purpose.

One of the highlights of my career was our SKO in Las Vegas at the Fontainebleau Hotel - a gorgeous venue with a state-of-the-art theater. The high-quality visuals, advanced tech, and a theme built around our innovations in AI made it an event that felt both premium and inspiring.

Every detail, from the sound to the design of the slides, was elevated, and it really made the team feel valued. This experience set a high bar, and the feedback we received confirmed that it was a success. But the most rewarding part was seeing our reps walk away with clarity, excitement, and a stronger sense of purpose for the year.

For me, this is the most rewarding part – seeing your sales reps nodding their heads enthusiastically during the keynotes, actively participating in the breakout sessions, and rushing up to me afterward to tell me how pumped they are - that's when I know we nailed it.

The work doesn't stop there. I always make a point to follow up with the team after kickoff to get their feedback using dedicated SKO survey templates and reinforce the key messages and takeaways. I want to make sure the energy and momentum we build carries through the rest of the year.

Post-SKO follow-up strategies

The work doesn't stop when everyone heads home. What you do in the weeks following your SKO often determines whether the event creates lasting change or becomes just another meeting.

I've learned to plan my post-SKO follow-up strategy before the event even starts. Within 48 hours, I send a recap email highlighting key takeaways, links to session recordings, and clear action items for each team. This prevents that "SKO high" from fading as reps dive back into their daily grind.

Feedback collection is crucial too. I use quick pulse surveys immediately after the event and more detailed assessments two weeks later. This helps me understand what landed well and what needs reinforcement. Plus, when reps see you acting on their feedback, they're more engaged in future events.

Most importantly, I create a reinforcement calendar. This includes monthly check-ins on SKO initiatives, refresher training on key concepts, and regular celebrations of teams implementing what they learned. Remember - transformation doesn't happen in two days. It happens in the consistent application of those lessons throughout the year.

Start with clear goals and a cohesive theme

Common SKO pitfalls to avoid

Over the years, I've learned as much from what went wrong as from what went right. Here are the pitfalls I now actively avoid:

Information overload is the silent killer of SKOs. I've sat through events where organizers tried to cram a year's worth of training into two days. Your reps won't retain it all. Focus on your most critical messages and provide resources for deeper dives later.

One-way presentations drain energy fast. If your agenda is just executive after executive talking at the audience, you'll lose engagement by lunch. Build in discussions, Q&As, and hands-on activities. Your salespeople are used to talking - let them.

Lack of relevance happens when content doesn't connect to daily realities. Every session should answer "How does this help me hit quota?" If presenters can't make that connection clear, reconsider including their content.

Poor follow-through wastes all your hard work. I've seen great SKOs fizzle because there was no plan for what happened next. Before your event starts, map out how you'll reinforce key messages throughout the quarter.

Final thoughts

If I had to boil down my advice into one essential takeaway, it would be this: just start.

It’s easy to feel overwhelmed by all that goes into an SKO. If you don’t know where to begin, start with the theme, then throw everything into a simple project plan template to help you organize. Taking that first step will get the momentum going, and from there, you can tackle each piece one at a time.

So, whether you’re planning your first SKO or your tenth, remember to start with clear goals, keep your team’s needs in mind, and don’t be afraid to ask for help.

Here’s to a successful SKO season ahead!

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"The Sales Enablement Collective Sales Kickoff course was great and gave me some wonderful ideas to put into practice for my organization's upcoming Sales Kickoff."

-Sharon Moore, Revenue Enablement Program Manager at SailPoint

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