Sales Team Management
Revenue Career Growth

The Essential Sales Kick-Off Survival Guide: 10 Tips for Running an SKO That Drives Revenue

Michaela Mendes
Head of Content & Strategy
Table of contents:

This year, don’t run your sales kick-off on muscle memory. 

It’s easy to fall into a pattern of using the same agenda, following the same rhythm, and then – getting the same outcome. This year, use this guide to ensure every single attendee leaves saying, “That was the best sales event I’ve ever experienced.” 

And most importantly – ensure your sales kick-off has a real impact on performance, and subsequently: revenue. 

What’s your sales kick-off budget?

When your sales kick-off focuses your team and drives results, it’s no longer a cost – it’s an investment. 

We polled attendees at a recent webinar we hosted with Saleshacker on how much money companies are investing per attendee on their sales kick-off this year. 

Most respondents are working with budgets of $2,000 per person or less: 

Sales Benchmark Index said the average cost per attendee reported in 2021 was $2,500-5,000. It’s not cheap to run an SKO – for just 50 attendees that could run between $125,000 to $250,000. For a large enterprise sales team, costs can run into the millions.

With that in mind, your SKO shouldn’t be a run-of-the-mill sales event – you need a clear “before and after” moment. This guide will help you stay focused on what matters in the planning process.

What makes a successful sales kick-off? 

There are three ultimate outcomes from a successful sales kick-off:

#1: SKOs should strengthen the organization 

A revenue team that has team-wide buy-in, believes in helping each other, and values encouraging each other is a step above the rest. 

“You should walk out of your SKO with a deeper level of trust built not only within your sales team, but also a greater level of trust in the leaders you're following in the company,” said Leslie Venetz, a three-time Head of Sales and Founder of Sales Team Builder.

#2: SKOs should give clarity

The larger your revenue team gets, the harder it is to maintain focus. Who’s the ideal customer? What do they care about? How do we ensure we’re telling the right story in the market? 

SKOs are about communicating revenue targets, but they’re also about clearing up confusion and giving the team a honed-in vision. What does the world look like if we do our job well and succeed? Who have we helped? 

“When people walk out, they should feel refreshed. They feel excited about what’s coming up. They feel clarity. They know exactly what their mission is,” said Tom Slocum, Founder of The SD Lab and one of the top 50 Sales Leaders to Follow.

#3: SKO should give you team a power boost that lasts all year

It’s inevitable that your team will face ups and downs throughout the year. What’s going to get them through it and keep them motivated? 

Think about how to extend the half-life of your sales kick-off so that the excitement continues.

“How do you carry through that energy, not just for a couple of days or a week afterwards. How do you carry it forward for the rest of the month? Another quarter? Go in with that mindset,” said Scott Ingram, Account Director at Relationship One and Founder of Sales Success Media and the Sales Tech Expo.

Slocum agreed: “What we’re trying to get out of this SKO is what happens in the future. It’s a micro-moment. What are we going to instill that comes three weeks from now, four months from now?”  

Having this perspective helps SKO planners hone in on what matters in the agenda.

Top 3 sales kick-off mistakes to avoid

There are three major high-level mistakes that will instantly derail the success of your sales kick-off:

  • Failing to align on the key initiatives
  • Overloading the agenda
  • Treating a virtual sales kick-off the same as an in-person event

Mistake #1: Failing to align on the key initiatives

Every sales kick-off, a planning committee is formed. Typically, that includes representatives from across the organization, from the C-suite to sales operations to team managers. 

There are a lot of opinions in the room. And there are a lot of different priorities. 

While it’s beneficial to have multiple voices contributing to the agenda, it’s impossible to please everyone. 

First, make sure your core group of decision-makers is able to get buy-in from executive sponsors on what the high-level golas are – the items that are non-negotiable. 

“If there’s misalignment on key initiatives, that’s going to be felt in the sales kick-off,” said Paul De Barros, Sales and Success Lead at Salesroom, and creator of NewTechnique, an interview series with sales leaders on product-led growth. 

“Zoom out and look at the whole agenda. Write down two or three key themes or feelings you want everyone to leave with. If it’s a little bit muddled or you’re confused on what the two feelings should be, then look at the executive sessions you have scheduled. Those are the biggest moments that you can use to double-click into the takeaways you want your team to leave with.” 

Mistake #2: Overloading the agenda 

The second biggest SKO mistake is treating the event like a marathon training session. 

“We tend to over-engineer and cram the agenda because the mindset is, ‘Oh my God, we’ve only got two or three days.’ You try to pack it all in. Leave space and give people time to process. Give people time to connect,” said Ingram.

Venetz takes it a step further: “Having a very training-focused SKO could actually take away from some of those higher-level more strategic conversations or moments of connection that could happen.” 

If your SKO agenda currently is jam-packed with training – it might be time to reconsider the priorities.

Mistake #3: Treating a virtual sales kick-off the same as an in-person event

We polled our Saleshacker webinar attendees and found that most respondents are planning on returning to an in-person, or mostly in-person experience this year: 

But if you’re one of the companies opting for online – experts say one of the biggest missteps is approaching a virtual event the same way you would an in-person event. 

Structure a virtual SKO so that attendees are active participants versus viewers. From polls, to online chats, there are plenty of ways to keep people engaging. 

Keep all sessions short – in fact, max them out at four hours. Instead of trying to pack an agenda of one to two full days, spread it out over a month. 

Don’t just slightly tweak the agenda in a virtual event – take an entirely different approach.

Top 10 tips for running an impactful sales kick-off

Here are the top 10 tips for ensuring a successful SKO and avoiding the most common mistakes: 

  • Communicate the goals in advance
  • Leave time for team-building
  • Train your team on the customer (not the product)
  • Get your data right – and make it mean something
  • Get work done together
  • Elevate the experts already on your team
  • Don’t just focus on the revenue team – build company-wide relationships
  • Give back to the community
  • Give ownership
  • Make a plan to continue momentum

Tip #1: Communicate the goals in advance

While it’s fun to have an air of mystery and suspense around your sales kick-off, your team will get more out of the experience when they know what to expect from you – and more importantly, what’s expected of them. 

Some information you could share with your team in advance: 

  • Speaker list: tell them which company executives or customers will attend so they can come prepared with questions
  • Data you’ll cover: share what reports you’ll go over so they can make sure their pipeline is clean and up-to-date
  • OKRs or revenue targets for the year: you can preview these in advance so they have time to digest and think strategically about new ideas to get there

It’s fine to keep some surprises on the agenda, but make sure your team shows up prepared to connect, engage, and learn.

Bonus: get your team involved in the planning process! Part of the pre-work could be submitting questions or topics the team wants to discuss. 

“Your sales teams typically have burning questions that can be beneficial for wide groups and ideal SKO topics. Solicit your teams and perhaps you’ll uncover some beneficial agenda items,” said Randall Kirk, Head of Sales at Modus.

Tip #2: Leave time for team-building 

Yes, sales kick-off is a good time to dive deep into data. But be careful of how you weigh the agenda. 

“Often SKOs are retros that involve understanding how we can use data to make better decisions going forward. That’s deeply important work,” said Venetz. 

“But I doubt that in six months when we ask somebody their favorite part of the sales kick-off, they’re going to say, ‘I love that pipeline workshop.’ They’re going to remember the white space moments for bonding – those are the inspirational moments.” 

What are some ways to actively create an environment that lends itself to team bonding? 

  • Design small group breakout sessions: Plenty of people (even outgoing salespeople) aren’t comfortable sharing in a larger group setting. Pair people up in groups of two to four to talk through a specific business challenge. This allows for richer conversations, and the takeaways can be shared outside the small group. 
  • Add rest time to the agenda: making team bonding time too open-ended may lead to people using the session to catch up on email or simply rest. Make sure you delineate between team bonding time and personal rest and recharge time on the agenda – that way people will be more likely to participate.

Tip #3: Train your team on the customer (not the product) 

It’s rare to find a sales kick-off without a product roadmap session on the agenda. 

And it’s beneficial to hear what’s coming down the road directly from your product team. 

But if you want your sales kick-off to instantly elevate the conversations your sales team is having with prospects, focus more training time on learning about the target customer. 

“Teach your sales teams how to begin and have meaningful conversations with buyers throughout the sales process,” said Randall Kirk. “Customers expect sellers to help them in their decision-making, with a real focus on their specific pain points. Pick a few key wins and not only highlight and describe the win, but provide details on the conversations that took place between the buyer and seller.”

Scott says to get deeper into the day-to-day life of your primary stakeholders. He recommends interviewing them and asking questions such as: 

  • What is your top challenge right now? 
  • What are you measured on? 
  • When do you get a bonus? 
  • How do you get promoted?

“Think about this as customer training versus product training. The more that we can understand about our customers, the better we can relate to them, and that’s going to make us better sellers,” said Ingram.

Whether it’s a live conversation, or a pre-recorded customer interview, work with your customer success team to identify at least two or three helpful candidates who are willing to share these insights at your SKO. 

Tip #4: Get your data right – and make it mean something

There’s nothing worse than putting up a slide deck full of sales performance numbers, and having the data be chock full of mistakes or inconsistencies. 

When you have incorrect sales data on display, you risk demotivating the team by not properly crediting them for their wins. Or, even worse, bad data could cause negativity and frustration – not the spirit you want at your SKO. 

Quality, correct sales data is central to getting team-wide buy-in on the rest of the strategy. 

“From a sales perspective, there’s attribution on where revenue is coming from, and if that data isn’t accurate, you’ve got SDRs getting frustrated at their AEs, or AEs are blaming marketing. Now there’s little murmurs in the back rooms of your SKO and you have to watch out because it will leak into those relationships,” said Slocum.

“The data has to be super clean, everybody is bought in, and you’re communicating.” 

He recommends sharing numbers in advance – that could mean having sales managers share pipeline data with their teams in advance, or having department heads work together to clean up any attribution inconsistencies.

Beyond just having clean data, Ingram said it’s critical to not just look at sales activity volume. Instead, you should also highlight the metrics that show which reps are getting the biggest payoff from their process. 

For example, ask and answer questions like: 

  • Which reps are the most profitable? 
  • Which reps have the highest conversion rates from discovery to demo?
  • Which reps have the fastest close rate?

“What are they doing that we’re all missing? How are they communicating value in a way that we can all pick up?” said Ingram. He recommends identifying and tracking success signals as a first step to building better best practices. 

“The reason we do a retro is so that we can figure out what we want to carry forward and what we want to leave behind, and it makes it very difficult to make the best decisions for our reps and for our companies if we don’t have that validated data.” 

Tip #5: Get work done together 

Don’t forget – your SKO is an opportunity to get your teams working together. Literally. 

Take a break from learning and absorbing information. Schedule workshop time that actually makes a dent in the pile of tasks you all want to get done. 

De Barros recommends breaking people out into groups to work on real projects because colleagues can start collaborating with each other in a new way – by getting tactical – and it gives the team a power boost the week following sales kick-off.

“It’s time-bound, so it’s not going to be perfect. But if you leave SKO with three sequences written, or your top 20 accounts identified from LinkedIn Navigator, you’ve already started your way up the mountain. I think that helps teams jump into the following week with something already accomplished.” 

Tip #6: Elevate the experts already on your team

There’s nothing wrong with bringing in outside experts to coach your team – but it may not be the best use of your team’s time, or your SKO budget. 

Your existing team members know the customer, the product, and the market, so why not learn from them? 

“Look at the superpowers of the top performers on your team and give them the stage. Give them the opportunity to share the things that they're doing to win,” said Ingram. 

Here are some ideas for skill-sharing sessions your top performers can lead: 

  • Cold email tips and tricks
  • Negotiation strategies 
  • Multi-threading tactics 
  • Objection handling
  • Competitor insights

Tip #7: Don’t just focus on the revenue team – build company-wide relationships 

Revenue doesn’t succeed in a vacuum. Use your sales kick-off as a way to start building relationships cross-functionally. 

“Bring other departments to your SKO. Bring customer success, bring accounting and finance. Everybody makes this happen and all of those relationships are important as we serve our customers. I need all of their help to deliver a great experience,” said Ingram. 

Here are some ideas to make your sales kick-off cross-functional: 

  • Review the attendee list: don’t just invite the C-suite. Make sure the directors and managers who work day-to-day with the revenue team are included in the guest list. If it doesn’t make sense for them to join for the entire SKO, plan one day that’s centered on organization-wide sessions that will be a good use of their time, such as customer training. 
  • Survey other teams in advance: what are the biggest challenges other teams have right now when working with the sales team? What do they not understand? This will help you find blind spots you can actively work to correct at your SKO. A good breakout workshop could be refining the process of how teams work together. 

Tip #8: Give back to the community 

Teams who serve together, stay together. 

If you’re gathering in person, reserve an afternoon and volunteer for a meaningful cause in the nearby area. 

Not only does this give your team a break from information overload, but it shows attendees the company values more than numbers. Sales kick-off can and will enhance performance when it provides individuals with learning opportunities – but it also should show team members why they’re happy they chose this particular employer. 

“We all know we need revenue, but that’s not going to be enough for me to stay in a company anymore. I need to know the organization that I’m working for is tracking towards goals that are slightly more meaningful,” said Venetz. 

Tip #9: Give ownership 

Sales kick-off is not about telling your team exactly how to hit their number for the year. It’s about enabling them to find the answer for themselves. 

“The ideal outcome for me is I want people walking away feeling like, ‘I got this. This feels totally achievable. I know the things I need to do. I know the people that are going to help,’” said Ingram. 

“We’re giving them the components that will allow them to assemble their plan, and now they have ownership of their process and results.” 

How do you make sure your team feels confident and in control after your SKO? 

  • Prep targets ahead of time: it’s tough to make sure you have the entire year’s numbers ready in advance, but work with revenue leadership to get as close as possible to having targets finalized before SKO. You don’t want your team leaving with uncertainty about what they need to achieve this year. 
  • Show them a sales enablement roadmap: communicate when certain check-ins will happen throughout the year with their manager, with the larger team, and what’s on the schedule for training. For example, maybe you’re launching a new tool in Q2. Perhaps you’re bringing on more support in Q3. Give them a vision for the resources they’ll have throughout the coming quarters. 

Tip #10: Make a plan to continue momentum 

Don’t let all of your hard work go to waste. Your sales kick-off should function as the first spark of a fire that burns bright all year. 

One way to make the momentum continue is to have a plan up-front to ensure all content is accessible post-event. 

“You may have just delivered the perfect QBR or SKO, and engagement was off the charts. But, what about post–event when your sales team needs to revisit that new product launch material, training information, customer success story?” said Kirk. 

“Being able to provide that needed info anytime, anywhere, before, during, and after the event maximizes the impact, learning, and adoption.”

What’s the best way to repurpose and redistribute SKO materials for the greatest impact all year long? 

  • Identify what resonated most: first, figure out what was most helpful for the team. Run a post-SKO survey and ask which sessions they found valuable. 
  • Use results to inform future training: build on what works. Take the topics that were most helpful to your sales team and go deeper in future sales enablement sessions. 
  • Build a resource library: turn customer interviews into video clips or shareable quotes your sales team can instantly use or add to slide decks. Document all training and make recordings easily accessible. 

Get ready 

Use our free CRM Health Grader to see if you’re missing critical sales data ahead of your SKO.

You can also watch the full webinar, “A Sales Leader’s Guide to a Killer SKO” here: