GUIDE TO SKOs Mastering Sales Kickoff Excellence

With this playbook you'll, learn what it takes to strike success at your sales kickoff — including how to get your sales team hyped for the year ahead (and their new comp plans). Read the entire report below, or download a PDF.

The Impact of a Well-Executed SKO

Within the dynamic realm of sales, a world where targets constantly shift, and customer expectations evolve by the day, one event marks a pivotal moment in the calendar of sales and revenue operations leaders: the Sales Kickoff (SKO).

This gathering isn’t just another corporate meeting.

It’s a celebration of last year’s wins and a time to set the tone (and playbook) to achieve your organization’s strategic goals in the new year with your team’s full buy-in and alignment.

But not all SKOs wrap up with the magical buzz, motivation, and energy leaders hope for. 

Some SKOs leave reps more frustrated after leaders try to bury compensation plans and quota adjustments in the mix of team-building, motivational speakers, and celebrations.

In fact, according to data from TaskDrive, a research analytics firm for B2B and marketing teams, nearly 75% of sales kickoff attendees report that their company’s sales kickoff doesn’t merit an A grade.

What’s more, 29% rate it a C or below.

This guide will help you prepare an A-grade worthy event. And one of the best ways to secure an “A” is through preparation.

No matter how long or how little your runway is to plan your next SKO, make sure your agenda carefully addresses the following:

  • What’s essential to the organization?
  • How does the work of the employees connect to the goals of the organization?
  • Is there a strategic plan or financial target?

“You’ve got to nail all three of these things or don’t do anything at all,” said EverView Executive Vice President Of Revenue Operations Dennis Dube. “In doing so, you’re creating alignment around the organization, how it impacts the individual, and letting them know there is a plan to drive that alignment.”

This is the magic of a well-executed SKO, and it’s the subject of our guide.

Inside, learn how to deliver a packed, punchy, and meaningful SKO and extend its impact long after the event.

25% of Revenue Leaders

Say “alignment to business goals” is most needed area of improvement when it came to sales compensation management.

Purpose of an SKO

An SKO sets the tone for the entire sales team for the coming year.

It serves as a platform to align the team’s goals, strategies, and expectations, providing a unified direction to propel the company forward.

More importantly, a well-executed SKO can have a profound impact on the sales team’s performance, motivation, and overall success.

The event creates a sense of camaraderie and fosters a culture of collaboration, ensuring that everyone is working toward a common objective. By bringing the entire sales team together, an SKO provides an opportunity for knowledge sharing, skill development, and learning from the experiences of top performers.

This not only enhances individual sales reps’ abilities but also strengthens the team as a whole.
Additionally, a well-executed SKO can boost morale, instilling a renewed sense of energy, urgency, and enthusiasm among the sales team. This is especially critical after this past year, when 91% of teams missed quota.

With everyone aligned and motivated, the impact of a successful SKO can be seen not only in increased sales figures but also in improved customer satisfaction and long-term business growth.

A well-executed SKO can have a profound impact on the sales team’s performance, motivation, and overall success.

What every successful SKO includes

So, what should you include in your SKO’s itinerary to ensure success?

Successful SKOs share several key elements, activities, and sessions in common. Take a look.

AgendaA well-planned agenda is essential to ensure that your team covers all necessary topics and that there is a balance between informational sessions, interactive activities, and team-building exercises.
Speaker Line-UpInclude a variety of speakers to keep your team engaged and provide different perspectives. 


Top performers who can share their experiences, strategies, and best practices or take the team through their biggest win of the year.

Executives to speak to the company vision, set clear goals, and how they will cross-collaborate with sales to win. Think: C-Suite including Marketing, RevOps, CEO, VP of Sales, Customer Experience, and Product. 

Directors who can highlight team success stories and run a workshop or exercise that supports the SKO message. 

Keynote guest speaker whose address aligns with the theme of the SKO or overarching goals. Customers and partners make the best guest speakers.
Learning SessionsBreakout sessions and workshops are standard in successful SKOs, providing opportunities for skill development, knowledge sharing, and interactive learning.

These could include sessions on:

Product or new technology trainings
Sales methodologies
Objection handling
Marketing 101 (campaigns, personas, messaging)
Ideal customer profiles
Negotiation skills 
Sales presenting
Time management and productivity
Digital selling and social media
Account planning
Lead generation and prospecting
Roundtable small group discussions with end users
Compensation Plan RolloutA dedicated session is essential to align your sales team with the company’s goals and set clear expectations for their performance. 

Do not let the SKO be the first time your team learns of their new plan.
Award and recognition ceremonyRecognition and rewards for outstanding achievements further boost morale and foster a positive and motivated sales team. 

Some awards you could highlight include: 

Salesperson Of The Year
Rookie Of The Year
Top Sales Performer By Region Or Market
Deal Of The Year
Customer Satisfaction Award
Most Improved Salesperson
Team Player Award
Leadership Excellence Award
Innovation In Sales
Consistency Award
Cross-sell/Upsell Champion
Customer Retention Award
Market Penetration Award
Sales Team of the Year
Customer Advocacy Award
Community Outreach Award
End-of-day team eventFollowing a day of content and activities, a night out with the team presents an excellent opportunity to celebrate and build team camaraderie.

Consider a team dinner or an activity: Bowling, shuffleboard, pickle ball, indoor miniature golf, Top Golf, ping pong, darts, pool, karaoke, comedy show, volunteer event, axe throwing, improv class, barbecue, or trivia

Remember to consider your team’s preferences, inclusivity, and comfort levels when planning these activities.

And never end your SKO on a breakout. Ensure your entire team is together before you close out the agenda.

SKO Best Practices

In addition to a well-thought-out agenda, the most impactful SKOs follow a set of best practices that begin well before the event.

Remember, planning and running a successful Sales Kickoff (SKO) is a complex task that requires careful consideration of various factors.

To help, consider the course of action below.

1. Early Planning

Your SKO deserves a headstart on planning to ensure all logistics are in place. This includes booking venues, securing speakers, and arranging accommodations if necessary.

If you’re hoping to host a successful SKO event in January, the best time to start planning is Q4.

Gather your team, collect feedback from reps, brainstorm ideas, and create a detailed agenda that aligns with your company’s goals and objectives for the coming year.

Ensure your SKO is an inclusive event for everyone by making it accessible to all team members, considering any special needs or requirements.

By starting early, you’ll have ample time to secure a venue, arrange accommodations, and coordinate with speakers and trainers. Additionally, early planning allows for flexibility and the chance to address any unforeseen challenges that may arise.


2. Cost Control

The best SKOs don’t have to burn your budget.

You can create a memorable event in a cost-effective manner. Here are a few tips from seasoned sales leaders and SKO organizers:

  • Hosting your SKO virtually or at your office
  • Skip an outside motivational speaker/coach by bringing in-house or in-network speakers
  • Partnering with sponsors or vendors who can provide financial support or in-kind contributions in exchange for exposure
  • Host meals and coffee breaks in-house
  • Negotiate discounts with vendors
  • Streamlining the agenda to focus on the most critical topics and activities to reduce the duration of the event


3. Align SKO objectives with Company Strategy

The most important part of planning your SKO content is defining the specific goals and outcomes you aim to achieve through the event.

Your outcomes should include (but are not limited to) aligning the team with the new year’s company objectives, introducing new products or strategies, and boosting morale and motivation.

To ensure your SKO aligns with the company’s overall strategy, weave your event’s content through a theme that communicates the strategic direction and goals for the upcoming year.

For example, ​​let’s say the company’s primary objective is customer retention. An ideal SKO theme could be “Building Lasting Relationships.” This theme would emphasize the importance of nurturing existing customer connections and finding innovative ways to keep them engaged and satisfied.

By focusing the SKO around customer retention, employees would be motivated to explore strategies to go above and beyond in meeting customer needs, ultimately leading to higher customer loyalty and increased business growth.


4. Audience-Centric Content

Next, make sure to tailor your SKO’s content to your audience.

Consider the needs and interests of your sales and revenue operations teams. You may need different tracks for new biz vs. expansion reps or for SDRs vs. account managers.

For instance, before planning the next SKO, EverView’s team runs an employee survey to uncover recommendations and initiatives for the new year.

Key findings from the survey then inform the SKO agenda.

“The feedback from the survey allows us to hold ourselves accountable and to help our people feel heard,” Dennis said. “We then line up the SKO agenda according to what’s important to them.”

5. Varied Content Formats

Mix up the content formats to keep the event engaging. Avoid one-way talking to your revenue team as much as possible.

Consider incorporating workshops, interactive sessions, and guest speakers to facilitate group discussions.

For instance, you could host an interactive role-playing exercise. This session allows sales representatives to step into the shoes of 
different customer personas and practice their selling techniques in a realistic setting.

Employees can refine their skills and gain confidence in their ability to handle various customer scenarios by receiving immediate feedback and guidance from their peers and sales leaders.


6. Incorporate Team Building

Your SKO should also include team-building activities to foster collaboration and bonding among team members.


  • Problem-solving challenges
  • Trust-building exercises
  • Friendly sales competition

Indeed shared this great list of team-building activities that includes scavenger hunts, a cold calling competition, Shark Tank pitch-offs, 
and more.

These activities not only strengthen relationships among team members but also enhance communication skills and develop a sense of unity and camaraderie. By incorporating such interactive sessions into the SKO agenda, companies can create a dynamic and collaborative environment that ultimately drives productivity.


7. Use of Technology

Leverage technology for presentations and to facilitate interactive sessions. Consider using SKO apps or platforms for agenda updates, surveys, trivia, Q&As, and feedback.

At QuotaPath, one of our favorites to encourage audience participation and interaction is Slido.

Alas, remember to have a backup plan if something goes awry.


8. Feedback Mechanisms

As crucial as it is to collect input ahead of the SKO, it’s also recommended to collect feedback afterward through anonymous surveys or questionnaires. Both will help you understand what worked well and what needs improvement for future events.

Additionally, you may find it beneficial to hold focus groups or one-on-one meetings with reps to gather more detailed feedback and insights before or after the SKO.


9. Compensation Discussion

It is imperative that the SKO is not the first time your team hears about compensation changes.

Open and transparent communication is critical in this process.

Start by clearly outlining the new compensation plans well before the SKO, giving your sales team ample time to review and understand the changes. You could host sessions or workshops before the SKO to explain the rationale and math behind the new plans.


It takes reps an average of 3 to 6 months to understand their compensation plans and how they are paid.

Your sales compensation communication plan needs to:

  • Include sales-leader-driven workshops to review any changes or adjustments to the plan
  • Explain the why behind the changes and the math
  • Share how the company will support the team with the new objectives
  • Create a safe space for the team to ask questions

This creates a safe space and dedicated time for reps to ask questions and for you to address any concerns or misconceptions.

Then, have your VP of RevOps or Sales run a dedicated session at the SKO to further align and connect your reps’ output directly to your organization’s targets — and how you will compensate them for driving performance.

This approach not only ensures a smooth transition but also sets the stage for a successful SKO where your sales team can focus on learning, collaboration, and driving business growth.

Compensation Discussion

The length of your compensation rollout session at your SKO can vary depending on several factors, including the complexity of your compensation plan, the number of salespeople attending, and the specific details you need to cover. However, it's essential to balance providing comprehensive information and not overwhelming your sales team.

  • Reiterate the North Star metric or goals
  • Connect how the work of your team connects and contributes to those metrics through engaging visuals
  • Explain the math behind the comp plan
  • When a rep/team hits X, the organization hits Y
  • Include how the company will support the team in hitting those targets
  • Resources
  • Enablement
  • Training

  • Workshops
  • Professional development
  • Technologies
  • Cross-departmental collaboration
  • Allow time for a Q&A
  • Set and present clear timelines on when comp plans go into effect
  • Collect sign-off on compensation structures to secure an understanding
  • Provide visibility into their compensation structures so reps have a place to reference their plans and see progress toward goal

10. Recap, Action Items, and Follow-Up

End the SKO with a recap of key takeaways and action items. Ensure that your team leaves with a clear understanding of what’s expected next.

Remember that the success of your SKO goes beyond the event itself. It’s about how well you can translate the energy and motivation from the SKO into actions and results in the field.

Consistent follow-up and support are essential to make an SKO genuinely impactful, which you can achieve through regular check-ins, coaching sessions, and training opportunities.

In the days following the SKO, we recommend:

  • Providing a go-to virtual location for resources discussed during the SKO (recordings of sessions, documents, templates, etc).
  • Sending a follow-up email to your team with links to these resources and an outline of the key takes from the event (personalize it by recapping specific wins and stories from the day)
  • Sending out compensation plans for their review and signature
  • Considering a “fast-start” SPIF as part of your post-SKO incentive plan that ties back to a critical business target highlighted during the event
  • Scheduling a follow-up coaching or training session with your immediate team to dive deeper into one or multiple SKO workshops
  • Hosting a personal goal-setting session with your reps one-on-one to deepen their connection and involvement to the company-wide goals

Furthermore, creating a culture of accountability and recognition 
is crucial.

Set clear expectations and goals, track progress, and celebrate achievements that regularly tie back to events and sessions outlined during the SKO.

  • Team meetings and communication channels can facilitate continuous learning, collaboration, and knowledge sharing based on SKO themes, initiatives, and targets.


If one of your themes at your SKO is on adjusting to today’s market, your sales team could model recurring continuous knowledge sessions at their weekly team meetings centered on “Adapting to Changing Market Trends.”

This provides reps an opportunity to share what they’ve learned and present on:

  • Identifying emerging market trends
  • Understanding customer needs and preferences
  • Adjusting sales approaches to align with changing 
market dynamics

These ongoing knowledge sessions tie back to the SKO and serve as a platform for sales reps to share their insights and experiences in navigating market shifts, enabling them to learn from each other’s successes and challenges.

By investing in consistent follow-up and support, leaders can maximize the impact of an SKO and drive long-term success for their sales team.

11. Stay Agile

Lastly, be prepared to adapt to changes or unexpected circumstances. Flexibility is critical to overcoming challenges that may arise during 
the SKO.

These curveballs can include last-minute changes in the agenda, technical difficulties with presentations or equipment, or even unforeseen conflicts among team members.

However, skilled leaders who organize SKOs can overcome these challenges by maintaining a flexible mindset and adapting quickly. Communicate effectively with the team and address concerns head-on.

Additionally, proactive planning and contingency measures can help leaders anticipate potential challenges and have backup plans. This proactive approach can minimize disruptions and allow leaders to handle unexpected situations with ease.


In the event of technology failure, leaders can have a backup plan to include alternative methods of delivering presentations, such as using printed materials or relying on pre-recorded videos.

You could also have a backup device or equipment on hand to quickly switch to if the primary technology fails.

Celebrate your SKO with us

Throughout January and February, QuotaPath will host a series of SKO Celebration Happy Hours in a city near you. Register below, and we look forward to celebrating with you in person.

Austin, TX – Jan. 18, 2024

Join us at Punchbowl Social Downtown at 522 Congress Avenue.

Boston, MA – Jan. 23, 2024

Join us at Lucky Strike Fenway located at 145 Ipswich Street.

New York, NY – Jan. 25, 2024

Join us at Frames Bowling Lounge located at 550 9th Avenue.

Washington, DC – Jan. 30, 2024

Join us at The Eleanor located at 100 Florida Avenue NE.

San Francisco, CA – Feb. 1, 2024

Join us at Lucky Strike located at 200 King Street.

Chicago, IL – Feb. 26, 2024

Join us at Pinstripes located at 435 East Illinois Street.

Streamline calculating and managing sales commissions

Whether you are rolling out new compensation plans at your SKO or looking to enhance your ongoing commission management processes, QuotaPath is your partner for driving sales excellence and maximizing revenue growth.