With every coming new year comes the annual sales kickoff event — undoubtedly the biggest meeting of the year for the sales organization. Sales kickoffs, also known as SKOs, are not only an opportunity to share strategic insights for the coming year, but they’re also a unique opportunity to showcase and reinvent one’s sales culture. To pull off a successful SKO, it’s key to provide enablement and relevant stakeholders ample time to plan accordingly. With that in mind, here’s a go-to guide for hitting a SKO home run in the new year.

What is a Sales Kickoff?

A sales kickoff is an annual gathering of the sales organization, the goal of which is to generate momentum for the year’s upcoming go-to-market strategy, to lay the foundation of new initiatives, and to recap on accomplishments of the previous year. A well-designed SKO should contribute three main purposes for the sales organization:

Educate: Inform the sales teams of what the goals are for the next year, what specific sales strategies they’ll adopt to get there, and any critical updates regarding new products, services, or capabilities that reps need to know before heading out onto the field.

Celebrate: Make reps feel appreciated and valued by leadership through toasting last year’s big wins and major accomplishments.

Inspire: Reinforce key company values and the overarching vision of the organization, creating a strong sense of culture and community for the sales team. This is also an ideal opportunity to spark a renewed culture and set of principles that adequately reflects the diversity and inclusion that the organization should strive for.

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utilize those departments to support the execution of their sales kickoffs

Fundamentals of Sales Kickoff Planning



Set objectives of what the SKO should accomplish

SKOs are typically large-scale events that require a substantial investment of time, energy, and resources. This is why it’s essential for sales enablement and sales leadership to collaborate on the main goals and objectives for the SKO to ensure alignment throughout the planning process.

This starts with establishing what the goals are for the sales org in the upcoming year, and ensuring SKO sessions, meetings, and activities ladder appropriately. 

Then, sales enablement and those involved in developing sessions should be sure to communicate early and often what the value proposition is for sales reps in attending and participating in SKO activities: 

  • Are there new products that they’ll be informed of and receive preliminary training on?
  • Is leadership addressing issues from the past year, with their proposed path of resolution?
  • Is there anything impacting morale that should be addressed?


Make “fun” an absolute

Not only is it important to keep spirits and engagement levels high for the SKO, but organizations should view them as a critical opportunity to reinforce a positive sales culture that prioritizes the well-being of their employees. In order to achieve this, keep SKOs fun and exciting, and make it the event that sales reps look forward to year after year.

Choose a theme:  Select an appropriate theme that can be reiterated throughout the entire event. Ensure themes are relevant to the morale, culture, and goals of the sales organization. Theme ideas can center around company slogans, popular movies or TV shows, or concepts that reflect new goals such as technology or customer-centricity. Go all out, if possible, and create a theme-branded logo for SKO-related emails and for hand-out materials, like the event’s agenda.

Create momentum weeks ahead: Get your sales teams excited for the event by building hype ahead of time. If there are speakers on the agenda that are particularly interesting, provide teasers that reveal or hint at who they are. Come up with a catchy theme-related hashtag and start using it in communications before the event so it begins to resonate with reps. Weeks before, start sending out “countdown” emails once a week with reminders about notable sessions or workshops.

Incorporate games and prizes: Between longer or more process-heavy workshops, build in gamified sessions where reps have to compete on teams for prizes. Games can focus on quizzing reps about product offerings, competitors, or sales methodologies. Games and incentives are key to increasing engagement and knowledge retention during SKO sessions, which is critical to maximizing ROI for the event and delivering on desired objectives.

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Determine necessary resources and expected ROI

Stakeholders should meet early in the planning process to determine a viable per-head budget for the event. Once all of the costs of the event have been taken into consideration and the number of participants finalized, then leadership can decide what the expected impact on revenue will be. One method of determining the ROI is to measure the expected revenue influenced or generated per sales rep as a result of the SKO’s outcomes.

In the case of virtual sales kickoff events, many organizations will likely notice lower overall operating expenses. However, to ensure a successful event, consider re-allocating some of the original budget towards meal delivery gift cards and special swag packages delivered to rep’s homes. For the grand prize of the event’s biggest game or competition, invest in something special that will get the reps and attendees excited.


How much will your organization spend on their annual sales kickoff this year, on a per rep basis?

Sales Kickoff Panels, Keynotes, & Workshops

While sales kickoffs should always be fun, they should also be informative and have tangible value for sales reps. Panels and workshops are great ways to provide content that’s impactful and tied to their success and professional development. Consider the following types of sessions:

Selling techniques

This is a chance for reps to learn from the best. Interview high-performers from the previous year to gain insights into their process, and translate that into an actionable approach for the coming year. Consider having top performers participate in live role-play sessions or real-life phone calls with prospects that demonstrate what “good” looks like.

Case studies

Take a look back at some of the biggest closed deals of the year and reflect on their attributes. Consider inviting the customer to speak at the event to provide their perspective and experience in working with the company. Take it a step further and allow reps to ask them questions in order to glean the most relevant insights and promote discussion.

Product updates

The SKO is the ideal place to not only demo and showcase updates to the product that reps will be selling, but it’s a key opportunity to deliver tactical information on how to position these new features with their customers or prospects. Again, always be tying the purpose of a session to how it creates lasting value to the reps in attendance.

External speakers

Bring in industry leaders, subject matter experts, or motivational speakers to give a keynote presentation. Speakers should align with the theme or slogan, as well as the morale and culture of the organization at the time of the event. For smaller panels, consider bringing in consulting firms who can speak to emerging business trends and/or market research on the industry your organization is involved in.

Fireside chats with leaders

An alternative to presentations or traditional Q&A’s are fireside chats, with a moderator that guides the conversation with the presenter. The presenter, ideally, should be a person within the company that sales reps typically don’t get a lot of face time with, like the CEO or VP of sales. Consider having an option for reps to submit their own questions to get the full engagement from the audience.

Cultural Refresh

In today’s current economic and social climate, leadership should use the sales kickoff event as an opportunity to address some of the concerns that their sales teams might have. With many organizations working towards a more diverse, inclusive, and collaborative culture, the sales kickoff event can be an ideal time to kick-start that change for the new year, and in turn creating lasting trust and loyalty among employees.

It’s important to not be apathetic about culture. An apathetic culture can get really toxic, really fast. It’s on us as enablement leaders, but also on our sales leaders, our HR teams, and others to jump in and be able to shape that culture every single day.

Kayde Givens

Senior Revenue Enablement Manager, Carta

Learn more about using the SKO as an opportunity to kick-start culture change for the sales organization:

Read the Article

Planning Your Virtual Sales Kickoff

Although the pandemic has put a hold on domestic travel and large gatherings, that shouldn’t prevent the sales organization from having the biggest team-building event of the year. In fact, now more than ever, these types of events are an opportunity to remind sales reps of how much their dedication during these trying times is appreciated. Here are some tips and considerations for planning a virtual sales kickoff event that will keep reps engaged and pumped up for the coming year.

In order to ensure that contents of panels and workshops are well-presented and that transitions run smoothy, be sure to conduct practice runs of sessions with internal and external stakeholders. Running tests are not only ideal for getting feedback on quality, but they’re also helpful for sussing out any technical issues. Be sure to establish contingencies for day-of problems that arise, with support teams alert and ready.

jamin fochtman

Some organizations have sales teams on different coasts or on different continents, so it’s important to be mindful of these when writing out agendas. If sales teams are global, consider customizing the panels and sessions to better reflect experiences within a respective time zone and geography.

michelle dotson

Similar to virtual learning or training programs, SKO sessions should be shortened to prevent fatigue from sales reps. Consider chunking workshops, panels, and keynotes into 15 or 30-minute increments, and incorporate breaks far more frequently than one would in-person. Use music, sound effects, and lively graphics to introduce speakers or presentations and incorporate throughout to keep the energy high.

virtual learning

In a virtual SKO, games are even more important in creating an interactive, engaging atmosphere that more closely mimics the inclusivity of in-person events. Not only do games drive engagement, but they can also improve the gathering and retention of key informational materials being presented.

mary tafuri podcast

Post-Sales Kickoff Planning

Video conference

In order to get the maximum ROI from your in-person or virtual sales kickoff, ensure that post-SKO programs are in place to reinforce the principles, educational experiences, and concepts that laid the foundation of the event.

  • Have a plan for the rest of the year: Plan in advance when leadership and managers can reinforce key messages or values. Use the SKO hashtag or tagline throughout the year in internal emails and social media platforms.
  • Use a takeaway template: At the end of the SKO, give all reps a template or form to fill out that has them reflect on the three most prominent takeaways of the event. Then, prompt them to write down how they’ll apply those takeaways throughout the year.
  • Use surveys to get feedback: After the SKO is over, send out anonymous surveys that sales reps are highly encouraged to fill out regarding their evaluation of the event. Be specific in the questions you ask to get meaningful feedback. Then, next year, make a point to address and reference the feedback to demonstrate to sales reps that leadership is concerned about their experience.


With a strategic approach that prioritizes the desired outcomes of what the sales kickoff should accomplish -- along with a creative and versatile pathway for getting there -- the annual SKO can be a triumphant event that creates lasting momentum for the new year's initiatives and goals. Always remember that the goal of the SKO is to educate, celebrate, and inspire, and you'll be well on your way to delivering a successful event for the revenue-facing teams that deserve it. For more resources, view all of Sales Enablement PRO's expertise as it relates to sales kickoffs.

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