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How to Plan a Successful Sales Kickoff

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The end of the year offers the opportunity to reflect and reset. For many enablement practitioners, this can culminate in planning for an organization’s annual sales kickoff (SKO) event.

The SKO is an annual meeting that ideally sets the tone and strategy for the year ahead. It can be an ideal time to spark new motivation and introduce new changes in an organization’s go-to-market strategy. For enablement practitioners, the SKO can be a key tool to align with executive leaders to help boost confidence among sales teams and prepare them for what’s to come in the new year.

And amid the changes happening across industries and throughout the economy, the significance of a successful SKO may be more critical than in previous years to keep morale high and share the goals and initiatives that sales teams should be laser-focused on throughout the year.

Whether the kickoff is in-person, virtual, or hybrid, there are several things to keep in mind as enablement professionals start to tackle the launch of a successful SKO, including gaining executive buy-in and identifying key stakeholders, determining a theme, setting an agenda, and delivering meaningful pre-work for all attendees.

Below, learn four key best practices to consider when first crafting a new SKO event, and download the planning checklist to kickstart efforts.

1. Secure Executive Buy-In and Identify Key Stakeholders

Understanding the audience enablement should keep in mind when planning a SKO is paramount to its success. Gather the enablement team and identify key stakeholders that will need to be involved to ensure cross-functional alignment is achieved.

“What we wanted to do is really set the stage with anybody who manages team members in our revenue organization and let them know what we were planning to focus on, get their support, and really introduce our leaders to the theme,” said Callie Apt, vice president of global revenue enablement at Near. “That was also a chance for us to review the operational cadences and the focus areas that we required this year.”

Locking in executive buy-in is also crucial for a successful SKO as it helps enablement teams to align to the organization’s overall mission and strategy for the year and can make the planning and setting of the agenda a more seamless experience.

A well-rounded group that will be instrumental in contributing their ideas and strategies for the event may include C-suite executives, sales leaders, product management, and marketing. Plus, if the event has an extensive hybrid or virtual component, it’s essential to tap IT for support to ensure the logistics of hosting a hybrid event run smoothly.

2. Determine a Theme and Set Goals and Objectives

A successful SKO often has a clear throughline connecting all of the sessions, breakouts, training, and more. Establishing a central theme that ties all of the components of the event will help ground the messaging, strategy, and expectations for attendees and participants. Themes are also an excellent opportunity to celebrate the culture or aspirations of an organization and can be used as a motivational tool for teams to carry with them well after the event. Implementing the theme throughout the SKO agenda can also help reinforce the main takeaways attendees should expect.

“Some of the big milestones that we had that we set out months before the actual event were first setting that theme because it drives all of our content creation and strategy,” said Apt.

Once a theme is determined, it’s time to set objectives that enablement wants to accomplish. SKOs are often used to motivate, celebrate, and set the scene for a new sales methodology or strategy. Objectives can then set the stage for detailing specific outcomes to expect coming out of SKO.

For example, if one of the main objectives is to motivate teams, it may be helpful to try and track if there is an increase in retention or engagement. SKO can be used as an effective tool in tapping into that engagement across teams and ensuring that people feel like they can collaborate and understand each other in new and exciting ways.

“Engagement is a critical word in terms of how we’re coming together as teams, and that’s not just meeting in virtual environments and discussing in virtual environments,” said Terry Bird, vice president of sales enablement at Vonage. “I think sometimes we have to get away from work completely and take extra lengths to really understand each other as people and how we interact as a team and interact with each other.”

3. Plan the Agenda

After engaging with cross-functional teams on what they’re looking to gain from attending SKO, crafting a comprehensive agenda can dig into the meat of the event and provide an overview of the topics and sessions that will be covered.

An effective agenda may include time for bite-sized training, keynote speakers from the executive team, a mix of presentations and breakout sessions with peers, product demonstrations, and more. Plus, finding opportunities for creative celebration and socialization that reflect a company’s culture.

“Being able to understand what motivates salespeople is key and understanding their personality,” said Joseph Tonye, EMEA regional director of sales enablement at Ivalua. “Once you get a better idea of what is important for salespeople, it becomes much easier. Some people like activities, like kickoffs, some people like to be recognized for their efforts, and some sales reps like to get better knowledge or experiences.”

A key to a successful SKO agenda is to focus on areas of improvement or exciting new developments in products or services that sales reps will want to be knowledgeable on. This is why weaving the overall SKO theme throughout the agenda can be an essential part of planning, as it helps narrow the focus and determine what ultimately needs to be accomplished for reps to walk away with tangible insights.

4. Deliver Pre-Work to Complete Ahead of the SKO

To maximize the value sellers get from the kickoff, consider assigning pre-work so reps can get properly trained prior to more in-depth training or exercises. This will not only help prioritize key learning and reinforcement opportunities during the kickoff, but it will also pave the way for a more engaging event throughout.

SKO isn’t an isolated event, and delivering valuable pre-work for attendees to complete prior to participating can help ensure that reps understand at the onset what to expect and what they hope to accomplish during the sessions and training. It can help reinforce the concepts and knowledge covered throughout the event and put it into practice to maximize the ROI from the kickoff.

SKO is a critical initiative for enablement to put together and can be thought of as much more than just a break from the typical day-to-day of a salesperson. Enablement can help craft a strategy that ensures topics, speakers, and initiatives all relate back to the goals established at a company-wide level. The sales kickoff is a prime opportunity for teams across the revenue-facing organization to come together and collaborate in a meaningful way to take action and work toward those bigger bets in the coming year.

Download our SKO Planning Checklist to get started. 



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