Sales Kickoff Planning: A Comprehensive Checklist

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Sales kickoffs present an unmatched opportunity to catalyze widespread action against a company’s strategic goals for the year ahead. An event that gathers teams across the revenue engine together, it is a unique chance for organizational leaders and sales enablement to build alignment around a collective vision for success.

For many sales enablement practitioners, the sales kickoff represents one of the largest and most critical initiatives of the year. This means it requires proactive, intentional planning and coordination with multiple stakeholders to curate an event that moves the needle on revenue performance.

“The biggest takeaway for anyone planning a sales kickoff is it’s never too early to get started,” said Callie Apt, senior director of global sales enablement and proposals at Domo, Inc. “It’s really like an external event almost, except it’s internal. There are a lot of different players involved.”

As the ways in which sales kickoffs are delivered have drastically changed for many over the past two years, with shifts between in-person, virtual, and now hybrid events, the planning process this year calls for sales enablement to think strategically about the content, communication, and delivery to ensure it resonates. Here are key steps to take when planning a sales kickoff to ensure effective execution.

Define the “Why”

Before crafting an agenda or recruiting speakers, it is important first and foremost to take a step back and center on what the purpose of the sales kickoff is this year. The overarching reasons why companies conduct a sales kickoff each year can transcend industry, market, and geographical lines, from unveiling new company initiatives to communicating business goals and celebrating past successes. However, practitioners can dig deeper into what the desired outcomes of the sales kickoff are in order to create an event that inspires the right actions.

To get to the root of the event’s “why”, consider these three steps:

  • Pick a theme: Themes help to create continuity across the entire event experience from start to finish. This can help drive engagement from the audience by creating a recognizable throughline to follow between sessions. Not to mention, it can also serve as a springboard for creating activities, building buzz, and encouraging participation.

“[The theme] drives all of our content creation and strategy,” said Apt. “We leveraged our own internal creative team to bring our theme to life, which was ‘Elevate’ this year…It’s really important to get that early because if you don’t have that, it’s hard to plan and to get things done. Set the theme early and then that can help you set your agenda.”

  • Identify objectives: To drive alignment with all stakeholders involved as well as ensure expectations for reps are clear, setting a few actionable objectives upfront is necessary. In identifying the right objectives, start by aligning with leaders on the larger company objectives that they have defined for the year ahead. Then, enablement can map those to the behavioral outcomes that are needed to achieve them.
  • Craft a cohesive message: With the theme as the foundation and objectives as the anchors, enablement can create cohesive messaging that can be used to both communicate the event and its purpose to key audiences as well as align speakers and leaders on the common language that can be used to reinforce that purpose.

“[Our leadership team] had to have a consistent message,” said Michelle Dotson, head of sales enablement at Zoom. “They needed to anchor to the same pillars…We really focused on having a cohesive message, strategy, pillars, and objectives for the events that all of the leaders knew about, agreed to, and reinforced throughout every session.”

Rally Stakeholder Support

With an enticing theme, structured objectives, and clear messaging, practitioners can evangelize these foundational pillars to engage partners and secure support from key stakeholders. In the planning phase, support needs to come from the top-down. To rally stakeholder support, take action across three levels:

  • Gain executive buy-in: Leadership must be bought into the direction event, as their presence and engagement in the event itself can serve as a core source of motivation for reps to both attend and actively participate. Messaging can carry more weight when it is reinforced by the top leaders of the organization. Similarly, it helps validate that the strategy and purpose the sales kickoff is driving toward will help deliver value against company goals.

“We always make sure to invite our entire C-suite and actually have them be extremely engaged,” said Jamin Fochtman, head of sales enablement at Addepar. “Our CEO, CFO, COO, they all take part in our sales kickoff.”

  • Engage subject matter experts: No sales kickoff can be executed by one person alone. It is important for cross-functional partners to be involved from the beginning to contribute expertise and share feedback. Not only can they help provide guidance on the direction of content, but they can also help build excitement for the event among their teams.
  • Set regular communication cadences: Engaging key stakeholders is not just a one-time event. Rather, it’s important to consistently provide updates in order to improve visibility and ensure stakeholders remain informed on important decisions and progress.

“You really want to get leadership input, so regular meetings, regular communications are important,” said Apt. “You feel like they’re getting sick of you, but in the end, it’s all worth it.”

Craft an Engaging Agenda

Building the agenda for the sales kickoff is both an art and a science. It is an art in the sense that the sessions outlined can take the audience on a journey and help them think about critical topics in new ways to spark innovation. At the same time, it is a science in the sense that the formats chosen and the way that information is presented can impact how it is digested and retained. In balancing the art and science of agenda building, consider these steps:

  • Identify key topics: In determining the topics to focus on, use the theme as the guide. Then, think about how different key stakeholders, both internal and external, could add value for reps as it relates to the objectives for the event that were outlined at the onset. It’s important that topics can align around the common theme, but offer unique value to keep the audience engaged and the information fresh.
  • Determine session formats: The format for sessions is highly dependent on the environment in which the event takes place. For example, highly interactive, longer-form sessions can do well in in-person environments where part of the value lies in building relationships and connections. On the other hand, short and digestible sessions that minimize opportunities for distractions are critical in virtual environments. Similarly, if the event contains virtual components, it is necessary to account for the different time zones and regions that people will be logging in from.

“We asked: who is attending, what time zones are they in, what’s their tenure, how do I tailor this event so that from the moment they are logging on they are engaged and it’s relevant to them,” said Dotson.

  • Invite unique and diverse speakers: In sourcing people to present sessions, think about including both those who have platforms that can carry weight with attendees as well as those who have valuable perspectives to share who may not often get this high level of visibility with those in the audience. Including diverse voices can help build resonance with diverse audiences and introduce people to perspectives that can motivate them to think in new ways.

“There’s a lot of great speakers out there, and I would just say to build in time for something different, something outside of the norm,” said Apt. “Not something about how to get more leads, but something a little bit fun and different.”

Practice and Gather Feedback

Just as reps need to practice and receive constructive feedback on new skills before engaging externally with customers, it is also important for enablement to carve out time in the planning process to test the event, gather feedback, and ensure quality standards are met. To do so, follow these steps:

  • Review content and ensure quality: To validate the quality of the sessions, it can be a worthwhile exercise to enlist a team of cross-functional representatives to review content and provide feedback. This can help catch any gaps or misalignments, as well as any overlaps that can be avoided to ensure each session delivers unique value.

“We had any content that was being presented go through what we call our SKO content review committee because we wanted to make sure that everything was aligned with our go-to-market strategy, that we had quality control, and just make sure that we had proper representation from all the groups and regions at Domo,” said Apt.

  • Test event execution: Similarly, the systems and logistics also need to be thoroughly tested in advance to work out any kinks and establish contingency plans as needed. As part of this, be sure to establish clear roles and responsibilities for anyone who will be involved in behind-the-scenes execution.

“It was really helpful for me to do a dry-run with just a 45-minute team meeting,” said Fochtman. “I just wanted to test out a few different workflows…That was critical for my planning phase in terms of using the functionality and seeing how the team responded to that functionality.”

  • Offer a central place to gather feedback: For both the content and logistical testing, ensure all people taking part in the testing have a centralized location to submit their feedback. Even better, standardize the format of feedback using a form or survey to make it easier to identify trends and create solutions.

Build Momentum

Finally, dedicating some time and effort in the planning process to promoting the event and building hype will help drive engagement during the event itself. This requires thorough communications plans for the lead-up to the event, crafting positioning around the benefit for attendees, and planning how to reward attendees during the event to keep them engaged and motivated.

  • Create communications plans: Establish methods for how important information regarding the event will be communicated to attendees, including when certain messages will be broadcast to build interest and excitement. For example, perhaps a movie-like trailer can be produced to reveal the theme or a game can be facilitated to unveil the agenda. The timing, method, and actual content of the communication are all key considerations.
  • Justify the audience value: Attendees want to know what is in it for them to participate in the event, especially since it will require reps to shift their focus away from their day-to-day selling activities for the duration of the event. It can be helpful to enlist the support of frontline managers in communicating and reinforcing the value of the sales kickoff for reps in the days and weeks before.

“We actually held a manager kickoff before we held our sales kickoff,” said Apt. “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.”

  • Plan extrinsic and intrinsic rewards: One of the key aspects of a sales kickoff is recognizing and celebrating the achievements of the previous year. In doing this, think creatively about how reps can be rewarded through both extrinsic means such as gift boxes as well as intrinsic rewards such as career development workshops. Making space for both of these during the sales kickoff can help boost morale, and teasing some of these benefits ahead of time can also serve to further validate the benefits of attending.

Creating a sales kickoff that is not only an enjoyable experience for attendees but also an event that truly sets the tone for success for the year to come can be challenging – especially in a continually evolving business landscape where there is no standard office environment across in-person, virtual, and hybrid. This means that thoughtful and structured planning is more important than ever. By following these steps, practitioners can ensure they check all the necessary boxes to bring an impactful sales kickoff to life.

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