The Sales Kickoff 101 Guide

The end of the year is fast approaching, which means two words are on the mind of every sales enablement practitioner: Sales Kickoff. The sales kickoff (SKO) is no small task; it’s an organization’s chance to set the tone for their go-to-market strategy for the entire year, jumpstart any change management initiatives, and set teams up for success to accelerate revenue as the year takes off.

A rare opportunity to gather all salespeople regardless of team together in one room, the SKO is also a critical tool to boost seller morale and amplify a positive, collective sales culture. Sales culture is a rising priority for sales enablement practitioners, especially given the massive costs associated with employee churn. The Sales Enablement Analytics 2019 report found that it costs businesses an average of $150,000 to replace a salesperson.

Sales culture is one of the core areas sales enablement can impact to retain good talent. Sales enablement has a massive opportunity to scale a positive sales culture by creating a dynamic SKO that effectively meets three core purposes:

1. Educate reps with proven effective knowledge: sales strategies, product updates, and best practices.
2. Celebrate past accomplishments, letting salespeople know their contributions are seen and appreciated.
3. Inspire reps with confidence and momentum to drive their success throughout the year.

To create a truly memorable SKO that starts the year off on the right footing, sales enablement professionals need to think beyond PowerPoint lectures and consider how to inject energy into the event’s entire look and feel. Being able to match this high energy with compelling and important information that can be leveraged year-round will ensure the event lays the foundation for a positive sales culture that can be built upon throughout the year.

Getting Started: The Foundations

Before the SKO can successfully get off the ground, it needs a rock-solid foundation to launch from. Every SKO planning phase should begin by assembling key building blocks: objectives, the right people, a detailed agenda, a clear budget framework, and ideal timing.

The Objectives:

Before scheduling the SKO, a critical first step is to look at the big picture and fully consider if, and how, you will be adding value with the event. If there are not clear goals and measurable outcomes for the event and how the event will improve the culture, then organizations need to reanalyze why they’re throwing it in the first place. Sales enablement practitioners should be able to articulate the return the company will see as a result of its investment in an SKO.

The Team:

Start by staffing the initial planning committee. At a minimum, the committee should include the sales enablement practitioners that are ultimately responsible for the event, event planners, subject matter experts assisting with content for sessions, and audio and visual support. SKOs are a cross-functional effort, so ensure you engage the right people across all departments to leverage knowledge and creativity throughout the company. In turn, this promotes and demonstrates the value of a collaborative culture.

“It is a forcing function that allows you to bring different people across the company to drive those strategic conversations and drive alignment,” said Carrie Bustillos, senior director and chief of staff to the senior vice president of worldwide field operations at Autodesk.

The Agenda:

Agendas will vary greatly by the size, goals, and resources of a company. However, all should include some level of built-in dynamism and adaptability.

Rather than planning out the day minute-by-minute for every participant, consider adding in some options for participants such as different track sessions or break-outs specific to different teams or roles. This helps adapt the agenda to the varying needs of different teams while still promoting a unified theme and culture. It’s not uncommon to find it helpful, or even necessary, to rewrite an agenda many times as one prepares their SKO.

The Budget:

Early in the planning process, meet with stakeholders to determine the budget per head. This includes how many people will be required to attend, if there are any teams where attendance should be optional, and who will be traveling in and for how long. This will impact the selection of theme, location and venue, catering, event staffing, and more.

Prepare a solid case for the budget you need to execute the event successfully and be ready to defend the value of every expense in order to secure the necessary funds. Help draw the correlation between the outcomes you anticipate in culture improvement and employee retention to illustrate the potential impact of the event.

The Timing:

Typically, SKOs should take place within the first few weeks of the fiscal year. But since they often span at least one full day, and sometimes multiple days for certain teams, it is especially important to be mindful of when the event is likely to cause the least disruption to workflow. For example, try to avoid the end of the month or quarter. Also, consider scheduling for the middle of the week to add a buffer for those traveling in from out of town. This helps promote a healthy sales culture because it demonstrates to the sellers that the organization understands the demands of their jobs and respects their time.

“It’s critical to be very sensitive and very aware of the seasonality of [the sales team’s] time,” said Marcela Piñeros, senior director of sales enablement at NewRelic. “So, what weeks are completely off-limits, what months are completely off-limits, when are you more likely to get their attention?”

With clear and defined goals, a strong team of experts, an agile agenda, a realistic budget, and thoughtful timing, sales enablement practitioners can ensure the SKO is set up for success from the beginning.

Core Strategies to Build and Amplify SKO

Once a solid foundation is in place, dig deep into the details to design an experience that will leave a lasting impression on the participants. Here are three core strategies to amplify the effectiveness of any SKO.

Sell the Value Early and Often

It’s easy for individuals to dismiss their company’s sales kickoffs as “back-to-school”, either not worthy of their time or unnecessary for them. Sales enablement needs to sell the value of SKO and its necessity to the rest of the organization in encouraging a healthy sales culture. This means building excitement and anticipation across the entire sales organization through consistent, compelling, and fresh information that hooks people in before the event kicks off.

Selling sales kickoffs also means making the event enjoyable with a theme that engages all participants and unifies the event content, sessions, and materials. Ultimately, this helps deliver a more memorable and cohesive experience that will help elevate a consistent, positive culture. Begin promoting this theme weeks in advance to build excitement. Find out where reps spend time daily and set up visual cues there, for example with posters around the office or themed messages in their email or instant messaging platforms.

Finally, start at the top by engaging with department leaders and turning them into champions for the event. This can cause a ripple effect through the teams in their orbits.

Keep the Energy High

While SKOs offer a crucial opportunity to educate reps on new tool rollouts, process changes, and updated messaging for the go-to-market teams, it’s important to pay attention to the format this information is delivered in. A long agenda of lecture after lecture can overwhelm the audience and derail their attention, which can negatively impact the cultural atmosphere at the event. Rebuilding excitement after it has gone stale is an uphill battle, so it is crucial to build energy at the start and maintain momentum. Consider the creative ways you can deliver information in an interactive way that invigorates the audience.

“We make sure they get face-to-face interaction with subject matter experts, they get to ask questions, we play games with them, and it is their critical time for learning, for understanding what they need to know to be successful,” said Laura Welch, director of sales enablement at HP.

To keep spirits lively throughout the event, stagger heavier content sessions with more entertaining sessions such as a role play contest or a hype video celebrating team wins. Beyond just the delivery and format, leverage audio and visual resources throughout to set the mood in the look and feel of the event — there’s no understating the value of a good playlist to keep morale high in between sessions.

Emphasize Past Wins and Future Aspirations

Celebrating key wins and success stories from the past year is a no-brainer, but too many SKOs stop here. Instead, take the opportunity to scale a supportive culture of learning across the entire organization by using celebrations as teaching moments. Demonstrate proven patterns for success and break down the best practices used by top performers that others can emulate.

Similarly, SKOs are a perfect venue to involve first-hand customer perspectives to explain the best practices that led to their decision to buy from your company. Inviting important clients to speak about how salespeople have provided them with excellent buying experiences can provide reps immeasurably valuable insight into what behaviors translate to wins. Furthermore, it can spark curiosity from reps to dig deeper into best practices and seek out learning opportunities beyond the SKO to refine their own skills, ultimately fostering a culture that values learning.

As you plan your sales kickoff this year, take time to consider what you can do to educate, celebrate, and inspire the company with a memorable and effective experience that scales a positive sales culture across the company. Begin by building a strong foundation that aligns to key goals for the company. Then, leverage your team and subject matter experts to craft an agenda that will energize the sales team and give them the tools to be successful all year long. Start building the momentum now to take your next SKO to the next level, and improve the sales culture as a result in the year ahead.

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