Step-by-Step Sales Kickoff Plan (with Checklist!)

Step-by-Step Sales Kickoff Plan (with Checklist!)
October 21, 2021
SKO Planning

Planning an effective sales kickoff (SKO) event has never been easy, and it’s become even more complicated with virtual and hybrid options thrown into the mix. There are presenters to wrangle, execs to convince, apps to configure, objectives to set, activities to coordinate, and venues to book, among many other tasks. This step-by-step guide (with accompanying, printable checklist) will help you organize all of the aforementioned and plan a kickoff that not only pays for itself, but boosts team morale and revenue all year long— while keeping your stress level in hand.

Step-by-Step Guide to SKO Planning

#1. Identify and Form Your Kickoff Planning Committee 

Identifying who will be planning your sales kickoff is the first essential component to determining the strategy behind the event no matter whether your event is in-person, virtual or hybrid. Who are the key stakeholders that need to be involved to ensure cross-functional alignment?  

Be sure to involve a well-rounded group of members with the right expertise to maximize the SKO experience and impact, such as senior sales leaders, sales enablement, product management, product marketing and event planning personnel. When planning a large-scale virtual event, it's also often necessary to include IT. Then, determine the core planning committee.   

The committee typically meets weekly or bi-weekly, with responsibilities including: 

●    Inform and secure buy-in from executive leadership 
●    Explain plans to department leadership  
●    Convey feedback 
●    Draft, review, and tweak SKO plans and agendas 
 
You can also survey the sales team to identify the top pain points or concepts they’d like addressed during kickoff. For example, if sellers want time to ask sales leaders about their vision, schedule a panel. If reps want to know where the product is headed, spend more time covering the roadmap. This makes it easier on your planning committee, but it also makes reps feel more invested in the event, knowing their ideas and concerns were heard.  

Tip: There will be specific individuals that you'll need buy-in from, such as sales managers, who don't necessarily need to be a part of the official committee. Bring them in periodically to approve essential details.  

#2. Consider Your Kickoff Audience 

Your SKO is incredibly beneficial to the sales organization, but other teams also get value from participating. Consider inviting groups tasked with increasing customer satisfaction and retention, such as customer success, professional services, and implementation (or delivery). Like sales, they must be well-versed in your company's strategy and able to deliver a consistent message to customers. 

In the past, budgetary concerns might have precluded having a bigger audience. But there’s more flexibility now with virtual or hybrid events.

#3. Set Objectives 

Once you’ve defined your audience, it’s time to set kickoff objectives. Your objectives are the same, or similar, whether your event is in-person, virtual or hybrid. 

When setting objectives, focus on what you can feasibly accomplish. Your objectives, for example, might include: 

●    Motivate the teams 
●    Celebrate success 
●    Conduct skills development 
●    Launch a new product or service 
●    Introduce a new methodology 
 
Review objectives with executive leadership before setting anything in stone so everyone is aligned. 

#4. Define Expected Outcomes and Metrics 

Once you’ve established your objectives, think about how you’ll measure success. Define expected outcomes, along with what success looks like. Be specific, and include both attainable and “stretch” goals. 

For example, if one objective is to motivate your teams, what benefits do you expect from that? You might conclude that you'll see an increase in retention and engagement. Quantify that too – e.g., 5% increase in retention; 3% increase in engagement. To measure these metrics, you might partner with your HR team, which likely already has attrition- and retention-tracking mechanisms in place.

#5. Decide on Content Themes 

To make your kickoff a cohesive event, consider establishing a central theme. This will help presenters find common ground in their messaging and tie everything together for attendees. Themes can have motivational undertones, like "Breaking Barriers" or "Beat [Competitor],” for example. 

For example, the theme of “Knowledge" could encompass requests for peer-to-peer sharing, team exercises, virtual productivity hacks, and connection-building, among other elements. A “Product” theme could include updates and the company’s vision/roadmap. “Recognition” could include celebrating customer wins, acknowledging high-performers and anniversaries, and creating buzz while recognizing the challenges of the prior year. 

Bake your themes into and throughout the agenda – not as tracks, but as types of information to incorporate within sessions.

#6. Focus on Logistics 

By going virtual, you’ll encounter various logistical considerations, both big and small. Some include: 

  • Event timeframe – Will you hold your kickoff in a jam-packed day or two or spread-out sessions over multiple days? To best hold participants’ attention, limit distractions and drive knowledge retention, it often works well to schedule 2-to-3-hour sessions spaced out over a week. 
  • Live vs. pre-recorded – Whether everything is live, pre-recorded or a mix of the two often depends on the geographic distribution of your teams. If you can support at least some live sessions, that typically helps everyone feel included and acknowledged. 
  • Technology platform(s) – Decide on the primary platform to support your virtual event. If portions are live, you might select a conferencing tool such as Zoom that helps with breakout sessions. For pre-recorded elements, platforms like Brainshark let you present information impactfully and track consumption. 
  • Cameras required? Choose what works best for your company culture. In general, requiring cameras to be on helps companies drive and monitor engagement and foster accountability. 
  • Virtual-friendly presentations – Make sure all your speakers have engaging presentations well-suited to your virtual format. That applies to company and customer presenters, as well as any motivational speaker you choose to include. 
  • Event monitors – Choose someone with a strong voice who is willing to jump in if speakers run overtime. You’ll also need someone to make sure audience members remain on mute unless they're involved in a specific portion and monitor feedback that comes in over the chat. 
  • Q&A – In some cases, you may want sessions to be highly interactive throughout. Often it's best for flow to take and respond to questions at the end of a presentation. 
  • Recording a live event – While recording an event can be expensive in a physical setting, it's easier and cost-effective virtually. Your technology platform likely supports this so that you can archive valuable knowledge. 

#7. Plan Your Agenda

After you’ve polled your audience to determine what they are looking to get out of this event, your committee can start to craft a rough agenda. Keep in mind that the agenda you initially put in place isn’t set in stone. Speakers, topics, and times may shift throughout the planning process – and that’s okay!  

Tip: Sales kickoff is not about beating up on the sales team for what they did wrong. Focus more on areas of improvement and talk about action plans.  

Here’s an overview of what an agenda should include: 

  • A reasonable timeframe –The agenda should include "bite-sized" training, which is more easily remembered. 
  • Executive presence – This underscores the importance of the event/subject matter. 
  • Clearly defined daily objectives – Attendees know what’s expected of them and what they should get out of the day’s sessions/what’s in it for them. 
  • Mix of speakers – You can reduce boredom and conferencing fatigue by varying speakers, keeping attendees engaged. 
  • Peer-to-peer learning – Reps often appreciate input and lessons from successful peers “in the trenches.” 
  • Knowledge application – Brief homework, including video-based activities, can reinforce knowledge, help reps apply what they learned, and enable presenters to tailor upcoming content to the skill levels demonstrated. Standout video submissions can also be recognized the following day.  

Where appropriate, also find opportunities for creative celebration and socialization that reflect your company culture. 

#8. Design and Deliver Pre-Work And Onsite Activities 

It’s not optimal to walk into a meeting with no advance knowledge of the topics or proceedings. But, many organizations treat their SKOs this way. More than 6 out of 10 companies (62%) don’t deliver pre-work to sales reps in advance of their kickoff, and 84% don’t conduct advance training – neglecting to provide a foundation on the skills and topics covered.  
To maximize the value your sellers get from the kickoff, it's essential to prioritize key learning and reinforcement opportunities at the event. 

Assign pre-work so sellers are adequately trained beforehand provides more time for team building exercises, peer-to-peer learning, and breakout sessions during the day. This makes for a much more engaging and exciting sales kickoff, allowing you to make the most of your reps’ time.  

#9.  Review, Rehearse, Refine  

Don’t leave out this often-overlooked step: review, rehearse and refine each of your presenters' content. The key here is to ensure that all presentations align with your kickoff strategy and overall goals for the event.  

  1. Review: Make sure that all content fits within the overall theme of the kickoff event and that there is no overlap between presenters.  
  2. Rehearse: Sales kickoff is not immune to Murphy’s Law. If your event is in-person, show presenters the stage, confidence monitor, and slide advancer before their session, so they know what to expect. If virtual make sure to walk your presenters through the platform you will be using. Encourage the presenters to do a dry run and suggest leaving time for questions at the end of their session.  
  3. Refine: Much like reps, presenters often need to be coached. If you feel like some of your speakers are weak on presentation skills, don’t let that take away from the value of their message; consider hiring a presentation coach.  
  4. Tip: Compile the master slide deck in advance. That way, if presenters request any last-minute edits (which happens often), you are aware of the changes and can ensure they are included in the final deck.  

#10. Learn from The Experience and Get Real-Time Feedback 

SKO is a critical initiative and should be much more than just a break from your typical day-to-day . There must be a carefully crafted strategy involved to make sure the topics, speakers, and activities resonate with the sales team and what they hope to achieve in the coming year. 

Too often, companies wait too long after the event to ask for feedback on the event. Be proactive about taking the pulse of the sales team during the event.  

Tip: Send push notifications to get reps to respond on the spot – this way, you'll get valuable thoughts about how they're feeling about the event before they forget. 

11. Keep the Momentum Going With Post-Work 

Your SKO isn't just a single, isolated event. It should be a springboard for the fiscal year. Your team has put a lot of blood, sweat, and tears into making sure your sales kickoff was worthwhile. Essential concepts and knowledge covered should be reinforced, put into practice, and expanded on to get the most ROI from your event. 

This is an area where many organizations fall short – more than 7 out of 10 (71%) don’t deliver SKO post-work or follow-up training to reps. 

Before reps leave the event, remind them of the sales strategy that you set at the event. It will be up to them and their sales managers to execute it locally. Hold them accountable for the next 90 days and beyond by setting some goals for prospect meetings or even closed deals. 

TIP: Don’t forget to send a high-level overview of the learnings and goals set at sales kickoff to loop in the rest of your organization. 

Print the checklist below to us as a companion to this article in order to organize and track your progress while planning your event.

Download the checklist

Happy planning!

If SKO is coming faster than you can prepare, reach out to Brainshark to learn how our solutions can help you deliver your best Sales Kickoff ever.