What is a sales kickoff?

Kickoff events bring revenue-generating teams together to launch new initiatives, provide important training, inject energy and set the tone for the year – these annual events can be called Sales, Revenue, or Go-to-Market Kickoffs depending on which teams attend. Kickoffs typically always include Sales, but they have evolved to include Marketing, CS, AM, and even sales engineers (when appropriate). Kickoffs are opportunities to dedicate multiple days to discuss the prior year’s learnings, prepare your revenue-generating teams for the year ahead, and energize team members after the crunch of  Q4.

What is the purpose of a sales kickoff?

Highlight important learnings from the prior year – provide a realistic view of what worked, what didn’t work, and what the team learned from the year before. Focus on insights that validate your team’s experience/performance and lead into the upcoming year’s priorities. If the prior year was challenging, be honest about what was difficult.

Reset the revenue organization’s priorities and roll out new strategic initiatives – set expectations for the new fiscal year. Attendees should come away with a clear understanding of their organization’s priorities for the year and how the teams will need to execute to support the company-wide objectives. Kickoff is also an ideal venue to level set and prepare your revenue teams for big shifts like an exciting product launch or other significant changes that will impact them.

Conduct skill- and collaboration-based training – kickoffs are a unique opportunity to bring people from different teams or locations together. Live training sessions can level up product knowledge, collaboration, and key selling skills while invigorating the team. Although more costly than virtual events, in person events tend to create greater impact.

Celebrate success and create energy to start the year with momentum – revenue generation is an emotional rollercoaster with significant highs and lows. Sales roles also have unique priorities, ongoing skill development requirements, and high levels of risk. To reward them and balance some of the inherent stress, it’s important to use this opportunity to inject energy into the new fiscal year and start  on a high note.

Planning

How far in advance should you start planning a Sales Kick-Off (SKO)? What does the planning 

Ideally, give yourself a full quarter to plan and prepare – the SKO is Enablement’s primary focus during Q4 and the part of Q1 leading up to the event.

Proactively engage stakeholders to keep preparations on track – be aware that critical SKO prep work occurs when revenue leaders and reps are busy with their end-of-year push to maximize revenue. Follow a realistic timeline to avoid misalignment and ensure you get the input you need to plan a successful event.

Sample Enablement Team Planning Timeline For an Early January Kickoff
Timing		Activities
October		Reach out to subject matter experts, revenue leadership, and other key stakeholders to align on SKO priorities, objectives, and set the agenda.
November		Conduct knowledge gathering and start  session content design.
Late November/December		Finalize content and event planning/logistics without requiring significant input from revenue-generating teams.
Early January		Finalize content, and rehearse all sessions with presenters

Note: timing for outreach shifts based on the SKO date – early January kickoffs require more prep work to be finalized in October, whereas events that go live in February have a few weeks of extra leeway. Either way, collect as much input as possible before revenue leaders get extremely busy closing in on the last 4 – 6 weeks of their fiscal year.

Who should be invited to the kickoff? 

The learning audience (and event name) depends on the goals of the event  – traditional Sales Kickoffs were intended for just the Sales team. It has become more common for organizations to host more inclusive events with broader audiences. For example a Go-to-Market Kickoff includes all the pre- and post-sales teams, technical sales, and marketing.

Consider the value the kickoff provides an attendee vs. the business impact of their attendance –  if you can’t include a team that would benefit from the kickoff, consider alternatives. For example, some companies offer shorter, more targeted kickoffs or invite certain teams (e.g., Customer Support ) to specific sessions that are most relevant to them as a way to mitigate the disruption caused by their attendance at a longer event.

Consider whether people beyond your learning audience should attend – your priority is to make the kickoff as valuable as possible for the audience that will help the revenue organization achieve its goals. However, inviting people outside of that targeted audience can benefit both your team and theirs.

Non-learning attendees sometimes include:

• Subject matter experts – who will be a speaker/session leader and educate the learning audience on an important product update or skill (e.g., people from the Product team come to introduce a new functionality).
• Key partners – as attendees, they can develop a better understanding of their role and the challenges faced by the revenue organization. This insight can help them become better partners.

SKO Agendas & Content

What should the kickoff agenda look like?

Expect the SKO to make up the bulk of the revenue-generating team’s week – by design, kickoffs leave space for valuable team building and learning opportunities, but kickoff programming generally flows across the entire week. Here is a sample schedule for reference.

		In-person Events		Virtual Events
Duration		2-3 days, mid-week		Programming blocks across 1 week
Sample schedule		• Monday – travel day • Tuesday – ½ day of afternoon programming • Wednesday – full day  • Thursday – ½ day of programing + team fun event • Friday – travel/catch-up day		4 hour block of programming for 4 -5 days

What makes for effective content during your kickoff? What types of content should you share?

Content should align with the goals of the Sales Kickoff – content strategy is not one-size-fits-all. Content should ladder up to the goals you want to achieve during your kickoff.

Content should reflect 4 key qualities: 

• Balance – programming should have a healthy balance of education, celebration, fun, and team building/networking focused sessions/events.
• Focus – choose a main topic or initiative that all skill development content supports. Identifying a single focus area facilitates planning and assessing the kickoff’s success.
• Participation – sessions should be as interactive and activity-based as possible.
• Audience relevance – consider each role that will attend the session and tailor the content accordingly. Every attendee should get value out of each session they attend.

The Three Content Types
Typical Content Category		Example Agenda Item		Sample Allocation
“Talk at you” sessions		CEO/Senior Leadership keynote  about conversations with the board		10-15%
Interactive sessions		Cross-functional training sessions, interactive learning games, etc.		50-60%
No learning agenda (pure fun) sessions		Happy hour, laser tag, picnic, bowling, comedy show, etc.		25-40%

Remember that effectiveness is more important than allocation – kickoffs are generally successful when they follow the above allocation mix. However, content should reflect the event’s goals. For example, if your priority is to ensure that your entire organization can smoothly demo a new product, most of your content should be dedicated to product education and demo execution.

Create an enjoyable team experience – even “talk at you” segments can create a sense of shared purpose and camaraderie. Designing an enjoyable experience for attendees is as important as delivering on your focus areas and can be achieved in many creative ways.

Balance focus with fun – don’t forget to plan activities that are fun for the sake of fun. Also, try to infuse fun elements into the rest of your content. Ideas include: thoughtful details like warm daily openings and closings, music, food, decor, etc.

What are good sources of SKO session content?

Content Category		Examples & ideas
Face-to-face customer perspectives – many of the most valuable (and highest rated) SKO sessions involve real customers		Fireside chat/panel – invite customers to participate in a session where you ask questions that you probably wouldn’t be able to ask for a case study (e.g., What was it like to go through the sales process with us? Why did you choose us and not a competitor?).
		Break out group/casual happy hour – after the panel, give your team an opportunity to get to know the customer on a personal level.
		Invite senior level or user level customers – both levels have unique insights and provide a rare opportunity for your team to understand how different members of customer organizations feel and think about the product and/or sales process.
Wins and losses – find creative ways to get team members to analyze what has and hasn’t worked in the past.		Win/loss “speed dating” – each person has an opportunity to share a significant  win and difficult  loss while working in a pair with a colleague. When they describe the win, they should also reflect on what could have been improved. Similarly, when they describe the loss, they should include what went well even though the deal was lost in the end.
		Internal vs external perspective – have someone from your selling team present their win to the group, including their analysis of why the customer converted. Then, have the customer that was sold to participate in the session and explain why they converted. In the next segment, have your team consider the differences in perspective and what they learned from the comparison.
		Important loss – have a top-performing (i.e., highly confident) rep share about a loss they had in the past year, what they learned, and what they could have done differently.
Outside speakers (on Day 3) –  outside sales coaches, external subject matter experts, or admired board members can bring a change of pace and energy boost to attendees.		Outside speakers can add legitimacy to your kickoff objectives – hearing from someone outside the organization who can reinforce what leadership is saying can sometimes validate the effort the team is putting in. However, keep in mind that speakers who aren’t part of the board or your portfolio ecosystem tend to be expensive.

What is an example of an effective collaborative learning segment that you have recently facilitated at a SKO? 

Start-up incubator style pitch competitions tap into the team’s competitive side with a collaborative simulation activity – collaborative learning exercises encourage teamwork while developing important skills in a fun, energizing format. This simulation had high engagement and positive feedback:

• Goal – develop account management skills by improving collaboration across all roles involved in the customer journey.
• Premise – each team represented a fictional “start-up”. They chose their start-up’s name and mission and assigned a role to each person on their team. They went through all the steps of the account management process and made their pitch to the incubator judging panel. Only 1 of the “start-ups” could earn “funding”.
• Motivation – revenue people love competition, so the pitch competition framework was naturally energizing. Furthermore, the audience they pitched to was composed of people they wanted to impress, such as board members. Participants were driven to win bragging rights and medals, not just prize money.
• Result – assigning different roles helped develop a better understanding of what other roles within an organization do. This changed how the teams interacted with each other going forward and provided opportunities to learn new skills while demonstrating the importance of research and presentation skills.
• Tracking impact – indirectly measure the success of the session based on whether collaboration and account planning for top accounts improved after the session.

What are some agenda ideas for running a SKO after a tough year?

Use challenges as learning opportunities – acknowledge what was challenging in the previous year, show that the company has learned from these challenges, and explain how the business is making changes to improve results going forward (e.g., pivoting to a different type of customer or buyer persona, changing pricing strategy, developing a new product functionality, etc.).

Provide tools to improve performance – give people a concrete reason to believe that this year will be better For example, if a lack of a certain skill limited performance last year, prioritize developing/re-honing that skill throughout the rest of the kickoff. Connecting training to performance helps give your team a sense of control and optimism about the year ahead.

Find wins to celebrate – the fastest way to get a sales team out of a slump is to boost their confidence. Even if you didn’t hit quota last year, find something that did go well (e.g., reduced churn, coveted new logo wins, taking market share from a competitor) and celebrate it.

Don’t underestimate the power of positive reinforcement (also applicable after strong years!) – celebrating wins—especially small wins that often go unnoticed—showing appreciation for team members, recognizing individual and team-wide accomplishments, and acknowledging hard work is a meaningful and direct way to motivate a revenue organization.

Day-before and Day-of Logistics

What pre-event logistical prep is important for in-person SKOs?

Steps to support smooth event logistics  – to ensure things will run as seamlessly as possible, always prepare backup solutions and session facilitators before the event goes live. Several things that can make a big difference:

• Designate a single computer to use for the entire event and ensure that the computer is equipped with all the capabilities and applications needed for the event.
• Download backup versions of all presentation materials so you have them in case the master copy gets corrupted, lost, or is otherwise unusable.
• Create a run of show that maps out how the day will flow, when presenters need to be ready, catering logistics, etc.
• Share the run of show with all applicable stakeholders and presenters.
• Create a detailed catering schedule; they should know when to have food available and where to set up water and coffee throughout the day.

Do an in-person tech rehearsal the day before – confirm that the necessary software is working on the designated presentation computer. Tech rehearsals are also an opportunity to:

• Familiarize yourself with the space and AV setup.
• Make sure you can hardwire the presentation computer to the AV system.
• Test the WiFi in the event space.
• Test microphones and make sure they’re working correctly.
• Test music, video, or live demo content.
• Troubleshoot any issues that arise in your rehearsal.

Have IT backup – you need to be able to use your Enablement expertise to facilitate/run the event, so it’s important that you don’t also need to act as a tech expert. Evaluate whether bringing someone from your own IT team vs using someone from the hotel or event space is more appropriate. Your IT support should be present for the tech rehearsal and the entire event.

Be prepared for presenters to fall through – assume that at least 1 presenter will wake up sick and be unable to participate or have some other emergency. Have a back up plan such as a recorded rehearsal video of their presentation on hand, an understudy who’s familiar with the presentation, or a backup presenter who can step in.

What elements of a kickoff need to change to accommodate a virtual/remote setup?

Content/Agenda:

• Virtual kickoffs require a different approach – 1 day’s worth of in-person content must be spread over at least 2 days of virtual programming. Shorter attention spans and the effects of screen fatigue must be considered when you’re not in person.
• Plan extra breaks – build in a short break on the top of every hour for virtual events. You can’t read the room when attendees are remote, so you should assume that people will need 5 – 10 minutes to stretch their legs or use the bathroom once an hour.
• Consider holding multiple events for different time zones – it’s often difficult to avoid early morning starts, encroaching on evenings, and different meal times when attendees are in different time zones or continents. Try to schedule programming blocks in the middle of the day for as many attendees as possible.

Logistics:

• Each presenter will be using their own computer – in addition to holding a tech rehearsal, have each presenter practice presenting and testing their WiFi in the location they will be in during the event.
• Have remote IT backup ready to jump in at any moment – IT support should sit in on all sessions and be prepared to resolve the technical issues that will undoubtedly occur (e.g., someone’s speakers aren’t working) so you can focus on the event itself.
• More variables are out of your control – if attendees work remotely, you have no way of knowing or controlling what else is happening in their work environment while they are attending the kickoff. This is especially important if you have teams from multiple time zones joining the same sessions.

Post-SKO

How do you make sure that SKO content is reinforced after the event is over?

Position the kickoff as the beginning of a journey – conclude the kickoff with a promise to support the initiatives you focused on throughout the year. Follow through on that promise by using kickoff materials and content that expands on it in additional Enablement programs and resources. Measure progress against important initiatives during QBRs.

Use recorded sessions as refreshers throughout the year – record all sessions and break them into micro-learnings that you use in onboarding and just-in-time resources available to the selling teams.

Enable frontline leaders to reinforce kickoff priorities – kickoff content isn’t designed to exist in isolation. Frontline leaders are a valuable resource that can provide support for their teams, reinforce training, coach team members, and push out communications that help forward the key objectives established during the kickoff.

How can you measure the success of an SKO and determine ROI?

Identify indicators that correspond to the kickoff goals – track metrics that are indicators of the skills or changes you introduce during the kickoff. For example, if the kickoff supports rollout for a new product, you can measure how much the new product appears in the pipeline, how quickly it moves through the funnel, and how much revenue it generates.

What other kickoff-type events might you have throughout the year? 

Other Kickoff-type Events
	Purpose	Duration	Location
Mid-year kickoffs	Recharge the team as you go into H2	1-2 days	In person, virtual, or Enablement travels to offices to conduct separate events in each time zone/continent
Quarterly kickoffs	Continue training for sales and/or success teams	1 day, after QBRs	In person or virtual

Tips: 

Mid-year kickoffs are a good opportunity to pivot – if you need to make a significant change in H2, a Mid Year kickoff is an efficient way to introduce updates and adjust strategies.

Budget

How should you budget for a kickoff?

Kickoffs typically cost approximately $2.5 – $5k per person – costs can range depending on location, extent of travel, accommodations, food, events, and programming.

They’re becoming more expensive, but large events give you negotiating power – larger attendance gives you more levers to negotiate with vendors. For example, if you’re using a presentation space at a convention center, you might be able to get special pricing on rooms at that hotel.

How can you save money on a kickoff if you face budget constraints?

Prioritize the most important things – don’t be afraid to spend on what matters and cut costs on non-essential elements. Evaluate the priorities and culture of your organization and choose things like accommodations, menus, extra events, and amenities accordingly. 1 area where you should not compromise is safety; choosing a more affordable hotel is a reasonable option unless it causes any of your attendees to feel unsafe.

Look for resources within the organization – people have myriad talents outside of work. See if you can leverage that talent. For example, someone on your team might be able to DJ, assist with content creation, or help with other entertainment.

Reevaluate the need for prizes and goodies – confirm whether attendees want swag and if they would be satisfied with more basic options. Also consider whether you need to offer cash prizes, or if you can find a creative way to use bragging rights as a reward. Sometimes those provide even better motivation for training exercises.

How can you involve partner sponsors? 

Partner/vendor sponsorships are win-win – well-designed sponsorships strengthen important relationships, provide value to the partner, and reduce your costs.

Sponsorships often work best when you pair educational content with more relaxed programming:

• Meal/drink sponsorship – give your partner airtime in a late afternoon session followed by a happy hour where they sponsor the event/hosted bar. Alternatively, invite them to the event itself and encourage your reps to interact with them for an additional learning experience. 
• Swag sponsorship – conduct an activity with your partner, then have them give out swag and/or sponsor an event that evening.

Overall 

What’s important to get right?

Set expectations so stakeholders understand that their partnership is important – one of the most critical times of the year for stakeholders (especially revenue leaders) overlaps with the critical planning period for SKOs. Work with your stakeholders to set expectations and ensure they understand the importance of the SKO. Doing so will go a long way towards gaining their commitment to providing the support and insights you need to deliver an impactful kickoff for their teams.

Big events are a purposeful investment – kickoffs are typically the most expensive investments a company will make on an internal team. In addition to venue and programming costs, you must be able to justify the opportunity cost of taking every revenue-generating employee away from selling activities for the duration of the event.

What are the common pitfalls?

Don’t sacrifice engagement to didactic content – it’s tempting to devote as much time as possible to focus-style content. However, overscheduling focused activities undermines kickoffs because it’s equally important that attendees feel motivated and optimistic about working with their team going forward.