Sales Kick-off: Best Practices From Top Enablement Leaders

Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.

Introduction

This article is a part of a series on the subject of sales kick-offs. Make sure to check out the articles on sales kick-off planning, sales kick-off themes, and sales kick-off mistakes as well.

Sales kick-offs (SKOs) are more than an annual get-together.

They are a chance to unify the sales organisation (or even an entire go-to-market unit) around shared goals, introduce fresh ideas, and build momentum that carries well past opening day.

Yet, I’ve seen firsthand how the impact of SKOs can vary wildly. 

Some leave reps fired up, clear on their strategy, and ready to execute. 

Others? 

A blur of slide decks, scattered sessions, and a lot of enthusiasm that fades within days.

Many leaders I’ve spoken with share the same frustration: How do you make an SKO truly valuable rather than just another corporate event? How do you ensure the time, energy, and resources put into it translate into real sales impact?

To discover what really works, I reached out to 16 enablement leaders with experience at companies such as Yahoo, IBM, Salesforce, GitLab, Writer, and SAP. 

Alicia Avrach  – Head of Sales Enablement

Beverlie Heyman –Director of Revenue Enablement

Eric Mingorance – Sr. Director of Sales & Field Enablement

Ivy Holt – Head of Global Revenue Enablement

Kelley Shirazi – Director, Global Sales and Customer Success Enablement

Lauren Channell – Senior Manager, Enablement Business Partners

Leah Levitte – Director, Revenue Enablement

Liz Chavez – Senior Director of Revenue Enablement

Louisa Morassutti – Senior Director GTM Enablement

Mat Hill – Sr Director, Revenue Enablement

Monti Bray – Director, Sales Enablement

Nina LaRouche – Director, Revenue Enablement

Paul Harvey – Head of Sales Learning and Practises – Global VP

Russell Wurth – Head of Revenue Enablement

Tim Carlson – Director Of Sales Enablement

Todd Lienart – Director – Revenue Enablement

As you are about to see, their insights blend real-world lessons and candid advice, shining a light on what makes a great sales kick-off. 

In the following sections, I break down their best practices into clear themes, showing how a well-executed SKO can rally your go-to-market teams for the months ahead.

SKO best practices

While each contributor had a unique perspective, certain recurring overarching themes quickly emerged as umbrella topics for a variety of more focused, specific aspects of a successful sales kick-off.

The four main themes and their sub-section are here summarised for reference: 

Let’s begin by looking at the foundational strategies needed to set your sales kick-off on solid ground.

1. Strategic foundations

Many of the leaders I surveyed and spoke to stressed the importance of laying a strong groundwork before diving into any event details. 

They insisted that a birds-eye view of the SKO is the foundation on which everything else will be built. 

In order to build these strategic foundations, you need to identify the business goals for the sales kick-off, align with executives and managers, decide on the scope of the SKO, and work out a budget and venue. 

These are all inputs that will guide everything else that you will be doing and it is of utmost importance to set those foundations as best as you can.

We will start with what is arguably the task which sets the tone for everything else going forward – engaging the main go-to-market executives and uncover the key business goals to which the SKO should align.

Identify clear business goals and align with the executives

To continue on the thread of what I just mentioned above, an SKO can only be as strong as its connection to top-level objectives. 

Paul Harvey, the Global VP of Sales Learning and Practises at a leading global wholesale provider of insurance and reinsurance products, framed it as understanding “the Business Goals for the year,” emphasising that they shouldn’t stray from what matters to the wider organisation. 

This view was also shared by Louisa Morassutti, the Senior Director GTM Enablement at a leading provider of talent acquisition technology, who described the importance of alignment with CRO and C-suite right from the start, before even you start the planning process.

Beverlie Heyman, the Director of Revenue Enablement at a company behind a revolutionary human experience healthcare platform, suggested over-communicating with execs and sales leaders on outcomes in particular because silence or assumptions can lead to missed targets. 

She also recommended viewing the event “through the lens of the sales team,” so that everyone – sales reps, managers, and executives – focuses on the same outcomes. 

Liz Chavez, the Senior Director of Revenue enablement at a leading company for identity threat protection, goes wider and sees sales kick-offs as relevant for other go-to-market teams in addition to sales:

“I use SKO as a forcing function to ensure GTM teams are aligned in vision and goals.” 

The takeaway of this entire subsection is perhaps best explained also by Liz:

“I need a clear vision of what I want people to do, feel, say coming out of SKO.”

Plan early, budget carefully, and involve multiple teams

Many of the contributors mentioned the pitfalls of last-minute planning and unrealistic budgets. 

For instance, Kelley Shirazi, the Director of Global Sales and Customer Success Enablement at a household-name DevSecOps platform, advocated a runway of at least six months: 

“There are numerous moving parts to running an effective SKO and giving yourself less than three months to plan… ultimately leads to a poor or negative experience for the entire sales organization.” 

She also suggested incorporating lessons learned from your previous event right away, rather than waiting until planning pressure sets in again:

“I recognize it’s difficult to start planning three months after delivering a sales kickoff, but simply taking the first steps to outline lessons learned is a powerful start. 

Planning in advance also protects your enablement and event teams from burnout, which not only results in logistical missteps but can put your team members’ health and wellness at risk.”

The budget side of things is closely tied to your timeline. 

Liz Chavez emphasised the need to be transparent about the kind of SKO experience your organisation wants, saying: 

“Expectations can explode over SKO.” 

By meeting with finance early on, you can avoid a scramble once deposits and contracts are on the table. 

Todd Lienart, the Director of Revenue Enablement at one of the most popular generative AI platforms for marketing, took it a step further, reminding us that everything – from venue choice to outside speakers – impacts both costs and overall engagement. 

These are decisions that deserve careful thought, not a rushed sign-off two weeks before the event.

Several leaders also stressed the importance of not trying to do everything alone. 

Monti Bray, the Director of Sales Enablement at one of the internet’s legendary companies, suggested creating an entire team, a cross-functional committee to share responsibilities, while Leah Levitte, the Director of Revenue Enablement at a company behind an intelligent auditing and finance automation platform within Excel, suggested being meticulous in your planning:

“Plan everything down to the minute and always remember everything takes longer than you think, so bake in extra buffer time for everything you do.”

That way, small mishaps cannot derail the entire show.

Decide on the event scope and location

Several leaders highlighted how the venue and event scope can either elevate or undermine all your hard work.

Kelley Shirazi was very straightforward about the value of in-person gatherings:

“If you do not have the budget to pull teams together in person, don’t have an SKO”.

In other words, she sees the virtual sales kick-off or hybrid events as a compromise that undercuts team bonding and overall excitement:

“Without the opportunity for extended deal teams to meet in person, you lose the value of building deeper relationships that lead to trust, and ultimately better outcomes. 

And please, don’t play it halfway and resort to a hybrid event either. 

Keynotes are important but no one wants to have four hours of their day hijacked, for two or more days, listening to how well the company is doing while sitting alone in front of a computer. 

The cognitive dissonance alone of that strategy only reduces trust in the organization and defeats the purpose of SKO, which is typically to celebrate, motivate, inspire, and importantly, learn.”

Kelley did, however, suggest holding smaller regional get-togethers if your budget simply won’t stretch to include everyone in one venue.

Todd Lienart echoed that a strong location is key, framing it as a location/logistics matter. 

His reasoning was that the space itself can influence how people engage with the event. 

In short, take your team’s distribution, budget, and overarching business goals into account before locking in a single large event. 

With the basic foundational recommendations in place, it’s time to dive deeper into the specifics of the SKO agenda

2. Designing the sales kick-off agenda

Many leaders I spoke with believe an SKO is only as effective as its agenda. 

Even if you’ve laid the most stable strategic foundations, if the agenda feels scattered or bloated, you risk losing engagement and failing to meet your goals. 

A thoughtful structure helps teams connect each session to what really matters – equipping them with practical strategies to win in the field.

So let’s find out how the contributors approach this.

Keep the content concise, practical, and outcome-focused

“Less is more, when it comes to content”

…said Todd Lienart. 

“Trying to do too much is a recipe for frustrating everyone.”

Mat Hill, the Senior Director of Revenue Enablement at a Healthcare CSPM and MDR services, echoed that sentiment, suggesting: 

“Spend less time on theoretical, and more time on practical.”

Both see it as a matter of respecting your reps’ time and attention. 

If a session doesn’t provide immediate, real-world value, it probably belongs on the cutting-room floor.

Tim Carlson, the Director of Sales Enablement at a company that builds mathematically accurate network digital twins, recommends sales leadership involvement in properly qualifying content and presenters:

“Sales leader-supported gatekeeping of content and presenters.  

Critically review all requested topics to ensure they are: 

a) relevant to the goals of the SKO, 

b) are on message/in alignment, 

c) that SKO is the best venue for delivering (avoiding the “this could have been an email” scenario)”

Far too often, people who organise SKOs are happy to have as many speakers and events that they forget to check them all and truly make sure that they will fit the overall flow and the direction in which the kick-off should go.

Minimise theory or executive-heavy sessions

Paul Harvey was very straightforward when driving his point about limiting executive keynotes:

“Limit main stage time for execs and concentrate on outcomes for the whole sales team.” 

That is actually one of the most common SKO mistakes – having too many keynotes on sales strategies, the sales process, and similar concepts that drain energy, especially when reps are looking for practical tips they can apply the following week.

Similarly, Ivy Holt, the Head of Global Revenue Enablement at a world-renowned platform for real-time operations, underlined the power of role-based tracks: 

“Emphasise enablement and practice – role-based offerings/tracks if at all possible.” 

She wants every rep to feel they’ve gained tangible skills that match their responsibilities. 

Tying in with one of the ideas from the strategic foundations, Lauren Channell, the Senior Manager of Enablement Business Partners at a leading full-funnel retail platform, emphasised the importance of having the objectives at the top of one’s mind when coming up with the sales kick-off agenda: 

“Every session, speaker, and activity should tied back to these goals.”

Consider the flow and leave room for breaks

Even when the individual parts of the agenda are fantastic, the sales kick-off event should never feel like a disjointed collection of talks and sessions. 

In other words, it needs a clear flow which ensures that all activities are coherent and that everyone involved is pointing towards the same shared goals.

Mat Hill suggested you write a storyboard so sessions flow together like chapters in a book or scenes in a movie. 

Nina LaRouche, the Director of Revenue Enablement at a leading full-funnel retail platform, similarly noted that content should tell “a cohesive story” and involve leaders or reps in its delivery.

As you map out each session, think about fatigue. 

Eric Mingorance, the Senior Director of Sales & Field Enablement at a cloud-based and on-premises software-defined video platform, recommended scheduling brief breaks up front: 

“Plan plenty of breaks throughout the day and communicate those breaks to attendees before the event… so they can be fully present for SKO sessions.”

Short interludes help your people stay focused and assimilate new ideas.

It’s easy to overlook downtime, but a few minutes of decompression often mean the difference between energised engagement and blank stares.

Invite outside speakers for fresh perspectives

If your budget allows, consider an external keynote or workshop. 

Todd Lienart argued that outside speakers are more effective than internal presenters because they bring perspectives company insiders may not have. 

A concise keynote from an external expert who has tackled similar challenges in other contexts can give your team fresh inspiration and help them see their everyday challenges and ways of doing things in a new light. 

Monti Bray frames this inclusion of outside expertise as one of the ways to make SKOs stand out from your average sessions or training:

“Don’t run a session or lead a training that you can do any day of the week; make it feel special and unique to get reps focused and inspired; I personally like bringing in third parties to lead a workshop or keynote.”

Todd, however also points out that, unfortunately, the first thing to be cut from SKO budgets are, in fact, external experts.

With all of this in mind, it’s important to understand that no one really wishes to be talked at for hours on end, which brings us to our next big theme: engagement and collaboration.

3. Engagement and collaboration

Events can feel dull or disconnected if attendees spend all day sitting and listening. 

This is why many of my contributors emphasised the need for interactive experiences that bring people together across functions, so the kick-off stays lively from start to finish.

Make sessions interactive with hands-on exercises

Kelley Shirazi provided more than a few suggestions on how to make the sessions interactive and effective:

“SKO breakout sessions should be focused on hands-on, practical application exercises. 

Teams have already sat through hours of keynote lectures and have limited engagement capacity. 

Use these sessions as an opportunity to prepare field teams for success in the coming fiscal year by incorporating pre-work like eLearning modules, knowledge checks, or pre-SKO workshops to teach key concepts. 

Provide opportunities for messaging and pitch reviews or bring real opportunities for teams to workshop together.”

Eric Mingorance pointed out that interactive sessions offer multiple benefits beyond just breaking the monotony of too many keynotes – the most important (in my opinion) being reinforcement: 

“Incorporate activities, interactions, and opportunities to apply what attendees are learning during the event. 

Not only does this break up the monotony of being lectured to, but provides an opportunity to actually accomplish things as a group on-site and reinforces the material so it’s not immediately forgotten.”

Alicia Avrach, the Head of Sales Enablement at a world-renowned full-stack generative AI platform for enterprises, added a few more ideas for interactive activities, some going beyond the formal setting, such as dinners, for example:

“Interactivity always. 

Nobody wants to listen to monologues with boring slides. Get them out of their seats, outside, and interacting with their peers. 

Reinforce learning through games and competitions, whiteboarding exercises, role plays, and improv. 

Design team building and dinners around your goals, and add elements of surprise.”

This concept of surprise is especially important for salespeople with plenty of experience who have probably attended more than a few SKOs and who have seen it all, so to speak.

Mix participants to break familiar patterns

Leah Levitte recommended mixing up seating plans and breakout groups so that people meet colleagues outside their usual circles: 

“Find ways to mix up groups. 

Kickoffs are a perfect time to meet new people, but folks end up sitting with people they already know. 

It’s possible they will get annoyed at first when they don’t get to sit with their BFFs, but they always come back around and are happy they spent time with new people.”

This is personally one of my favourite pointers that were shared by the contributors for a number of reasons. 

For one, it breaks the routine. 

It can help break up cliques that may form within the sales organisation. 

Additionally, it nudges people to talk to “strangers” which is something salespeople should regularly engage in. 

Finally, it is far more likely that a sales rep will learn something new from someone they don’t see or talk to every day, all day.

It is the perfect example of a small change that can spark fresh ideas and uncover best practices that might never have come up in standard team meetings.

Get people moving with short exercises

Not every session has to be a formal workshop or a lecture that lasts for hours. 

Leah Levitte put it somewhat jokingly: 

“The average adult attention span is around 8 seconds” 

That is why she and a number of other contributors suggested short exercises and getting people out of their seats and moving. As Leah suggested: 

“Get people moving around if the sessions are longer than 45 minutes.”

Ivy Holt and Nina LaRouche recommended including energisers and quick interactive breaks to keep everyone alert, with Nina briefly proposing a format for doing so:

“Incorporate plenty of interactivity, breaks and energizers to keep the audience engaged and alert. Customer and/or internal team panels are always a big hit.”

Involve multiple go-to-market roles

One aspect of SKOs that often gets forgotten is that they are a great opportunity for the entire sales team to talk to other go-to-market roles. 

This is beneficial on a number of levels – from making sure that everyone’s on the same page business-wise to (in)formally sharing insights that might have been siloed, to building connections on a personal level.

Paul Harvey insisted on inviting as many of the customer-facing teams as possible, so everyone shares the same knowledge and vision. 

Kelley Shirazi expanded on this idea:

“Breakout sessions should be inclusive of the entire extended deal team where that makes sense; SDR/BDR, AE, SA, CS and Partner teams should have the opportunity to attend at least one breakout session together to enhance trust, align on key processes and foster collaboration so they can execute throughout the sales cycle.”

When different groups tackle a breakout exercise side by side, they start to see how their roles intersect, which pays off later when they collaborate on deals or other initiatives. 

In order to make sure everything has a pay-off down the line, it is important to reinforce everything that has been learnt during an SKO and that is what the next section is all about.

4. Follow-through and reinforcement

The excitement and energy from a successful SKO can fade quickly without a clear plan to sustain them.

Many contributors insisted on turning post-event energy into ongoing progress, by turning new knowledge, fresh ideas, and heightened morale into ongoing habits that support sales success.

Easy access to materials

Arguably the easiest and the most practical way to reinforce the agenda from the SKO is to make the content readily available and logically organised as quickly as possible. 

Russell Wurth, the Head of Revenue Enablement at a cyber risk detection and response platform, highlighted the forgetting curve, stressing that even an inspiring session can fade fast if reps can’t revisit what they learned. 

Tim Carlson echoed this, recommending posting all content and videos nightly if possible, or at least as soon as the SKO finishes (I can only presume that he had multiple-day SKO in mind). 

This should really be the bare minimum that should be done as a way of immediately reinforcing new knowledge that people have (hopefully) absorbed.

Manager-driven accountability

I often advocate building great relationships with sales managers due to their enormous influence on all things enablement, and the same goes for SKOs. 

Frontline managers play a central role in reinforcing and extending the lessons covered during SKO. Alicia Avrach underscored this point:

“If there are certifications or expected actions for the team to take, you need to get on them immediately afterwards, and continue the drumbeat until they’re adopted.”

She sees managers as the driving force behind ensuring these tasks actually happen, rather than letting them slip through the cracks. 

Lauren Channell offered a similar perspective:

“It’s easy for reps to walk away inspired but unsure how to apply what they learned. 

Equip them with post-SKO resources, reinforcement sessions, and clear next steps to turn knowledge into execution.”

Managers should always be there to support their teams in those next steps.

Keeping the momentum going

Reps often return to overflowing inboxes and looming deadlines once the event ends, making it easy for new ideas to get drowned out. 

Russell Wurth suggested scheduling regular post-SKO enablement or refresher sessions to ensure the main takeaways stay top of mind. 

Alicia Avrach was even more direct: 

“The SKO vibe should permeate your entire first quarter.” 

She believes leaders should keep that energy alive for weeks (or months) afterwards with ongoing check-ins, group workshops, or even bite-sized coaching challenges. 

The crucial takeaway here is that the SKO should never be an isolated event with a few new insights that are forgotten the next week. 

I am a big proponent of reinforcement in all things enablement and the same goes for SKOs. 

Conclusion

Far too often, a sales kick-off can feel like a monumental effort that, underwhelmingly, yields only fleeting enthusiasm. 

Yet, if you take the steps my contributors laid out, it can become an event that truly shifts (or reinforces) the trajectory of your sales organisation and delivers sustained impact well beyond its final day.

From establishing firm strategic foundations and scrutinising every speaker request, to crafting an agenda that respects your reps’ time and builds in genuine collaboration, this article shows that a successful SKO is the product of thoughtful planning, clear objectives, and genuine engagement.

It doesn’t end when the sessions wrap, either. 

By making content accessible, empowering frontline managers, and scheduling ongoing refreshers, you ensure that what’s learned on SKO day continues to shape sales behaviour tomorrow, next month, and throughout the upcoming year.

Above all, it’s clear that a great SKO is neither a race to jam in “just one more presentation” nor a parade of executive keynotes.

Instead, it’s a dynamic shared experience, bringing together cross-functional teams, creating real connections, and reigniting a sense of purpose for the whole sales or GTM organisation.

I’d like to extend my heartfelt thanks to Alicia, Beverlie, Eric, Ivy, Kelley, Lauren, Leah, Liz, Louisa, Mat, Monti, Nina, Paul, Russell, Tim, and Todd. 

Their collective wisdom, drawn from years of leading and refining enablement approaches at top companies, is what helped bring these best practices to life. 

My hope is that by reading their advice (and applying it), your next SKO will drive the kind of momentum all revenue leaders dream of.