Are your sales kickoff events actually driving revenue, or are they just expensive company parties?
If you're spending millions on SKOs without clear paths to productivity, you might be missing the mark. According to insight shared during SellMeThisPen podcast by Ashton Williams, Director of Slack Enablement at Salesforce, most companies are approaching their SKOs all wrong.
"If it's not about seller productivity, it's not worth the millions it costs,"
says Ashton, who has transformed how Slack approaches sales enablement and led their most successful SKO to date.
In this article, we'll analyze the common pitfalls of traditional sales kickoffs and share Ashton's proven blueprint for creating an SKO that actually drives revenue growth and upskills your sales team.
Let's be honest – most sales kickoffs today follow a predictable and ineffective pattern:
The result? Wasted budget and disengaged sellers who return to their territories without the tools they need to succeed.
Sales leaders often fall into the trap of viewing SKOs as marketing events rather than strategic enablement opportunities. SKOs agenda is usually packed with executive speeches and product presentations, leaving little time for what truly matters: practice, collaboration, and actionable learning.
Before diving into how to create an effective SKO, Ashton offers a provocative perspective: sometimes, you shouldn't have one at all.
According to Ashton, don't bother with an SKO if:
This might sound harsh, but when you consider the enormous investment that goes into planning and executing an SKO – not to mention taking your entire sales team away from selling – it's worth asking if the return justifies the expense.
Ashton Williams shares a comprehensive approach to sales kickoffs that breaks down into three critical phases: before, during, and after the event. Let's explore each stage in detail.
1. Create resources early
The most successful SKOs don't start when everyone arrives – they begin weeks in advance with careful preparation of enablement resources:
"Give sellers a treasure map – each session should unlock pieces they need," explains Ashton.
This preparation ensures that everyone arrives with a clear understanding of what they'll learn and how it connects to their success.
2. Move keynotes to pre-SKO virtual sessions
One of Ashton's most counterintuitive recommendations is to move traditional keynote content (like CEO vision and company updates, product roadmap overview or high-level strategy discussions) to pre-SKO virtual sessions.
By shifting these information-heavy presentations to pre-work, you free up the valuable in-person time for activities that truly benefit from face-to-face interaction. This approach respects sellers' time and ensures they arrive at the SKO ready to engage in higher-value activities.
1. Fill in-person time with high-value activities
With the informational content handled in advance, your in-person SKO can focus on activities that drive real results:
"Being together changes how people hear and take in information," Ashton notes.
The energy and collaboration of in-person interaction create learning opportunities that simply can't be replicated virtually.
2. Enable real-time action
One of the most powerful aspects of bringing your entire sales organization together is the opportunity for immediate action. At Slack's SKO, sellers were regularly stepping out of sessions to:
This real-time problem-solving is "the magic of in-person SKOs." It creates immediate impact and shows sellers the value of the event.
3. Hold live Q&As with product teams
Perhaps surprisingly, one of the most valuable sessions at Slack's SKO isn't a flashy keynote or high-profile speaker – it's direct access to product experts.
"To this day, our reps say Q&A with product teams is the single most valuable session every time," says Ashton.
These sessions work because they provide real-time answers to pressing questions by experts who rarely interact with sales and deep product insights from the creators themselves. they also allow immediate clarification on complex features.
To illustrate how these principles come together, Ashton shares an example from Slack's SKO: the Big Deal workshop.
During this session, sellers brought actual deals they were working on for live review with executives. What made this workshop particularly valuable was the cross-functional participation.
This collaborative approach transformed theoretical training into immediate action on real revenue opportunities.
1. Measure success meaningfully
When evaluating your SKO, Ashton warns against focusing on superficial metrics like number of sessions delivered, attendance rates and presentation quality scores.
Instead, you should measure what truly matters:
Do people feel confident they'll hit quota?Is there a culture of continuous learning?Do sellers believe in the product they're selling?Are leaders bought in and modeling the right behaviors?
These qualitative measures provide a more accurate picture of your SKO's true impact on sales performance.
2. Make learning ongoing
The most successful sales organizations recognize that enablement isn't a one-off event but an ongoing process. Ashton recommends extending the SKO impact through:
By building these ongoing learning structures, you ensure that the investment in your SKO continues to deliver returns throughout the sales cycle.
Sales kickoffs represent a significant investment for any organization, both in terms of budget and opportunity cost. By reimagining your SKO strategy with Ashton Williams' blueprint, you can ensure that this investment delivers real returns in sales productivity and performance.
The key takeaway? Stop treating your SKO as a marketing event or information dump. Instead, design it as a strategic enablement opportunity focused on practice, collaboration, and immediate action. With this approach, your next sales kickoff can become a genuine catalyst for revenue growth and seller success.
In this episode of SellMeThisPen Podcast, Michael talks with Ashton Williams about transforming sales kickoffs from expensive corporate events into productive enablement opportunities. They discuss why traditional SKOs often fail, what makes an SKO truly valuable, and how to implement a before-during-after strategy that drives real results.
Ashton Williams is the Director of Slack Enablement at Salesforce. She has led Slack's most successful SKO and continues to drive impactful initiatives that transform how teams learn and operate at scale. With her extensive experience in sales enablement, Ashton provides practical insights for sales leaders looking to maximize their enablement investments.
