How To Plan An Effective Sales Kickoff (SKO)
Align your sales and GTM teams to kickstart 2025 with the following "pro-tips", plus templates for budgeting and setting an engaging SKO agenda.
A well-planned Sales Kickoff (SKO) is one of the most critical team retreats your company will plan each year.
It's not just another meeting—it's an opportunity to align your sales force with your company's strategic objectives, energize the team, and set the tone for the coming year.
Whether you’re leading a team of dozens, or hundreds, and regardless of whether everyone shares a couple distributed offices or is fully remote, planning an effective SKO requires intention, precision, and an understanding of what will truly resonate with your team.
Below, we’ll cover essential tips for planning an impactful SKO that not only motivates but also drives results. You can also dive deeper on budgeting, locations, and other topics of interest with previous posts on The Offsite Blog below:
I know you’re busy, so below we’ve put together the high-level packet of resources you’ll need to plan an effective Sales Kickoff.
When you're ready to dive deeper into planning your 2025 SKO, set up a free Offsite account and then reach out to me directly at jared@offsite.com.
Time is money, so let’s get into it…
Don’t forget to download our 2025 Sales Kickoff Template as well as our free Offsite Budgeting template.
Of course, visit offsite.com whenever you plan your next Sales Kickoff.
Define Clear and Measurable Objectives
Every SKO should have clearly defined goals that align with your company's broader business strategy.
What do you want your sales team to walk away with?
Is it a deeper understanding of new product offerings? A renewed focus on pipeline generation? Or perhaps a stronger alignment on key account management strategies?
Whatever your objectives, ensure they are specific, actionable, and measurable. Consider these potential objectives for your SKO:
Strategic Alignment: Ensure the entire sales team understands and is committed to the company’s revenue goals for the year.
Skill Development: Focus on building or refining sales techniques that align with your company’s current market position.
Motivation and Morale: Reinforce the company culture and values while recognizing top performers to drive morale.
Cross-Departmental Collaboration: Foster stronger connections between sales and other key departments, such as marketing or customer success.
By setting specific goals, you provide a clear framework for the event and a benchmark against which success can be measured.
Gather Pre-Kickoff Feedback from Your Sales Team
Your sales team is on the front lines, interacting with customers and prospects every day. Their insights are invaluable in shaping the agenda for your SKO.
Before the event, send out a survey to gather feedback on what your team feels are the most pressing issues, areas for development, and topics they’re most interested in exploring.
This not only ensures the content is relevant but also fosters a sense of ownership and engagement among participants.
Sample questions for your pre-SKO survey might include:
What challenges are you currently facing in the sales process?
Are there any specific products or services you need more training on?
What kind of motivational content or speakers would you find most inspiring?
What skills do you want to develop further?
This feedback will help you tailor the SKO agenda to the real needs of your team, ensuring that the event is both impactful and engaging.
Send out a basic feedback form to your executive team well in advance (Google Forms work just fine!). You should also sort out practical stuff like meal choices or room requirements while you’re asking for pre-SKO feedback.
Example prompts to get the basics right:
Do you have any food allergies or dietary restrictions?
Do you have any specific needs for accessibility?
Are there any dates you absolutely cannot attend the retreat?
Find out what issues they think need addressing, what skills they want to build, and what kind of activities they'd enjoy. After the retreat, you can ask for their feedback on how it all went to make the next one even better.
Choose An Inspiring And Practical Venue
The venue for your SKO can significantly influence the event’s success.
It should be a place that inspires creativity and collaboration but is also practical in terms of logistics and cost.
Whether you opt for a retreat-like setting that allows for deep focus and team-building or a more urban location that underscores efficiency and connectedness, the venue should align with your event goals.
At Offsite, we offer a curated Airbnb-style marketplace of venues that cater to a wide range of needs.
From boutique hotels to expansive resorts, we help you find a location that fits your budget while still providing an environment conducive to achieving your SKO objectives.
Plus, our platform streamlines the booking process, saving you time and reducing costs by up to 40% on room blocks, meeting space, and more.
To secure an inspiring and cost-effective venue, it's essential to consider factors such as location, ambiance, size, flexibility, and available amenities (such as meeting space, Wi-Fi speed, and activities).
Offsite also provides end-to-end offsite planning services to hundreds of remote and hybrid companies (like Buffer, Webflow, HiBob, Hampton, 15Five, Linear, Metabase, LinkSquares, Rattle, Airbyte, and others), so we are only an email away if you’d like to explore having our help with your Sales Kickoff planning.
Develop An Agenda Focused On The Business Objectives For Your Offsite
The agenda is the backbone of your SKO.
It should balance strategic sessions with motivational content, skill-building workshops, and opportunities for team bonding.
Start with the big picture—what are the main messages you want your team to absorb?
Then, break that down into sessions that build on each other throughout the event.
Here’s a simple framework to consider:
Opening Session: Set the tone with a keynote that aligns the team with the company's vision and goals.
Product/Service Deep Dive: Provide in-depth training on new or updated offerings.
Sales Strategies Workshop: Interactive sessions that focus on refining sales tactics and techniques.
Team-Building Activities: Foster camaraderie with activities that encourage collaboration and communication.
Recognition and Awards: Celebrate top performers to motivate the entire team.
Closing Session: Reinforce key takeaways and set clear action items for the coming quarters.
Remember to build in some flexibility to adapt to the energy and feedback from your team as the event unfolds.
For a detailed agenda, check out our 2025 Sales Kickoff Agenda Template.
Assign “Pre-Work” To Attendees
To get the most out of your SKO, your team needs to arrive prepared.
Assign pre-work that aligns with your agenda, such as reviewing sales reports or sales calls, preparing presentations on their regions, or completing e-learning modules on new products.
This not only ensures that everyone is on the same page but also maximizes the effectiveness of the in-person sessions.
Pre-work might also include:
Analyzing previous quarter’s sales data and preparing a brief presentation on findings.
Completing a survey on key challenges and opportunities in their territory.
Reviewing case studies that will be discussed during the SKO.
Here’s how to set up effective pre-work:
Inform the leadership team about the retreat's strategic focus weeks in advance, encouraging them to gather pertinent data and insights to support their strategic planning suggestions.
Organize sessions for quarterly/annual retros, strategic planning for the upcoming quarter/year, and long-term vision-setting so that each conversation occurring during the offsite will be high ROI.
Set up a timeline for attendees to submit their “pre-work”, allowing for thorough review. This guarantees that everyone is prepared before the meeting.
By ensuring that your team comes prepared, you can hit the ground running and make the most of the time spent together.
During The Offsite
During the SKO, the last thing you want is for logistical issues to distract from the content.
Whether it's technical glitches or scheduling conflicts, any disruption can diminish the impact of the event.
If you are a Chief of Staff, Executive Assistant, People Leader, or even a CEO reading this, and want to fully participate in your Sales Kickoff as an attendee, consider hiring a company like Offsite or working with a “day-of” coordinator at minimum (like a wedding planner!).
Here’s how we help:
Venue Coordination: We liaise with your venue to ensure everything is set up to your specifications.
Technical Setup: Our team works to guarantee that all AV and tech requirements are met, minimizing the risk of disruptions.
On-Site Support: We provide day-of coordination to address any issues that may arise, ensuring a smooth experience for all attendees.
Turning Insights Into Actionable Plans
The real value of an SKO lies in what happens after the event.
To ensure that the insights and strategies developed during the SKO are implemented, establish a clear follow-up process.
This might include regular check-ins, progress tracking on key initiatives, and continued training sessions.
Key steps for post-SKO follow-up:
Debrief Session: Gather key leaders to review the outcomes of the SKO and prioritize next steps.
Action Plans: Assign ownership of key initiatives to specific team members, with clear deadlines and deliverables.
Ongoing Communication: Keep the momentum going with regular updates and check-ins on progress.
By turning the ideas and strategies from your SKO into actionable plans, you’ll ensure that the event has a lasting impact on your team’s performance.
Want More?
I could write for days on how to plan an effective Sales Kickoff, or really any type of offsite. Every company is different, and so the team at Offsite is committed to being a resource for you as you work to ensure your team(s) remain agile and ready to tackle whatever problems and opportunities come your way.
Email me anytime at jared@offsite.com, or visit offsite.com for client case studies to see how other companies are planning their offsites.
If you haven’t already, subscribe to The Offsite Blog below for agenda templates, budgeting spreadsheets, and more thought leadership like this post around offsite planning, remote work, increasing employee engagement, and more.
And of course, when you’re ready to plan your 2025 Sales Kickoff, make a free account at offsite.com to search our curated marketplace with over 1000 premier offsite venues.
Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why companies like Buffer, Webflow, 15Five, Linear, HiBob, Metabase, Hampton, and others trust Offsite for their team retreats.
Thanks for reading!
-Jared
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