Kickoff season is upon us! While most teams are likely to have their plans locked and ready (and maybe already underway), we’re happy to share a few best practices to ensure your event — for sales teams and beyond — goes off without a hitch.

Our portfolio company QuotaPath recently hosted a webinar on this topic, featuring a panel of seasoned sales leaders and Stage 2 LPs: Steve Goldberg (CRO, Salesloft), Hayden Stafford (President & CRO, Seismic), and AJ Bruno (Co-Founder & CEO, QuotaPath). We recommend listening to the conversation in its entirety, but we’ve summarized for top 5 takeaways for those of you who want the TL;DR.

1. Pick a theme for the event (and the year ahead)

A theme provides a central focus, aligning content and discussions around specific objectives, ensuring all activities contribute to the overall goals. It also serves as a source of motivation, creating excitement and energy, turning the kickoff into a memorable and engaging experience. Steve shares an example of a recent theme that worked really well at Salesloft:

“There’s this analogy out there — what’s the difference between a cow and buffalo. They’ve very similar, but they act differently in a storm. We correlated a storm with what’s happening in the market, talking to our sellers about what they do in a storm — for instance, a cow runs away from the storm, gets tired, and lays down. A buffalo runs through because it knows it will get through the storm much faster. Our goal was to have an SKO that enables everyone to become buffalos, and charge straight through the storm.”

2. Identify a North Star metric, and reinforce it at SKO

Communicating a clear north star goal focuses the attention of participants on a common objective. This shared focus helps in driving engagement and ensures that attendees leave the kickoff with a clear understanding of what needs to be achieved, even if their individual KPIs differ. AJ describes how QuotaPath does this:

“It’s all about getting alignment around one key thing. Our north star metric is tied to compensation. Whether you’re on a corporate bonus or have variable comp, you should feel like you can impact it. The north star metric [should also] be centered around the customer, and how they see success in your platform, which is really important for the team and the company to understand.”

3. Tailor sessions to your organization’s structure

Kickoffs, especially for smaller orgs, can be expanded to include other functions. From fostering cross-collaboration, to emphasizing a customer-centric focus, to improving team building and morale, there are countless positives that an organization-wide kickoff can offer. Steve shares how they’re doing this at Salesloft:

“We call ours a RKO because it’s a Revenue Kickoff. We bring in Customer Success, Consulting, Product, and Marketing — it’s really anyone who touches or influences customer outcomes.”

When it comes to your kickoff’s sessions, you have the option of running the entire event as a group forum, hosting smaller sessions by department/function, or doing something blended. Hayden explains Seismic’s approach:

“I’m a big fan of smaller tracks. There’s a time for collective audiences, but there’s also a time for more specific tracks to hone in on a key message. Kickoffs don’t have to be one large forum over several days. Instead, perhaps it’s one large forum that goes in separate directions.”

4. Incorporate discussions on comp… or don’t

At most kickoffs, compensation discussions serve as a powerful motivator. Clearly communicating how performance is tied to rewards, bonuses, or commission structures 1) sets realistic expectations, 2) inspires your team to set higher personal goals, and 3) reinforces the importance of achieving targets that contribute to the overall success of the company. 

Hayden describes these events as an opportunity to align on customer outcomes, then inform teams on how they will get paid on those outcomes:

“We call this operationalizing outcomes. We measure outcomes around multiple categories — for instance, our sales and success teams have a component of their comp tied to value sold vs. value realized. At our event, we will anchor on messaging around those outcomes, and host workshops on how team members contribute to those outcomes, along with the impact it will have on compensation.”

On the other hand, some feel like these conversations should have already taken place. For Steve and the team at Salesloft:

“It’s really important for sellers to walk into the RKO with their comp plan and their territory, so that when they leave, they know exactly what they’re doing. It’s imperative to have our annual operating plan completed before kickoff, so we can focus on execution in the year ahead.”

5. Maintain focus, motivations, and learnings throughout the year

The theme and north star metric established during a kickoff serve as guiding principles — continuing to emphasize them throughout the year ensures that your team's efforts and initiatives remain closely aligned with the overall objectives of the company. Hayden remarks: 

“Stay with the theme and continue with exercises, workshops, consultants that tie back to it. I would even advocate for a mid-year event, if budget can hold, to reinforce the theme even further.”

Steve also shares his final thoughts:

“[Try to prioritize] in-person QBRs and make sure there’s space for the team to come back together. Once your employees lose connections with the company and their peers, you’re at risk.”

While this isn’t realistic for all companies, reserving time for quarterly reflections is essential. If it can’t be in person, get creative with dedicated time for a remote event. Gathering the team to reflect on themes and continue learning together is critical. 

Implementing SKO best practices not only cultivates a culture of excellence and continuous learning, but also positions your team for sustained success by aligning with organizational goals and fostering a positive and adaptive workplace environment. 

Have tips of your own? Share them in the comments below!