A sales kick-off, when meticulously planned, flawlessly executed, and continuously validated, can be a catalyst for driving success for your GTM organization.

Annual sales kick-offs (SKOs) are often considered a formality – a check-the-box exercise to appease stakeholders and provide a brief overview of targets and strategies for the upcoming year. In my role working with Go-to-Market teams, I’ve found that companies that are forward-thinking have recognized the potential of turning sales kick-offs into a transformative experience that sets the tone for success year-round.

A sales kick-off, when meticulously planned, flawlessly executed, and continuously validated, can be a catalyst for driving success for your Go-to-Market (GTM) organization. Few companies understand this better than Stratix, which specializes in enterprise managed mobility solutions and services.

I partnered with Kip Wagner, Chief Commercial Officer at Stratix whose sales kick-offs have been instrumental and can be directly tied to the success of a GTM strategy, to offer some of the best practices for sales kick-offs in this GrowthBit. We’ll also share firsthand examples from Stratix’s SKO playbook to visualize these concepts in action and help drive results year-round.

Involving interdepartmental stakeholders helps to enrich your SKO’s agenda quality and promotes cross-functional alignment in the planning process.

Crafting your SKO: Bridging teams for year-long success

A sales kick-off should be more than just a company gathering; it’s an opportunity to inspire, educate, align and energize your sales teams.

“My goal is to unify the sales team with the entire organization, ensuring mutual support and shared objectives. I prioritize this by breaking down silos, cultivating interdepartmental relationships, and collaboratively shaping a forward-looking strategy for our sales kick-off, where every facet of our organization is engaged to help drive collective growth.” – Kip Wagner, Chief Commercial Officer and head of Sales Kick-Offs at Stratix

1. Plan and execute with cross-functional collaboration top of mind.

Start early and set clear objectives. The sooner you start planning, the more time there is to solidify key themes, create tailored content, ensure smooth logistics, and establish your budget to develop a well-strategized SKO. First start by defining goals, reviewing last year’s feedback, and, most importantly, identifying the current year’s roadblocks to success. Whether it’s roadmap updates, product and services launches, revamping sales strategies or reinforcing core values, the goal is to instill key objectives into the kick-off.

Involve cross-functional leaders from start to finish. Sales kick-offs should extend beyond the sales team. Involving interdepartmental stakeholders not only helps to enrich the quality of content at the SKO, but also promotes cross-functional alignment in the planning process. This sets the tone and aligns with your organization’s objectives, fostering a united front and equipping your sales team with the resources necessary for yearly success.

Kip’s SKO Insight: I typically assemble a team of six to seven leaders across Go-to-Market to begin SKO planning in August/September. We collectively talk through key themes we want to address this year, as well as the growth trajectory for next year to promote forward-thinking in everything we do. This gives time to ideate themes, solidify branding and messaging, and curate relevant topics and training together to establish what’s going to really drive a strong scope for a well-rounded, cohesive SKO.

2. Curate actionable content and agenda.

Your content should focus on the themes identified with your planning team of internal stakeholders to help equip sales and the broader organization to achieve yearly goals. Examples of topics I’ve seen that help drive value are company challenges, industry trends, cross-functional updates, and continuing education on internal tools. While utilizing engaging formats like panel discussions, workshops, and interactive sessions to maintain participant engagement and investment.

Kip’s SKO Insight: My agenda for the first day focuses on “sales success.” This is a balance of continuous training on technology and processes coupled with dedicated time for marketing, customer success and solutions architect teams to communicate program updates, new offerings, and roadmaps. Day 2 dives into supporting departments, featuring sessions on everything from product and services updates, operational enhancements, strategic partnerships, project management, order management, finance processes and other supporting functions. The goal is to enrich the perspectives of the sales team and foster a collaborative work environment that is engrained well after the SKO is over. I also ensure time is allocated throughout for open-floor Q&A sessions, partner-sponsored lunch-n-learns and/or kick-offs, and in-person workshops.

Connections formed during the sales kick-off meeting can help to streamline communication and promote idea exchange throughout the year.

3. Maximize the time you have together for professional and personal development.

Time spent together is a strategic investment in the team’s cohesion and effectiveness long-term. This is a unique opportunity to align teams, not just professionally, but also personally. Allocate time for team-building activities and networking. The connections formed during the sales kick-off meeting can help to streamline communication and promote idea exchange throughout the year.

Kip’s SKO Insight: I make sure to build cross-functional working sessions and breaks as well as team dinners, lunches and happy hours into the SKO agenda. Partner-sponsored networking sessions also allow our partners to showcase new products for the upcoming year and connect with Stratix sellers and customer-facing teams. Now, I see my remote sales reps engaging with other functions when they’re in town, building on the foundation laid during the SKO to fortify cross-functional relationships. One tip to help ensure there is ample time for networking at the SKO is to decide what information is best communicated beforehand. Ask yourself, “What can I address in advance to free up time for more strategic, meaningful conversations during our two or three days together?” Tackling topics like organizational changes, promotions, and commission plans beforehand enables you to focus on both high-impact discussions and networking opportunities.

4. Leverage technology and gamification.

Sales kick-offs are often seen as obligatory exercises for employees too, leaving them feeling as though they’re ticking boxes for leadership. Remember your employees are the ones immersed in the day-to-day operations, tasked with implementing the strategies and objectives discussed at the SKO. Their input is invaluable and could directly impact both their performance and the overall success of the organization.

Leveraging technology can transform this environment, allowing a safe and inclusive way for (potentially anonymous) feedback from the team, and making sure they are heard. Make your SKO sessions more engaging and informative by incorporating technology like real-time polling and Q&A apps. Platforms like Sli.do, Aha Slides, and Vevox help to gather immediate feedback, conduct live polls, and facilitate rapid-fire Q&A sessions. This not only enriches the dialogue but also adds a dynamic and interactive element, helping to ensure the insights gained are as actionable and relevant as possible.

Gamification also helps promote engagement and fosters healthy competition. One example is to break into small teams and simulate a difficult customer objection teams have to respond to. The winning team is then rewarded with a prize.

Kip’s SKO Insight: During one session, our partners organized a game with our sellers, quizzing them about their products and offering rewards. In 2024, we plan to host a speed dating/happy hour session where partners will have face time with each of our customer-facing teammates, encouraging them to incorporate a game related to their products or services.

Think: 1) Here is how we impacted the client. 2) Here is the process and how we executed. 3) Here is what we can learn from this for next year.

5. Have an engaging and inspiring keynote speaker.

Your keynote speaker can help to put yearly goals into perspective, inspire on a career and personal level, and light a fire underneath employees to connect the dots between effort put forth in the coming year and the benefit of accomplishing these goals for their individual careers. They help serve as a catalyst for change and improvement within the team. This multifaceted connection provides a breath of fresh air for the standard SKO agenda creating a deeper engagement that should translate into increased motivation, productivity, and unity among teams.

Kip’s SKO Insight: In the past, we have leveraged our own executives (CEO, CCO, Chief Strategy Officer) as keynote speakers. This year, we plan to engage an external motivational speaker with expertise speaking at B2B SaaS, technology and other team events as well as sports teams. I encourage leaders to first explore their own networks for high-quality, budget-friendly external keynote speakers.

6. Incorporate customer stories and insights.

Building on your keynote’s inspiration, now is an excellent time to spotlight the real-world success of your clients; emphasizing the importance your employees played in positioning your product to solve customer pain points. These success stories should highlight the efforts of your teams (territory expansions from sales, upsells from customer success, new business wins) and tie them directly to next year’s goals.

Think:

  • Here is how we impacted the client
  • Here is the process and how we executed
  • Here is what we can learn from this (and replicate it) next year

All of which lends credibility to the goals and initiatives laid out for the upcoming year, solidifies your product’s impact, and fosters a sense of camaraderie among your employees.

Kip’s SKO Insight: I typically wrap up the SKO by celebrating customer success stories and sharing best practices, setting the trajectory for the upcoming year. This ensures the SKO is not just motivational but also educational, helping to set the stage for a successful year.

Validate SKO success year-round: What’s measured gets improved

Your sales kick-off is over. How do you help ensure your team is trending toward the goals you carefully outlined? The true value of your SKO lies in how you sustain that momentum and build on it. Below are four ways to measure and drive continuous impact throughout the year. This should be communicated to your teams at the SKO so expectations are clear.

  • Establish clear accountability and prioritize consistent communication: Clarify roles and responsibilities, outlining who is responsible for what outcome. Make a regular dialogue plan after the SKO to emphasize key takeaways and strategies. Share success stories, goal updates, and emerging trends to build on momentum.
  • Facilitate ongoing training and development: Offer continuous learning opportunities through regular training sessions, webinars, and workshops to sharpen skills and update teams on industry shifts.
  • Implement and track performance metrics: Utilize measurable indicators to track progress toward goals, and celebrate achievements by recognizing and rewarding high-performing individuals and teams, fostering a culture of accountability.
  • Validate intended outcomes: Set up reviews on a quarterly basis to assess progress towards executing the key initiatives of the SKO.

Kip’s SKO Insight: After our last SKO, I gave my team a list of 20 to 25 essential hard and soft skills (time management, empathy, and negotiation to name a few) crucial for sales success, having each person self-assess on a scale of one to five in each category. The exercise wasn’t just for the sales team; it involved customer service reps, account managers – anyone who interacts with customers – to help improve on how to think differently and thoughtfully when approaching the market and helping existing customers. I collected this data and used it to identify collective strengths and weaknesses. The weaknesses helped to lay the foundation for targeted ongoing training sessions to address the team’s collective ‘blind spots,’ in addition to the “traditional” sales trainings. As a result, our team is becoming stronger, more agile, and more attuned to the nuanced needs of their customers. This exercise has allowed us to validate the ongoing success of the SKO initiatives, and helping to ensure that we are always evolving and improving.

Here’s the bottom line.

Your sales kick-off serves as the spark for your Go-to-Market team’s measure of success in the forthcoming year. It demands meticulous planning and cross-functional leadership to help maximize its potential. Beyond merely setting annual goals, a well-executed SKO can help serve as a creative platform to inspire your teams to discover their “why” for the year. However, remember that a strong SKO is just the beginning. To help ensure continued progress, it’s crucial to implement a robust tracking system, communication plan, and ongoing training to monitor your team’s trajectory toward achieving the objectives set during the SKO.

This GrowthBit is featured in LLR’s 2024 Growth Guide, along with other exclusive insights from our portfolio company leaders and Value Creation Team. Download the eBook here.