The New Sales Kickoff: Optimise Your Regular Sales Meets for a Quarterly Sales Boost

January is traditionally Sales Kick-Off (SKO) time for many companies: an opportunity to get the team together and focus on the year ahead. However after the last two years the “normal” SKO format doesn’t seem that viable anymore and a fresh take on the traditional concept is now needed more than ever to keep it relevant.

It’s fair to say that 2021 has been another challenging one — as the economy bounced back from COVID, it was met by supply chain disruption, an energy crisis and creeping inflation. Economic uncertainty has slowed things down again, and your sales team has likely felt the pinch in their end of year results for the second year running. And if we’re honest, even two years later, we’re still adjusting to making remote working the new normal.

So amid the current wave of the pandemic and working from home orders in place, how do we kick start the new year successfully when face-to-face events are less of an option? Team engagement is critical now to get everyone on board and motivated by the goals set out for the year ahead.

Current restrictions and the inability to set plans for the new year complicate things a lot, but this presents a unique opportunity to review the concept of what a sales kickoff is and to introduce a new way of engaging and motivating staff.

The new sales kick-off

SKOs are an integral part of doing business, starting the new year with a fresh injection of clarity, motivation and plan of attack. But as with any meeting, they need planning to make sure they are both purposeful and valuable, not just another tick box exercise to place on your sales teams. Let’s start by looking at the main ingredients of a successful SKO.

At a minimum, the following should be part of your agenda:

  • Review what was achieved in 2021 versus set goals
  • Focus on celebrating success, both teamwide and of individuals
  • Set the scene for 2022; what can we do more, better, different and less
  • Explain why we are doing a sales kick-off
  • Layout how the team will hit their targets for the next 12 months

Sales targets across the board will have taken a hit this year, and be sure to highlight that rather than singling out bad performance. Look at what has been achieved despite the barriers to doing business in 2020/21. Your job is to focus on the data, not your team’s performance. But this is a prime opportunity to get input from your sales staff to tell you how they can do better, rather than the other way around.

A Sales Kick-off is an interactive session, not a presentation

Your sales team is not your audience; they are equal partners in a successful SKO. Don’t be trapped into reusing slides from your end of year leadership team meeting and just listing off OKRs that have been approved at C-level. This is the quickest way to turn your SKO into what seems like added pressure. And if you’re holding it virtually, your participants will quickly turn off.

Before the session, share the agenda with the team. Let them know what you’ll run through and ask for input. It might be beneficial to ask a team member to do a 5–10 minute presentation, either of what they saw as the highlights of 2021 or to collate feedback from their colleagues. Make sure they don’t hold back; you want to encourage an honest discussion when it comes to your SKO.

Ensure people are equipped for a Q&A session and a brainstorm as you go through each part of the agenda. You could ask questions ahead of time such as:

  • What, why and how can we achieve more than last year?
  • What could we do more, better, different or less to improve day-to-day performance?
  • What tools, training, or resources could we embed this year to make the job of sales easier?
  • What parts of the role do people not enjoy? How can we streamline/reduce time spent?

You’ll motivate staff by letting them set the tone for 2022. They are a crucial part of defining the how. Starting off the year fresh with team input is great for engagement, but it’s essential that you are all held accountable for the actions set as you move through Q1 and the rest of the year.

What’s next?

To recap, a successful SKO is achieved by three things. (1) Focus on success, (2) explain the what, why and how of your sales strategy, and (3) high and active participation from your sales team. Despite the virtual meeting setting, you should all end on a high and be clear on the next steps.

But don’t let motivation and engagement wane. This is an opportunity to turn a traditional annual meeting into a recurring event to keep the team on track, add some fun, and refresh your operating rhythm. The SKO becomes a Sales Booster — a quarterly event somewhere between a sales kick-off and a Quarterly Business Review (QBR).

A Sales Booster achieves two things. Firstly it’s easier for salespeople to maintain momentum with another results-based meet at the end of Q1 rather than the following year. And while a QBR is effective at the executive level, the focus on historical performance does little to engage the team or set a plan of action for the following three months.

Get the most out of a Sales Booster

Regularly reviewing, adapting and stretching team performance is good for morale. However, holding mini SKO-type meetings at the end of every quarter won’t achieve this. OKRs aren’t fluid. New products and propositions take time to roll out. Not enough happens in a three-month window to make a quarterly SKO not feel repetitive or valuable. A new approach is needed.

New is the keyword here; teams stay motivated by constantly trying and being involved in new things. They want to be updated on global strategy and company challenges and be aware of the progression and pitfalls encountered. Knowing this will help your team understand what role they play and understand their purpose in the business.

Remember that hybrid working is difficult for many, especially when the shift is towards working from home with minimal office time. Sales is agile and reactive — a scaling fintech with a constant conveyor belt of new products, processes and market strategies means continuous learning needs and professional development. These opportunities are lost when sales teams don’t have optimal F2F time together. People need to see and taste the progress that all their efforts are contributing to. And they need exposure to the broader business and a chance to collaborate with their peers.

Talking with many fintech companies over the past 18 months, we’ve seen that the best performing teams are those that challenge and motivate themselves through regular workshops.

Workshops allow virtual meetings to become interactive sessions. The content should span a wide range of topics, and the format varied so as not to feel repetitive. But they should all include hands-on exercises, some group activities, and at the end to review the takeaway message together.

Having a qualified third party host these workshops is almost a guarantee of success. They bring a fresh perspective, show you have invested in your team’s development, and let staff share their honest struggles and challenges with managers out of the picture. Staff welcome external advice.

Next steps

The core ingredients of a sales kick-off haven’t changed, but the approach has. This is a chance to improve engagement and motivation and encourage new ideas. What’s essential to their success is that these Sales Boosters are held quarterly and focus on the actions agreed in the previous session.

It’s hard to run a successful SKO or QBR on your own. Remember, the metric to success is team engagement and ultimately stronger performance. Humble Technology can help you plan and execute your meeting and make sure to get the most desired outcome — a high-powered sales team.

Our innovative workshops are designed to guide you through the process, elicit buy-in through open feedback and align staff to your strategic revenue goals. We tailor the content of these workshops to your roadmap for 2022 but keep it fresh using our expertise to drive more value for your team.

Annalisa Sarasini — Partner Humble Technology



CEO of Humble Technology — Commercial Advisory for Fintech. CEO of Humble Grape — wine bar, wine merchant, and events company.

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James Dawson

CEO of Humble Technology — Commercial Advisory for Fintech. CEO of Humble Grape — wine bar, wine merchant, and events company.