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Planning a Successful Sales Kickoff - 16 Tips from Marketing Leaders

It’s that time of year again -- when we gather the entire sales team together, energize them, educate them, and align them for success in the new year. This effort often falls to the team that we frequently turn to for connecting and communicating across teams: Marketing. It’s no small feat to tackle this annual event, so we turned to marketing leaders to get their tips for a successful kickoff and hear what they’re struggling with this time around.

Goals for Annual Kickoffs

1.) Identify your goals - not just the activities.
“Most sales kickoffs (SKOs) are focused on sales ‘fun’ and less on the goals. Think about what you want to get out of the event and the rare opportunity to have your team all together. Even if the result is ‘fun activities,’ identifying your goals will allow you to tailor those events.” -- Jeanne Hopkins, Chief Marketing Officer at Lola

2.) Recharge your team.
“The kickoff is a time to recharge the team, reset the mission, reinforce what we do, and provide more compelling examples of how we accomplish that. Our kickoff is one week long, and we spend the first half focused on energizing the team, and the second half turns to training and launching new initiatives. We find that you just can’t replicate the energy you get from this face-to-face event.” -- Jim Williams, VP Marketing at BlueCat

3.) Align, inspire, and connect.
“The primary goal of our kickoff is to create alignment around our 2019 goals for the whole company, as well as inspire our team for an amazing year. We also learned that our employees are really interested in what’s happening in other departments, so we are creating more time to allow employees to opt in to learn about other areas of the business.” -- Kelly Esten, Sr Director of Product & Partner Marketing at Toast

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4.) Focus on customer value.
“The primary goal of our kickoff is for customer facing members of our team to walk away better equipped to qualify, sell, and deliver value for the customers they work with. If it doesn’t pass a test of, ‘will this meaningfully help folks do their day-to-day job better?’ it doesn’t make the agenda.” -- Jonah Silberg, Sales Manager at Wistia 

Kickoff Planning & Leadership

5.) Collaborate on the planning itself.
“SKO leadership should include a combination of people. We include both management team members and ambassadors - employees who know the ins and outs of the business and team. While Marketing often leads the charge, we lean on other teams to nail down themes, key points, activities, etc.” -- Jeanne Hopkins

6.) Engage outside support when needed.
“Last year was our first time using an outside event agency to help plan the event logistics, branding, and activities. It was a good test run and we have even bigger plans this year to make it a truly memorable, and more interactive, event.” -- Jim Williams

7.) Get representation from across the company.
“Our kickoff is an all-company kickoff, which means it’s important to have content for everyone, regardless of their role. A cross-functional team leads our company kickoff - the executive team and a lead from each department joins a kickoff committee that creates the agenda. There’s also a separate team that manages the logistics - from travel and IT needs to securing locations and food and organizing fun events - they’re who really makes it all come together! For the first time this year, we are creating a sub-committee to own each ‘track’, which has been working really well.” -- Kelly Esten

8.) Bring people together on neutral territory.
“We fly in all of our employees to a new destination every year. Our team is spread out over many locations, and this is a key opportunity to bring everyone together.” -- Jenn Steele, Chief Marketing Officer at Madison Logic

9.) Expand beyond sales.
“Over the past year, our company has successfully focused on sales and marketing alignment, and so our ‘sales’ summit is now officially a ‘sales and marketing’ summit with integrated and separate content for both functions. We think this will send a strong message to the company on the importance of working and planning cohesively throughout the pipeline, as well as allow us to accomplish some practical sessions relevant to both groups.” -- Mike Kaplan, VP Marketing at ENGIE Insight

10.) Don’t wait all year.
“Our Revenue team (Marketing, Customer Success, and Sales) does a two-day Quarterly Business Review where we reflect on last quarter’s results and discuss how we’ll accomplish our goals for the upcoming quarter. The quarterly cadence allows the team to celebrate key wins and spread out critical learning that occurred during the quarter -- key wins and learnings that might be lost in the run of a year. It also allows us to measure quarterly success against annual goals and adjust / create a clear plan for continued or improved success in the next quarter. And we also get the opportunity to foster more team bonding and morale on a regular basis.” -- Justin Blackburn, Product Marketing Manager, Affinio

Sales Kickoff Themes & Content

11.) Lead with Energy.
“It's so tempting to pack the day, cover everything you possibly can, and deliver a kitchen sink of enablement material. Last year was our first full day sales kickoff. A big focus was to limit ‘lecture style’ sessions and keep things as interactive as possible. Even so, during the course of the day there were clear peaks and valleys of energy in the room that prompted some changes in our 2019 agenda. This year we'll jump right into a full-group role play activity first thing in the morning, rather than having the team sit and listen to a recap of goals and strategy. While that information and context is critical, it's been shared in advance of kickoff and there's been opportunity for questions. Thus it doesn't necessitate a full walkthrough.” -- Jonah Silberg

Bonus: “Also, humor never hurts! We start the day with a fun video to get the energy up right from the start.” Here's Wistia's kickoff hype video from 2018:


12.) Mix up the formats.
“This year, we’re minimizing the talking heads sessions - instead focusing on interactive sessions to maintain interest and energy levels. We’re doing a mix of exercises, case studies, and town halls in addition to the typical classroom style presentations.” -- Jenn Steele

13.) Keep it short and sweet.
“We’ve learned to be more efficient with our timing and discussions. We get updates from each team, reflect on our results, and drive action items. While open discussions can be great, they often lead to long and unnecessary tangents that pull the team away from the most valuable topics.” -- Justin Blackburn

14.) Hear straight from your customers.
“The kickoff presents a great opportunity to bring customer stories to your whole company. The first day of our kickoff this year will be a meeting of our Customer Advisory Board, and a few of the customers will stick around to participate throughout the week as keynote speakers and panelists. Particularly in an industry where it’s hard to share customer stories publicly, this is a huge opportunity for employees to hear directly from our customers the impact that we have on their businesses.” -- Jim Williams

15.) Focus on alignment.
“Our sales team craves training, but we’ve learned that the kickoff isn’t the right place for it. The sales kickoff is a great opportunity to energize and align the team and do some collaborative training sessions. But deeper dive training will be reserved for kickoff follow up, when sales reps can spend more time digging into product details.” -- Jenn Steele

16.) Don’t do everything.
“The hardest part is fitting everything in. There are so many sessions that can add value for the sales team, but ultimately you need to make difficult decisions based on what’s critical to the business and team capabilities, as well as what other channels you have to train and communicate throughout the year. My advice when considering content is to assess what is most valuable to have everyone in the room for (which is likely rare) and what really needs to be communicated during the summit versus elsewhere.” -- Mike Kaplan

Have your own lessons learned for your company or sales kickoff? Let us know!

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Ellie Mirman
Ellie Mirman, a Crayon alum, is currently CMO at Mulberry, the consumer-first product protection platform. Previously, she was VP of Marketing at Toast, where she built and led the marketing function across demand gen, content marketing, product marketing, branding, and customer advocacy. Ellie also held multiple marketing leadership positions at HubSpot during its growth from 100 customers to IPO. She loves working at the intersection between marketing, sales, and product, and building marketing from startup to scale-up.