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Salespeople are perpetually busy throughout the year, as they strive to find their next customer and hit their quotas.

While it’s great to see a motivated sales team working hard day in and day out, it’s important for them to take a step back and regroup every once in a while. Sales professionals thrive when given the opportunity to learn, develop new skills, and interact with one another. That’s what makes the annual sales kickoff meeting so important.

With that being said, not all sales kickoffs are created equal. Some are incredibly valuable, while others are enjoyable but mostly frivolous and inessential. Or worse, a bad sales kickoff can become an interminable slog featuring presentation after presentation that bores employees to tears.

When a sales kickoff is executed to perfection, it fuels your sales team throughout the entire year. And as with any event, the success of your sales kickoff depends on your planning and preparation.

The following guide comes from Patrick Purvis, ZoomInfo’s Senior VP of Revenue. Prior to ZoomInfo and DiscoverOrg joining forces in 2019, Patrick played a key role in planning many of DiscoverOrg’s annual sales kickoffs — and he’s got plenty of tips to share! Let’s get into it.

How to Create a Great Sales Kickoff

Planning a sales kickoff depends on many different factors, from the size of your sales team to the location of your company, and more. But, the following steps are a great place to start for anyone looking to plan a memorable sales kickoff:

  1. Identify specific goals for the event.
  2. Choose an intimate, non-corporate environment.
  3. Set an agenda with actionable tips that can be implemented on Monday morning.
  4. Use data-driven content.

These four areas of focus have helped make our events one that our sales team looks forward to all year long — and gives them a boost of energy which they carry throughout the following year.

1. Identify the specific goals of the sales kickoff.

Before we pick a theme or discuss any of the other fun components, we think about the goals and outcomes we want to get out of the gathering. How do we achieve these goals? And how do we measure them?

Our objectives always fall into three buckets: bonding and morale-boosting; improving our sales team’s knowledge of our product and space; and improving soft sales skills.

We make sure the event is not three days of product training.

“We focus on honing our craft and finding new strategies in sales and customer success,” says Steve Bryerton, our Vice President of Sales. “The content changes a lot from year to year.

“We have different people lead sessions, so it’s not just sales leadership. It’s also our CMO, we bring in outside thought leaders. We bring in a customer to come in and talk — to gain insight into how his team uses our product and what changes they’re seeing.”

Example

Bryerton offers this example from our 2017 event. “Selling to Marketers” was the focus of the event. As marketing departments handle an increasing percentage of a company’s budget, one of our sales goals was to sell more to marketing buyers. Following the event, we had a higher win rate and a higher deal size for marketing buyers. The SKO played a major role in that result.

While our event is obviously sales-focused, we invite other departments for at least part of the 2- to 3-day weekend. Marketing, customer success, operations, and learning & development all play an important role in the SKO. For this example, the marketing team had a larger role as we discussed tactics to improve our ability to sell to a marketing audience.

Find an area of opportunity — say, breaking into a new market, or adopting a new approach, such as social selling — and build out the agenda from there.

2. Select an intimate, non-corporate environment.

Culture is incredibly important at our company. Sales kickoffs provide the opportunity to reward your team with a fun experience — while also educating them and providing them with tools for success. That means no boardrooms and button-up events.

“We all go to an out-of-town retreat,” says Tom Studdert, Vice President of Learning and Development. “It sends a message that this isn’t a corporate event; it’s for learning and retreat. A physically different space means that it’s a different world. I like that message.

“The cool thing about our SKO is that it doesn’t feel corporate,” Studdert says. “We don’t go to a corporate hotel, we don’t go to boardrooms. We go to retreats with outdoor time, with evening activities that we plan: we have a campfire, musicians bring guitars, we have a dodgeball night. Everyone is together. We all love it.”

Of course, sales professionals still love an opportunity to get dressed up. Our SKO ends with a black-tie gala and awards banquet, where we recognize the amazing work our sales teams do every day.

“The awards ceremony ensures that stand-out performance is recognized in front of peers and significant others,” Bryerton says. “That’s a very proud moment, a very big moment. We get to see everyone in a different world, dressed up, excited. We’re all thinking, ‘I work at a company that’s not just amazing but supports me in my growth and experience.’”

Example

With our office in Vancouver, Washington, a great choice for our SKO was an outdoor retreat in nearby Bend, Oregon. It’s a few hours’ drive south. The rustic environment is different enough that our team is excited, but also out of their comfort zone.

Everyone brought dress clothes for the concluding ceremony, but the event had an otherwise casual atmosphere. It was easy to learn in a relaxed environment, and our sales team enjoyed interacting with one another outside of the day-to-day office grind.

3. Set an agenda with actionable tips that can be implemented on Monday morning.

By this point, we’ve made it clear that kickoffs should be enjoyable, fun experiences for a sales team. But above all else, an SKO is about learning and development. For us, the weekend is filled with workshops for intensive learning around a specific agenda.

“We’re not concerned with getting on stage and lecturing to a crowd,” says David Sill, Senior VP of Sales. “If everyone doesn’t walk away with skills they can turn around and use Monday morning, we’ve failed. It’s very development-oriented. We have a strict rule: no pontificating to the masses.”

Here are some examples of specific skill sessions we’ve used in the past:

  • The Socratic Method: The Art of Selling Through Questions
  • Let’s Get a Bigger Share of the Biggest Wallet: Selling to Marketing
  • The Narrative Advantage: How to Leverage Storytelling
  • Selling Value: Using Stories and ROI to Illustrate Value
  • A Day in the Life of a Customer
  • Wait. How Did We Get Here? Mapping the Buyer’s Journey

“We’re really keen on the idea of getting out of one’s comfort zone,” Sill says, “from our CEO, Henry Schuck, right down to the newest employee. If you’re putting on the jersey every day, you shouldn’t get too comfortable. Comfort zones are deadly.”

Cross-functional empathy is another important part of our agenda. Sales kickoffs are a great way for sales workers in different roles to interact and learn about each other’s day-to-day processes.

“Our Customer Success Managers (CSMs) need to know life of Account Executive, and vice versa,” Sill says. “We paired people into cross-functional groups, and each team had to present on a particular use case. For example, spinning up an SDR team, or executing ABS for the first time. Everyone got to roll up their sleeves together in a practical way, so they all walked away with something they can all use. We’re aiming for practical value in every session.”

Example

The following is a perfect example of how an SKO can be informative and provide actionable value, while still being fun. Sill recalls a kickoff from a couple years ago, where everyone had to memorize a spirited soliloquy from a movie.

“Our premise was that if you’re on the phone trying to retain business, it’s paramount to express conviction. If you don’t sound like you believe what you’re saying, how can you expect the prospect or client to? And still, most people aren’t going nearly far enough verbally to sound like that. Everyone had to perform their soliloquy in front of the entire crowd.”

While the performances were fun and entertaining, the real learning experience came afterward.

“We recorded it and played it back,” Sill says. “You think you’re pouring it on thick, but the truth is, you can pour it on much thicker. And that’s a great teaching moment when, individually, you listen to yourself and think, ‘Yeah, it’s true, I could have gone a lot harder there.’ So yes, we force people outside their comfort zone. It’s the only way we can all grow beyond where we are now.”

5. Use data-driven content.

The quality and depth of your content is crucial to the success of your sales kickoff. But, it can be difficult to determine how effective your content is and how your sales team responds to it. Through tests, surveys, and other forms of analysis, you can test and optimize your content so that it improves with each and every event.

“We want to walk away with everyone better at certain skills, particular talk tracks,” Bryerton says. “Our L&D department helps retest and redeliver on that content throughout the year. We circle back in team meetings to refer to it, so that the knowledge isn’t lost. We’ll continue to harken back and build on those things that we learned over the coming year.”

Example

We implemented a pre- and post-kickoff test, based on the outcomes we generated, presentations we delivered, and any other content that we shared throughout the event. Attendees were tested on their knowledge on account based marketing, storytelling, the Socratic Method (selling through listening), pipeline management, selling to marketers, the buyer’s journey, and more.

“We saw a 13% point increase in knowledge gained following the SKO on these topics,” Studdert says.

Final Thoughts on SKOs

A sales kickoff represents much more than a fun getaway or an informational learning session. The most effective kickoffs create a sense of unity among your team, motivate them to strive for greatness, and help them develop into their best selves.

We hope our experiences planning sales kickoffs gave you some fresh ideas for your next gathering. Remember this: when it comes to sales kickoffs, fun and informational are equally valuable tones to strive for, and they are not mutually exclusive.

Patrick Purvis is the senior VP of revenue at ZoomInfo, where he is responsible for strategic account growth. Formerly Chief Revenue Officer, Purvis is a graduate of Oregon State University where he studied Economics.

To learn more about how ZoomInfo can dramatically scale and improve all aspects of your go-to-market strategy, contact our sales team today. We offer the most intelligent B2B contact database on the market.

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