Supercharge Your Year with a Powerful Sales Kickoff

Before founding SalesHood, a sales enablement platform company, in 2013, Elay Cohen worked for much of the early 2000s at the CRM behemoth Salesforce. He recalls meeting with Salesforce co-founder and CEO Marc Benioff to review the agenda he helped develop for an upcoming sales kickoff.

Cohen’s plan included a number of breakouts over the multiple-day event for small groups to receive training, but Benioff nixed it. There is ample time before the kickoff for training and plenty of time afterward to certify salespeople on training, Cohen remembers Benioff saying. He wanted the kickoff — one of the few times during the year that the whole sales team would be together — to be about connecting, sharing successes and swapping ideas.

“I want you to use the time when we’re together to motivate, inspire and get people pumped up. I want to do things in person that we can’t do remotely,” Cohen recalls Benioff saying.

Why Kickoffs Matter

“Connecting” and “motivating” are words we heard repeatedly from those we spoke with about constructing effective sales kickoffs. Other frequently mentioned concepts: “alignment,” and “celebrate.”

Sales Kickoffs (SKOs) are almost as old as sales itself. In strong economies, companies start the year by bringing their entire sales team and maybe marketing and sales support staffers to an offsite that lasts two to three days. However, in an era of tighter budgets and decreased business travel, some companies may be tempted to eliminate this annual event.

That could be penny wise and pound foolish.

“Sales kickoffs are pivotal events that set the tone for the entire year,” Max Shak, founder and CEO of digital solutions company NerdDigital, said in an email exchange. His key objectives for kickoffs:

Alignment – Ensure the entire sales team is aligned with the company’s overarching goals and sales strategies for the upcoming year.

Team building – Foster a sense of unity and camaraderie by facilitating team-building activities and networking opportunities.

Motivating – Energize the salesforce by reinforcing the value of their work and highlighting their potential to achieve targets.

Training – It doesn’t need to be the focus of a kickoff, but Shak notes there should be room on the agenda for training, whether on new products, updated sales processes or the latest market trends. “You have to equip salespeople with the knowledge they need to excel,” he said.

Make Room for Micro Discussions

Caitlin Begg helps B2B sales teams close more deals by improving their social selling skills. Her company, Authentic  Social, is all about helping salespeople enhance the authenticity of their business relationships in an increasingly digital business world. Sales happens less and less in person, yet Begg helps companies bring a more human touch to their business interactions.

Her company is an extension of her 2016 Harvard University sociology thesis on virtual impressions and how digital communication affects the way we interact as well as form and develop relationships. She is frequently tasked with helping clients create effective sales kickoffs.

“One thing that we like to make sure is integrated into sales kickoffs is a balance of the spectacular and the everyday,” Begg said. “There should be big talks and big things going on. Where I often see companies fail with sales kickoffs is they focus too much on the spectacular.”

So many of those we spoke with about SKOs emphasized the importance of creating numerous opportunities for informal conversations. Begg calls them “micro discussions.” They occur during breaks between formal presentations, over meals and any other spaces between more formal agenda items.

“This is how best practices are shared and what helps people grow,” Begg said. “Getting people together, establishing camaraderie and sharing best practices are the most important thing about sales kickoffs.”

Use Your Technology

Sharing success stories will hopefully happen informally and throughout an SKO, but Cohen said sales leaders need to remember to use the technology that’s available to them to make sure the best strategies get circulated. His SalesHood  sales enablement platform allows reps to record practice pitches or success stories from the past year. Managers can review these, rework any that need it, and incorporate them into an event’s content.

By having sales reps prep before the event, the learning starts early and the participants are more engaged once the kickoff begins. Moreover, they literally have a voice in the content that is presented.


SKOs set the tone for the rest of the year. Don’t overpack the agenda but do load it up with energy and inspiration — what the SalesHood SKO guide calls “bigger than you motivation.”

“A sales team can only be the best they can be if they know what success should look like — and if you make it personal to them,” the SalesHood guide states. “Communicating the difference your company makes to the lives of your customers — or the world at large — will deliver the motivation that everyone is part of something much larger. Present the big picture, then clarify each person’s role in the big picture.”

The reliance on virtual meetings during the COVID pandemic has proven difficult for many businesses to abandon. Employees want to continue working remotely while companies like the savings from drastically reduced business travel. It may be tempting to shift to a virtual SKO or cancel it altogether, but doing so could send the wrong message.

Bringing a sales team together in person not only presents an opportunity to reinforce goals and processes, it’s a culture- building experience.

“Getting your team away from the office really makes a difference in their perception of your investment in them,” said Michael Butler, vice president of sales at Brightspot, a provider of incentive programs and offsite events.

Brightspot’s “The Complete Guide to Sales Kickoffs” states, “Why SKO? The message you are sending your sales team when you make the important decision to bring them all together for sales kickoff meeting is, ‘You are important. We care about your needs and we are committed to your success.’ This is the very first point we make, because culture is arguably the most important, but by far not the only good reason.


Kickoffs should set the tone for the rest of the year and establish overarching goals, but there should be room on the agenda for celebrating past successes as well. The feel of an SKO is decidedly different than a President’s Club incentive travel event, which brings only the top performers together. However, a kickoff can be a great time to call out the most recent President’s Club winners and announce this year’s incentive program.

Butler recalls a client of theirs who ended an SKO by announcing a first-quarter incentive program that awarded three-year leases for Porsche sportscars to the two reps who turned in the strongest start to the year. The vehicles were on display with their engines revving at the kickoff.

Also, having top performers share their success stories and insights with the team at the kickoff keeps them engaged and gives them a well-deserved pat on the back.

Sending attendees home with a small gift can go a long way toward driving enthusiasm and instilling loyalty. Scott Fristachi still has a scarf he was given at a sales kickoff more than a decade ago when he worked for the online real estate company Zillow. Fristachi is now senior director of North American sales at Extu, a provider of channel marketing solutions and incentive programs.

Kickoffs are to educate, celebrate and inspire people,” he said. When he was at Zillow, the company had an annual SKO in Seattle that brought more than 1,000 team members together for several days. The scarf was part of a team outing to a professional soccer game.

Alternatively, sending a follow-up token of appreciation to SKO attendees a few weeks after the event provides an opportunity to reinforce the main messages and inspire them all over again.

Follow Up

Every SKO should be followed up with a survey of attendees. What did they like best about the event? What was missing? Are there skills they wanted more training on? Was the pre- work assignment helpful? Did they have ample time to network informally? Are there team members they would have liked to network with who were not present?

Undoubtedly, you will get comments about the choice of restaurants or the temperature of conference rooms being uncomfortable. Don’t disregard those, but the bigger-picture insights that can help you make next year’s SKO better are what you’re after.

Keep Key Objectives In Mind

SKOs are an important part of company alignment. They energize and align teams by bringing people together. The SalesHood SKO Guide states that agendas should be designed to motivate and to support activities that are only possible to do together as a group. Do not try to cram a year’s worth of training into one week or a few days.

“People jam way too much into their agenda,” says SalesHood’s Cohen. “They put too much emphasis on training and not enough on the storytelling, the collaboration — the real connections that can happen in person.”


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