InsightSquared held our official Sales Kickoff this week, starting the quarter with a bang.

The event included presentations from the VP of Sales, CEO, Chief Product Officer, VP of Marketing, and more — all focused on educating the sales team, inspiring them to work hard, and making next quarter our best yet.

The InsightSquared sales team didn’t just have a quick Kickoff for a few hours in a conference room in the office. Instead, the entire team arrived bright and early at the Cambridge Innovation Center (CIC) for a full day of sales presentations, education, and training all focused around one central theme.

“There are two objectives for a Sales Kickoff: motivation and education,” Sales VP Steve McKenzie explained. “For this one, we focused on operational excellence.”

We know this event is a little unusual for a company our size. Most startups like InsightSquared don’t have an official, day-long Sales Kickoff. In fact, most people think of Sales Kickoffs as something only done by massive enterprise sales teams with hundreds of reps.

However, we believe that even if your company is small, you should still invest in a team-wide quarterly Kickoff. While it is expensive to take every sales rep off the phones for a full day, it’s completely worth it.


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This type of event is hugely beneficial to your sales team — boosting morale, promoting a sense of teamwork, and offering an opportunity to do serious sales training. Here are the 3 things you should get out of a Sales KickOff:

1. Align with Company-Wide Goals

The first priority for the Kickoff was full transparency from the Executive level and other departments. The day started with a candid presentation by Co-founder and CEO Fred Shilmover, who looked back at the company’s growth so far and shared his vision for the future. He revealed the InsightSquared business strategy to the entire sales team, including goals for hiring, revenue, and more. This kind of open and transparent discussion of company strategy helps the sales team see the bigger picture, so they understand that they’re working toward a larger goal.

After Shilmover’s presentation, Co-founder and CPO Sam Clemens gave a presentation on what the engineering team is building and how the product will be improving in the future. He explained that they’re working to build much-requested new features, making the product even easier for the sales team to sell. Then the VP of Marketing shared how the marketing team has implemented lead scoring to improve the quality of the leads handed to sales, and how this will improve sales results. These two presentations helped to remind the sales team that everyone is working together to help sales close deals.

2. Look Back, and Forward

A big part of the Kickoff is looking back at the last quarter, and celebrating wins. McKenzie recognized every sales rep by name who had exceeded their quota, dubbing them the “100% Club.” He called out specific deals that were key to achieving goals, and asked reps to share stories of their successes. However, it wasn’t all about wins. McKenzie also talked about the misses across the sales team, and how they can improve going forward. He reviewed historical performance in detail, highlighting conversion rates down the sales funnel, Win/Loss reasons, and overall sales pipeline growth.

With that information in mind, McKenzie then revealed the higher sales goal for next quarter, and talked honestly about how hard the team will have to work to achieve this goal. He talked about changes to the sales strategy, how marketing’s lead generation changes will help, and what sales is up against. By reviewing the wins and losses of last quarter and looking forward, the entire sales team now knows the top-down priorities for next quarter.

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3. Train for Success

While it’s important to review historical performance and align with other departments, the Sales Kickoff is also about education. Your entire team is in one place, and it’s an opportunity to offer everyone training and best practices going forward. While the morning sessions were devoted to high-level business operations and team-wide performance, the afternoon was far more tactical. There were presentations from sales directors and sales trainers, focused on improving sales skills, learning best practices for the sales process, and working on new talk tracks.

“The reality is, we need to constantly push ourselves to understand what it means to drive quality business for InsightSquared,” Daniel Marzinotto, Senior Manager of Sales Training explained. “It’s about getting away from the minimum standards for the job and going the next couple steps to make sure we’re driving the right business.”

One presentation looked at defining an MQL, a Meeting, and a Meeting Scheduled in Salesforce. Another presentation helped reps define Opportunity Stages as opportunities move through the funnel. The day ended with a live roleplay of a demo between a rep and a sales director, offering practical advice on how to improve sales results next quarter. Reps took notes about these presentations, and will be implementing what they learned in the office as they chase new deals.
The InsightSquared Sales Kickoff was tailored to our sales team specifically, but the general principles can apply to sales teams everywhere. A great Sales Kickoff can help you start off every quarter with a refreshed, inspired, and prepared sales team that is ready to close deals and hit quota.

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