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SKO: A Million-Dollar Investment in Your Reputation

SKO: A Million-Dollar Investment in Your Reputation

It’s January, which means thousands of sellers are getting on planes for Sales Kick-Off. For many, it feels like a reward for surviving the Q4 gauntlet or a chance to blow off steam. But if you’re looking at it that way, you’re already missing the point.

As a leader who has designed and authorized many SKOs, I can tell you that these events are the most fraught dates on the executive calendar. They cost millions. Every time I leave for SKO, it’s an event whose budget I’ve had to defend to my CFO and Board multiple times. I do so by telling them that sales is the most important team in the company for hitting our annual goals. We need you motivated, we need you trained on the new products we’ve also spent millions developing, and—most importantly—we need you excited.

SKO is a high-stakes performance. But as much as I see you as my primary audience, you’ve got an important audience of your own. And it’s not your peers – It’s the people who decide your future.

The Great Emotional Reset

The timing of an SKO is no accident. We’ve just come out of December, a month where we probably parted ways with a few underperformers. The people in the room at SKO are the people we want there.

But the energy in that ballroom is mixed.  There are “Club” winners who made a small fortune last year sitting next to talented sellers who had a brutal year and are questioning their place in the company. But regardless of which camp they’re in, on January 1st, the quota attainment was reset to zero – and both are wondering if they want to stay at this particular company.

The SKO is designed to win your hearts and minds during this vulnerable transition. We want to convince you that this is the year, this is the product, and this is the team that will win. We’re trying to build camaraderie and culture in a few short days for folks that usually only see each other on Zoom.

But because that environment is so emotionally charged and often accompanied by an open bar, it can be a killer for professional reputations.

The Tragedy of the “Top Performer”

Every year, it happens. A top performer—someone who just spent twelve months crushing their number—gets carried away. They overempahsize the “celebration,” say or do something offensive to a colleague, and a few short hours after I’ve handed them a huge trophy, HR and I are asking them to turn in their laptops.

It stinks to fire a top-tier revenue generator because of something that happened at SKO.  The company loses great talent, and the individual loses a career’s worth of momentum. Don’t let your “best year ever” be the reason you lose your job in the first week of January.

The Lesson of the Orlando Pool

But it doesn’t  have to be that way. I’ll never forget an SKO I hosted in Orlando. We had a new BDR who had flown down from the freezing North. It was one of his first business trips ever – exiting enough – and this brought him to the Florida sun, too.

On our final night, we held a formal dinner and reception around the resort pool. Towards the end of the night, he came up to me on the pool deck, and asked, “Are we allowed to use the pool? I’ve got a swimsuit upstairs, and I haven’t had a chance to use it all week.”

I told him that we didn’t have an actual rule – but asked “What do you think is best?”

He paused.

I held my breath, hoping he’d make the right choice.

After surveying the crrowd of VPs and eecutives in their business casual attire, he decided. ““You know, this isn’t really about the pool, is it?” 

He stayed out of the water, he networked, and he strengthened his reputation as the mature, focused pro that he is.

Visibility in a Virtual World

In an era where we spend 50 weeks a year as two-dimensional squares on a Zoom screen, these rare, face-to-face times together are huge for building “reputation equity.”

An SKO can be an informal, multi-day interview for your next promotion. When the leadership team sits in a room to discuss who is ready for a Management or Director role, they don’t just look at your CRM data. They remember the seller who showed up to the 8:00 AM session on time and engaged after a long evening the day before.  The employee who treated hotel staff with respect? And they remember the ones who made less-great decisions.

The things you do at SKO will be talked about for months. There are some SKO stories that have been re-told for more than ten years.

As you head to SKO, you’re going to learn how to sell the new products, yes—but you are also there to sell yourself to the organization.

Enjoy the camaraderie, celebrate the wins, but never forget: the “O” in SKO stands for “Off,” but you always need to be “On.”

About The Author

JD Miller

JD Miller began his technology sales career during the dot-com boom as employee number 26 of a company that was eventually acquired by Vignette – a web content management company that had one of the largest public market valuations of the time at $9 billion. Eager to repeat that experience, JD built a career with a series of progressive leadership roles at international organizations seeking sales transformations – whether that be strong increases in revenue, preparation for merger, acquisition, or IPO. His career has included roles at LexisNexis, West Monroe Partners, Workplace Systems, BravoSolution, Motus, and Kantata - backed by or exiting to private equity firms including Lloyds Development Capital, Insight Partners, Accel-KKR, and Thoma Bravo. Currently, he is a go-to-market Operating Advisor for Five Arrows Capital Partners. ​With a PhD in organizational communication, JD's leadership is marked by the intersection of technology, business and humanity. He serves as a Board advisor, prolific author, and conference speaker on these topics, and is the author of the book "The CRO's Guide to Winning in Private Equity."

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