Can the Magic of the Sales Kickoffs (SKOs) Come Online? Why We Have to Try!


Why SKOs Matter

I first got indoctrinated to the power of a well run sales kickoff (SKO) back in 2014, when I was running DoubleDutch.  My co-founder and VP Sales had made the case that an SKO was important to get the team fired up out of the gates to start the new year..  While I was a little skeptical (“I don’t see the finance team approving starting off the year with a party!?”), I didn’t have enterprise sales experience, and my co-founder did, so off we went.

The big stated goals of our SKO were:


And this last item, camaraderie, was huge.  

Good salespeople tend to be coin operated.  They optimize their behaviors to maximize their earnings, which sometimes can mean competing with their peers for scarce resources; leads, deals, contacts, etc.  It is not unusual for a top performing salesperson to be a lone wolf; you may rarely see or hear from them during a quarter, until you realize that they crushed their quarter, again. Yet, the best performing sales teams tend to be collaborative; they share customer intel, they coach each other, and they lift each other up. Balancing this tension between enabling star individual performance while still fostering a winning team culture is one of the biggest challenges of sales management.

At the time of our first official SKO, we were scaling quickly and had a lot of new members of the sales team - SDRs, inside sales, and more seasoned enterprise sales folks.  The team skewed male and young, and for many of them, DoubleDutch was their first or second job out of school.

We rented a venue for dirt cheap (a live music venue down the street that was unused during the day), and the sales leaders planned the agenda. The big content blocks were as follows:

  • Sales Leader Welcome; rah, rah, get people going
  • Founder Kickoff; lay out the vision, the strategy, the direction
  • Product Deep Dive (led by product team); show some roadmap, get people excited about all the new stuff to sell
  • Sales Ops and Finance; sales process, tools, etc, not really the most electric part of the agenda, but you have to do it.
  • Awards and Recognition; call out the sales reps who were doing great
  • Team Bonding and Happy Hour

If you haven’t been to a SKO, you have to realize that they hit a bit different than other internal meetings.  Music is typically blasting between sessions.  Folks are animated and legitimately fired up. There is almost a playoff sports electricity in the air, particularly for companies that are growing quickly, like we were.  For lack of a better word, SKOs are fun.

But looking back at our early SKOs, despite all of the effort that we put into content and education, it was the team bonding that probably mattered the most to the long term health and productivity of the team.  

SDRs got to hang with the senior Enterprise Reps they supported in a social setting.  Reps got to forget about competing for deals and $$, and trade war stories. Managers got to learn more about their reports, and vice versa.  These were the relationships that would carry the team through the rough patches, and would lay the groundwork for a team that lifted each other up.  And our sales leadership knew this.  We did not cut the happy hour off.  We let it go deep into the night.  It wasn’t about the partying or the alcohol; it was about the intentional time to build connection.  At later SKOs we would head to the park and play lawn games, or have trivia contests.  What mattered was the time together.

Can a Virtual SKO still be great?

The existential question here for SKOs in the age of remote & hybrid work is whether this sort of magic and connectivity can still be delivered online.  I’m a big believer that the face to face offsite has never been more important. At twine, we do in person offsites once a quarter, and it’s hard for me to imagine running the business without them.  But with larger teams, is it financially feasible to fly in your full revenue team and all the supporting functions every quarter?  Probably not.  So virtual and hybrid SKOs look to be a reality going forward.

As we close out 2021, here is what we know:

  • We know remote work is not going away, and the best companies are leveraging remote work to hire the best talent, wherever they may be geographically.
  • We know that top down content has moved effortlessly online.  There is no need to fly your sales team in to listen to a product keynote from your Chief Product Officer; this content can be delivered over Zoom, Teams, or Streamyard.
  • We know that employee connection and camaraderie is more mission critical than ever; the Great Resignation is a real thing, and sales teams where vision, connection, and fulfilment are not obvious are getting hit.

As far as moving connections and camaraderie online, I am hopeful.  

Over the last ~18 months, we have all learned a lot about online engagement, beyond just the top down dissemination of content.  Solutions like twine, Weve, and online activities like virtual escape rooms and trivia are already being used to deliver team engagement. At the macro level, huge investments are being made in “the Metaverse,” virtual event platforms, and other online spaces making it easier to move your SKO online without losing the magic.

Let’s Design a Virtual SKO

OK, let’s take a shot at designing your virtual SKO.  Here are the blocks as I see them:

  • Compelling Content.  Get your team excited about your product, your market, your strategy.  Tuck in some education and training in short, digestible pieces. Again, the medium shouldn’t matter here - if your content is strong, you can get it across IRL or on a Zoom.
  • Recognition.  Sales teams like to see success; they like to have a goal to aspire to so make sure your team gets to see and hear from the folks who are crushing it.
  • Gamification.  See if you can weave some healthy competition throughout your SKO.  Trivia tied to education works great online, as do digital leaderboards. Gamification can happen before, during, and after your event to drive buy-in and retention.
  • Think Regionally. Depending on the scale and geographic distribution of your team, consider sponsoring some local meetups to ensure the face-to-face interactions can still happen in a smaller setting.
  • Watercooler and Camaraderie.   Skip this piece at your peril.  This is where all the relationship building, connection, and friendship are built. It's likely the hardest part to create online, but arguably the most important element of your SKO.

A team that has each other's backs when adversity hits is a team that will succeed. A well-designed SKO that creates strong camaraderie among your sales team will deliver plenty of ROI.

I don’t believe that a virtual SKO can match the energy of an IRL happy hour or park day for your sales team - at least not yet.   But one thing I know is this: for a great SKO whether it be IRL or virtual, ignore connection building at your peril.  The best performing sales teams care about each other, and these relationships will not happen by themselves. So different as it may be to try to deliver the magic of an SKO online, you certainly have to try.


Designing awesome virtual SKOs is a problem we're excited to work on and we love talking about it with our community and clients. If you want to learn more about how you can redesign your SKO in a remote world, join us at our upcoming #twineTalks event on November 23, 2021 where we will be discussing different strategies for designing an engaging SKO for your team.

Lawrence Coburn is the CEO & Co-Founder at twine.

To learn more about twine, set up your own space for free here or schedule a time to chat with our team here.

Written by
Lawrence Coburn

Foster camaraderie & connection

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