The 2020 Bitglass SKO Recap and More

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Every year before now, I’ve attended sales kick-off (SKO) without having to work on preparing an agenda, but I’ve marveled at the amount of work that goes on to put on such an event. I’ve thought about the reasoning behind certain sessions that I have attended and the adjustments I would make.

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This year, I had the opportunity to put on our 2020 SKO, and with the help of my peers, we managed the scheduling, sessions, speakers, and more.  To add to that, this year we had a customer advisory board meeting on the Monday before, which took a lot of work.The preparation of SKO is much longer than the event itself.

There is a lot of information to jam into a short period of time, and it must be done in a fashion that keeps everyone’s attention (late nights lead to short attention spans during the day☺).

SKO generally covers these topics:

  • CEO vision – where we are, where we are headed
  • Product updates, roadmap, etc.
  • Competitive updates
  • Marketing updates
  • Business development updates
  • Channel updates
  • Outside speakers (customers, partners)

By the time you cover the topics above, you don’t have a lot of time for anything else (a few hours).  In the past, this would be filled by ‘pitch’ competitions. We’d form teams and pitch the solution to management.  Management would then vote and finally you settle on a winner after a few hours. Most participants hated this (at least the people pitching).  The rules of the contest are typically set in a way that would never happen in a natural situation, so the event was a failure. Last year we had 20 minutes to present the solution, while ensuring three people spoke (never happens).  With that being said, we decided to ‘ditch the pitch’. This freed up three hours to do something different.

If you look at the topics above covered, what you’ll notice is that there were updates from everyone EXCEPT the sales teams working in the field.  We wanted the teams executing in the field to hear from their peers. We came up with two topics:

  • Whiteboarding session
  • Customer wins

Whiteboarding session: Working in the CASB field, we receive a ton of questions that are not black and white as to how you answer.  We live in a world where different companies have different ideas on how to secure cloud data, and the questions we receive from customers/partners (in many cases) may be influenced by what they’ve learned from other vendors.  This is fine as long as you are comfortable with how to answer them, but how did our best and brightest answer these questions? We gathered up six people to the stage and had prepared questions in advance to ask. The people gathering on stage had no idea we were going to call them up.☺ We called it a whiteboarding session, meaning if you have nothing but a whiteboard, piece of paper, or are having coffee with someone can you answer these questions (with additional feedback/questions coming from the audience). 

Customer wins: Again, we didn’t prep any of the teams we called up to discuss notable wins for the quarter prior.☺ We didn’t want anyone preparing for this, instead we wanted the conversations to flow naturally.  We called the teams up one by one, asked them all about the deals. Let them describe the deal to the rest of the company, their peers, every detail from cold call to signed contracts. It was fascinating to see the interaction between everyone who attended this session.

What did I learn from Bitglass 2020 SKO?

  • We have a GREAT team!  Many field teams were brought on in the past 12 months as we expanded, they are fantastic and starting to run like a well-oiled machine.
  • I’ve never worked for a company with executives that cared more about what and how we are doing things, than Bitglass.
  • Let our sales teams in the field have stage time.  The whiteboarding and customer wins sessions were fantastic.  People want to hear from their leaders, but they want to communicate with their peers as much or maybe even more. 
  • Everyone is jacked about 2020. 

Lessons learned/thoughts?

  • We are gathering feedback from everyone that attended, on what they liked and disliked, to improve for next year.  This event is for the people in the trenches, give them more power to decide the agenda.
  • How much more alert would everyone be if we had intravenous (IV) therapy available for those that like to stay out late?

Lastly, kudos to the Bitglass team members for coming in from all over the world to learn and leave with an excitement to go win the market in 2020!

See you all next year!

*** This is a Security Bloggers Network syndicated blog from Bitglass Blog authored by Shane Moore. Read the original post at:

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