Why Building Sales Contests to Drive Revenue is the Wrong Mindset

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When it comes to deciding on contests prizes for sales teams several things should be considered BEFORE you choose the prizes.

Whether it’s an SDR Team, Inside Sales Team, Enterprise Sales team we recommend “bucketing” the prize types into 5 primary buckets:

  1. Solo Event
  2. Rep +1 Event
  3. Team Event
  4. Money
  5. Educational

Of course there could be others, and they can and often do overlap.

From here you need to look at some bigger issues and in particular “selling the executive” on the expenses.

The primary outcome of a contest is NOT to drive revenue. It’s to reinforce the right behaviors. If the behaviors occur, the muscle memory lasts, you win the long game of revenue growth.

Additionally, if you are trying to incentivize the rep with money at the end of a month, quarter, or year, you may be doing too little too late. If its the EOY and you are trying to drive new business from October 1 – December 31 because you are behind, it’s most likely too late. This should not be blamed on the sales team. Equal blame can go around to marketing, executive team, and product or engineering team (especially if release deadlines have passed)

Here are some hints to help you understand how you got here, or better yet, how to avoid ever getting here:

  1. If your CFO isn’t letting you spend money, then s/he got the pan and greased it for the sh*t pie
  2. If your CEO is afraid to try things throughout the year, then s/he made the sh*t pie filling.
  3. If the marketing has not been cooperating, they forgot to warm the oven that the sh*t pie is being baked in.
    1. How many new case studies did they write this year?
    2. How many press releases around new customers did they put out?
  4. If sales have been letting their egos dictate too much, then they often get to take the first bite of the sh*t pie.
  5. Irrational discounting throughout the year. That piece of sh*t pie goes to the CEO, VP of Sales, and maybe event the Board

So now, what kinds of incentives should you have in Q4??


  1. Big Cash $, like $500, $1000, $2000 minimum
    1. Make some individual
    2. Make a few team oriented. If everyone does XX then everyone gets $1000. is some psychology to this one. It rarely happens, but you have to willing to play the “If the Browns/ Jets win the superbowl all TV purchases are FREE” (No offense to Clevleand fans. Actually hoping they get there.”


  1. All expense paid a trip to _____
    1. Go big or go home. Make it somewhere out of the country, not “Vegas”
  2. All expenses to Disney World for the family. Not kidding on this one. If you know members of your team have a family, then, by all means, send them there. Help them teach their family the value of hard work and what it means. Plus you will increase loyalty from the “family” level.


  1. Offer to pay off the equivalent of the trips in student loan debt
  2. Offer to send someone to a sales-related event like SalesLoft Rev 2020, Outreach Unleash, SurfAndSalesIV, Saastr

Now here is the clincher, if you have real enterprise deals that 6-9-12 months long. Then you should be talking now about driving business for 2020. If you have a 9 month sales cycle, that means you have from now, October until March 31 to drive new inbounds. What are you doing about that now so you aren’t here again next year?

Good luck

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