Q2 Sales Contests That Will Boost Your Sales

Sales reps deal with more indifference, rejection, and bad attitude throughout their workday than most. Sales contests are used as fun ways to lift their spirits, remind them of their larger goals, and keep them motivated – while simultaneously driving results in specific areas.

We at InsightSquared believe in building a culture that rewards teamwork, competitiveness, and fun. We operate like a sports team. That’s why we run competitive programs all the time – quarterly ones, monthly ones, weekly ones, and a few additional, random ones along the way.

Remember to run a tight ship when you run sales contests. Set a strict start/end date and time, center each contest on a clear and specific goal, talk about the running contests at every meeting, test them afterward and share results, and ask for feedback.

This post is meant to give you an insider’s look into our sales contests that I run regularly here at InsightSquared – rules included.  Your teams may be smaller or larger so you will have to adjust for how many sales reps are eligible to win Presidents Club and other contests.

Take note of the key abbreviations we use for our different sales reps:

  • iSDRs = inbound sales development reps

  • oSDRs = outbound sales development reps

  • ISRs = Inside Sales Reps (closing reps)

1) President’s Club

  • When: Quarterly (yes, you read that right, quarterly and not annually!)

  • Who: Everyone on the sales team is eligible (but only a few winners will go)

  • What: Top producers from each team (1 ISR, 1 iSDR, and 1 oSDR) win a 3-day weekend getaway together. Past getaways include Florida and the Caribbean. The top producers are measured by:

ISR: Top Bookings over monthly quota

iSDR: Top Opps over monthly quota

oSDR: Top in total opportunities sourced that month

  • Why: I don’t believe in designing all our contests such that our top reps always win, but they do deserve to be rewarded for long-term, exceptional performance. We also want to retain our top talent, and this reward is one incentive we use. The prize is an opportunity to bond with members of the sales team that have different jobs and therefore are not always in contact with one another.

2) Fantasy Sales Team (like a Fantasy Football Team)

  • When: Monthly

  • Who: Teams of 3, consisting of 1 ISR, 1 iSDR, and 1 oSDR each. To make teams, ISRs pick the names of 1 iSDR and 1 oSDR out of a hat.

  • What: All ISRs are measured on sales points. At the end of the month, the team with the most points goes to professional sports game. Sales points work like this: each deal can be worth up to 5 points, and reps can gain points by doing the following:

    • 1 point gained automatically for closing the deal

    • 1 point if that deal is multi-year

    • 1 point for selling live support on top of the software

    • 1 point if the customer pays upfront

    • 1 point if no discount is given

  • Why: Another opportunity for bonding across the different teams, this time celebrating small wins that could push one team ahead of another. Boston is the greatest sports hub in the country, so sports games are coveted prizes around here.

3) Individual Quota Over-Achievement Award

  • When: Monthly

  • Who: ISRs (closers)

  • What: The top ISR with the highest % over $ quota receives a price. This month, the prize is a bottle of Exclusive Limited Edition Avion Tequila.

  • Why: Reps should feel relieved when they reach their quota, and should be rewarded when they exceed their quota. We don’t believe in resting on our laurels – otherwise, reps might be incentivized to stall deals until the following month to help them reach their next-month quota, rather than closing as much new business nowas possible.

4) Team Quota Over-Achievement Award

  • When: Monthly

  • Who: ISRs (closers)

  • What: If the closing team as a whole overachieves their $ quota by 130% or more, we order a limo and send the whole team to a casino with $200 each, in addition to a steak dinner on the company at the casino.

  • Why: Similar to the Individual Quota Achievement Award, we want everyone to strive to overachieve their goals – even if it looks like they won’t win the individual award. Individual rewards are great, but we want reps on the lower end of the performance spectrum to exceed their goals, too. And we want the top performing reps to coach and encourage them along the way. The prize is also an opportunity for the closing team to bond in a unique environment.

5) Telethon

  • When: 1 random day every month

  • Who: The iSDR & oSDR teams

  • What: Telethons always lasts one day, and that day is picked at random – I announce it the day before at 5pm. The contest goal is different every time – switching up your prizes keeps reps engaged. This month, our telethon goal was that each iSDR schedules 2 meetings and each oSDR schedules 1 meeting on a single, given day. The goal can be anything, though – 200+ dials per rep, for example. If the team succeeds, they win a night at a local bar paid for by the company, or a delivery from the best gourmet pizza in the city.

  • Why: Everyone has to meet the goal to get the prize, so every SDR is extra motivated because they don’t want to be the reason the whole team doesn’t win. I also find that everyone helps each other, coaches each other, and encourages each other. The prize is an opportunity to bond with the rest of the team.

Key takeaways:

Make sure you have contests for closers, for SDRs, and for both to encourage high performance and collaboration across all levels. Run contests constantly, not just once per quarter or twice per year! And make most of the prizes something members of the team can share, like an experience or a “trophy” for their desk.