The 6 Key Elements of an Effective Sales Contest

You can use a single question to determine how experienced a sales manager is: “What has a bigger impact on your team’s success, sales skills or motivation?”

Newer managers tend to say the former, while more experienced ones pick the latter.

The reality is, motivation isn’t just a little more important than sales skills — it’s far more influential. While individual selling styles, methodologies, and processes might differ, core sales techniques don’t change.

Keeping your team members engaged, uplifted, and inspired is often far trickier than teaching them what to say on a connect call or in a prospecting email. A well-designed sales contest is one of the best tools in your arsenal.

Here are ten of our best sales contest ideas for you to try out in your office — whether in person or virtual. Many of these sales contests can be run simultaneously or within the same time period.

The prizes for these contests would vary; check out our list of sales contest prizes below. Whichever one(s) you choose to run, don't miss our sales contest best practices.

1. Daily Prizes

Run a daily sales contest and give away a daily prize. Each day could have its own goal (e.g. most calls on Mondays, biggest sale on Tuesdays, etc.), or you could run the same contest every day and reward a daily prize to each winner.

2. Salesperson of the Month

Salesperson of the Month is a pretty common sales contest. Choose a top salesman, either quantitatively by most sales or biggest deal or qualitatively based on manager's choice. He or she would then be Salesperson of the Month and receive a recurring prize.

3. Conversion Contest

Run a sales contest to reward the salesperson with the most lead-to-customer conversions. You could reward this winner on a daily, monthly, or quarterly basis. 

Note: Be sure to strengthen your marketing and sales alignment for this contest so your sales team can access and convert any marketing-qualified leads (MQLs).

4. Upsell or Cross-Sell Contest

This contest rewards the salesperson with the largest or most significant upsell or cross-sell. This encourages your sales team to find opportunities to make additional sales with current customers, such as additional software or a larger subscription plan.

5. Retention Contest

Similar to the previous two contests, a retention sales contest rewards the salesperson with who's retained the most customers or perhaps has the longest-running customer for the month, quarter, or year. This encourages your sales team to boost your customer retention and, therefore, your ROI.

6. Customer Reviews

This contest is a little different from the others on this list. A sales contest centered around customer reviews essentially rewards the salesperson with the most or most positive customer reviews. This type of contest is a bit more involved as it requires your sales team to ask for customer reviews after sales calls or meetings. But this can be a good thing — it encourages your team to collect live feedback and learn more about their customers' experiences and how to improve them. Additionally, your team can report these reviews at large sales meetings and perhaps to your broader team and organization.

7. Sales Bingo

Sales bingo is a multifaceted sales contest that allows your sales team to pursue many different, smaller goals. Similar to normal bingo, sales bingo requires a 5 x 5 bingo chart filled with objectives such as:

• Book a meeting with a director
• Schedule three demos
• Make 25 calls
• Send five LinkedIn messages

You'd then pass out the sales bingo cards and ask your team to mark off the objectives as they complete them. (Don't forget the Free box in the middle!) The first person to get five in a row would then win a prize. Tip: Run your sales bingo contest within a certain time period (monthly or quarterly) so it doesn't go on for too long.

8. Most No's

A "most no's" sales contest is another unique yet positive one. I don't know anyone — including sales people — who enjoy hearing the word "No". This sales contest essentially rewards the salesperson on your team who receives the most "No's" within a week or month (or a time period of your choice). This contest gets your team comfortable with hearing the word "No" and encourages to make as many calls as they can, pushing past objections and refusals.

9. Best Pitch

This is the only sales contest on the list that can be held either internally. A sales contest for the best pitch rewards the person on your team that has the best sales pitch. You can determine this winner in a couple ways — either hold a meeting where everyone can present their pitch and then vote for the best (but not themselves) or have your team present to VPs and executives to receive feedback.

10. Sales Bracket

The last and perhaps most involved sales contest is a sales bracket contest, similar to March Madness. In fact, I've seen it called "Sales Madness". To run this contest, create a bracket including your entire sales team. Set a threshold for each pairing (salesperson with most sales, biggest sale in the month, most "Nos", etc.) and choose a winner to move on to the next round. Eventually, you'll end up with a "championship" round that will result in an ultimate winner. The sales bracket contest is unique as you can run a different sales contest for each round, raising the stakes as it nears the championship round.

Curious about what you can reward your sales team with when they win your sales contest? Here are 10 sales contest prize ideas. Note how some may be more appropriate for larger, longer sales contests and some are a good fit for those daily and weekly contests. Tip: If you're wondering what will incentivize your sales team — ask them. Run an anonymous survey for prize ideas.

1. Monetary Prize

A monetary prize is pretty straightforward — simply reward your sales contest winner with a dollar amount provided in cash or as a bonus on a paycheck. (Don't forget to talk with your accounting team if you opt for this decision.) Larger monetary prizes are more appropriate for long-term sales contests and keep your sales team interested and engaged.

2. Gift Card

A gift card prize is a fun way to support a local or beloved business and can be perceived as something outside a normal compensation structure. Consider gift cards for restaurants, movie theaters, gas, or prepaid all-purpose gift cards.

3. Electronics or Equipment

Give away electronics or equipment as sales contest prizes. This could include a computer or phone, or even non-work-related "toys" like a grill, luggage, camera, or coffeemaker.

4. Complimentary Meal(s)

Reward your sales contest winner with free lunches for a week or month. Perhaps you offer to order in or cater lunch for the time period or have your winner expense their meal. Tip: Set a spending limit so you can predict the cost.

5. Boss for the Day

Put your sales contest winner in charge for the day, literally. Let them work in your office, park in your parking spot, or even run or join a meeting they otherwise wouldn't

6. Free Task from the Boss

This reward gives away something arguably more valuable than money — time. Reward your contest winner with a free task to be completed by you. This gives your winner a chance to give away a task or project that you can take care of for them.

7. Free Vacation Day(s)

Everyone loves a day off. Give away a free vacation or personal day as a sales contest prize. Since this one is so valuable, save it for a longer, larger sales contest that runs on a less-frequent basis.

8. Free Personal Development

Reward your sales contest winner with a free sales training seminar or educational stipend they can use for personal development or college. Be sure to consider the demographic and interests of your sales team as some folks may not be interested in or have time for this prize.

9. Floating Trophy

A floating trophy prize is exactly how it sounds — a trophy or plaque that is rewarded to and passed between the winners of a weekly or monthly sales contest. This type of prize is typically paired with a smaller incentive like a gift card or small monetary prize, although it carries bragging rights in and of itself.

10. Winner's Choice

Lastly, provide your sales contest winner with a variety of prizes to choose from, whether listed here or not. This keeps your entire sales team interested and engaged in your contest and working toward the prize regardless of their interests.

How to Run an Effective Sales Contest

In the past three decades, I’ve learned a great deal about effective sales contests (often by making mistakes). Here are six of my biggest takeaways.

1. Keep it simple.

Your salespeople shouldn’t have any trouble understanding the rules of your contest. When it’s hard to understand how to win — or who’s currently in first place — their enthusiasm about participating takes a hit.

What does a simple contest sound like? You could reward every salesperson who meets a certain target for meetings set, or give prizes to the five reps who increase their calls-to-demo rate by the highest percentage.

Aim for a contest you can explain in two sentences or less. And if you’re still unsure if it’s confusing, ask one of the senior salespeople on your team for their feedback. (As an added benefit, they might spot loopholes or problematic rules you’ve missed.)

Along similar lines, only hold one contest at a single time. This guarantees you won’t distract your team from the behavior or outcome you’re trying to promote.

2. Make it fun.

Contests should have an element of fun. A little levity helps your salespeople bond and makes the competition more memorable.

To give you an idea, I used to give away my services to the winning salesperson. I’d wash the rep’s car, pick up their dry cleaning, even clean their house — whatever they wanted.

It’s always fun to see your boss doing a menial task. This type of prize also shows your team you’re devoted to their success (and have a great sense of humor!)

Try crafting your contests around office inside jokes as well. For example, perhaps the winner gets to take everyone to lunch at a local restaurant the entire office loves.

3. Involve your sales team in the planning process.

Alternatively, let your reps choose what they’ll win. I used to get everyone in a room and ask, “Do you need a team motivation program?”

The answer was always yes. I’d explain the contest rules, then say, “You’ve got X dollars — decide what the prize or prizes will be.”

This strategy has three effects:

• Your reps are more invested. Having direct control over a major aspect of the competition drives buy-in from the start.
• The reward isn’t what you think they want, it’s what you know they want.
• Your salespeople will feel gratified by your decision to hand over the reins.

4. Give daily or weekly updates.

Few people stay committed to a competition if they don’t know where they stand. Strive to give daily or weekly updates, depending on how quickly each salesperson’s status changes. At HubSpot, we typically put up a live dashboard so every rep can check on their progress whenever they’d like.

Some salespeople will check it every hour -- that’s how intent they are on being number one. Imagine losing this powerful motivator just because you didn’t keep your team up-to-date.

5. Don’t make false promises.

It might sound obvious, but never promise a prize you can’t deliver on. In 2002, a waitress who won a sales contest for a new Toyota was understandably furious when she was presented with a toy Yoda instead.

She sued her employer — and won.

If you don’t deliver what you promised, your salespeople will lose trust in you (not to mention, all motivation to engage in future competitions). Before you announce a prize, calculate what you’ll be on the hook for if your reps do as well as possible. You might not be able to afford the reward if they really blow it out of the park. When in doubt, skew conservative.

6. Hand out prizes ASAP.

I once gave my salespeople their prize money nine months after they’d won it. Needless to say, they weren’t happy.

You’ve set a deadline for the contest — why should the deadline for the award be less important?

The takeaway is, distribute prizes as quickly after the contest ends as possible. It’ll be far easier to rally your team for the next contest if they’re not still waiting for their prizes from the last one.

Sales Contests = Sales Results

Follow these sales contest ideas, prize recommendations, and guidelines, and your sales contests will noticeably impact your team's motivation, camaraderie, and, just as importantly, their results.

Editor's note: This post was originally published in February 2017 and has been updated for comprehensiveness.