26 Sales Contest Ideas to Motivate Your Sales Team in 2023

With economic turbulence and drastic changes in work environments, your sales team is likely burnt out right now. A well-designed sales contest is one of the best tools in your arsenal to combat this burnout.

Keeping your team members engaged, motivated, and inspired is often far trickier than teaching them what to say on a connect call or in a prospecting email. Check out this list of sales contest ideas and execution to motivate your sales team and make selling fun again.

Table of Contents

• 15 Engaging Contest Ideas
• 11 Motivating Prize Ideas
• How to Run an Effective Sales Contest

15 Engaging Contest Ideas

Here are 15 of our best sales contest ideas to try out in your office — whether in person or virtual. Many of these sales contests can be run simultaneously or within the same period.

Pro tip: Use several contest ideas during the year to allow salespeople with different talents to get a moment in the spotlight.

1. Daily Prizes

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

Pro tip: Create an atmosphere of fun surrounding daily prizes by having a drumroll or hype song before declaring the winner.

2. Salesperson of the Month

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

Pro tip: Bring up the current salesperson of the month topically in meetings (with applause) to both recognize their efforts and encourage participation.

3. Conversion Contest

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

Pro tip: Strengthen your marketing and sales alignment for this contest so your sales team can access and convert any marketing-qualified leads (MQLs).

4. Upselling or Cross-Selling 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.

Pro tip: Regularly discuss new techniques to upsell and cross-sell, letting your sales staff share success stories so everyone can learn.

5. Retention Contest

Similar to the previous two contests, a retention sales contest rewards the salesperson 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.

Pro tip: Check out this article on retention techniques and share it with your sales team.

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.

Review contests are a bit more involved, as they require 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.

Pro tip: Customer reviews are vital for local SEO, so try to get customers to review your sales team and organization online.

7. Sales Bingo

Sales bingo is a multifaceted sales contest that allows your sales team to pursue many 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. (Remember the Free box in the middle!) The first person to get five in a row would then win a prize.

Pro tip: Run your sales bingo contest within a specific period (monthly or quarterly) so it doesn't go on too long.

8. Most No's

A “most no's” sales contest is another unique yet positive one. I don‘t know anyone — including salespeople — who enjoys 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 period of your choice).

This contest makes your team comfortable with hearing the word “No” and encourages them to make as many calls as possible, pushing past objections and refusals.

Pro tip: Getting lots of no’s can be stressful. Take the pressure off with a lighthearted discussion where sales staff can share funny “no” stories and commiserate.

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 with the best sales pitch.

You can determine this winner in a couple of 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.

Pro tip: Regular role-playing sales pitches can improve closure stats, so include sales scenarios regularly in meetings.

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 the 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.

Pro tip: Make sure your leaderboard/bracket is viewable to everyone and frequently updated.

11. Most Improved

A most improved contest gives your low-performing sales team members a chance to shine. Determine at least one KPI you want to measure, such as meetings held, phone calls, new customers, etc., and track which member of your team blows their previous records out of the water.

Pro tip: If you choose this contest, you must meet one-on-one with all sales staff to establish their past averages so they know what goal they should have in mind.

12. Raffle

A raffle with several prizes lets people bet on the items they want. Choose which KPIs to incentivize and track and give your team members tickets when they experience success.

Pro tip: Make each prize worth around the same amount, or you will have a lot of competition for the big prize and not much interest in the smaller ones.

13. Buddy Selling

Try a collaborative selling contest idea with buddy selling. Pair your team members and have them work together to see who can close the most sales. The pair that generates the most revenue or closes the most deals wins a prize.

Pro tip: Consider pairing high-performing salespeople with lower-performing ones so everyone can learn.

14. Increased Commission

This is a contest that everyone can benefit from. Choose a day when commission can be raised a couple of percentages, and let your team know. During those 24 hours, sales teams can make more commission and will be incentivized to make more sales.

Pro tip: You can hold this increased commission day during your slow season, giving you and your sales team a much-needed boost.

15. Content Contest

Did you know that content can improve conversion rates by 161% across all industries? Work with your marketing team to identify key pieces of content you want pushed, such as a guide, white paper, or webinar. The salesperson who gets the most downloads or attendees for the content wins!

Pro tip: Be sure to include an entry in your form field that lets leads put in who referred them to the content so they can get credit.

11 Motivating Prize Ideas

Curious about what you can reward your sales team with when they win your sales contest? Here are 11 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.

Pro tip: If you're wondering what will incentivize your sales team, ask them. Run an anonymous survey for prize ideas.

1. Monetary Prizes

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.

Pro tip: Include prize amounts in your quarterly sales budget so executives know about this upcoming expense.

2. Gift Cards

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.

Pro tip: Buy gift cards that the winner will actually use. For example, if one of your salespeople is a vegetarian, they likely won’t appreciate a gift card to a steakhouse.

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.

Pro tip: If you’re not planning on covering the taxes included in a prize, let your sales staff know so they can choose whether to accept the prize and pay those taxes.

4. Complimentary Meals

Reward your sales contest winner with free lunches for a week or month. Perhaps you offer to order in, cater lunch for a period of time, or have your winner expense their meal.

Pro 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.

Pro tip: Make this prize even more fun by giving them an outfit that mimics their boss’s daily wear. For example, if you have a mustache and wear glasses, give them these props as part of their prize.

6. Free Tasks 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 you can take care of.

Pro tip: Let your team know they can choose a funny task outside of work, such as cleaning their house, washing a car, or cooking a meal.

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 less frequently.

Pro tip: Consider also giving a certificate to watch a movie or a pass to an amusement park so your winner can make the most of their day off.

8. Free Personal Development

Reward your sales contest winner with a free sales training seminar, educational stipend, or book they can use for personal development. 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.

Pro tip: Consider letting your winner use their personal development stipend on a non-work related prize such as a pottery or photography class.

9. Floating Trophies

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.

Pro Tip: If you want your winner to get attention from other departments and visitors, be sure to choose an eye-catching and unique trophy they can display on their desk.

10. Promotions

If a new position opens up, consider motivating your team with a promotion. Salespeople typically thrive off competition, especially if something as big as a promotion is available. So, let your team know that the contest winner might be the next boss.

Pro tip: Consider being transparent about salary increases and title changes before awarding the promotion so everyone can manage their expectations.

11. Winner's Choice

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.

Pro tip: Similar to a complimentary meal prize, you will want to set a limit for the cost of a winner’s choice prize.

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.)

Pro tip: Be sure to hold only one contest at a 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!)

Pro tip: 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.

Pro tip: Even if you don’t use an idea for a particular contest, keep a record of it in case your team wants to use it for future contests.

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.

Pro tip: Have your team log sales in HubSpot’s free CRM software so everyone can be updated in real time.

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.

Pro tip: Supply chain issues can make finding prizes like tech difficult. If your winner wants something you can’t find, let them know quickly so you can get them an alternative prize or offer a gift card so they can buy it when it is available.

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?

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.

Pro tip: Create a reminder for yourself at least a week out to purchase the prize or make plans for delivering the chosen incentive.

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.