Remote sales teams get a bad rap for being “disconnected,” but let’s be honest—most contests fall flat even in person. If you want to use contests to motivate a remote sales team, you need more than a leaderboard and some cheesy graphics. You need structure, clarity, and a platform that doesn’t get in the way.
This guide is for sales managers, ops folks, and team leads who want to run genuinely motivating contests using Hoopla. I’ll walk you through the setup, point out the pitfalls, and share what’s actually worth your time.
Why Bother With Sales Contests in Remote Teams?
Let’s cut through the usual buzzwords. The point of a contest is to get people focused and motivated—ideally, without creating resentment or confusion.
Well-designed contests can: - Make boring metrics (like calls made) feel like a game. - Highlight progress in real time, even when no one shares an office. - Give new reps a fair shot, not just reward the usual top dog. - Break up the grind and inject some fun.
But: messy contests, unclear rules, or “winner takes all” setups can backfire, especially when people are remote and already feeling isolated.
Step 1: Get the Basics Right in Hoopla
Before you start, double-check that Hoopla is set up to pull in the right sales data. If your CRM integration isn’t working, nothing else matters.
Checklist: - Is Hoopla connected to your CRM (Salesforce, HubSpot, etc.)? - Are the fields you want to track mapped correctly? (e.g., “Deals Won,” “Meetings Booked”) - Do all reps show up as users in Hoopla? - Can you run a test “contest” just for yourself to see if the numbers update automatically?
Pro tip: Don’t trust one-off exports or manual uploads. If you need to do this, fix your data pipeline before running a contest. Otherwise, expect headaches.
Step 2: Pick the Right Contest Format (Not Just “Top Seller Wins”)
Hoopla offers a bunch of contest types, but you should choose the one that fits your team’s goals—not just what looks flashy.
The main options: - Leaderboards: Classic “who’s on top” setup. Fine for big teams if everyone has a shot. - Race: First to hit a target wins. Good for short sprints or to encourage quick adoption of a new behavior (like booking demos). - Points-based games: Assign points to different activities (e.g., 1 point per call, 5 per meeting, 10 per deal). This can level the playing field. - Teams: Group reps and let them compete together. Works well for big orgs or when you want to build camaraderie.
What to ignore:
- Overly complex multi-metric contests. If you can’t explain it in one sentence, it’s too much.
- “Winner takes all” formats every time. You’ll lose engagement from everyone who isn’t in first place after day one.
Step 3: Define Clear, Simple Rules
This is where most contests fall apart. If people don’t know what counts—or think the rules are unfair—they’ll check out fast.
Keep it simple: - What exactly can people do to earn points or win? - When does the contest start and end? - Are there daily/weekly resets or is it cumulative? - What counts—and what doesn’t? (e.g., are only closed-won deals counted, or pipeline created?)
Communicate it like you’re talking to a busy rep: - “Every call logged = 1 point.” - “Book the most demos between Monday and Friday, and you win.” - “Top 3 on the leaderboard split the prize.”
Pro tip:
Write the rules out in plain English and run them by a couple of reps before launching. If they have questions, your rules need work.
Step 4: Set Up the Contest in Hoopla
Here’s what you actually need to do in the Hoopla platform:
- Create a New Contest
- Go to the “Contests” section and click “New Contest.”
- Choose Your Format
- Pick from leaderboard, race, points, or teams—based on your earlier decision.
- Select Participants
- Add the reps or teams involved. For remote teams, double-check everyone’s included (especially new hires).
- Define Metrics
- Choose the exact data fields that count toward the contest. Map each one to a point value if using a points-based format.
- Set the Timeline
- Enter clear start and end dates/times. For remote/global teams, clarify the time zone.
- Add Prizes (Optional, but Encouraged)
- Enter rewards (gift cards, “champion” badge, Amazon credit, etc.). Don’t overthink prizes—just make it something people actually want.
- Customize Notifications
- Configure alerts for big wins, streaks, or lead changes.
- Set up Slack or Teams integrations if you want updates in chat.
What not to do:
- Don’t turn on every single notification. It gets noisy fast.
- Don’t put in silly “prizes” like a trophy emoji unless your team actually likes that stuff.
Step 5: Launch and Communicate—Without the Hype
Don’t oversell it. Just be clear and direct:
- Announce the contest in your main communication channel (email, Slack, Teams).
- Post the rules, point system, and prizes in one place.
- Tell people how to check their progress in Hoopla.
- Remind folks it’s optional (if it is), but participation makes it more fun for everyone.
Sample kickoff message:
“Starting Monday, we’re running a one-week contest: every meeting booked in Salesforce = 5 points. Top three scores win $50 Amazon cards. Check the leaderboard in Hoopla to track your progress. Questions? Slack me.”
Pro tip:
If someone asks a question, answer publicly (or update the contest rules) so everyone’s on the same page.
Step 6: Keep Engagement Real (Not Forced)
Contests peter out if leaders ignore them or if it feels like busywork. Some ways to keep things moving:
- Post updates mid-contest (“Leaderboard as of Wednesday: Sarah in the lead, but three people close behind!”)
- Recognize small wins, not just the big ones.
- Encourage friendly trash talk—if your team’s culture supports it.
- Don’t drag contests out. A week or two is plenty.
What doesn’t work: - Constant, automated “You’ve been passed!” pings. It gets old. - Publicly shaming people at the bottom. Just… don’t.
Step 7: Wrap Up and Get Feedback
When the contest ends:
- Announce winners and distribute prizes right away.
- Thank everyone, not just the winners.
- Share quick stats (“Our team booked 30% more meetings this week!”) if you have them.
- Ask for feedback—did the contest feel fair, fun, and worthwhile?
Pro tip:
If you notice a few folks are always winning, try team-based or randomized rewards next time.
What Actually Works (And What Doesn’t)
Works: - Simple, transparent rules - Short timeframes (1-2 weeks max) - Small but meaningful prizes - Team-based contests for variety
Doesn’t work: - Complex, multi-metric scoring no one understands - “Winner takes all” every time - Forced “fun” that doesn’t match your team’s vibe
Final Thoughts: Start Simple, Iterate Fast
Don’t get caught up in making the “perfect” contest or chasing every Hoopla feature. The best contests are easy to explain and quick to run. Try something basic, see how your team reacts, and adjust for next time.
In remote teams, real motivation comes from clarity, recognition, and a little friendly competition—not from a dashboard full of fireworks. Keep it simple, stay honest, and you’ll get the results you want.