Walking Challenge Launch Playbook
Suggested timeline, copy-paste emails, engagement tips, and incentive ideas for your walking challenge.
How to use this page
Use the timeline and email templates for a standard rollout: save the date, launch, mid-challenge nudge. For a try-before-you-buy option with a small free pilot, open Running a pilot? below.
Copy and edit freely. Replace placeholders like {{company_name}}, {{trail_name}}, and {{join_qr_or_link}}— we email you the real join link and QR from Walk The Distance after we create the group or pilot on our side. To start that, or to change trail or head-count tiers, reply to your Walk The Distance onboarding email (that thread is the right channel, not a generic support form).
Suggested Timeline for Your Challenge
Example only— adjust timing and steps to match your org.
Decisions & setup
- ✓Contact me so I can create the group for your organization in the app
- ✓Required: set the route for the company challenge. Compare options on the walks page.
- ✓Optional: add a sub-goal for the route.
- ✓Suggestion: create a team challenge for the company.
- ✓Optional: pre-organize teams, or have people self-organize after they join the team challenge — you don’t have to set that up ahead of time.
- ✓Lock your incentive structure and any prizes
- ✓Contact me if you need help with any of these details, or the walk calculator can help too.
Announce the challenge
- ✓Send Email 1 (Save the Date) to everyone who will be invited
- ✓Create a dedicated Slack / Teams channel for the challenge
- ✓Post a teaser in your company newsletter or all-hands
Go live
- ✓Send Email 2 (Launch Day) first thing in the morning, pasting the QR and join link we shared with you
- ✓Post a short welcome message from a leader in Slack / Teams
- ✓Share a screenshot of the leaderboard later in the day to build momentum
Billing period start
- ✓The first two weeks after go live are a join grace period — people can still get in, and head count is not final until the period ends
- ✓Your first monthly billing period starts after that two-week window, based on active head count at the end of the grace period. See pricing for per-participant tiers and plan details.
Sustain engagement
- ✓Send Email 3 (It’s Not Too Late) around week 2 to anyone who still hasn’t joined
- ✓Celebrate milestone checkpoints in all-hands or Slack as the group hits them
- ✓Forward the weekly auto-report from Walk The Distance to leadership
- ✓Run a mid-challenge “walking meetings day” or team photo contest
Running a pilot?
Optional free pilot: up to 20 people, 30 days on us, then you can go company-wide. Skip if you don't need it.
Pilot timeline
After the pilot, pick up the main timeline from save-the-date through launch, or the alternate save-the-date below (add pilot quotes if you like).
Recruit and form the group
- ✓Send the pilot recruit email to a shortlist of likely champions (e.g. 30–50)
- ✓Close recruitment, lock your pilot participant list (up to 20), and confirm the pilot run dates and the trail for the walk
- ✓Contact me so I can create the pilot group in the app
Decisions before the pilot
- ✓Required: set the individual route. Compare options on the walks page.
Help me pick a pilot route (two strategies)
With 30 days to run, you basically have two good options for what individual route the pilot group walks:
Option 1— Pick a short route the group can finish inside 30 days
Great if you want the whole pilot group to cross a real finish line together before the pilot ends. Top picks:
- Boston Marathon (26.2 mi)— short enough that most teams finish well inside 30 days.
- Shenandoah National Trail (106 mi)— a little longer, still realistic to finish in the pilot window.
Option 2— Pick a longer trail you'd want to continue after the pilot
If you already know you want to roll this out company-wide, start on a trail the group would be excited to keep walking. When you go company-wide, you have two choices:
- Keep going: the pilot group rolls smoothly into the full rollout on the same trail, with their existing progress intact.
- Reset to zero: when the company-wide challenge launches, I reset everyone back to zero so the whole organization starts from the same line on day one.
Not sure which fits? Just reply to your onboarding email and we'll pick one with you.
- ✓Optional: add a sub-goal for the individual route.
- ✓Suggestion: create a team challenge for your group.
- ✓Optional: pre-organize teams, or have people self-organize after they join the team challenge — you don’t have to set that up ahead of time.
- ✓Contact me if you need help with any of these details, or the walk calculator can help too.
Save the date to participants only
- ✓After the list is set, email the one-week-out save the date only to your confirmed up-to-20 participants
Kick off the pilot
- ✓Send the pilot launch email to that same list, pasting the QR code I share with you for the pilot
- ✓Create a small Slack / Teams channel for the pilot group, or an email thread
- ✓Ask one enthusiastic pilot to post their first miles to break the ice
Run the pilot (up to 30 days)
- ✓Share a weekly leaderboard screenshot in the pilot channel
- ✓Collect 1–2 short testimonials and a screenshot for the company-wide kickoff, if you go that route
- ✓Nail down trail, teams, and incentives for the company-wide challenge; email me when you're ready to set up the full org group in the app
Roll into the full challenge
- ✓Debrief with pilots, lock your company-wide start date, and reuse the main timeline above (save the date, final week, launch day, and weekly reminder emails).
- ✓If you want pilot quotes in the announcement, use the “After pilot — company-wide save the date” template in this section instead of the main Save the Date copy.
- ✓Stuck on sequencing? We help teams with this all the time — reply to your onboarding email.
Email templates for a pilot
Pilot — Recruit up to 20 volunteers
Recruit up to 2 weeks ahead of time, lock 20, then email your Walk The Distance contact the list and run dates so we can create the pilot in the app before the 1-wk, participants-only save-the-date.
Subject
Want to help us pilot a walking challenge? (first 20 people)
Body
Hi,
{{company_name}} is exploring a company-wide walking challenge. Walk The Distance plots real-world steps onto a virtual route along a famous long trail (e.g. the Appalachian Trail) with checkpoints and team progress. Before we roll it out to everyone, I'm putting together a small pilot group — first 20 people who commit.
You don't need to be a runner or a fitness person. We want a mix — walkers, hikers, or folks who just want to move more. If you're in, reply "I'm in".
Pilot runs {{pilot_start_date}} to {{pilot_end_date}}. I’ll take the first 20 who commit, lock the list, and about a week before we start I’ll email that group a save-the-date. On the morning of {{pilot_start_date}} you’ll get the email with the QR code and link to install, join the group walk, and connect your tracker. After the pilot we’ll ask for quick feedback and decide whether to roll it out company-wide.
Thanks,
{{your_name}}Pilot — Save the date to participants (1 week out)
One week before {{pilot_start_date}}. Only the confirmed list (up to 20), and only after Walk The Distance has created the pilot group from your email request.
Subject
Save the date: walking pilot for {{company_name}} starts {{pilot_start_date}}
Body
Hi everyone,
Save the date: we start the morning of {{pilot_start_date}} (pilot runs through {{pilot_end_date}}). On the morning of {{pilot_start_date}}, I’ll email the QR code and the steps to install Walk The Distance, join the group walk on {{trail_name}}, and connect your tracker. No app install until that launch message.
Questions? Just reply to me.
— {{your_name}}Pilot — Launch (QR, walk, tracker, team)
Send the morning the pilot starts. Paste the QR and join link from the admin email we send you after we set up the pilot group.
Subject
Pilot starts today — how to join Walk The Distance
Body
Hi everyone,
Today we kick off our small walking-challenge pilot for {{company_name}}. Your real steps get plotted on a virtual route for {{trail_name}} — a famous long-distance path with checkpoints. The app works with the devices and apps you already use: Apple Health, Garmin, Fitbit, and Samsung Health (or your phone alone). How to get started:
1. Scan the QR code (or tap the link on your phone). It takes you to download Walk The Distance. After the app is installed, you should join our pilot group automatically; if not, scan the QR again.
2. When prompted, join our group walk on {{trail_name}}.
3. When prompted, connect your desired tracker.
4. (Team challenge only) On the company page, make sure you join a team for the team challenge.
{{join_qr_or_link}}
What we're walking: {{trail_name}} — low pressure, no daily check-ins. Share a line of feedback with me when the pilot wraps.
Let's go,
{{your_name}}
P.S. Every step counts — commute, lunch, walking the dog. No minimum or step target for the pilot.After pilot — Company-wide save the date (with pilot social proof)
Use in place of the main Save the Date if you’re announcing after a successful pilot. Drop in 1–2 real quotes and names from your pilots.
Subject
Save the date: {{company_name}} Walking Challenge kicks off {{start_date}}
Body
Hi everyone,
Save the date — on {{start_date}}, {{company_name}} is kicking off a company-wide walking challenge. The Walk The Distance app maps your steps onto a virtual route for {{trail_name}} (a real long trail with checkpoints, like the Appalachian Trail) so the team advances along the same path together.
A small pilot group has been testing this, and the feedback has been great:
"{{pilot_testimonial_1}}"
— {{pilot_participant_1}}
"{{pilot_testimonial_2}}"
— {{pilot_participant_2}}
How it works:
• Every step you take (walking, running, hiking) moves the team along that virtual path on the map
• Free Walk The Distance app on your phone; it connects to Apple Health, Garmin, Fitbit, and Samsung Health (phone-only is fine too)
• We plan to group teams by {{team_split}} (department, office, region, self-organize) — leaderboards, milestones, and {{incentive_summary}}
• No new equipment required — use the trackers and apps you already have
Watch for the launch email on {{start_date}} with the join link and QR code. Questions in the meantime? Just reply.
Looking forward to walking with you,
{{your_name}}Copy-Paste Email Templates
Three company-wide emails: save the date, launch, nudge. Swap the placeholders. Piloting first? See Running a pilot? for recruit, launch, and post-pilot save-the-date.
Email 1 — Save the Date
Send 1–2 weeks before launch once you’ve picked the trail and locked the incentive. You confirm the trail and group setup with Walk The Distance by email; the launch-day QR in Email 2 comes from us.
Subject
Save the date: {{company_name}} Walking Challenge kicks off {{start_date}}
Body
Hi everyone,
Save the date — on {{start_date}}, {{company_name}} is kicking off a company-wide walking challenge. The Walk The Distance app maps your real-world steps onto a virtual route along a famous trail. For this challenge, we're all hiking {{trail_name}} together — think real checkpoints, mile markers, and team progress on a route like the Appalachian Trail.
How it works:
• Every step you take (walking, running, hiking) moves you and the team along that virtual path on the map
• You'll use the free Walk The Distance app on your phone; it works with the trackers and health apps you already have: Apple Health, Garmin, Fitbit, and Samsung Health
• We plan to group teams by {{team_split}} (department, office, region, self-organize) — leaderboards, milestones, and {{incentive_summary}}
• No new gear required — your phone is enough if you don't use a wearable
Watch for the launch email on {{start_date}} with the join link and QR code. Questions in the meantime? Just reply.
Looking forward to walking with you,
{{your_name}}Email 2 — Launch Day
Send the morning the challenge starts. Paste the QR and join link from the Walk The Distance admin email we send you after the group is created.
Subject
We're walking! Join the {{company_name}} challenge today
Body
Good morning {{company_name}},
Our walking challenge is officially live. Your real steps get plotted on a virtual route for {{trail_name}} — a famous long-distance path with checkpoints, just like the Appalachian Trail. The app works with the devices and apps you already use: Apple Health, Garmin, Fitbit, and Samsung Health (or your phone alone). How to get started:
1. Scan the QR code (or tap the link on your phone). It takes you to download Walk The Distance. After the app is installed, you should join our group automatically; if not, scan the QR again.
2. When prompted, join our group walk on {{trail_name}}.
3. When prompted, connect your desired tracker.
4. (Team challenge only) On the company page, make sure you join a team for the team challenge.
{{join_qr_or_link}}
What we're walking: {{trail_name}} — {{trail_distance}} miles as a team
First milestone to aim for: {{first_checkpoint}}
How we're celebrating: {{incentive_summary}}
A word from {{leader_name}}:
"{{leader_quote}}"
Let's get moving,
{{your_name}}
P.S. Every step counts — on your commute, at lunch, walking the dog. No minimum, no step target. Just show up and walk.Email 3 — It’s Not Too Late
Send around week 2 to anyone who hasn’t joined yet. Shows current standings to drive FOMO.
Subject
It's not too late to join the walking challenge
Body
Hi team,
Quick update: {{company_name}} has walked {{current_miles}} miles on the {{trail_name}} together so far. We just passed {{latest_checkpoint}} — great work to everyone who's been logging steps.
If you haven't joined yet, there's still plenty of trail ahead. The app maps your steps onto the same virtual route as everyone else ({{trail_name}}) and works with Apple Health, Garmin, Fitbit, and Samsung Health — or just your phone. Hop in today:
1. Scan the QR code (or tap the link on your phone). It takes you to download Walk The Distance. After the app is installed, you should join our group automatically; if not, scan the QR again.
2. When prompted, join our group walk on {{trail_name}}.
3. When prompted, connect your desired tracker.
4. (Team challenge only) On the company page, make sure you join a team for the team challenge.
{{join_qr_or_link}}
Current standings:
• Top team: {{top_team}}
• Top walker: {{top_walker}}
• Next milestone: {{next_checkpoint}}
Deadline to join and still qualify for {{incentive_summary}}: {{join_deadline}}.
Questions? Just reply.
— {{your_name}}Want us to tailor these for your company? Just reply to your onboarding email and we'll help fill in the blanks.
Incentive Patterns That Work
Four patterns you can mix, skip, or adapt. Prizes aren't required, but they can boost sign-ups.
Participation raffle
Anyone who joins and logs a minimum distance (e.g. 25 miles by month end) is entered to win a gift card, extra PTO day, or company-branded swag.
Why it works: Low effort to administer, high participation lift.
Milestone tiers
Small rewards at trail checkpoints— e.g. 100 mi bronze, 500 mi silver, 1,000 mi gold. Walk The Distance auto-emails admins when members hit milestones, so you don't have to track anything manually.
Why it works: Keeps people engaged for the full length of the challenge.
Team vs. team
Winning department picks the next team lunch, the charity for a matched donation, or a similar non-monetary perk. Cheap to run and drives social pressure inside teams.
Why it works: Turns walking into a shared team goal, not a personal chore.
Charity match
Company matches a dollar amount per mile (e.g. $1 / mile) to a cause employees vote on. Country Bank raised $28,000 for their local communities with this exact pattern.
Why it works: Purpose-driven motivation scales beyond what prizes can.
Walk The Distance sends admins automatic weekly and monthly progress reports with participation data and leaderboards, so you have the numbers you need to run any of these patterns without manual tracking.
Tips for Sustained Engagement
A few habits keep momentum going after launch.
Celebrate milestones publicly
When the team passes a major trail checkpoint, call it out in your next all-hands or a pinned Slack / Teams message. Takes 30 seconds and keeps the challenge top of mind.
Share leaderboard screenshots weekly
A weekly “Here's where we are on the trail” post in Slack or Teams drives way more engagement than email. One screenshot is enough.
Get an exec to participate visibly
When a senior leader posts their own miles or a checkpoint photo, it signals that the challenge matters. One post a week from a VP beats ten posts from HR.
Run a “walking meetings” day
Mid-challenge, designate a day when any meeting under 30 minutes should be a walking meeting (in person or phone). Gives everyone permission to log miles during work hours.
Share photos from the real trail
Walk The Distance surfaces photos and descriptions of the real checkpoints as your team passes them. Reposting those in Slack or Teams makes the virtual journey feel real.
Ready to Launch Your Challenge?
Book a free demo and we'll have your group set up in minutes. Already running one? Just reply to your onboarding email with questions and we'll help tailor any of these templates.
Want to learn more about the program itself? See our Employee Wellness page