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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: open the join window two weeks before launch, celebrate launch day (with a heads-up if you reset everyone’s miles), then a mid-challenge nudge. People can keep joining at any time. 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.

2–3 wks before launch

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.
  • Decide whether you’ll reset everyone’s trail progress to zero on launch day so the whole org starts together, or let early-access miles count toward the team total. Either is fine — just call it out so people know what to expect.
  • Contact me if you need help with any of these details, or the walk calculator can help too.
2 wks before launch

Open the join window

  • Send Email 1 (Open the Doors) with the QR code — this is the first email people get. They install the app, join the group, and pick a team during the two weeks before official kickoff.
  • Pick a comms channel for the rollout: a dedicated Slack / Teams channel works great for orgs that already live in Slack, or use the built-in in-app group chat that comes with every Walk The Distance group. Drop the QR wherever folks will see it.
  • Encourage early sign-ups so launch day is a celebration, not a scramble — but anyone can keep joining at any point during the challenge.
  • Remind folks whether early-access miles will count toward the team total or whether you’ll reset everyone on launch day.

Jump to Email 1

Launch day

Go live & billing starts

  • Send Email 2 (Launch Day kickoff) the morning of launch — reminds people whether their early-access miles got reset to zero or carried over, and welcomes anyone who still hasn’t joined to scan the same QR.
  • Optional: reset everyone’s trail progress to zero so the whole organization starts at the same point on launch day. (Skip this if you’d rather let early-access miles ride.)
  • Post a short kickoff message from a leader — in Slack / Teams, the in-app group chat, or both — celebrating that the challenge is officially on.
  • Share a screenshot of the leaderboard later in the day to build momentum.
  • Your first monthly billing period starts on launch day. People can keep joining at any time during the challenge see pricing for per-participant tiers and how active head count is tracked from month to month.

Jump to Email 2

Ongoing

Sustain engagement

  • Send Email 3 (It’s Not Too Late) around week 2 of the challenge to anyone who still hasn’t joined — people can keep joining at any time, the whole challenge through.
  • Celebrate milestone checkpoints in all-hands, Slack / Teams, or the in-app group chat 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

Jump to Email 3

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).

1–2+ wks

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

Jump to the pilot recruit email

1–2 wks

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:

    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.
  • Decide whether you’ll reset everyone’s pilot trail progress to zero on Day 1 so the group starts at the same line, or let early-access miles count toward the pilot total.
  • Contact me if you need help with any of these details, or the walk calculator can help too.
Pilot T–1 wk

Open the join window (grace period)

  • Email the pilot Open-the-Doors message to your confirmed up-to-20 participants with the QR code so they can install Walk The Distance, join the pilot group, and pick a team this week.
  • Set up your pilot comms channel (Slack / Teams, the built-in in-app group chat, or just an email thread) so people can ask install questions and chime in early.
  • Anyone who installs early gets the app paired with their tracker before Day 1 — the 30 days then become a real mini-challenge instead of a setup scramble.

Jump to the pilot Open-the-Doors email

Pilot Day 1

Kick off the pilot

  • Send the pilot launch-day email reminding people whether their early-access miles got reset to zero or carried over, and welcoming anyone on the pilot list who still hasn’t installed to scan the same QR.
  • Optional: reset everyone’s pilot trail progress to zero so the whole pilot group starts at the same point on Day 1. (Skip this if you’d rather let early-access miles ride.)
  • Ask one enthusiastic pilot to post their first miles in the comms channel to break the ice.

Jump to the pilot launch-day email

During pilot

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
After pilot

Roll into the full challenge

  • Debrief with pilots, lock your company-wide start date, and reuse the main timeline above (open the join window two weeks before launch, then the launch-day kickoff and the mid-challenge nudge).
  • If you want pilot quotes in the company-wide rollout, paste 1–2 short pilot testimonials into the top of Email 1 (Open the Doors) before sending it out.
  • 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 and lock the list. About a week before {{pilot_start_date}} I’ll email that group with the QR code so you can install Walk The Distance, join our pilot group walk, and pick a team in advance — that way Day 1 is a real mini-challenge instead of a setup scramble. After the pilot we’ll ask for quick feedback and decide whether to roll it out company-wide.

Thanks,
{{your_name}}

Pilot — Open the Doors (early access, ~1 week before pilot)

Send about a week before {{pilot_start_date}} to your confirmed up-to-20 participants — only after Walk The Distance has created the pilot group from your email request. Paste the QR and join link from the admin email we send you. Onboarding ahead of time is what turns the pilot month into a real mini-challenge instead of a Day-1 install scramble.

Subject

Get the app: our walking pilot starts {{pilot_start_date}}

Body

Hi everyone,

Our walking pilot officially kicks off the morning of {{pilot_start_date}} and runs through {{pilot_end_date}}. To make Day 1 a real mini-challenge instead of a setup scramble, the join window is open today — about a week early — so you can install Walk The Distance, join our pilot group walk on {{trail_name}}, and pick a team before we start.

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 set up 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 pilot group automatically; if not, scan the QR again.
2. When prompted, join our pilot 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}}

A heads up about Day 1 ({{pilot_start_date}}): {{pilot_reset_note}} — e.g. "we’ll reset everyone’s pilot trail progress to zero so the group starts at the same line on Day 1," or "your early-access miles already count toward the pilot total — jump in now and get a head start."

Questions? Just reply to me.

— {{your_name}}

Pilot — Launch Day kickoff

Send the morning of {{pilot_start_date}}. Reminds early-access folks whether their pilot miles got reset to zero or carried over, celebrates that the pilot is officially on, and gives anyone on the pilot list who hasn’t installed yet one more nudge with the same QR.

Subject

We’re walking! Our pilot is officially live

Body

Hi everyone,

Today’s the day — our walking pilot is officially on. Every step you log from here moves us along {{trail_name}} together.

A heads up about your trail progress: {{pilot_reset_note}}. (Examples: "we just reset everyone to zero so the pilot starts at the same line today," or "your early-access miles already count toward the pilot total — no reset, you’re already on the trail.")

What’s next:
• Pilot runs through {{pilot_end_date}} — that’s our mini-challenge window
• Leaderboards and team standings update in the app throughout the day
• Share a line of feedback with me as you go so we can shape the company-wide rollout

Anyone on the pilot list who didn’t install during the early-access window — same QR as last week:

{{join_qr_or_link}}

Let’s go,
{{your_name}}

P.S. Every step counts — commute, lunch, walking the dog. No minimum or step target for the pilot.

Copy-Paste Email Templates

Three company-wide emails: open the join window (two weeks before launch), launch-day kickoff (with a heads-up about any mileage reset), and a mid-challenge nudge. Swap the placeholders. Piloting first? See Running a pilot? for recruit, launch, and post-pilot save-the-date.

Email 1 — Open the Doors (early access)

Send the morning the join window opens — about two weeks before {{start_date}}. Paste the QR and join link from the Walk The Distance admin email we send you after the group is created. This is the workhorse email of the rollout: people install, join the group, and pick a team in advance so launch day is just a celebration, not a scramble.

Subject

Get the app: our Walking Challenge starts {{start_date}}

Body

Good morning {{company_name}},

{{company_name}} is kicking off a company-wide walking challenge — and the join window opens today, two weeks before our official kickoff on {{start_date}}, so you can install the app, join the group, and pick a team in advance.

Your real steps will 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 set up 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}}

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}}
We plan to group teams by {{team_split}} (department, office, region, self-organize). No new gear required — your phone is enough if you don't use a wearable.

A heads up about launch day ({{start_date}}): {{launch_reset_note}}. We’ll send another note that morning so no one is caught off guard.

A word from {{leader_name}}:
"{{leader_quote}}"

See you on the trail,
{{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 2 — Launch Day kickoff

Send the morning of {{start_date}}. Reminds early-access folks whether their trail miles got reset to zero or carried over, celebrates that the challenge is officially on, and gives anyone who hasn’t joined yet one more nudge with the same QR.

Subject

We’re walking! Our Walking Challenge is officially live

Body

Good morning {{company_name}},

Today’s the day — our walking challenge is officially on. Every step you log from here moves the team along {{trail_name}}.

A heads up about your trail progress: {{launch_reset_note}}. (Examples: "we just reset everyone to zero so the whole org starts at the same line today," or "your early-access miles already count toward the team total — no reset, you’re already on the trail.")

What’s next:
• First milestone to aim for: {{first_checkpoint}}
• How we’re celebrating: {{incentive_summary}}
• Leaderboards and team standings update in the app throughout the day

Haven’t installed yet? You can still join at any time — same QR code as before:

{{join_qr_or_link}}

A word from {{leader_name}}:
"{{leader_quote}}"

See you on the trail,
{{your_name}}

P.S. Every step counts — commute, lunch, walking the dog. No minimum, no step target.

Email 3 — It’s Not Too Late

Send around week 2 of the challenge to anyone who hasn’t joined yet. Shows current standings to drive FOMO. People can keep joining for the entire challenge.

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, a pinned Slack / Teams message, or the in-app group chat. 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 / Teams or the in-app group chat 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 / Teams or the in-app group chat 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