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Walking Challenge Launch Playbook

A timeline, copy-paste emails, and incentive ideas to launch your walking challenge.

How it works

Follow the timeline and send the three copy-paste emails: open sign-ups two weeks early, kick off on launch day, then nudge stragglers mid-challenge. People can join anytime. Want to test it first? Open Running a pilot? below.

Copy and edit freely. Replace placeholders like {{company_name}} and {{trail_name}}. We email you the real join link and QR after we set up your groupreply to your onboarding email to start or to change your trail.

Suggested Timeline for Your Challenge

Example only adjust timing and steps to match your org.

2–3 wks before launch

Decisions & setup

  • Contact me to create your company group
  • Pick your route (required)compare options on the walks page.
  • Lock in your incentives and any prizes.
  • Optional: add a route sub-goal and a team challenge. Teams can self-organize after they join.
  • Decide: reset everyone to zero on launch day, or let early miles count? Either works—just tell people.
  • Stuck on any of these? Contact me or use the walk calculator.
2 wks before launch

Open the join window

  • Send Email 1 (Open the Doors) with your QR code. People install the app, join the group, and pick a team.
  • Share the QR in a Slack / Teams channel or the built-in in-app group chat.
  • Push for early sign-ups—but people can join anytime.

Jump to Email 1

Launch day

Go live & billing starts

  • Send Email 2 (Launch Day kickoff) the morning of launch.
  • Optional: reset everyone to zero so the whole org starts together.
  • Post a kickoff message from a leader and share a leaderboard screenshot.
  • Billing starts on launch day. See pricing for per-participant tiers.

Jump to Email 2

Ongoing

Sustain engagement

  • Send Email 3 (It’s Not Too Late) around week 2 to anyone who hasn’t joined.
  • Celebrate milestone checkpoints in Slack / Teams or the group chat.
  • Forward the weekly auto-report to leadership.
  • Run a walking-meetings day or a team photo contest.

Jump to Email 3

Running a pilot?

Optional free pilot: up to 20 people, 30 days on us, then go company-wide. Skip if you don't need it.

Pilot timeline

After the pilot, pick up the main timeline above (add pilot quotes if you like).

1–2+ wks

Recruit and form the group

  • Send the recruit email to a shortlist of likely champions (e.g. 30–50).
  • Lock your participant list (up to 20) and confirm the run dates and trail.
  • Contact me to create your pilot group

Jump to the pilot recruit email

1–2 wks

Decisions before the pilot

  • Pick your pilot route (required)compare options on the walks page.
    Help me pick a pilot route (two strategies)

    With 30 days to run, you have two good options:

    Option 1 A short route the group can finish in 30 days

    Best if you want everyone to cross a finish line together. Top picks:

    Option 2 A longer trail to continue company-wide

    Best if you already plan to roll out wide. When you go company-wide:

    • Keep going: the pilot group rolls into the full rollout with progress intact.
    • Reset to zero: I reset everyone so the whole org starts from the same line.

    Not sure? Reply to your onboarding email and we'll pick one with you.

  • Optional: add a route sub-goal and a team challenge.
  • Decide: reset everyone to zero on Day 1, or let early miles count?
  • Stuck on any of these? Contact me or use the walk calculator.
Pilot T–1 wk

Open the join window

  • Send the pilot Open-the-Doors email with your QR code so people install and join.
  • Set up a comms channel (Slack / Teams, in-app group chat, or an email thread).
  • Early installs get paired with their tracker before Day 1—so the 30 days are a real challenge, not a setup scramble.

Jump to the pilot Open-the-Doors email

Pilot Day 1

Kick off the pilot

  • Send the pilot launch-day email.
  • Optional: reset everyone to zero so the group starts together.
  • Ask one enthusiastic pilot to post their first miles 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.
  • Lock in your trail, teams, and incentives for the full rollout, then email me to set up the company-wide group.
End of pilot

Collect participant feedback

  • Send the pilot feedback email a few days before the pilot ends.
  • Pair it with the auto-reports and leaderboard data for the full picture.
  • Capture pros, cons, and quotable lines for your stakeholder pitch.

Jump to the pilot feedback email

After pilot

Roll into the full challenge

  • Debrief, lock your company-wide start date, and reuse the main timeline above.
  • Want pilot quotes in the rollout? Paste 1–2 into the top of Email 1.
  • Stuck on sequencing? Reply to your onboarding email—we help with this all the time.

Email templates for a pilot

Pilot — Recruit up to 20 volunteers

Send ~2 weeks out. Lock your list of 20, then email me the names and run dates so I can create the pilot group.

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 ~1 week before the pilot to your confirmed participants. Paste in the QR and join link we email you. Onboarding early turns Day 1 into a real challenge, not an 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 the pilot starts. Confirms any mileage reset and nudges anyone who hasn’t installed yet.

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.

Pilot — Feedback request (near end of pilot)

Send a few days before the pilot ends, while it’s still fresh. Gets you honest feedback for the company-wide rollout decision.

Subject

Quick feedback on our walking pilot?

Body

Hi everyone,

Thanks for being part of the {{company_name}} walking pilot. As we wrap up our 30 days on {{trail_name}}, I’d love your honest feedback so I can bring it back to leadership — we want to properly evaluate whether to roll Walk The Distance out company-wide as a paid program.

Even a short reply with bullet points helps. A few things I’d love to hear:

1. Did Walk The Distance change how active you were, or how you think about daily movement?
2. Anything you loved — favorite features, moments on the trail, or checkpoints?
3. Anything that didn’t work well, or that you wish were different?
4. Would you keep using it if {{company_name}} kept the program going? Why or why not?
5. Anything else you think leadership should know before we decide?

If you’re OK with me sharing a short quote from your reply with leadership (or in the company-wide kickoff if we go that route), just put "OK to share" at the top of your reply.

Please send your thoughts by {{feedback_deadline}}. I’ll pull everything together and bring it to our stakeholders so we can make an informed call on whether Walk The Distance becomes part of the {{company_name}} wellness program going forward.

Thanks for being our trail blazers,
{{your_name}}

Copy-Paste Email Templates

Three emails for a company-wide rollout. Swap the placeholders and send. Piloting first? See Running a pilot? for the pilot versions.

Email 1 — Open the Doors (early access)

Send ~2 weeks before launch, when sign-ups open. Paste in the QR and join link we email you. This is the workhorse email—people install and join early so launch day is 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 launch. Confirms any mileage reset, celebrates that the challenge is on, and nudges anyone who hasn’t joined.

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 to anyone who hasn’t joined. Shows current standings to drive FOMO—people can join the whole challenge through.

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 logs a minimum distance (e.g. 25 miles) is entered to win a gift card, PTO day, or swag.

Why it works: Low effort to run, high participation lift.

Milestone tiers

Rewards at checkpoints e.g. 100 mi bronze, 500 mi silver, 1,000 mi gold. We auto-email you when members hit milestones, so there's nothing to track.

Why it works: Keeps people engaged the whole challenge.

Team vs. team

Winning department picks the next team lunch or a charity for a matched donation. Cheap to run, and drives friendly competition.

Why it works: Turns walking into a shared team goal, not a chore.

Charity match

Company donates per mile (e.g. $1 / mile) to a cause employees vote on. Country Bank raised $28,000 this way.

Why it works: Purpose motivates beyond what prizes can.

We send you automatic weekly and monthly reports with participation data and leaderboardsso you can run any of these without manual tracking.

Tips for Sustained Engagement

A few habits keep momentum going after launch.

Celebrate milestones publicly

When the team passes a checkpoint, call it out in an all-hands or a pinned Slack / Teams message. Takes 30 seconds, keeps the challenge top of mind.

Share leaderboard screenshots weekly

A weekly “here's where we are on the trail” post drives more engagement than email. One screenshot is enough.

Get an exec to participate visibly

When a leader posts their own miles, it signals the challenge matters. One post a week from a VP beats ten from HR.

Run a “walking meetings” day

Pick a day where any meeting under 30 minutes becomes a walking meeting. Gives everyone permission to log miles during work hours.

Share photos from the real trail

The app surfaces photos of real checkpoints as your team passes them. Repost them in Slack / Teams to make the 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