H01: Listing Optimization

Dynamic, quality-score-driven coaching tips to help hosts improve their listings and earn more money.

Flow Architecture — Complete Redesign

Previous approach: 5 static emails on a fixed schedule (Day 1, 3, 5, 14, 21). Every host got the same tips regardless of listing quality. This didn't work.

New approach: Dynamic, conditional tips based on actual listing data. Each email contains only the tips relevant to that host's listing gaps. If a host already has 10+ photos, they don't get the photos tip. If pricing is competitive, they skip the pricing tip. The goal is to increase the quality score of every listing so hosts earn more money.

Entry: Listing goes live (status = active). Timing: Tips sent based on listing quality score and what's missing, not a fixed calendar. Day 1 fires immediately. Subsequent tips fire every 2-3 days, only for gaps that still exist. Exit: Quality score reaches target threshold OR first booking received OR 30 days.

Quality Score Signals (need from eng): photo_count, price_vs_local_avg, description_length, response_time_avg, amenities_count, availability_days_next_30, has_instant_book, listing_views_last_7d.

Voice: Supportive coach, not a nag. "Here's how to earn more" not "your listing is bad." Every tip ties back to earnings. Data-driven where possible ("hosts near you who did X earn Y% more").

NEEDS ENG DYNAMIC H01 / Engineering Requirements @Nikhil Arora
⚠️ Why This Needs Eng
The entire flow is conditional. Each tip only renders if the host's listing has that specific gap. We need listing quality signals exposed as custom attributes or event properties in Braze so we can conditionally render tip modules.
Required Custom Attributes (Braze)
listing_photo_count — int, number of photos on active listing
listing_price_vs_local — float, host's hourly price / avg hourly price in area (1.0 = average, >1.3 = high)
listing_description_length — int, character count of description
listing_avg_response_minutes — int, avg response time to inquiries in minutes
listing_amenity_count — int, number of amenities listed
listing_availability_next_30 — int, available days in next 30 days
listing_has_instant_book — bool
listing_quality_score — int (0-100), composite quality score
listing_views_7d — int, listing views in last 7 days
Conditional Logic
Each email assembles dynamically from tip modules. A host with few photos + high pricing gets the photos tip + pricing tip in one email. A host with great photos but no availability gets only the availability tip. The canvas checks which gaps exist and renders only relevant modules. If no gaps remain, the host exits the flow.
Fallback
If custom attributes aren't available at launch, we can start with the static version (current drip content) and migrate to dynamic as eng delivers the data. The brief below includes both the dynamic trigger conditions and the static tip content so nothing blocks design.
Dynamic Tip Modules

Each tip is a standalone module. The canvas assembles emails from whichever tips are relevant to each host's listing gaps. Tips are ordered by impact on booking conversion.

DYNAMIC H01 / Tip 1 Highest impact Photos Are Everything 📷
Trigger Condition
{% if {{custom_attribute.${listing_photo_count}}} < 8 %}
When to show
Host has fewer than 8 photos. Listings with 8+ photos get 3x more bookings.
Subject (when this is the lead tip)
Subject
Your listing is live! Here's the #1 thing guests look at first.
Preview
Listings with 8+ photos get 3x more bookings. Here's how.
Tip Module Content
TIPPhotos: The #1 Booking Driver
🎨 Creative Concept
This is the highest-impact tip. Guests decide in seconds based on photos. The module should show the host their current photo count vs the target (8+). Make it feel achievable, not overwhelming. "Done beats perfect. But great photos change everything."
Headline
You have {{listing_photo_count}} photos. Hosts with 8+ get 3x more bookings. 📷
Body
Guests scroll photos before they read anything else. Here's what top-earning hosts shoot:

✓ Wide pool shot from across the yard (shows the whole space)
✓ Water-level angle (makes guests picture themselves in it)
✓ Lounge/seating area (where people hang between swims)
✓ Night/evening shot if you have lighting (extends bookable hours)
✓ Amenities close-ups (grill, hot tub, speakers, towels)

Pro tip: Shoot in the afternoon when the light is warm. Phone camera works great. Done beats perfect.
CTA Button
Upload More Photos 📷
DYNAMIC H01 / Tip 2 High impact Pricing Strategy 💰
Trigger Condition
{% if {{custom_attribute.${listing_price_vs_local}}} > 1.3 %}
When to show
Host's price is 30%+ above local average. New listings priced high get fewer first bookings. The strategy: start lower, build reviews, then raise.
Subject (when this is the lead tip)
Subject
The pricing move that gets new hosts booked in days
Preview
Start a little lower. Build reviews. Then raise it. Here's the math.
Tip Module Content
TIPPrice to Get Booked, Then Raise
🎨 Creative Concept
Sensitive topic. Don't say "your price is too high." Instead, show what similar hosts nearby charge and frame the strategy as smart business: "start competitive to get reviews, then raise." Include local pricing data if available. Earnings-focused: "hosts who start at $X/hr in {{city}} get their first booking 4x faster."
Headline
Hosts near {{city}} charge around ${{local_avg_price}}/hr. Here's why that matters. 💰
Body
Your first few bookings are the most important ones. They build your reviews, your ranking, and your reputation. Hosts who start at or slightly below the local average get booked faster and earn more in the long run.

The playbook:
1. Start at or just below ${{local_avg_price}}/hr to attract your first guests
2. Get 3-5 great reviews
3. Raise your price $5-10/hr at a time
4. Top hosts in {{city}} charge ${{top_host_price}}/hr after building their reputation

It's not about being cheap. It's about getting booked, getting reviewed, and earning more over time.
CTA Button
Update My Pricing 💰
DYNAMIC H01 / Tip 3 Medium impact Description That Sells ✍️
Trigger Condition
{% if {{custom_attribute.${listing_description_length}}} < 200 %}
When to show
Description is under 200 characters. Short descriptions don't convert. Guests want to know what the experience is like before booking.
Subject (when this is the lead tip)
Subject
Your listing description could be working harder for you
Preview
Paint a picture. Guests book feelings, not features.
Tip Module Content
TIPWrite a Description That Books
🎨 Creative Concept
Don't criticize what they wrote. Instead, show them what great looks like. "Guests book feelings, not features." Give them a simple framework: start with the experience, then details, then logistics. Include a before/after example if possible.
Headline
Guests book feelings, not features. ✍️
Body
A great description makes the guest picture themselves there. Here's what to include:

Open with the experience: "Imagine floating in a heated saltwater pool while the sun sets behind the palm trees..."

Then the details: Pool size, depth, temperature. What's included (towels, chairs, speakers, grill). What makes your space unique.

Then logistics: Parking, check-in process, house rules, what to bring.

Aim for 300+ characters. Top-earning listings average 500+.
CTA Button
Edit My Description ✍️
DYNAMIC H01 / Tip 4 High impact Reply Fast, Book More ⚡
Trigger Condition
{% if {{custom_attribute.${listing_avg_response_minutes}}} > 60 %}
When to show
Average response time over 60 minutes. Hosts who reply in under 1 hour get 60% more bookings. Also trigger if instant book is off.
Subject (when this is the lead tip)
Subject
Hosts who reply in under 1 hour get 60% more bookings
Preview
Guests compare listings. The fastest reply almost always wins.
Tip Module Content
TIPSpeed Wins Bookings
🎨 Creative Concept
Frame as competitive advantage, not a complaint. "Guests are comparing options. The fastest reply almost always wins." If instant book is off, pitch turning it on as the ultimate speed hack.
Headline
Guests compare listings. The fastest reply wins. ⚡
Body
When a guest sends a booking request, they're usually messaging 2-3 hosts at once. The first one to reply almost always gets the booking.

Your average response time: {{listing_avg_response_minutes}} minutes
Top hosts in {{city}}: under 15 minutes

Two things that help immediately:
✓ Turn on push notifications so you never miss a request
✓ Enable Instant Book so guests can book without waiting for a reply

Hosts with Instant Book on get 60% more bookings. One setting, major difference.
CTA Button
Turn On Instant Book ⚡
DYNAMIC H01 / Tip 5 Medium impact Amenities That Sell 🎉
Trigger Condition
{% if {{custom_attribute.${listing_amenity_count}}} < 5 %}
When to show
Fewer than 5 amenities listed. More amenities = higher in search results and more booking appeal.
Subject (when this is the lead tip)
Subject
The small details that make guests pick your pool over others
Preview
Towels, speakers, a grill? List them. Guests filter by amenities.
Tip Module Content
TIPList Every Amenity
Headline
You have {{listing_amenity_count}} amenities listed. Top hosts list 10+. 🎉
Body
Guests filter by amenities. Every one you add makes you show up in more searches. Don't forget the small stuff:

🏊 Pool noodles, floats, toys
🎵 Bluetooth speaker
🍖 Grill or BBQ
🧬 Towels provided
🚿 Outdoor shower
💡 Pool lighting (for evening bookings)
👦 Shallow end / kid-friendly
🐶 Pet-friendly

Even "shaded seating area" or "private restroom" matters. If you have it, list it.
CTA Button
Add Amenities 🎉
DYNAMIC H01 / Tip 6 High impact Open Up Your Calendar 📅
Trigger Condition
{% if {{custom_attribute.${listing_availability_next_30}}} < 10 %}
When to show
Fewer than 10 available days in the next 30. Low availability means fewer search impressions and missed bookings.
Subject (when this is the lead tip)
Subject
More available days = more bookings. Here's what we're seeing.
Preview
Guests search by date. If you're not available, you're invisible.
Tip Module Content
TIPCalendar = Visibility
Headline
You have {{listing_availability_next_30}} days open in the next month. 📅
Body
Guests search by date. If your calendar doesn't have open days, you won't show up in results. More availability = more impressions = more bookings.

Quick wins:
✓ Open weekends through the end of next month
✓ Add weekday evenings (popular for after-work swims)
✓ Block only the days you truly can't host

Top hosts in {{city}} keep 20+ days open per month. You can always block days later if plans change.
CTA Button
Update My Calendar 📅
H01 / Tip 7 Day 14+ with no booking Free Listing Review 🔍
Trigger Condition
{% if days_since_listing_active > 14 AND booking_count == 0 %}
When to show
Listing has been live 14+ days with zero bookings. This is the "let us help" escalation. Always the last tip in the sequence.
Subject
Subject
Want a real person to look at your listing? Free review from the Swimply team.
Preview
We'll send you specific feedback on what to fix. Takes 2 minutes to request.
Tip Module Content
TIPHuman Help
🎨 Creative Concept
This is the safety net. The host has been live 2+ weeks with no bookings. They might be frustrated or confused. This should feel like genuine help, not "we noticed you're struggling." More like "we do this for every new host." Warm, human, zero judgment.
Headline
Let us take a look at your listing. 🔍
Body
Sometimes a fresh set of eyes makes all the difference. Our team will review your listing and send you specific, actionable feedback: what's working, what to tweak, and what might be holding you back.

It's free. It takes 2 minutes to request. And hosts who've done it see an average 40% increase in listing views within a week.

No catch. We want you to succeed because when you earn, we grow.
CTA Button
Request a Free Review 🔍
Push + SMS Nudges
H01 / Push + SMS Supporting channels — tied to tip triggers Supporting Nudges
Push Notifications (fire 1 day after email tip)
Photos tip follow-up
Listings with 8+ photos get 3x more bookings 📷 You have {{listing_photo_count}}. A few more could change everything.
Pricing tip follow-up
Hosts near you start at ${{local_avg_price}}/hr and raise after reviews roll in 💰 Smart strategy.
Response time follow-up
Guests are comparing options right now ⚡ Turn on Instant Book and never lose a booking to a slow reply.
Availability follow-up
You have {{listing_availability_next_30}} days open this month 📅 More days open = more bookings. Quick update?
Free review
Want the Swimply team to review your listing? Free, personalized feedback 🔍 Takes 2 min to request.
SMS (fire 2 days after email tip, only if no action taken)
Photos tip
Quick tip: hosts with 8+ photos get 3x more bookings. You have {{listing_photo_count}}. A few more could make the difference 👉 [link to upload]
Pricing tip
Hosts near {{city}} who start around ${{local_avg_price}}/hr get booked faster and earn more long-term 👉 [link to pricing]
Response time
One setting that could change everything: Instant Book. Hosts with it on get 60% more bookings 👉 [link to settings]
Free review
We'd love to review your listing and send you specific tips. Free, no catch. Takes 2 min 👉 [link to request]
Inspiration & Creative Direction
FOR THE DESIGNER H01 / Creative Direction Visual Strategy & References
Design Philosophy
These emails need to do the heavy lifting visually. The host isn't going to read paragraphs. They'll scan, see a number, see a visual, and either act or not. Every module should feel like a friend showing you how to earn more, not a platform lecturing you about your listing.
Key Visual Patterns That Work Across Marketplaces
Pattern 1: The Data Callout
One big stat, large type, impossible to miss. "Hosts with 10+ photos earn 2x more." Airbnb, Turo, Uber Eats all lead with this. Make the number the hero.
Pattern 2: The Before/After
Split view showing a bad example vs a good one. Dim, poorly-angled pool photo on left, bright golden-hour shot on right. Works for photos, descriptions, and pricing.
Pattern 3: The Progress Bar / Scorecard
Show the host where they are vs where they could be. "Your listing: 4/10. Top hosts in your area: 9/10." Etsy, Walmart, and Airbnb all use this. The incomplete progress bar creates motivation.
Pattern 4: The Peer Comparison
"Hosts near you earn $X. You earned $Y." Show context, not just advice. Makes it personal and competitive.
Pattern 5: The Checklist
Simple checkboxes. Done/not done. Makes improvement feel manageable. Works great for the final "listing review" module.
CREATIVE DIR. Module 1 Photos 📷
Lead With
"Hosts with 8+ photos get 3x more bookings" (or similar Swimply stat) in large, bold type.
Visual Approach
Before/after split. Left: dark, cramped, poorly-lit pool shot taken from the porch. Right: bright, wide-angle golden-hour shot with loungers staged, pool water sparkling. The contrast should be dramatic.
Inspiration References
Airbnb
Pro Photography Program: hosts with pro photos see 20% more bookings and 20% higher earnings
Turo
Listings with verified photos get 30% more requests
Uber Eats
Restaurants with photos on all items see 88% higher monthly sales
Poshmark
Listings with 4+ photos are 70% more likely to sell
Specific Shot Types to Show as Visual Guide
Shot 1
Wide establishing shot (whole pool + yard)
Shot 2
Water-level angle (makes guest picture themselves in it)
Shot 3
Lounge/seating area (where people hang between swims)
Shot 4
Night/evening shot with lighting (extends bookable hours)
Shot 5
Amenity close-ups (grill, hot tub, speakers, floats, towels)
Tone
"Done beats perfect. But great photos change everything." Make it feel achievable, not intimidating.
CREATIVE DIR. Module 2 Pricing 💰
Lead With
"Hosts near {{city}} charge ${{local_avg_price}}/hr. Here's why that matters." Use a pricing range bar or market comparison chart.
Visual Approach
A simple horizontal bar showing price range for pools in the host's area. Mark where the host falls (probably high, since this only triggers for overpriced listings). Show the "sweet spot" zone in green. Make it feel like data, not judgment.
Inspiration References
Turo
Automatic pricing optimizes based on local market + demand + seasonality ("let the algorithm do the work")
Airbnb
"Research comparable listings in your area" with market data visualization
Key Creative Note
This is sensitive. Don't say "your price is too high." Say "here's what the market looks like, and here's a strategy that works." The playbook is: start competitive, get reviews, raise later. Frame it as smart business, not discounting.
Tone
"This isn't about being cheap. It's about getting booked, getting reviewed, and earning more over time."
CREATIVE DIR. Module 3 Description ✍️
Lead With
"Guests book feelings, not features." Short, punchy, then show what good looks like.
Visual Approach
Before/after text comparison. Left: "Private pool in backyard. Available for booking." Right: "Imagine floating in a heated saltwater pool while the sun sets behind the palm trees. Towels, speakers, and cold drinks included. Your private escape is 10 minutes from downtown." The difference should be visceral.
Inspiration References
Etsy
"Put your most important keywords first in your title"
Turo
"Articulate what makes your car great to encourage guests to book"
VRBO
"Your headline is the first thing travelers see"
Fill-in-the-Blank Template
Provide this template in the email itself: "Imagine [experience]. [Unique feature]. [What's included]. [Logistics]."
Tone
Make writing a description feel easy, not like an essay. A template removes the blank-page problem.
CREATIVE DIR. Module 4 Response Time ⚡
Lead With
"Guests compare options. The fastest reply wins." Use a clock or timer visual with response time tiers.
Visual Approach
A visual timer/speedometer showing response time zones: Green zone: < 1 hour (top hosts). Yellow zone: 1-6 hours (you're losing bookings). Red zone: 6+ hours (guests already booked elsewhere). Show where the host currently falls with a marker.
Inspiration References
Thumbtack
"A one-hour delay makes it 21x less likely you'll book" (most dramatic stat)
Etsy
"Sellers who respond within 24 hours are 5x more likely to make a sale"
Airbnb
90%+ response rate required for Superhost, impacts search placement
Key Creative Note
Swimply bookings are often same-day or next-day (weather-dependent, impulse decisions). A 6-hour delay means the guest already booked elsewhere. This urgency angle is UNIQUE to Swimply vs Airbnb where trips are planned weeks ahead. Lean into this.
Instant Book Pitch
Frame as "the set-it-and-forget-it solution." One toggle, 60% more bookings. Make it feel like a cheat code, not more work.
CREATIVE DIR. Module 5 Amenities 🎉
Lead With
"You have {{amenity_count}} amenities listed. Top hosts list 10+." Show a checklist with the gap.
Visual Approach
Two-column checklist. Left column: amenities the host HAS listed (with checkmarks). Right column: amenities guests search for that the host is MISSING (with empty circles). Make the gap visual and obvious.
Inspiration References
VRBO
Amenities function as search filters. More amenities = more filter matches = more visibility.
Uber Eats
Customization options make ordering easier. Same for pool amenities making booking easier.
Pool-Specific Amenities Guests Filter For
Amenity List
Pool floats/noodles, Bluetooth speaker, BBQ/grill, towels provided, outdoor shower, pool lighting (evening), shallow end (kids), pet-friendly, shaded seating, private restroom, changing room, parking, heating/hot tub, diving board, waterslide, fire pit
Tone
"If you have it, list it. Even 'shaded seating area' matters to the right guest."
CREATIVE DIR. Module 6 Availability 📅
Lead With
"You have {{available_days}} days open in the next month." Use a calendar heat map visual.
Visual Approach
Mini calendar showing the next 30 days. Green = booked. Gray = blocked by host. Red/orange = peak demand days the host is missing (weekends, holidays). The visual story: "Look at all this money you're leaving on the table."
Inspiration References
Poshmark
"Relisted items sell 30% faster" (refreshing/updating has algorithmic impact)
Fiverr
Daily activity and keeping gigs updated improves ranking
Airbnb
Active calendars rank higher in search
Key Angles to Emphasize
Weekday Daytime
Underutilized goldmine for WFH parents
Evening Swims
Date night positioning
Pre-season
"Open your summer weekends NOW before demand hits"
Tone
"You can always block days later if plans change. But you can't get bookings on days you never opened."
CREATIVE DIR. Module 7 Free Listing Review 🔍
Lead With
"Let us take a look." Use a scorecard/report card visual showing the host's listing grades.
Visual Approach
A "Your Listing Report Card" with letter grades or score bars per category (Photos: B-, Pricing: A, Description: C+, etc.). The CTA: "Want us to help you turn those C's into A's? Book a free listing review." Make it feel like a helpful assessment, not a failing grade.
Inspiration References
Airbnb
Pro Photography Program: free, invitation-only, creates exclusivity
Walmart
Listing Quality Score: 0-100 with category breakdown
Key Creative Note
This is the safety net. By Module 7, the host has seen 6 emails with specific tips and hasn't acted. This email says: "We get it, it's a lot. Let a human help." Sign from a named team member (Bunim or a real person). Make it feel personal, not corporate.
Tone
"No catch. We want you to succeed because when you earn, we grow."
DESIGN RULES All Modules General Design Principles
Apply to Every Tip Module
1. One Stat Hero
The big number IS the visual. Make it 48px+ type. One stat per email, impossible to miss.
2. One Clear CTA
Deep link directly to the edit screen in the Swimply app. Don't make them navigate.
3. Mobile-First
Hosts check email on their phones. Single column, big buttons, scannable.
4. Progress Feels Good
If the host acts on a tip, celebrate it in the next email. "Your listing just improved."
5. Data Removes Subjectivity
"You have 4 photos, top hosts have 12" is inarguable. "Your photos could be better" is dismissable.
6. Peer Comparison Motivates
"Hosts in {{city}} who did X earn Y% more" is more compelling than "Swimply recommends X."
7. Seasonal Timing
Send the calendar/availability tip before peak season. Send the pricing tip when the host hasn't been booked in 2 weeks. Context makes tips feel relevant, not random.