The Challenge
Skylight is a $300M+ bootstrapped startup transforming family connectivity with products loved by millions. You'll own their digital presence across Walmart, Target, and Costco—driving conversion, visibility, and growth at the intersection of retail media and performance marketing.
Your Mission
Audit and optimize all Skylight product detail pages (PDPs) across Walmart, Target, and Costco for conversion rate, ensuring best-in-class content and merchandising
Launch and operationalize retail media strategy across Walmart Connect, Target Roundel, and platform-specific ad networks with baseline performance benchmarks
Establish measurement framework tracking traffic, conversion rate, share of search, and ROI across all three retailer platforms
Build and document retailer-specific playbooks including keyword strategy, content testing protocols, and promotional calendar alignment
Achieve 15-25% lift in conversion rates through systematic A/B testing of PDP content, A+ content, and promotional tactics
Scale retail media spend to hit CPA targets set by Finance while maintaining positive ROAS across all channels
Establish quarterly testing roadmap with 4+ active experiments per retailer testing pricing, creative, positioning, and merchandising
Develop 3-4 new visibility and growth opportunities with retailer teams (category placement, featured positioning, co-marketing)
KPIs You'll Own
Conversion Rate by Retailer
Track PDP-to-cart conversion % across Walmart, Target, Costco with weekly monitoring and monthly targets.
Retail Media ROAS
Return on ad spend across Walmart Connect, Target Roundel, and other retail media platforms against CPA targets.
Share of Search
Percentage of relevant retail search impressions captured for Skylight products within each retailer ecosystem.
Traffic & Volume
Monthly visits and product impressions to Skylight's digital properties across all three retailers.
Content Performance Index
Composite scoring of PDP effectiveness including engagement, dwell time, and conversion contribution by asset type.
Tools & Stack
Your Team
Your Manager
Head of Growth or VP Marketing (not specified)
Current Team
Cross-functional: Sales, Growth, Creative, Analytics, Finance teams
New role
The Package
Salary
$120K-$160K base
Remote
On-site (location not specified, but US-based)
Benefits & Perks
Company Intelligence
Skylight builds the OS of the family with products like Skylight Calendar (millions of users) and Calendar 2. Founded by ex-VCs and serial entrepreneurs, they've scaled to $300M+ ARR while remaining completely bootstrapped and profitable. Their mission: connect loved ones through simple, meaningful products that improve family life.
Funding
Bootstrapped (no VC)
Customers
Millions of families; featured in Wired and The Wirecutter
Culture
Smart, hardworking team obsessed with meaningful products. No investor pressure. Family-first mentality.
Is This Role For You?
- You've shipped retail media or retailer.com campaigns and understand Walmart Connect, Target Roundel, or similar platforms
- You're obsessed with conversion optimization—A/B testing, PDP content, keyword strategy—and can tie it to revenue
- You thrive working across Sales, Creative, and Analytics; you speak their languages and translate strategy into execution
- You want ownership of a $XX million channel with clear metrics and the autonomy to test, learn, and scale
- You need a remote setup; this role is on-site only
- You're used to vanity metrics (impressions, clicks) without connection to conversion and revenue
- You prefer big agency/vendor relationships over hands-on platform optimization and testing
Interview Process
Initial Screening
Phone conversation about retail media experience and understanding of retailer ecosystems
Portfolio & Case Study
Walk through a past retail media or retailer.com campaign: strategy, execution, results, learnings
Team Interviews
Conversations with Growth lead, Sales leader, and Analytics partner to assess cross-functional fit
Strategy Exercise
Develop a 90-day retail media plan for Skylight across one retailer platform (Walmart, Target, or Costco)
Interested in this role?
Apply now and hear back within days, not weeks.
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About Growth Marketing Roles
Growth marketers drive user acquisition, activation, and retention through data-driven experimentation. They sit at the intersection of product, data, and marketing — running A/B tests, building funnels, and scaling what works.