Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families (plus Wired and the Wirecutter). Our latest product is Calendar 2, which just launched to rave reviews.

Our mission is to connect loved ones by creating the world’s simplest products and services that improve family life. Our founders are former venture capitalists and serial entrepreneurs who have scaled this business to $300M+ in annual revenue while being completely bootstrapped and profitable. We get to grow a happy, healthy company focused on making products our customers love without investors breathing down our necks.

Smart, hardworking people who care about making actually meaningful products love working here. People like you. We’re busy inventing new ways to simplify family life and help parents raise great kids – and we need your help! Come invent something new with us.

About the Role:

We’re looking for a Retail Digital Marketing Manager to own how Skylight shows up and wins across key retail.com platforms—specifically Walmart, Target, and Costco. This role is ideal for a highly analytical and execution-focused digital marketer who understands how to drive conversion, visibility, and growth within retailer ecosystems.

You will be responsible for optimizing Skylight’s presence across retailer websites, leading digital merchandising, retail media strategy, and on-site conversion tactics. Working closely with Sales, Growth, Creative, and Analytics, you’ll ensure every digital shelf is best-in-class and built to scale.

This is a high-impact role that sits at the intersection of performance marketing, digital merchandising, and retail strategy.

Key Responsibilities:

• Own Skylight’s digital presence across retailer websites including Walmart, Target, and Costco —ensuring best-in-class product detail pages (PDPs), brand stores, and on-site content.
• Lead retailer-specific digital merchandising strategy, including SEO optimization, keyword strategy, content testing, and conversion rate optimization
• Manage and optimize retail media investments across platforms such as Walmart Connect, Target Roundel, and Best Buy Ads to drive traffic and sales
• Partner with Sales to align on key business priorities, promotional calendars, and product launches, translating them into high-performing digital campaigns
• Develop and execute retailer-specific activation plans, including seasonal campaigns, product launches, and promotional events.
• Collaborate with Creative to develop and adapt digital assets tailored to each retailer’s platform and audience, as well as leveraging best in class content, campaigns and key learnings.
• Monitor performance across retailer platforms, including traffic, conversion, share of search, and content effectiveness—turning insights into actionable optimizations
• Build and maintain a testing roadmap across PDP content, A+ content, media tactics, and promotional strategies to continuously improve performance
• Partner with Analytics and Finance to track ROI, measure incrementality, and inform future investment decisions
• Strengthen relationships with retailer media and merchandising teams to unlock new opportunities for visibility and growth.
• Develop and manage a retailer media budget for each major retail channel, with inputs from Sales on revenue expectations and Finance around CPA targets. 
• Create KPIs and measurement tools for evaluating marketing spend and tactics employed in effectiveness of building :  1) Sales, 2) Brand awareness and 3) Competitive landscape positioning.
• Develop and execute Retail Influencer and Affiliate programs for Walmart, Target, Costco and Best Buy.

Requirements

• 4–6+ years of experience in eCommerce, digital marketing, retail media, or shopper marketing—preferably with hands-on experience managing retailer.com channels
• Deep expertise in retail media platforms such as Walmart Connect, Target Roundel, and/or Best Buy Ads.
• Highly data-driven, with strong experience analyzing performance metrics like conversion rate, ROAS, share of search, and digital shelf health
• Understanding of digital merchandising fundamentals, including PDP optimization, content strategy, ratings & reviews, and search ranking factor.
• Experience managing cross-functional initiatives with Sales, Creative, and Analytics teams
• Comfortable owning budgets and optimizing spend based on performance and business priorities
• Ability to thrive in a fast-paced environment and can balance strategic thinking with hands-on execution
• Clear communication skills and ability to translate data into compelling insights and recommendations

Some travel required to retailer meetings and company events

Benefits

Our competitive compensation package includes:

• Competitive Salary + Equity Package
• 401K matching
• Wellness, learning, and home-office budgets
• Health, Dental & Vision Medical Plans
• Tremendous autonomy to set the direction of your work
• Unlimited PTO
• Company holidays on the first Friday of every month (Excluding November, December, and January)

Equal opportunity employer

Skylight is committed to building a diverse and inclusive team. All qualified applicants will be considered without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, disability, protected veteran status, or any other factor protected by applicable federal, state, or local laws. If you’re the best person for the job, we want you on board!

We hire across the U.S., but for legal reasons, we have to list NY and CO separately.

For Colorado-based candidates, the range being offered for this role is $120k - 180k based on experience and for California-based candidates, the range being offered for this role is $120k - 180k based on experience. Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment for qualified applicants with criminal histories in a manner consistent with the requirements of this law.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.