Head of Ecommerce

Head of Ecommerce

Skylight · United States (Remote) · — · Posted 2026-10-16

Salary: USD 200,000–275,000

Workplace: remote

Description

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.

The role
Own Skylight’s D2C website and channel P&L. The site generates a significant share of company sales and is the only channel where customers can buy hardware and subscriptions together. It is also Skylight’s primary place to test positioning, bundles, and how its products work as an ecosystem. This high-impact role reports to Aviv, President, and oversees our only fully owned sales channel for the business - which includes several strategic goals simultaneously: increasing conversion rate to increase device sales, telling our brand story, using the site as an experimentation ground for strategic decisions on positioning, product pricing, messaging, plus pricing and positioning, and explaining our overall product lineup/ecosystem to a wide range of customers.

What you’ll do

• Own the P&L of myskylight.com. Work with finance, operations, demand planning, retail, GTM, and growth on assortment strategy, pricing, and forecasting to set up the channel to achieve growth and profitability targets.
• Own the vision for myskylight.com: Balance site performance with brand storytelling; our website is one of the primary destinations where omnichannel buyers learn more about Skylight. 
• Partner with our ecom team to guide our A/B testing strategy and major prioritization decisions on what business goal we’re trying to achieve: e.g., pricing, positioning, conversion optimization, product naming, etc. 
• Oversee the ecomm team (Product, Design, Engineering) to ensure the roadmap accomplishes our strategic vision for growth and brand. 
• Partner closely with growth marketing teams to drive site conversion and improve SEO.
• Set the priorities for the ecomm team across growth, product, design, and engineering functions. The ideal candidate has fluency across marketing and technical specializations to set clear goals and make trade-offs as necessary. 
• Own the data and outcomes. KPIs like traffic, conversion rate, AOV, revenue, margin. Report on performance to leadership regularly and turn insights into roadmap decisions.
• Set and manage the ecomm budget, covering headcount, tools, agencies, and the tech stack. Decide when to build, buy, or partner.

Requirements

• Strong head-of-ecommerce experience in an omnichannel consumer hardware business at $100M+ scale and strong strategic and business judgment.
• D2C P&L ownership, including close work with demand planners on inventory.
• Hands-on growth product and CRO results, with a track record of shipping features and tests quickly and owning conversion rate as primary metric. 
• A hungry, entrepreneurial, scrappy leader who can find a way to prove out business value with MVP execution, then scale. 
• Strong partnerships with marketing/growth, engineering, product, finance, and operations 
• ability to hire and lead a cross-functional pod.
• Needs to be high IQ, low ego, servant leadership style, with a significant track record of growing and developing people on their team. 

Nice to Have

• Knows and understands how to leverage self-serve tools and AI to increase velocity and empower the team. 
• Shopify SKU-architecture experience and interface with ERPs and 3PLs.
• Experience selling subscriptions alongside physical products.
• Experience working with headless commerce

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 (Except November, December. & January)

The anticipated base salary range for this position is $200K-275K per year. This range reflects the compensation Skylight reasonably and in good faith expects to pay for the position at the time of posting. Actual compensation will be determined based on job-related factors, which may include experience, qualifications, skills, education, geographic location, and internal equity. Skylight also offers benefits, including medical, dental, vision, and paid time off.

Equal Employment Opportunity

Skylight is an equal opportunity employer committed to building a diverse and inclusive team. All qualified applicants will be considered for employment without regard to race, color, religion, sex, national origin, age, disability, genetic information, or any other characteristic protected by applicable federal, state, or local law. Pursuant to the San Francisco Fair Chance Ordinance, Skylight will consider for employment qualified applicants with arrest and conviction records.

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Apply at Skylight

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