Senior Manager, Retail Operations

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 Wirecutter). Calendar 2 launched earlier this year to rave reviews, and our newest product, Skylight Buddy, was just named one of TIME’s Best Inventions of 2026.

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:

The Senior Manager Retail Operations will lead our retail operations team and own the long-term plan for how we ship to retailers. You will manage two Retail Operations Managers, who run the day to day for our retail accounts, and you will be the escalation point for retailer operations leaders when something goes wrong. You will also be the thought partner to our Senior Director of Global Fulfillment on the larger questions: which retailers to add, whether to go direct or through a distributor, how our systems and 3PL network should look in two years, and where our retail margin is leaking.

This is a player-coach role. About half your time is your team and the accounts; the other half is strategy and projects that need one owner. The ideal candidate has run retail operations for several national retailers, has coached managers, writes clearly, and can tell us when we are wrong.

Responsibilities:

• Lead and develop two Retail Operations Managers: set expectations, coach weekly, review their accounts, and build the standards they work to. Hire for the team as we grow.
• Own the retail operations strategy and 12-24 month roadmap: new retailers, new channels, international expansion, and the systems, 3PL capacity, and headcount needed to support them.
• Be the escalation point for retailer operations and vendor-compliance leaders. Run the quarterly reviews with our largest accounts alongside Sales.
• Own the cross-account scorecard: OTIF, fill rate, lead time, chargeback % of sales, freight cost per unit, and dispute win rate. Report it to leadership monthly with clear actions.
• Lead the chargeback and deduction prevention program: find recurring causes across retailers, fix them at the source with the 3PL and carriers, and quantify the savings.
• Own the retail order-to-cash process end to end with Sales, Accounting, and Planning: EDI (850 / 856 / 810), NetSuite, retailer portals, and where manual work should be automated.
• Work with Sales, Planning, and Purchasing on forecast-to-ship: how retailer forecasts turn into container loads, allocation rules, and inventory commitments.
• Work with the 3PL Manager on network design, site capacity, and retailer requirements at each warehouse.
• Evaluate build vs. buy and direct vs. distributor decisions with a clear business case, and present the recommendation to the executive team.
• Lead new retailer onboarding and large product launches as the single accountable owner.
• Own freight strategy for retail: broker and carrier mix, prepaid vs. collect, rates, and service.
• Build the operating rhythm: weekly team review, monthly business review, annual retailer compliance calendar.

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 Wirecutter). Calendar 2 launched earlier this year to rave reviews, and our newest product, Skyl...

• Bachelor’s degree in Supply Chain Management, Logistics, Business Administration, or related field
• 8+ years of experience in retail fulfillment operations or supply chain management, including 3+ years leading retail logistics for national retailers
• 2+ years managing people, including coaching and performance management of managers or senior individual contributors
• Proven experience managing fulfillment for multiple national retailers (Costco, Walmart, Sam’s Club, Target, Best Buy)
• Track record of designing and delivering a multi-quarter operational initiative with measurable results
• Strong financial skills: landed cost, freight cost, chargeback ROI, and building a business case
• Experience with EDI, ERP (NetSuite or similar), and retailer portals
• Excellent written communication and the ability to present to executives

Bonus Points for:

• Experience leading a team through rapid growth in number of retailers or volume
• Experience onboarding new retailers or running a distributor program
• Experience with international retail and ocean freight
• Experience with 3PL network design or a 3PL transition
• MBA or MS in Supply Chain Management, International Business, or related field
• Experience with consumer electronics or subscription hardware businesses
• Track record of successful change management in complex organizations
• Experience building dashboards or automation (SQL, Google Sheets, BI tools) yourself

Our Commitment:

We value diverse experiences, backgrounds, and perspectives—and we hire kind, thoughtful people who care deeply about their work. If you're reading this and think, “I don’t check every box,” but still feel excited about the role: Apply. We want to hear from you.