Senior Manager, Retail Operations

Skylight; United States; Remote; USD 150,000 - 180,000; Full time

Benefits offered by this job

Competitive Salary + Equity Package

401K matching

Wellness and home-office budgets

Health, Dental & Vision plans

Autonomy to set direction

Unlimited PTO

Company holidays

Job summary

Skylight is hiring a Senior Manager, Retail Operations to lead our retail operations team and own the long-term plan for shipping to retailers. You will manage two Retail Operations Managers, escalate retailer issues, and partner with senior leaders on network design and channel strategy.

The role combines hands-on team leadership with strategic initiatives, requiring experience with national retailers, complex forecasting, and cross-functional collaboration across Sales, Planning, and

Qualifications

• Bachelor’s degree in supply chain or related field.
• 8+ years in retail fulfillment operations or supply chain management.
• 3+ years leading retail logistics for national retailers.
• 2+ years managing people.

Responsibilities

• Lead two Retail Operations Managers and set expectations.
• Own the 12–24 month retail operations roadmap and expansion.
• Escalation point for retailer operations and vendor compliance.
• Own cross-account scorecard including OTIF, lead time, freight costs.
• Lead chargeback/deduction prevention and savings.
• Own end-to-end order-to-cash with ERP and retailer portals.
• Collaborate on forecast-to-ship and container planning.
• Design network with 3PL and warehouse requirements.
• Evaluate build vs buy and direct vs distributor options.
• Oversee onboarding of retailers and large product launches.
• Define freight strategy and operating rhythm.
• Build a strong, scalable operations team.

Education

Bachelor’s degree in Supply Chain Management, Logistics, Business Administration, or related field

Tools

EDI

ERP (NetSuite)

retailer portals

Job 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 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.

• 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: We want to hear from you.

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)

The anticipated base salary range for this position is $150k-$180k 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.