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 are seeking a strategic and results-driven Senior Director of Retail Sales to lead our expansion across the North American markets. In this pivotal role, you will drive and build our critical Retailer go-to-market strategy, evaluate and prioritize new retail and distribution opportunities, and build a high-performance North America Retail sales team.

You’ll work cross-functionally with Marketing, Finance, Operations, and Product to drive sustainable growth, develop channel management and pricing strategies, forecast inventory needs, and cultivate strong executive retailer, distributor and internal executive team relationships. We are looking for a high level strategic sales leader who has a deep understanding of the North American retail market and has excellent business skills to deliver profitable customer plans and market share growth. This role will report directly to the VP of Sales and manage all aspects of our business in North American retail markets.

Responsibilities:

Strategic Expansion & Market Development: Lead development of the retail growth strategy for North America: market selection, retail and channel prioritization, channel pricing management, sku assortments, future product development for key strategic exclusives and alignment on which channels deliver net new consumer markets.
Partner management: Set and manage joint business plans (JBPs), annual targets, and promotional calendars with key partners, building executive level relationships.
Channel Management: Build and execute best in class channel management and reseller enforcement strategies, tools, tracking and execution.
Market Analysis: Conduct competitive, consumer, and retail landscape analysis to identify high-potential opportunities, top new retail partners to unlock and which channels have best opportunities for growth.
Business development: Build business cases for expansion into new regions or retail partners, including financial modeling and risk analysis.
Market definition: Define and localize the channel mix strategy: direct retail, distribution, ecommerce, and hybrid models.
Distribution Management: Identify, negotiate, and onboard new retail partners and regional distributors

Evaluate new Distribution partners, conduct RFPs and pricing analysis, sourcing and logistic capabilities to identify and finalize new partners and contracts.
Manage and lead all onboarding activities for setting up new Distributors, Retail expansion or new direct retail accounts with collaboration between internal Operations and Finance teams.

Forecasting, Pricing & Commercial Planning: Own Retail (North America) pricing strategy: tiered retail, distributor, and landed costs to ensure margin and brand positioning targets

Partner with Operations to develop accurate inventory forecasts by retailer, product line, and retail partner.
Analyze sell-in and sell-through data to optimize channel inventory levels and minimize stockouts or overages
Work with Finance on contract terms, marketing investments, and contractual programs.

Cross Functional Collaboration: Work closely with Marketing to ensure retail campaigns are aligned with retail and distributor needs.

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.

Requirements

8–12+ years of retail sales leadership, preferably in consumer electronics, houseware products, or lifestyle brands.
Strong experience managing retail partnerships and distributor networks.
Experience with National Retailers like Walmart, Costco and Target, as well with large distributors and specialty retailers.
Proven track record of driving sales growth and managing retail partnerships in the United States and Canada.
Highly analytical, with proven success in forecasting, planning, and performance analysis.
Deep understanding of channel pricing, compliance, and commercial logistics required to support the National retail channel.
Excellent negotiation, communication, and relationship-building skills.
Ability to work independently and adapt to different cultural and business environments.
Willingness to travel as needed.

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 $200k - 250k with bonus potential based on experience and for California-based candidates, the range being offered for this role is $200k - 250k with bonus potential 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.

Senior Director of Retail Sales, North America