Strategy and Special Projects Lead

Skylight is a technology startup building the OS of the family. We make Skylight Calendar, the smart calendar loved by millions of families. 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:

As a Strategy and Special Projects Lead, you will help drive the future direction and key projects for the Operations team. You will lead the day-to-day execution of high-impact Operations initiatives with a strong focus on scaling our internal capabilities. This role is ideal for someone passionate about optimizing operations and building infrastructure that supports rapid growth across global retail and D2C channels. You will be responsible for managing special cross-functional projects that improve order fulfillment, logistics, and inventory management. You will work closely with Finance, Product, CX, and Marketing teams to align operations strategy for developing scalable tools and addressing reporting needs, and uncover insights to streamline workflows across the organization. The ideal candidate has strong analytical and project management skills, thrives in autonomous environments, and is motivated by solving complex problems with a customer-first mindset.

Responsibilities:

• Shape operational strategy: Partner with leadership to design and scale systems, workflows, and tooling that align with long-term company goals
• Build our data architecture and implement automated systems that transform operations from reactive to proactive
• Lead mission-critical projects with a hands-on approach:
  • Develop clear roadmaps aligned with leadership vision and stakeholder needs
  • Coordinate cross-functional teams (Ops, CX, Finance, Marketing) to ensure seamless execution
  • Run focused stand-ups that maintain momentum and accountability
  • Balance strategic oversight with a willingness to roll up their sleeves and execute when needed
• Elevate operational performance:
  • Identify and lead automation, tooling, and process initiatives that reduce manual work and unlock scale
  • Solve complex operational challenges with innovative solutions
  • Turn data into actionable insights that drive strategic decisions
• Create documentation that ensures knowledge transfer and sustainable implementation
• Validate new processes with methodical testing to guarantee flawless deployment

Requirements

What You Bring:

• 8+ years experience in Operations, Supply Chain, and eCommerce fulfillment in growth environments
• Proven track record of leading complex, high-impact Operations projects from conception to successful implementation
• Hands-on, roll-up-your-sleeves mindset: comfortable getting into the details, doing the work alongside the team, and directly solving problems—not just providing strategic direction or managing from a distance
• Hands-on experience with ERP systems (like NetSuite ) and operational technology (like Pigment , SPS Commerce , and transportation management systems)
• Strong strategic systems thinking: able to identify upstream inefficiencies and also execute on detailed solutions
• Demonstrated ability to cross-train and step into adjacent roles to ensure organizational stability and momentum
• Strong analytical skills for data-driven decision making
• Exceptional attention to detail and organizational abilities
• Clear communication skills that bridge departmental boundaries
• Comfort with ambiguity and a solutions-focused approach
• Experience creating effective SOPs and operational frameworks

Bonus Points for:

• Experience with e-commerce fulfillment operations and refurbishment
• Knowledge of emerging operations technologies
• Track record in change management
• Experience with Reverse Logistics management
• Solid people leadership experience: Ability to build and leverage the capabilities of a high-performing team

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)