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:
The Special Projects role 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:
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
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
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 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
A willingness and 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
Background in sustainability initiatives
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)
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 $120-160k based on experience and for California-based candidates, the range being offered for this role is $120-160k 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.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.
Skylight is a digital consultancy using design and technology to help government agencies deliver better public services. The company is at the forefront of a civic movement to reinvent how all levels of government serve families, patients, and others in today's digital world. They work with federal agencies in the health and civilian space, building and maintaining systems that handle sensitive personal data for millions of people. Skylight is led by a team of public interest technologists focused on delivering reliable, secure, and compliant software solutions that meet strict federal security standards.
