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:

You are the operational spine of Skylight's logistics function. Where our Director of Logistics owns strategy carrier contracts, compliance posture, SLA frameworks, and systems design you own execution: making sure that every shipment moves as planned, every forwarder and drayage partner is held to their commitments, and exceptions are caught and resolved before they become problems. You'll be the connective tissue between our freight forwarders, 3PL partners, and internal teams.

Responsibilities:

• Partner with our freight forwarders on day-to-day bookings, exception escalations, and performance follow-ups. You are the primary operational point of contact.
• Own the forwarder to drayage handoff: ensure cargo moves cleanly from vessel discharge to our FC’s  (Reno NV and Indianapolis IN) with no gaps in ownership or communication.
• Coordinate FC facility transfers, including inbound routing decisions, cross-dock timing, and delivery sequencing.
• Audit forwarder rates, accessorials, and SLA performance on a recurring basis — flag variances and drive them to resolution.
• Operate cargo tracking systems (TMS, Forwarder Systems, Internal trackers): maintain shipment visibility across all active lanes, escalate delays proactively, and keep stakeholders informed.
• Own data and documentation workflows: ensure all shipping documents (commercial invoices, packing lists, BOLs, ISF filings) are captured, filed, and accessible and build the habits and systems that make this reliable at scale.
• Lead exception and incident management: serve as the point person when things go wrong,  a delayed vessel, a drayage no show, a CBP hold, a cargo claim and drive resolution to closure.
• Provide compliance ops support to the Director of Logistics: assist with ISF filing coordination, CBP exam response, customs document collection, and UFLPA documentation workflows.
• Continuously improve the processes, tools, and documentation that underpin operational consistency across all lanes and partners.

Requirements

This role is not for everyone. You will thrive here if you:

• Can find the 1-2 things that actually drive outcomes or that will really make a difference for any given goal.
• Feel comfortable in ambiguity. You don’t need a roadmap handed to you—you’ll make one.
• Can both execute while designing repeatable processes that work in practice.
• Care deeply. You show up with curiosity, vulnerability, and good intent.
• Own the problem, fix the system. You don't patch the same issue twice — you find root cause and build a process that prevents recurrence.
• Bridge ops and tech. You can look at a workflow, articulate what a system needs to do, and work with engineers or no-code tools to make it repeatable and scalable.
• Own the problem,  fix the system.  Identify the root cause,  prevent the recurrence 
• Bridge Ops and Tech - translate workflow needs into buildable requirements

Must-Haves:

• 4–7 years of experience in freight forwarding, 3PL, or shipper-side logistics operations with hands-on carrier and forwarder management.
• Strong working knowledge of international freight: ocean FCL/LCL, air freight, and domestic drayage operations.
• Demonstrated ability to own exceptions, incidents, and escalations in a fast-moving environment you finish what you start.
• Comfortable with data: you can work in Google Sheets or Excel, build trackers, and produce reporting without needing someone to set it up for you.
• Baseline familiarity with customs and trade compliance workflows ISF, CBP entry process basics, document collection even if compliance is not your primary background.
• Clear written communicator: you correspond professionally with carriers, forwarders, and 3PLs, and draft internal updates that are crisp and complete.
• Entrepreneurial mindset: comfortable in fast-moving environments, able to deal with ambiguity, take ownership, and continuously improve.
• Process design and systems thinking: spots what’s broken, designs something better, and sees it through to adoption — has translated an operational need into a tool, tracker, or automation, and can work alongside engineers or analysts to build it right.

Nice to Haves:

• Experience working with major freight forwarders (Expeditors, Flexport, Crane Worldwide, or similar).
• Familiarity with drayage and 3PL coordination in transpacific lanes to LA/LGB, or the Midwest
• Experience with TMS or shipment visibility platforms (OSCA, Setlog, project44, FourKites, or similar).
• Customs brokerage coordination experience (CBP holds, ISF corrections, entry review, standard customs documentation).
• Experience in a consumer goods or eCommerce company with an omnichannel distribution model.
• Prior experience managing or mentoring junior logistics staff.

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.

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)

The anticipated base salary range for this position is $110k-$130k 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.