Role Description Our ideal candidate is an entrepreneur at heart and has deep experience talking to customers and building lovable products. This candidate is comfortable wearing many hats and has an innate curiosity that drives the direction of their work. You will report to our Chief Product Officer, working closely with the engineering, customer service, and marketing teams to transform Calendar into the operating system of the family, eventually used by millions of families daily. Responsibilities - The Family OS has many possible paths forward and your first job will be to define and validate the next major step forward. - Within your first few months, you’ll shape a roadmap, prototype and validate your ideas with customers and work with design and engineers to bring them to life. - Set the product vision: develop a deep understanding of the competition, the customer, and the ways Skylight can help families. Use that and your creativity to propose and validate new products. - Own the product roadmap: define the roadmap across and build features that both benefit customers and impact KPIs. You will ruthlessly prioritize features with a nose for value and scope a minimum lovable product to deliver features on time. - Collaborate cross-functionally: work across engineering, design, and marketing teams to take these features to market with smooth rollouts and high feature adoption. - Set and assess progress rigorously: you will set KPIs, monitor performance, and analyze data to deeply understand our users and the impact your product initiatives have. Your insights will drive future developments and organize the team around your strategy. Qualifications - You have 5-10 years of relevant experience. - You have a proven track record of building and owning impactful software products. - You are brimming with ideas, opinions and products that ought to be. - You have a knack for finding the novel insight and tend to be right. - You are endlessly curious and are on the edge of how product works in the AI-era. - You are comfortable operating independently, spotting ambiguity and proposing solutions. - You are data analytics savvy and take a data-driven approach to building product. - You are a great communicator and can simplify the complex. Benefits - 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) Company 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 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.

Role Description We are looking for a friendly and organized Insurance Client Relations Manager to help maintain strong relationships with existing clients. The main focus of this role is to contact current clients, schedule insurance review meetings, send reminders, and keep client information organized. This is not a high-pressure sales role. You will be speaking with people who already know or have worked with the business. - Contact existing clients by phone, email, or message - Schedule insurance review appointments - Send appointment confirmations and reminders - Follow up with clients who have not responded - Update client information and notes - Track birthdays, policy review dates, and important client milestones - Send simple follow-up emails after meetings - Ask satisfied clients for referrals, testimonials, or Google reviews - Help prepare newsletters, greetings, and client reminders - Assist with basic administrative tasks as needed Qualifications - Experience in customer service, appointment setting, sales support, or administration - Comfortable speaking with clients over the phone - Clear and professional English communication skills - Friendly, patient, and confident when speaking with clients - Organized and able to keep track of follow-ups - Comfortable using email, calendars, spreadsheets, and online systems - Able to handle client information with care and confidentiality - Willing to learn basic insurance processes and terminology Requirements - Nice to Have: - Experience in insurance, banking, mortgages, real estate, or financial services - Experience working with Filipino clients in Canada - Experience using a CRM or client database - Experience requesting referrals or scheduling review meetings Benefits - Remote - Part-Time (20–25 hours per week) - Long-term opportunity with room for growth

• Own Amazon search and display (DSP/OTT) performance advertising for an assigned set of clients • Create, implement, manage, and report on advertising strategies that align with client goals • Collaborate with internal and external stakeholders to maximize performance for the client’s business • Proactively research industry trends and best practices and communicate internally to knowledge share • Engage frequently and professionally with clients via email/slack, phone, and in-person video meetings • Strategic thinking, detail oriented execution, and insightful data analysis to identify areas of opportunity and deliver sales-driving initiatives • Utilize Amazon Attribution and Amazon Marketing Cloud to gain additional insights to increase performance • Mentor more junior Advertising Managers

• Own Amazon search and display (DSP/OTT) performance advertising for an assigned set of clients • Create, implement, manage, and report on advertising strategies that align with client goals • Collaborate with internal and external stakeholders to maximize performance for the client’s business • Proactively research industry trends and best practices and communicate internally to knowledge share • Engage frequently and professionally with clients via email/slack, phone, and in-person video meetings • Strategic thinking, detail oriented execution, and insightful data analysis to identify areas of opportunity and deliver sales-driving initiatives • Utilize Amazon Attribution and Amazon Marketing Cloud to gain additional insights to increase performance • Mentor more junior Advertising Managers