Executive Assistant

At Hi Marley, we’re not just a technology company—we’re on a mission to revolutionize the insurance industry with our conversational platform that makes communication simple, efficient, and delightful. Built for carriers, powered by SMS, and designed by insurance experts, Hi Marley connects people through seamless, friendly conversations that save time, money, and hassle. Our platform helps insurance carriers strengthen customer relationships while streamlining operations. With a focus on collaboration, coaching, and powerful analytics, we deliver the insights insurance teams need when they need them—creating a smooth, frictionless experience for customers along the way. We are looking for a highly organized and proactive Executive Assistant (EA) to support our CEO. This is a pivotal role and a true force multiplier, you will ensure the CEO’s time, priorities, and communications are managed effectively during an exciting period of growth and scaling. While the primary responsibility is to partner closely with the CEO, you will also support our CPO and COO, playing a central role in company operations, leadership alignment, and internal culture. This is an opportunity to learn, grow, and make a meaningful impact at the heart of Hi Marley’s leadership team. Teamwork and shared enthusiasm is a core part of our culture, which is why this role involves joining us in the Boston office for two days each week. What You’ll Do: Keep the CEO’s schedule running smoothly, balancing priorities with foresight and care. Draft, manage, and triage communications on behalf of the CEO, including monitoring the inbox, prioritizing critical issues, and ensuring messages are clear, timely, and aligned with our values. Coordinate travel with attention to detail. Support the Senior Business Operations Manager with logistics, materials, and follow-ups for board meetings, leadership sessions, and offsites (scheduling, pre-reads, deck formatting, AV/Zoom, notes, and action tracking), ensuring smooth execution of these high-priority events. Prepare and distribute briefing notes, agendas, and pre-reads for key meetings (CEO external conversations with customers, partners, investors, as well as people-related leadership sessions such as promotions or compensation). Anticipate needs and solve problems before they come up. Executive Team & Business Support Partner with other leaders when scheduling, planning, or logistics support is needed. Manage complex calendars and scheduling for the CEO, CPO, and COO, balancing one-on-ones, leadership meetings, sensitive employee-related discussions, and external networking. Work across teams to keep high-priority initiatives moving forward. Use tools like Outlook, Slack, and project trackers to keep communication flowing and details organized. Culture & Internal Engagement Play a central role in bringing our culture to life by planning and executing company-wide events and leadership gatherings. Represent the executive team in a way that reflects our values and builds trust. Embody and reinforce our values of humility, bravery, and ubuntu in every interaction. What We’re Looking For: Experience supporting a CEO or senior executive in a fast-paced, high-growth environment. Exceptional organizational skills and the ability to juggle multiple priorities without dropping the ball. Strong written and verbal communication skills and confidence drafting polished, thoughtful messages. Comfort with modern productivity tools and a willingness to learn new systems quickly. Integrity and discretion in handling confidential information. Flexibility and adaptability when priorities shift. A proactive, detail-oriented mindset that keeps you one step ahead. A collaborative spirit — you enjoy building relationships and being a trusted partner to leaders and teammates. Who We Are: Hi Marley has three core values that are the foundation of our company culture, which every employee embodies: Max Courage - we encourage our team, our customers, and their customers to dream big, try new ideas and maximize impact by measuring risk. Be Humble – we lead with appreciation and promote a culture of humility, compassion and openness to learn from anyone, anywhere. Ubuntu “I am because we are” - we believe true success is much bigger than any single individual or company. By aligning our individual aims behind a shared purpose we can achieve our fullest potential, together. Benefits and Perks: Full benefits package for employees working 30+ hours per week, including parental leave, a matching 401k program, and medical, dental, vision, disability, and life insurance. Open vacation policy - we all work hard and take time for ourselves when we need it Competitive salary and generous stock options - we all get to own a piece of what we’re building A fun, lively startup culture Core values-based leadership A culture of employee engagement, diversity and inclusion Ample opportunities to learn and take on new responsibilities in a fast-paced, growth-mode startup Hi Marley is proud to be an equal employment opportunity employer. We celebrate diversity and do not discriminate based on gender, sexual orientation, gender identity, religion, race, veteran status, disability status, or any other characteristic protected by applicable law. We are committed to building an inclusive work environment representing a variety of backgrounds, perspectives, and skills, where all employees are encouraged to be their authentic selves. Hi Marley participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. #J-18808-Ljbffr