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.

• 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.

• 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.

• 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.

• 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.

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…