Senior Executive Assistant at Digible (Remote)

ABOUT THE ROLE We’re looking for an exceptional Executive Assistant to support our CEO and CFO—someone who combines outstanding executive support with a highly modern, AI-native approach to getting work done. At its core, this is an Executive Assistant role. You’ll own the fundamentals exceptionally well: calendars, meetings, travel, communications, preparation, follow-ups, and day-to-day executive coordination. What makes this role different is how you do that work. Our company operates with an increasingly AI-native technology ecosystem. Many of the tools we use to communicate, meet, document, plan, and collaborate already incorporate AI, and that ecosystem will continue to evolve. We’re looking for someone who becomes exceptionally fluent in that environment—someone who understands how information moves between tools and uses AI, automation, and thoughtful workflows to create a seamless operating environment around our CEO and CFO. The goal isn't to add more process or more tools. It's to make sure the right information gets to the right executive, in the right format, at the right time—with as little friction as possible. WHAT YOU’LL OWN EXECUTIVE SUPPORT & CALENDAR MANAGEMENT * Own complex calendar management for the CEO and CFO, ensuring their schedules reflect their priorities. * Manage and triage executive email and Slack communications, helping prioritize messages, surface time-sensitive items, and ensure important requests receive timely follow-up. * Draft and send routine communications on behalf of executives, as appropriate, while exercising strong judgment around tone, context, and confidentiality. * Coordinate internal and external meetings across employees, customers, partners, investors, and other stakeholders. * Proactively identify and resolve scheduling conflicts. * Protect focus time and create appropriate buffers around high-priority meetings and commitments. * Coordinate travel, itineraries, reservations, and related logistics. * Manage recurring executive routines and administrative responsibilities. * Handle highly confidential information with exceptional discretion and judgment. MEETING PREPARATION & FOLLOW-THROUGH You'll make it easy for the CEO and CFO to walk into meetings prepared and walk away knowing exactly what happens next. * Own and maintain the annual ELT meeting calendar, proactively planning around key business cycles, company priorities, and other major events so the team can plan ahead. * Coordinate all logistics for in-person ELT meetings, including travel considerations, meeting space, meals, team dinners, reservations, and other on-site needs. * Partner with the CEO and ELT to ensure upcoming meetings and planning cycles are anticipated well in advance, with appropriate time, materials, and logistics accounted for. * Ensure meetings have the appropriate agendas, materials, attendees, and context. * Organize agendas, pre-reads, recurring meeting documentation, and supporting information. * Leverage AI-enabled meeting and productivity tools to capture notes, decisions, important context, and action items. * Ensure relevant meeting outputs are documented and accessible without requiring executives to manually organize them. * Surface follow-ups and reminders when executive attention or action is required. * Maintain continuity between recurring meetings so executives aren't rebuilding context each time. AI-NATIVE EXECUTIVE WORKFLOW This is a defining part of the role. We don't need someone who simply knows how to use an AI chatbot. We want someone who understands how to work in an environment where AI is increasingly embedded across the technology stack. You'll become a power user of the tools we use today while remaining curious and adaptable as those tools change. You'll understand how information moves across meetings, communications, documents, calendars, email, project systems, and other sources—and help connect those pieces into a cohesive executive workflow. You will: * Become highly fluent in our existing AI-enabled tools and internal systems. * Use AI capabilities within those platforms to summarize, organize, retrieve, connect, and surface information. * Connect information across systems so executives aren't manually piecing together context. * Reduce unnecessary searching, copying, summarizing, and context-switching. * Build repeatable templates, workflows, and lightweight automations for common executive activities. * Recognize when an existing tool or AI capability can eliminate a manual process. * Continuously explore new capabilities within our technology ecosystem and determine where they can meaningfully improve executive productivity. * Adapt as our technology stack evolves rather than becoming dependent on a particular set of tools. * Apply excellent judgment around confidentiality, accuracy, permissions, and when AI-generated information requires human review. The goal is simple: Our executives shouldn't have to be the integration layer between all of the information, conversations, and systems surrounding them. COMMUNICATION & INFORMATION ORGANIZATION * Draft and refine emails, messages, agendas, and other executive communications. * Organize information so the CEO and CFO can quickly understand what they need to know. * Turn meetings, conversations, documents, and other inputs into concise summaries when appropriate. * Maintain organized executive documentation and reference materials. * Help ensure important information is easy to retrieve rather than buried across multiple systems. * Route information appropriately and help reduce unnecessary noise for the executives. EXECUTIVE COORDINATION * Serve as a highly reliable point of coordination for people working with the CEO and CFO. * Coordinate logistics and information for leadership meetings, board meetings, investor meetings, company events, and other important executive interactions. * Maintain recurring executive cadences and ensure materials are prepared in advance. * Track requests made directly to the executive office and ensure the CEO or CFO has visibility when needed. * Build strong working relationships across the organization so executive coordination feels seamless. WHAT WE'RE LOOKING FOR You're likely a strong fit if you: * Have experience supporting senior executives in a fast-moving organization. * Are exceptionally organized and detail-oriented. * Have excellent written and verbal communication skills. * Exercise strong judgment and discretion. * Are comfortable managing competing priorities and frequent changes. * Anticipate needs rather than waiting to be told what to do. * Can interact confidently and professionally with employees, customers, partners, investors, and senior leaders. * Enjoy creating systems and improving the way work gets done. * Learn new technology quickly and genuinely enjoy becoming a power user. * Are comfortable experimenting with AI capabilities and figuring out where they are—and aren't—useful. * Can look across multiple systems and understand how information should flow between them. * Are energized by a technology environment that will look different 12 months from now than it does today. You don't need to be technical in the traditional sense. You don't need to code or build AI models. But you should be technologically fearless, naturally curious, and unusually good at figuring out how tools can work together. WHAT GREAT LOOKS LIKE After 6–12 months: * The CEO and CFO spend significantly less time coordinating, searching for information, and handling administrative logistics. * Their calendars are thoughtfully managed and reflect their priorities. * Meetings consistently have the right preparation and context. * Meeting notes, decisions, and relevant follow-ups are captured without requiring significant executive effort. * Information moves effectively across the company's tools and systems. * The CEO and CFO can quickly access the context they need without digging through multiple places. * You've developed repeatable workflows that make executive support faster and more consistent. * You've identified and eliminated unnecessary manual work through AI, automation, or better use of existing technology. * You've become a trusted expert in how the CEO and CFO work and how our evolving technology ecosystem can best support them. * The executives trust that the details are handled, the information is organized, and they'll be surfaced when something requires their attention. THE KIND OF PERSON WHO WILL THRIVE HERE You're exceptionally reliable and highly organized, but you're not stuck in traditional ways of working. You see a messy workflow and want to clean it up. You see someone manually moving information between systems and wonder if there's a better way. You discover a new capability in a tool and immediately start thinking about where it could save time or eliminate friction. You're comfortable saying, “I'll figure it out.” And you understand that the best Executive Assistants don't simply manage an executive's calendar. THEY CREATE AN ENVIRONMENT WHERE THE EXECUTIVE CAN OPERATE AT THEIR BEST. PAY RANGE FOR POSITION: $85,000 - $100,000 HEADS UP! WE BELIEVE IN TRANSPARENCY THROUGHOUT OUR HIRING PROCESS. TO HELP US ENSURE A GREAT FIT, WE'LL ASK YOU TO SHARE A FEW PROFESSIONAL REFERENCES DURING THE HIRING PROCESS WHO CAN SPEAK TO YOUR EXPERIENCE AND SKILLS. IT’S ALL PART OF OUR COMMITMENT TO OPEN, HONEST COMMUNICATION AND OUR CORE VALUES: FOCUS, AUTHENTICITY, HUMILITY, CURIOSITY, AND HAPPINESS.

Senior Executive Assistant

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