Executive Assistant

Job Description This is a remote position. About EntrepreNorth EntrepreNorth is a Northern and Indigenous-led organization that empowers Indigenous entrepreneurs to build sustainable businesses and livelihoods across the Northwest Territories, Nunavut, and the Yukon. We believe entrepreneurship is a powerful tool for self-determination, economic justice, and community wellbeing. Through culturally rooted business education, access to relational capital, storytelling, and ecosystem-building, we support entrepreneurs at every stage of their journey. Our work spans a growing suite of offerings for entrepreneurs: programming, eLearning, the Sinew Impact Fund, a podcast and films, a Policy Circle, and Northern events. We are a small, passionate team committed to decolonizing business education and supports, and we are scaling. The Opportunity This is a high-trust, high-responsibility role that sits at the operational centre of EntrepreNorth’s leadership team. The Executive Assistant will primarily support Xina Cowan, CEO (approximately 70% of the role) and Kristin Richard, Co-founder and Managing Director of the Sinew Impact Fund (approximately 30%). The ideal candidate brings significant EA experience, strong organizational instincts, and a genuine understanding of the relational and cultural dynamics of Indigenous-led organizations. This is not a traditional administrative role. It requires someone who can hold confidential information with care, anticipate leadership needs, and move fluidly between day-to-day operations and high-stakes communications. CEO Support (70%) Board Governance Prepare, compile, and distribute board packages and supporting materials Coordinate board and committee meeting logistics, including scheduling and platform setup Take accurate meeting minutes and distribute in a timely manner Maintain governance records, resolutions, and board documentation Coordinate board member per diems, travel, and logistics Funder Relations and Reporting Draft and coordinate funder reports across multiple funding relationships Manage a reporting calendar to track submission deadlines and lead times. Support grant tracking, acknowledgment correspondence, and funder communications Compile supporting data, appendices, and narratives for grant applications and reports Calendar and Scheduling Manage the CEO’s calendar with strategic prioritization, protecting time for leadership Schedule and coordinate internal and external meetings across time zones and territories Set proactive reminders for deadlines, contract renewals, and follow-up sequences Communications Management Triage and manage the CEO’s general email inbox, flagging what needs attention and handling routine inquiries Draft correspondence, briefing notes, and talking points on behalf of the CEO Prepare pre-meeting briefing notes: who you’re meeting, their background, and what is needed from them Handle general stakeholder inquiries with professionalism and cultural sensitivity Travel Coordination Manage end-to-end travel logistics: flights, accommodation, and ground transportation Navigate Northern travel complexities including limited carriers, connection logistics, and remote community access Build detailed travel itineraries that include meeting context, materials needed, and buffer time Handle last-minute changes, rebooking, and cancellations in real time Track receipts and prepare expense reports for sign-off following each trip Event and Convening Support Coordinate logistics for EntrepreNorth funder convenings and external speaking engagements Set up and manage event registration platforms; handle RSVPs and attendee communications Build run-of-show documents and briefing notes for day-of execution. Liaise with venues, caterers, A/V providers, and other vendors Prepare speaker prep materials and post-event follow-up communications Internal Operations Prepare presentations and supporting materials for leadership and external engagements Track action items and follow-ups from leadership and team meetings. Maintain an organized, well-labelled shared file system across Google Workspace Sinew Impact Fund Support (30%) Investment Operations Assist with scheduling Investment Committee (IC) meetings and preparing IC packages and supporting materials Take and distribute IC meeting minutes; maintain IC governance records and decision logs Coordinate fund-related correspondence and track follow-up items Stakeholder Coordination Support scheduling and communications with investors, investees, and ecosystem partners Support Indigenous Policy Circle coordination, including event registration, attendee communications, and session logistics Assist with event logistics for Sinew-related investor convenings and fund activations Administrative and Research Support Support document preparation, light research tasks, and presentation materials for the Managing Director Complete data entry in Zoho CRM and pull standard operational reports for leadership review Assist with drafting investor update emails, quarterly investor reports, and funder correspondence for MD review Who You Are You bring calm, capable energy to a fast-moving, high-trust environment. You anticipate what leadership needs before being asked, and you hold confidential and sensitive information — governance, investment, and organizational — with discretion and integrity. You move comfortably between structured, recurring processes and the unpredictability of last-minute changes, without losing your composure or your attention to detail. You bring genuine cultural awareness and relational sensitivity to your work, understanding how you support this team is as important as what you get done. You're a clear, professional communicator who can represent leadership well in every interaction, and a natural organizer who brings order to competing priorities across multiple leaders. Requirements Required 5+ years of experience as an Executive Assistant, Senior Administrative, or comparable leadership-support capacity Demonstrated ability to manage competing priorities across multiple leaders in a fast-paced, mission-driven environment Strong written communication skills, including experience drafting professional correspondence, board materials, and funder reports Proficiency in Google Workspace (Docs, Sheets, Slides, Calendar, Gmail) and video conferencing platforms High degree of discretion, integrity, and confidentiality — this role involves sensitive investment, governance, and organizational information Self-directed with strong follow-through and exceptional attention to detail Assets Assets Indigenous identity (First Nations, Métis, or Inuit); preference will be given to Indigenous applicants Experience working in Northern Canada or with Northern Indigenous communities and organizations Familiarity with non-profit governance, board processes, and funder reporting requirements Experience in impact investing, financial services, or Indigenous economic development contexts Experience coordinating executive travel in remote or Northern geographies, including limited-carrier logistics Familiarity with CRM systems (Zoho preferred) and financial software (Sage Intacct) Benefits Competitive base salary: $70,000 - $85,000 Comprehensive employer-paid extended health, vision, and dental benefits package starting on your first day of employment Annual Retirement Savings contribution $1,500 annual professional development budget 3 weeks of paid vacation 10 sick and personal days Winter office closure and Summer schedule Flexible, remote-first work environment Travel to the territories, connecting directly with the communities and entrepreneurs we serve A dynamic, inclusive team culture that fosters innovation and creativity