{"id":3461871,"url":"https://alion.io/job/d2l-executive-assistant","title":"Executive Assistant","company":{"id":3408,"name":"D2L","domain":"d2l.com","url":"https://alion.io/company/d2l","size_band":"1001-5000","is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Greenhouse","truth_index":{"grade":"B","score":84,"open_postings":7,"ghost_share":0,"stale_share":0.857,"repost_share":0,"time_to_fill_p50_days":16,"computed_at":"2026-10-31T05:58:55Z"}},"role":"Administrative","role_family":"Administrative","seniority":"middle","employment_type":null,"work_mode":"on_site","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["Kitchener, Canada","Winnipeg, Canada"],"countries":["CA"],"hiring_countries":[],"hiring_countries_total":0,"salary":null,"salary_estimate":{"min_usd":36000,"max_usd":57000,"period":"year","method":"role_seniority_country_remote_cell","sample_n":264},"experience_years_min":3,"visa_sponsorship":false,"relocation_package":false,"has_equity":true,"technologies":[{"name":"ChatGPT","optional":false}],"status":"live","first_seen_at":"2026-06-16T21:18:00Z","employer_posted_date":"2026-10-29","last_verified_at":"2026-10-31T08:56:54Z","board_verified":true,"closed_at":null,"days_open":136,"trust":{"level":"stale","repost_count":0,"flags":["stale"],"days_open":136},"description":"D2L is a cloud company that is modernizing education and building the Future of Work. The old models of teaching and learning are in the midst of the largest transformation in history, and D2L is at the heart of that fundamental shift. \nNew models of teaching and learning enable a personalized, student-centric experience - and deliver improved retention, engagement, satisfaction, and results for learners of all ages - in schools, campuses, and companies.\nD2L is disrupting the way the world learns, by providing the next generation learning environment and solutions to engage and inspire learners. And most importantly, by giving customers a platform that is easy, flexible, and smart. No other company provides a solution as robust and innovative as D2L.\nD2L has had a singular mission for 25 years and is dedicated to that same mission in the years ahead: to transform the way the world learns - and by doing so, we will help improve human potential globally.\nEvery application we receive is personally reviewed by a member of our Talent Acquisition team - yes, a real person looks at your resume! While we use AI tools internally to streamline tasks like meeting notes, summaries, and administrative work, these tools never rank resumes, make hiring decisions, or influence candidate evaluations.\nABOUT THIS ROLE:\nD2L is looking for an ambitious, highly organized, and exceptionally thoughtful Executive Assistant to support our Chief Product Officer and Chief Technology Officer. \nThis is more than a traditional administrative role. You will help two senior leaders operate effectively as partners, protect their time and attention, strengthen the quality of their leadership routines, and ensure important work moves forward. You will be trusted to exercise sound judgment, anticipate needs, improve how the offices of the CPO and CTO operate, and bring clarity and follow-through to a fast-moving environment. \nYou will report to the CPO and work closely with the CTO, their leadership teams, and partners across the broader D2L organization. \nThis role is based in either Kitchener or Winnipeg, with an expectation of working from the office at least three days per week. \nHOW YOU'LL MAKE AN IMPACT:\nEnable effective executive leadership \nManage integrated calendars for the CPO and CTO, balancing competing priorities, protecting time for strategic work, and ensuring both leaders are well prepared for the commitments that matter most. \nMake routine prioritization and scheduling decisions independently within established guardrails, escalating exceptional conflicts or sensitive matters as appropriate. \nExercise judgment and appropriate authority to challenge low-value meetings, ensure the right people are involved, and improve meeting quality. \nCoordinate meeting agendas, pre-reads, decisions, actions, and follow-through for the CPO, CTO, and joint leadership forums. \nPrepare concise executive meeting briefs that clarify the purpose, context, participants, desired decisions, and required preparation. \nManage incoming requests and information flow for the CPO and CTO, using sound judgment to triage, draft responses, escalate urgent matters, and ensure important commitments are not lost. \nMaintain visibility into key executive commitments and surface unresolved decisions, risks, or follow-up items before they become issues. \nSupport continuity when either executive is unavailable by ensuring delegation paths, decisions, and communications are clear. \nProvide limited coordination support to the Product and TED leadership teams. \nSupport travel coordination and expense management as needed. \nCoordinate and track budget-related administrative activities, including spending commitments, expense approvals, and inputs for budget reviews, in partnership with FP&A. \nStrengthen executive communication and readiness \nDraft, edit, and shape executive communications, leadership updates, presentations, talking points, and other materials. \nCoordinate the development of executive-team and Board materials, including gathering inputs, managing timelines, improving clarity, and ensuring materials are ready for review. \nHelp create clear, consistent narratives across Product and TED, while working with the appropriate functional leaders to validate content and decisions. \nHandle sensitive information with a high degree of discretion, professionalism, and sound judgment. \nPartner across Product and TED \nPartner with Product Operations and other functional leaders to support effective executive participation in planning, review, and leadership routines. \nBuild strong working relationships across functions and help remove friction at the executive level. \nPlan and deliver effective leadership offsites, events, team sessions, and other high-impact internal engagements. \nSupport priority leadership hiring, onboarding, and organization-transition activities as needed. \nImprove how the executive offices work \nIdentify practical opportunities to improve executive workflows, information flow, meeting practices, and communication. \nUse approved AI tools, including ChatGPT and Rovo, to improve preparation, drafting, meeting synthesis, research, action tracking, and other executive workflows. \nHelp the CPO and CTO adopt practical and responsible AI-enabled ways of working, with appropriate attention to confidentiality, accuracy, security, and human review. \nBring curiosity, initiative, and a continuous-improvement mindset to the role. \nWhat you will bring:\nAt least three years of experience supporting senior leaders in an Executive Assistant, executive coordination, or comparable high-trust role within a fast-paced organization. \nExcellent written communication skills and the ability to turn incomplete inputs into clear, concise, well-structured materials. \nStrong organizational discipline, attention to detail, and the ability to manage multiple priorities without losing sight of what matters most. \nExceptional judgment, discretion, and the confidence to respectfully push back, ask clarifying questions, and protect executive capacity. \nA proactive mindset: you anticipate needs, spot gaps, and bring forward solutions rather than waiting for direction. \nStrong relationship-building skills and comfort working with leaders across technical and non-technical functions. \nConfidence using modern productivity tools and practical experience using AI tools to improve the quality and speed of work. \nComfort operating amid ambiguity and changing priorities, with a calm and reliable approach. \nWhat success looks like:\nThe CPO and CTO have more time and attention for the work where they can have the greatest impact. \nTheir leadership routines are prepared, focused, and decision-oriented. \nImportant commitments, communications, and follow-up actions do not get lost. \nProduct Operations and other functional partners experience the role as a strong executive partner. \nLeadership teams receive timely, clear support and have confidence in the quality of executive preparation and communication. \nThe CPO and CTO are making effective use of approved AI tools to reduce administrative burden and improve decision readiness.\nThis position is to fill an existing vacancy.\nThe expected base salary range for a new hire in this role is listed below. The annualized base salary offered is determined by each candidate’s relevant knowledge, skills, education, training and experience. It is aligned to ensure both internal and external competitiveness using market data for the geographic location and industry. As part of the total compensation at D2L the role may be eligible for additional benefits including a Wellness Subsidy, Equity Grants, Variable Incentive, and more.\nBase Salary Range\n$75,000—$85,000 CAD\nDon’t meet every single requirement? We strongly encourage you to still apply! At D2L, we are committed to creating a diverse and inclusive environment. We encourage your application even if you don't believe you meet every single qualification outlined, because we love to help our people grow and develop!\nWhy we're awesome:\n\nAt D2L, we are dedicated to providing you with the tools to do the best work of your life. While some of our perks and benefits may vary depending on location or employment type, we are proud to provide employees with the following through #LifeAtD2L:\nImpactful work transforming the way the world learns\nFlexible work arrangements\nLearning and Growth opportunities\nTuition reimbursement of up to $4,000 CAD for continuing education through our SkillsWave Program\n2 Paid Days off for SkillsWave-related activities like exams or final assignments\nEmployee wellbeing (Access to mental health services, EFAP program, financial planning and more)\nRetirement planning\n2 Paid Volunteer Days\nCompetitive Benefits Package\nHome Internet Reimbursements\nEmployee Referral Program\nWellness Reimbursement\nEmployee Recognition\nSocial Events\nDog Friendly Offices Spaces at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne offices.","description_format":"text","description_chars":9010,"description_truncated":false,"requirements":{"experience_years_min":3,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":["Equity","Flexible schedule","Growth opportunities","Internet reimbursement","Pet friendly","Retirement plans"],"hiring_locations":[],"hiring_excludes":[],"relocation_offered":false,"industries":["EdTech Platforms"],"lifecycle":[{"event":"open","at":"2026-10-29T14:10:09Z"}],"visa":[],"liveness":{"score":6,"band":"cold","label":"Long shot","p_open":1,"p_active":0.199,"p_room":0.28,"age_days":136,"expected_fill_days":16,"reasons":["conf:0","velocity","win:tail","crowd:"],"computed_at":"2026-10-31T05:58:55Z"},"pay":null,"html_url":"https://alion.io/job/d2l-executive-assistant","json_url":"https://alion.io/job/d2l-executive-assistant.json","meta":{"generated_at":"2026-10-31T11:19:33Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":17360,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-11-01T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":3408},"rest":"https://alion.io/mcp/rest/get_company?id=3408"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fd2l-executive-assistant"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fd2l-executive-assistant"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fd2l-executive-assistant"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/d2l-executive-assistant\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fd2l-executive-assistant"}],"agent":{"mcp":"https://alion.io/mcp/jobs","mcp_open":"https://alion.io/mcp/open","next":[{"tool":"get_job","arguments":{"id":3461871}},{"tool":"search_jobs","arguments":{"company":"d2l.com","detail":"compact"}},{"tool":"match_people","arguments":{"job_id":3461871},"note":"people open to offers who fit this vacancy"}],"note":"The same data through MCP tools: https://alion.io/mcp/open needs no sign-in (compact searches, postings, people); https://alion.io/mcp with an Alion account has everything. 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