Executive Assistant

Lendesk

  • Windsor, ON
  • $68,500-103,000 per year
  • Permanent
  • Full-time
  • 5 hours ago
Executive AssistantAbout Lendesk
We’re a financial technology company on a mission to help people feel confident in their mortgage decision and deliver a seamless experience. Our flagship product is an advanced digital mortgage origination platform that connects borrowers, brokers, and lenders. We’re a fast-growing team of 70+ employees, composed of innovative and engaged individuals working collaboratively to deliver a unique digital home buying experience. We’re also a remote-first company with team members across Canada.At Lendesk, diversity is our strength. What makes us different, makes us stronger. We believe that a variety of backgrounds, cultures, beliefs, experiences, identities, and voices make for a better and inclusive workplaceThe RoleWe are looking for an Executive Assistant to the President and COO. This is a high-trust, high-impact Executive Operations role designed to increase leadership capacity and organizational clarity. This role exists to protect focus, increase decision velocity, and ensure follow-through at the highest level of the company.This individual operates as a force multiplier — bringing structure to ambiguity, converting discussions into decisions, and decisions into execution. While the core of the role is operational excellence, strong written communication skills are a meaningful advantage, enabling the amplification and sharpening of leadership messaging internally and externally.This role contributes directly to company performance by improving executive effectiveness, alignment, and execution quality.What you’ll be doing:
  • Own executive operations including calendar, travel, logistics, and expense management with precision and proactive foresight
  • Increase decision velocity by organizing information into concise, structured summaries (context → decision → recommendation)
  • Attend key meetings to capture decisions, identify action items, and ensure clear ownership and follow-through
  • Prepare structured daily and weekly briefs that clarify priorities, risks, decisions, and tradeoff
  • Anticipate friction points and design simple systems to reduce noise and inefficiency
  • Support strategic communications by drafting internal memos, summarizing key insights, and refining written content.
  • Ability to cover all Canadian time zones. Our executives are based in both PST and MST.
What you’ll bring to the team:Must have:
  • 5+ years experience supporting a senior executive in a fast-paced environment
  • Demonstrated ability to operate with high discretion and sound judgment
  • Exceptional organizational skills and proactive time management
  • Strong structured thinking and ability to synthesize information clearly
  • High agency with the ability to anticipate needs and solve problems independently
  • Strong attention to detail
Nice-to-Have
  • Experience in executive operations, business operations, or Chief of Staff–adjacent roles
  • Strong writing ability with experience drafting executive communications
  • Experience working in a high-growth technology or financial services company
  • Comfort participating in strategic discussions and distilling insights into clear summaries
  • Familiarity with productivity and project management systems that drive accountability and follow-through
You must be a current Canadian resident to be considered for this role. A candidate selected for this position must pass a criminal background check.Lendesk is committed to offering competitive salaries to all our team members. This role has a salary range of $68,500-$103,000. For experienced candidates, we typically hire near the midpoint of the salary band to ensure that there is room for growth and development. Compensation is determined based on the skills experience, and qualifications you bring to the team, as well as the impact you will have on the business and the growth you'll achieve in the role. Throughout your time at Lendesk, we'll continue to have conversations about your career and development and you'll have the opportunity to build an amazing career with us.

Lendesk