Executive Assistant to the CEO

4 weeks ago


Old Toronto, Canada DealMaker Full time

About This Role

We are seeking a highly skilled and experienced individual to serve as the Chief of Staff to our CEO. As a key member of our executive team, you will be responsible for managing priorities, removing bottlenecks, and overseeing cross-functional projects. With a focus on adaptability and proactive problem-solving, you will handle urgent needs, drive complex projects, and cultivate strong partnerships, freeing the CEO's time for visionary focus and empowering the organization to meet its strategic goals.

Your Responsibilities

  1. Manage priorities and remove bottlenecks to free up the CEO's time for strategic focus, handling both high-level strategy and daily tasks.
  2. Assist with fundraising efforts by preparing materials, managing investor relationships, and ensuring smooth due diligence processes to support financial growth.
  3. Analyze market trends and competitive threats to provide actionable insights that help shape strategic decision-making and maintain a competitive edge.
  4. Act as the key contact for investors, partners, and advisors, building strong relationships to support investment and strategic initiatives.
  5. Tackle urgent tasks or issues, ensuring efficient progress on the CEO's priorities and organizational objectives through adaptability and ownership.
  6. Manage complex, cross-functional projects in the business, from inception to execution, ensuring timely delivery and adherence to objectives.

What We Are Looking For

  1. Demonstrated experience in supporting C-Level executives in startups, tech, venture capital, consulting, or finance, with a deep understanding of high-growth business environments.
  2. Strong ability to analyze data, draw insights, and communicate findings clearly in both written and verbal formats.
  3. Proven experience in high-growth startups, particularly in navigating funding rounds from Seed or Series A to Series C/D.
  4. Experience in managing complex, cross-functional projects, with the ability to prioritize and handle multiple tasks efficiently.
  5. Ability to thrive in fast-paced, ambiguous environments, demonstrating flexibility and a proactive, hands-on approach to problem-solving.
  6. High level of integrity and professionalism, with the capacity to handle confidential information discreetly.
  7. Comfortable adjusting to shifting priorities and always willing to roll up your sleeves to ensure tasks are completed effectively.
  8. Nice to have: Master's Degree in Business or any other principle.

About Us

Founded in 2018 by leading capital markets lawyers, DealMaker has blazed its own trail as the leading online capital-raising platform. As a Series A tech startup, we are well-capitalized, firmly established in our market, and ready to scale. We offer a competitive compensation package with the opportunity to earn equity, a diverse & distributed team of doers, innovators, and experts, and a shared employee benefit plan (medical, vision, & dental). We also offer strong autonomy with support from leadership and annual learning support.



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