Diagram is a venture builder that conceives and launches technology companies in the financial services, insurance, and health industries. We've designed a unique platform for entrepreneurs who have a proven track-record or domain expertise to start their next business by combining access to venture capital investment, hands-on support, and access to a vast network of partners and incumbents. Since 2016, Diagram has raised over $250M and launched fifteen new companies across North America. Our ecosystem is home to 90+ angel investors, including 45+ entrepreneurs with >$15B in exits and an extended global network of corporate partners, investors, and builders.

We are looking for an up-and-coming high-performer to become Chief of Staff to our Partner & COO and be his right-hand. The Partner & COO leads our Investment team (post-seed and external investments) and our Venture Advisory team (finance, legal, talent, communications) which advises our portfolio companies and drives the operations of Diagram. He also supports our CEO in strategic planning and execution to achieve the firm's objectives while leading corporate development activities and the development of Diagram's ecosystem of LPs, co-investors, partners and advisors.

This Chief of Staff role is a multidisciplinary one crafted to supercharge both teams by supporting world-class operations with both internal (Diagram, Sagard) and external (Founders, Investors, Advisors) stakeholders. This role will encompass all teams of Diagram and provide the candidate with a diverse opportunity to gain deep experience in startups and the venture capital industry while balancing strategy and hands-on execution.

The role is Montreal-based with a hybrid work model with a start date expected by early October. All candidates will be considered on a rolling basis.

You’ll be responsible for:

  • Grow the capacity of Partner & COO to multiply impact and act as deputy as needed;
  • Quarterbacking strategic and/or operational initiatives with Partner & COO sponsorship;
  • Prepare, attend, and follow-up on meetings with internal and external stakeholders;
  • Support Partner & COO in leading his teams efficiently and encouraging collaboration across Diagram; 
  • Draft and quarterback key presentations that Partner & COO needs to deliver or financial analysis to be done in the context of Diagram’s strategy or portfolio management;
  • Drive the portfolio company CEO onboarding process and become main point of contact going forward while keeping track of all ongoing workstreams between our teams and portfolio company founders;
  • Support Partner & COO in managing portfolio by monitoring key metrics, returns, board meetings notes, key developments, and identifying relevant publications/conferences;
  • Help drive investor and internal/external stakeholder relations.

You should reach out if you have:

  • 2 to 4 years in a high impact environment like investment banking, private equity, management consulting, or startup operations (exposure to venture capital or investments an asset);
  • Strong organizational skills and work ethic with ability to run multiple time-sensitive matters;
  • Self-starter and keen teammate with strong interpersonal and communication skills;
  • Thrives in a work environment where autonomy and resourcefulness are essential;
  • Professionalism, integrity, confidentiality and discretion;
  • Proficiency in English and French, both written and spoken.

You will be offered:

  • An outstanding opportunity to contribute and be part of something big, meaningful, and different;
  • A role that will allow you to push yourself and have ownership with potential for outsized career growth;
  • A competitive compensation package, benefits, and long term incentive plan;
  • An ambitious and encouraging team that will help you grow, and provide a dynamic experience;
  • An exceptional experience and key role in the venture capital and startup industries.


Applying at Diagram

Diagram is an equal opportunity employer.  We appreciate your interest in working with us; however, only those applicants selected for interviews will be contacted. Diagram’s Ecosystem team may reach out to you about other possible opportunities you may be a fit for. We launch five new ventures each year in the FinTech, Health, and Insurance space and are continually excited to talk to founders and top talent who want to join us.

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