Chief of Staff to the CEO

Who we are: 

Diagram is a venture builder that conceives and launches companies in Fintech, Insuretech, Web3, and ClimateTech. We've designed a unique platform for entrepreneurs who have a proven track-record and 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 $320M and launched 22 new companies across North America. Our ecosystem is home to 200+ angel investors, including 60+ entrepreneurs with >$15B in exits and an extended global network of corporate partners, investors, and builders. 

Summary of the role: 

Diagram is looking for a new Chief of Staff to our CEO to be their right-hand. This person will work closely with the CEO and Partner group, leading several strategic and operational projects across Diagram, as well as provide leverage to the CEO and Partner group. This role will work with every team within Diagram, and provide the candidate with an opportunity to gain deep experience in startups and the venture capital industry while balancing strategy and hands-on execution. 

This is a 18-24 month growth role at the heart of the organization, collaborating closely with the senior executive team. You will have a unique vantage point to experience very diverse types of work, tackle challenges core to the business and help shape the future of Diagram. After your mandate, we expect that you will transition into another role within Diagram or our broader ecosystem (i.e., Sagard, Portage, our portfolio companies), in line with your interests and the business needs. 

You’ll be responsible for: 

● Providing day-to-day support and leverage to the CEO, and grow their capacity to multiply impact and act as deputy as needed 

● Quarterbacking several initiatives under CEO sponsorship at any given time

● Drafting and quarterbacking key presentations and financial analysis that CEO needs to deliver

● Supporting and quarterbacking Diagram fundraising in future funds, and supporting investor and internal/external stakeholder relations 

● Acting as a thought partner to the leadership team, and suggesting improvements / supporting Diagram scaling efforts 

● Leading key meetings, and ensuring follow up on action items with internal and external stakeholders 

● Maintaining & improving the Chief of Staff system, and sharing best practices with others at Sagard and Portage 

You will thrive in this role if you: 

● Enjoy being in a very fast-paced environment, appreciate diversity in your work (no two days are the same!), and approach new challenges with a can-do attitude 

● Are very proactive, organized, and detail-oriented, with an ability to anticipate needs/challenges and act on them accordingly

● Are comfortable with ambiguity and have strong business judgment - you’ll be empowered to problem-solve with little guidance 

● Work effectively under pressure and are at ease managing multiple time-sensitive matters with shifting priorities 

● Have a proven track record of over-performance in prior positions 

● Enjoy being stretched outside your comfort zone and are a fast learner 

At a minimum, we’re looking for you to have: 

● Undergraduate degree 

● 3-5 years in a high impact environment like management consulting, business strategy, corporate development, venture capital, private equity, or startup operations (exposure to venture capital an asset);

● Strong organizational skills and work ethic with ability to run multiple time-sensitive matters;

● Excellent written and oral communication skills in both English and French 

● Be based in Montreal and open to a hybrid work model 

What you'll get from us: 

● Work at the heart of the organization alongside the CEO and leadership team, and have an impact on a thriving company 

● Be part of a team of hard-working, ambitious and caring individuals that will help you learn & grow

● Competitive compensation, benefits and Long-Term Incentive Plan (LTIP) that will provide you with an economic interest in each new company co-founded by Diagram 

● A fully-funded group insurance program which includes a health spending account, an employee assistance program and access to Dialogue telemedicine services 

● A beautiful historic location at the heart of Downtown Montreal, with a fully stocked kitchen

● A role that will allow you to push yourself and with potential for outsized career growth

● Fun traditions – We have roasts, team lunches, fun games, quarterly offsites, team outings, and many more fun activities. 

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 several new ventures each year in the Fintech, Insuretech, Web3, and ClimateTech space and are continually excited to talk to founders and top talent who want to join us