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Chief of Staff

Strategy - Toronto

Reporting to our CEO, we are looking for a Chief of Staff to join our team. As a critical partner to the CEO, you will work with senior leadership to lead quarterly and long-term business planning, work with the CEO to manage fundraising, oversee internal company communications, and manage special projects (including product and business unit expansion). This role is expected to be a “tour of duty”, where you’ll be deeply immersed in the leadership team for 12-18 months and later transition to work within the business - this could mean anything from joining an existing team in a high impact role, to helping launch and scale a new business unit that you built the go-to-market strategy for while acting as Chief of Staff. 

About Properly:

At Properly, we are on a mission to make real estate customer-centric. We envision a future in which real estate transactions involve dramatically less friction and surprising simplicity, and where Properly is the first choice of all Canadians throughout the entire experience of buying, selling and owning a home. Check out our CEO’s note on the culture we are trying to craft at Properly. 

Properly is headquartered in Toronto. We have a foundation of experienced operators on our team (Uber, Wealthsimple, Wave, Ritual, Mozilla, McKinsey, Shopify, Blackberry, etc.) and have raised over $115 million in funding from investors including FJ Labs, Prudence, Golden Ventures, iNovia Capital, AlleyCorp (Kevin Ryan), Silicon Valley Bank and others. We are an equal opportunity employer and celebrate diverse experiences and perspectives because they make our team more successful.

What you will do:

  • Work with the CEO, Board and advisors on fundraising efforts, including creating and refining our narrative, creating supporting analysis, building fundraising materials, and engaging with investors during due diligence 
  • Work with the senior leadership team to study the industry and our business to help define our long-term strategy, and to support the team-wide planning of our quarterly and annual business objectives and key results
  • Work with the CEO to define and execute on investor, government and stakeholder relations strategy, including Board meeting preparation 
  • Manage special projects including the evaluation of new business units or product lines, running an acquisition process, establishing key partnerships, leading the search for an executive hire, etc.; work closely with Product, Marketing, Data, Engineering and Operations teams to execute recommendations and drive results
  • Manage company-wide All Hands meetings to ensure that the full team is aware of business performance and key priorities

What you bring to the table:

  • 4+ years of experience in private equity, venture capital, investment banking or consulting; additional experience at a high-growth technology startup is great to have but not a requirement 
  • You have past experience that combines day-to-day execution with strategic planning, business analytics, and project management
  • You are highly analytical and have a strong attention to detail 
  • You have entrepreneurial DNA - you're excited to build a business from the ground up, are comfortable making decisions in the face of ambiguity, and aren't discouraged by the inevitable challenges that will arise along the way
  • You're an effective communicator who can inspire trust and confidence whether giving an oral presentation to your team or conveying insights from your analysis on a slide

At Properly, you'll have:

  • Competitive cash and equity compensation
  • Unlimited vacation days and a flexible work day; we care about outcomes over schedule
  • Lots of team events and social activities
  • Top of market maternal and paternal leave
  • Excellent healthcare benefits
  • Personal development budget; we support our team members' growth
  • Employee discount on Properly’s services