VC Associate @ Staircase Ventures in Toronto, ON

Staircase Ventures

Based in Toronto, Staircase Ventures is a new early-stage venture firm with unparalleled dedication to helping founders accelerate their own development and perform at their best. Staircase leads seed-stage rounds into Canadian-based, B2B software companies. The Firm was founded by Janet Bannister, a nine-year veteran of early-stage investing and founder of

Staircase is seeking an experienced Associate to help identify and evaluate potential investment opportunities, support existing portfolio companies, and help manage and build the Staircase Venture firm.

Staircase Ventures is an equal opportunity employer. We work continuously on creating a culture and an organization that truly values diversity. We believe cultural fit doesn’t mean being culturally identical, and that diversity of thought enables us to challenge one another to think broader. We provide equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, colour, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity or gender expression.


We are looking for an outstanding individual to join the team and provide support across all aspects of the Firm. The Associate will be integral in supporting all aspects of firm operations and the end-to-end investment process. This is an outstanding opportunity for the right individual to learn about the venture capital industry, understand best practices for launching and building a successful tech company, become embedded in the Canadian tech ecosystem, and learn directly from the Staircase Ventures team. It requires an individual who is a self-starter, highly motivated, analytical, fast learner, and deeply passionate about start-ups and the role of technology in transforming industries.

Applicants must be legally eligible to work in Canada and reside in Ontario. Position is full time and the candidate will be expected to start within the next two months.


New Investments:

  • Qualify, manage and track a high volume of new investment opportunities.
  • Take initial screening meetings and identify the most promising opportunities.
  • Provide insightful due diligence including financial analysis, market research, and customer interviews.
  • Write investment memos and manage the investment processes.

Portfolio Support:

  • Support portfolio management and reporting.
  • Write quarterly updates on each portfolio company.
  • Track portfolio performance.
  • Oversee Founder Development Platform.
  • Develop and manage other portfolio resources.

Firm Operations:

  • Assist in LP reporting including quarterly and annual Fund financial reporting.
  • Assist in capital call management.
  • Oversee work done by the outsourced accounting firm to ensure timely and accurate bookkeeping and reporting.
  • Organize events for founders, LPs, Advisors, and others.
  • Develop content calendar, manage blog and social media content.
  • Support the Firm on special projects and executing ad hoc tasks.
  • Provide administrative support as needed such as taking meeting notes, booking meetings, and tracking legal documents.
  • Enhance Staircase Ventures’ internal efficiencies and communications by identifying opportunities to continually improve how we work.


  • University degree, preferably with a technical, finance or business background.
  • Minimum 5 years work experience including at least 3 years in venture capital or consulting.
  • Strong background in accounting and financial analysis.
  • Exposure to the Canadian tech ecosystem.
  • Demonstrated passion for early stage technology companies and trends.
  • Demonstrated ability to analyze market trends, conduct financial analysis, and draw concise conclusions.
  • Outstanding written and verbal communication skills.
  • Intellectually curious with a dedication to go the extra mile.
  • Very organized, reliable, highly responsive and excellent organizational skills.
  • Ability to work independently with little supervision.
  • Self-starter and problem-solver with strong initiative to improve processes.
  • Growth mindset.
  • Attention to detail.


  • A high-growth, fast-paced learning environment with strong mentorship.
  • Exposure to the Canadian tech ecosystem including opportunity to gain deep insights into venture capital, company building, and leadership.
  • Competitive salary.
  • Three weeks vacation.
  • Hybrid work environment.
  • Benefits package that includes health and vision care and flexible healthcare resources.


Every person who interacts with the Firm will “feel” the following values, embodied in all communications, decisions, and actions.

  • Give-first mentality: help others without the expectation of getting anything back.
  • Positive, high energy, and deep care for others, balanced with radical candor.
  • Unparalleled level of drive and hard work to help founders and deliver returns to LPs.