Associate/Senior Associate, Healthcare Investments Wittington Ventures

***To be considered for this position, please send your resume to: cdickson@wittingtonventures.com ***

Background

Wittington Ventures (WV) is a Toronto-based venture capital (and growth equity) firm backing bold entrepreneurs across North America who are using technology to redefine the future of commerce, consumer, climate, and healthcare. We are thesis-driven – we evaluate industry sub-sectors and invest in start-ups (companies) that share our conviction on the trends that we identify. WV has a unique set of investors that give us unparalleled access to some of Canada’s largest companies to help our portfolio of startups succeed; our affiliates include companies such as Loblaw, Shoppers Drug Mart, Choice Properties, Holt-Renfrew, Joe Fresh, and philanthropic Foundations focused on key healthcare and environmental areas. We pride ourselves on fostering a collaborative and inclusive work environment where creativity and initiative are encouraged. Our portfolio includes category-defining companies such as Abridge, Doctronic, Gatik, Lemme, and Noetik, alongside many other exceptional companies and founders.

Role Description

This role offers a unique opportunity to shape our healthcare investment strategy and work with a team that has invested in some of the leading healthcare technology startups. The Associate/Senior Associate will be an intellectually curious professional who will bring an understanding of the US healthcare system – ideally developed through investing, operating, or industry experience - and help sharpen our view of the digital health landscape across software, informatics, and tech-enabled services. Your time will span sector research, deal sourcing, diligence, investment execution, and portfolio support. Uniquely, you will be able to draw on WV’s relationships across Shoppers Drug Mart, Loblaw, and the broader Wittington network as a real-world channel to help portfolio companies validate products and reach patients and providers at scale. You will craft investment theses, identify non-consensus opportunities, and develop a view on how to predict and unlock meaningful returns.

You will bring to the team a background in science, engineering or business, a strong financial acumen, an analytical mindset, entrepreneurial spirit and collaborative approach to problem solving. This is a chance to join an ambitious team and unique investment platform that is backing founders and category-defining technology companies that will fuel the next century of innovation.

Responsibilities

Deal Sourcing & Execution

• Proactively source and evaluate healthcare technology investment opportunities across North America, building and maintaining a strong network of founders, co-investors, and referral sources.
• Lead comprehensive due diligence processes, including technical, market, and regulatory analysis.
• Develop detailed financial models incorporating healthcare-specific metrics and KPIs.
• Prepare investment memos and present recommendations to the investment team.

Healthcare Strategy & Thesis Development

• Lead development of investment theses in digital health and tech-enabled healthcare services.
• Identify and analyze key market opportunities, regulatory considerations, and technological innovations shaping the future of healthcare delivery.
• Build and maintain relationships with healthcare industry experts, entrepreneurs, investors, and strategic partners.
• Help build the firm's healthcare ecosystem through thought leadership and network development.
• Support portfolio companies around key strategic initiatives, talent sourcing, business development, and future financing or exit.
• Play a key internal role in managing the fund reporting process, including investment monitoring and valuation analysis, and quarterly reporting.
• Support LP reporting, annual meeting preparation, and fundraising materials.

Qualifications

• Bachelor’s degree, ideally with a quantitative, scientific, or business orientation.
• 3-7 years of work experience in the technology industry in a start-up, big tech, management consulting and/or as an investor with at least 2 years of experience in US healthcare technology investing or operations. Title and compensation will be calibrated to experience.
• Understanding of the US healthcare system, including technology trends, business models, and regulatory landscape.
• Must enjoy a versatile and dynamic environment in a small team.
• Outstanding financial and analytical skills.
• Exceptional business writing and data synthesizing capabilities.
• Proficiency in spreadsheet, presentation and other office productivity tools.
• Ability to research diverse areas and synthesize differing opinions on various technology topics.
• Ability to interact with start-up founders and corporate executives in a collaborative manner.
• Thoughtful, imaginative, and intellectually curious with strong interpersonal and critical thinking skills.
• Strong work ethic, self-driven with attention to detail and follow-through.
• Ability to juggle multiple workflows and responsibilities.

Location

This role is based in Toronto, with a hybrid in-office schedule. Given our US healthcare focus, we will consider exceptional US-based candidates.

Wittington Ventures is an equal opportunity employer committed to promoting a diverse and inclusive workplace. We know our success depends on the perspectives and contributions of all our employees. Diverse backgrounds and experiences make our business stronger. If you are contacted for a job opportunity and require accommodation, please email people.culture@wittington.ca. All requests are confidential and used only to meet candidate needs.

We may use artificial intelligence (AI) tools to support parts of our recruitment process, which could include screening, assessing, or evaluating candidates. All hiring decisions include human review and oversight.

We thank all applicants for their interest in this position. Only those selected for an interview will be contacted.

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