About the Company
We are excited to introduce a unique opportunity to join, Upward Trajectory Fund (‘UTF’), a newly established private investment vehicle spearheaded by a visionary entrepreneur with a proven track record of success. Leveraging strategic insights and financial acumen UTF is focused on investing in established small to mid-market companies within legacy industries, to drive growth and innovation.
Learn more about UTF by visiting www.upwardtrajectoryfund.com.
Scope of Position
As the Senior Investment Associate, you will be the first key hire, working directly with the principal investor to shape the UTF’s investment approach, conduct in-depth analyses, and drive the development of a robust portfolio. The role offers an exceptional chance to influence the foundation and future of the fund’s investment strategy, playing a central role in a transformative journey from the ground up.
Functional Tasks
• Source and evaluate attractive investment opportunities for UTF through in-depth due diligence, financial modelling and analysis.
• Assist the Principal in determining the appropriate amount of capital deployment for each investment by modelling projected return scenarios.
• Ensure that investments are made consistent with the UTF’s strategy.
• Proactive outreach and cultivation of relationships with owner-operators, market intermediaries and sponsors as well as other centres of influence and private equity funds for direct investing, co-investing and deal sourcing.
• Monitor existing investments to accurately predict return of capital timing and redeployment for efficient recycling of capital.
• Assist with developing systems, models and processes to optimize deal sourcing, evaluation and ‘go, no-go’ investment decisions.
• Develop operational and business systems, playbooks and best practices to create a sustainable, top-performing mid-market fund.
• Attend and participate as appropriate industry conferences, events and forums to develop the firm’s brand and market presence.
• As appropriate, monitor, oversee and interact with portfolio companies providing guidance and act as a sounding board.
Key Performance Deliverables
In light of the identified responsibilities, the following are specific deliverables that the position is designed to achieve.
• Capital preservation combined with a hurdle internal rate of return.
• Development and adoption of investment template models, playbooks and best practices.
Competency Profile
The following competencies listed below define the role of Investment Associate:
Commercial Acumen: Applies appropriate commercial and financial principles; Understands situations in terms of costs, profits, added-value and return on investment; Thinks broadly and investigates a wide-range of alternatives in developing a vision for the future. Selects the most promising vision from a range of alternatives and communicates this vision to others.

Results Orientation: Focuses strongly on achieving agreed upon outcomes and ensures that key objectives are met. Conveys a sense of urgency and drives issues to closure. Aims to improve upon past performance. Establishes aggressive personal targets and strives to achieve them.
Role Expertise: Demonstrates critical technical or professional knowledge/skills related to the role. Has thorough knowledge of relevant products, services and methods. Expands technical knowledge/skills and keeps up-to-date in own area of expertise.
Decisiveness: Gathers and interprets all available sources of information. Willing to make solid and quick decisions when necessary. Can commit to a course of action without delay when faced with limited information.
Strategic Approach: Develops a strategic plan to realize the vision. Revises strategy in light of changing circumstances. Takes a long-term view of organizational success. Works to clarify long term organizational goals. Able to stand back from immediate problems in order to focus on more far reaching ideas.
Initiative: Proactive. Seizes opportunities and acts upon them immediately. Takes responsibility for own actions and addresses problems before asked.
Drive: Adopts an energetic approach. Demonstrates capacity for sustained effort and hard work over long periods of time, even in the face of adversity. Works towards goals and willingly tackles demanding tasks.
Adaptability: Quickly adapts to new situations and approaches. Can alter own perspective and behavior in order to adjust to changing demands and plans. Open to change and readily adopts new methods in the face of shifting priorities and ambiguity.
Preferred Experience / Education
The following indicates specific industry, academic and functional experience/qualifications that are important to the successful achievement of the identified responsibilities and performance deliverables.
• Minimum of 8-10 years of prior investment experience with a successful track record of investing in small to mid-market legacy businesses.
• An undergraduate degree in business, sciences or engineering coupled ideally with an MBA, CFA or CPA.
• Strong analytical and quantitative skills in order to conduct original research and assess new investment opportunities.
• Ability to think critically, question the status quo and adapt to evolving market conditions.
• A visionary with a ‘partner’ mentality, long term perspective and commitment to sustainable wealth creation.
• An insatiable curiosity combined with an even greater work ethic, intelligence, integrity and strategic orientation.
• Well-respected and well networked to ensure that quality investment opportunities are in constant supply.
Remuneration & Benefits
• A compensation package commensurate with experience.
If interested, please contact:
Sal Rocco
StoneWood Group, Toronto
Cell: 416-500-7100 [email protected]
Shreya Rao
StoneWood Group, Toronto
Cell: 647.550.1654
[email protected]