Operating Principal

Trolley AI; Remote; CAD 100,000 - 150,000; Full time

Job summary

A venture capital firm is seeking an Operating Principal to manage deal operations and fund administration. This role involves sourcing, evaluating investment opportunities, and communicating with founders and investors. The ideal candidate will have 3–7 years of investment operations experience, strong financial analysis skills, and the ability to manage complex initiatives. This is a remote position with a commitment to diversity and inclusion in the workplace.

Qualifications

• 3–7 years of experience in investment operations or business operations.
• Proven ability to run complex, cross-functional initiatives end to end.
• Strong judgment and execution discipline.

Responsibilities

• Spearhead deal opportunities from discovery to close.
• Conduct market research and evaluate potential investments.
• Draft investment memoranda and maintain documentation.
• Communicate effectively with stakeholders.
• Coordinate with fund administration and compliance partners.

Skills

Financial analysis

Modeling skills

Communication skills

Project leadership

Job description

Job Overview

Kinship Ventures is seeking an Operating Principal to spearhead and manage all activities related to investment opportunities, from early-stage discovery through close and post-investment execution. This role is central to how Kinship evaluates deals, structures investments, manages fund operations, supports portfolio companies, and communicates with founders, partners, and Limited Partners (LPs).

This role combines deal operations, financial diligence, fund administration oversight, and investor communications, serving as a trusted operational partner to senior leadership while owning execution across the investment lifecycle.

Key Responsibilities

1. Deal Sourcing & Investment Operations
   • Spearhead all activities around deal opportunities from early-stage discovery through close and post-investment follow-through
   • Evaluate strategic and financial fit of potential investments
   • Own execution of approved deals across sourcing, diligence, execution, and post-close operations
   • Manage the full investment lifecycle, ensuring disciplined tracking and documentation
2. Diligence, Research & Market Analysis
   • Conduct market research on trends, emerging categories, and competitive landscapes
   • Review target company materials, including historical financials and projections
   • Rebuild and validate financial models, assumptions, and outputs
   • Perform opportunity sizing, sensitivity analyses, and scenario modeling
   • Develop and refine investment theses in partnership with senior leadership
   • Participate in diligence interviews, including cultural and values-based assessment
3. Investment Memoranda & Deal Documentation
   • Draft and own investment memoranda and presentation decks for internal and LP review
   • Develop Kinships financial and strategic case for each investment
   • Compile private transaction and public market comparables
   • Draft term sheets, offer letters, and operational deal materials (non-signatory)
   • Maintain clean documentation and tracking across active and closed deals
4. Stakeholder Communication & Fund Reporting
   • Communicate effectively with founders, venture partners, LPs, and C-level leadership
   • Prepare investment updates, partner memos, and ongoing deal status reporting
   • Produce bi-weekly internal updates and quarterly LP communications
   • Prepare LP-facing presentations evaluating portfolio companies and investments
   • Track LP sentiment, feedback, and key relationship signals
5. Fund Administration, Compliance & Vendor Oversight
   • Coordinate with fund administrators, CPAs, tax preparers, legal counsel, and compliance partners
   • Review (but do not sign) Income Statements, Balance Sheets, and Cash Flow Statements
   • Oversee preparation and coordination of K-1s, 1099s, Form D, and Blue Sky filings
   • Support investor onboarding workflows (DocuSign, subscription documents, W-9/W-8 collection)
   • Maintain secure storage of investor and fund documentation
   • Manage annual compliance calendars, renewals, and reporting requirements
6. Operations, Vendors & Fund Infrastructure
   • Support portfolio companies with guidance and operational coordination, in alignment with senior leadership
   • Monitor PR, marketing, and external developments related to partners and LPs
   • Coordinate founder forums, LP gatherings, and GP events
   • Serve as an operational bridge between portfolio companies and Kinship leadership

What We Are Looking For

• 3–7 years of experience in investment operations, fund operations, business operations, or project leadership
• Strong financial analysis and modeling skills
• Proven ability to run complex, cross-functional initiatives end to end
• High ownership mindset with strong judgment and execution discipline
• Excellent written and verbal communication skills across technical and non-technical audiences

Preferred

• Experience in VC, Corporate VC, fund operations, or portfolio management
• Background in consulting, investing, finance, or strategy
• Experience working directly with LPs and fund administrators

Job Details

• Location: Remote (Must work within PST or EST time zones)
• Hours: 40hrs/week

We are only reviewing candidates who submit their application through this link: https://forms.clickup.com/9017085020/f/8cqbk2w-82397/IJWOQDLG1NI3M9DPQS

Applications submitted elsewhere will not be considered.

About Us

Kinship Ventures is a unique team of seasoned entrepreneurs, founders, and investors with deep expertise across consumer technology (edtech, healthtech), Web3, and CPG (Beauty, Essentials, Wellness & Food). This includes founders, operators, and LPs who identify as POC, LGBTQIA+, and women.

Kinship Ventures Culture

At Kinship Ventures, we are committed to bringing diversity and inclusion to the cap table by deploying our privilege and access to uplift voices that have been historically marginalized. We take a long-term view of relationships because we are fundamentally in the relationship business. We value EQ as highly as IQ — being able to read the room, listen actively, and communicate thoughtfully is essential. Kinship Ventures proudly hires candidates of any race, color, ancestry, religion, sex, national origin, sexual orientation, gender identity, age, marital or family status, disability, veteran status, or any other protected status.

Learn more

Kinship Ventures

Be Part of the Future of Work

Currently, Kinship Ventures is a lean team of fewer than ten people, growing rapidly. We are looking to add exceptional individuals with backgrounds in investment, finance, or business operations who are motivated to make a meaningful impact in the investing ecosystem.

We operate with an AI-first mindset and look for people who use technology to work faster, smarter, and more creatively. AI is part of our everyday work, and we expect new hires to support a culture of curiosity, experimentation, and continuous improvement. We don\'t believe AI replaces human work or creative instincts, it enhances them by making our output more efficient and scalable.