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General Counsel & Compliance (Part-Time, Remote)

General Counsel & Compliance (Part-Time, Remote)

TripshepherdHalifax, Halifax County, Canada
4 days ago
Job type
  • Full-time
  • Part-time
  • Remote
Job description

General Counsel & Compliance (Part-Time, Remote)

Location : Nova Scotia (Remote)

Compensation : Part-Time, ~20 hours / week

Reports To : CEO, Daud Grewal

About Tripshepherd

Tripshepherd is redefining travel through authentic, community-driven experiences. As we continue to grow, we need a strategic and adaptable legal professional to oversee our corporate and regulatory compliance across Canada and the U.S. This role includes managing a variety of legal matters—from contracts and risk management to the occasional administrative law issue.

What You’ll Do

  • Regulatory & Compliance

Oversee compliance with tourism, payroll, and tax regulations in Canada and the U.S.

  • Develop internal policies and risk mitigation strategies that align with evolving legal requirements.
  • Coordinate necessary government filings and maintain proper records.
  • Contracts & Corporate Governance

    • Draft, review, and negotiate contracts (e.g., vendor, partnership, employment, independent contractor).

  • Manage corporate governance, including board / shareholder documentation and filings.
  • Create and refine tech-related legal documents (terms of service, privacy policies, etc.).
  • Litigation & Dispute Management

    • Address any legal disputes, including appeals or hearings before regulatory boards, when they arise.

  • Represent the company in proceedings as needed, engaging outside counsel sparingly for specialized matters.
  • Keep leadership informed on dispute status, potential outcomes, and recommended strategies.
  • Employment & Payroll Compliance

    • Ensure compliance with employment laws and payroll regulations across multiple U.S. states and Canadian provinces.

  • Advise on employment contracts, policies, and conflict resolution strategies.
  • Administrative Law (As Needed)

    • Provide counsel on administrative law matters that may impact operations or new initiatives.

  • Assist with regulatory board appeals or hearings, if they occur.
  • Strategic Counsel & Risk Management

    • Advise the CEO and executive team on broad legal implications of business decisions.

  • Identify areas of legal risk and propose proactive solutions to safeguard the company’s growth.

    • Who You Are

  • Licensed to practice law in Nova Scotia (Mandatory).
  • 5+ years of experience in corporate, regulatory, or general counsel roles (in-house experience preferred).
  • Familiarity with Canadian and U.S. legal frameworks, particularly payroll, tax compliance, and commercial contracts.
  • Exposure to administrative law or regulatory board proceedings is a plus (though not the primary focus).
  • Able to work independently, remotely, and flexibly (~20 hours / week), with occasional travel to Halifax if needed.
  • Skilled at juggling diverse legal tasks and making strategic decisions in a fast-paced environment.

    • What We Offer

  • Part-Time, Remote Role : Work ~20 hours per week from anywhere in Nova Scotia, with potential in-person appearances as required.
  • Growth Potential : Opportunity to evolve into a full-time position as the company scales.
  • Collaborative Culture : Join a mission-driven team focused on revolutionizing how people travel.

    • Hiring Process & Timeline

    We have urgent legal deadlines within the next 30 days and hope to fill this position quickly.

  • Initial Screening (30 minutes) : Introductory call to discuss your background and immediate fit.
  • Legal Case Study : Brief practical exercise to gauge your approach to typical startup legal challenges.
  • Final Interview : In-depth discussion with CEO, Daud Grewal, about strategy, culture, and next steps.

    • Seniority level : Mid-Senior level

    Employment type : Full-time

    Job function : Legal

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