Senior Director/VP, Legal Counsel

at  CaseWare

Caseware is one of Canada’s original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!
We are seeking a Senior Leader in Legal to join Caseware. As a key member of the senior leadership team, you will report directly to the CFO and play a pivotal role in shaping and scaling the legal function within our growing business.

QUALIFICATIONS:

• Active membership in the US State Bar membership (additional membership in the Law Society of Ontario).
• Minimum of 4-7+ years of relevant legal experience in a law firm or in-house at a technology company and demonstrated success in navigating the complexity of a growing global organization (relevant Canadian experience in a legal experience in a law firm or in-house technology company is a plus).
• Strong leadership skills with corporate business acumen.
• Experience managing and scaling a legal team in a fast-growth SaaS company.
• Significant experience drafting, reviewing, and negotiating commercial contracts for on-premise software and SaaS services.
• Working knowledge of employment law and corporate governance for international entities.
• Ability to mentor Legal Team members and take ownership of projects and initiatives.
• Expertise in data protection laws (CCPA, GDPR, UK Data Protection Act).
• Experience with M&A, legal due diligence, and communicating with Board Members and Investors.
• Familiarity with contract management software, trademark and patent processes, distribution channels, and international PeopleOps issues.
• Experience in the audit and accounting industry.

ADDITIONAL SKILLS:

• Comfortable advising all organizational levels, including Executive Leadership, Senior Management, Board of Directors, and Investors.
• Knowledge of SaaS, subscription agreements, reseller agreements, and technology-related offerings.
• High attention to detail and accuracy.
• Collaborative approach with other teams (Finance, Sales, People Ops, Product, Technology) and people leadership.
• Energetic self-starter with initiative and business judgment.

• Lead the Legal Team, providing day-to-day legal advice and guidance on risk mitigation, customer/vendor contracts, data processing and security, corporate leases, and insurance.
• Scale the Legal Team and establish departmental strategy.
• Oversee key customer deals and act as a collaborative partner internally and externally.
• Manage complex legal agreements focused on technology software and data privacy, including SaaS subscription services.
• Draft and maintain policies, procedures, and contract templates to meet regulatory requirements and improve internal workflows.
• Advise the Executive Leadership Team on changes to relevant laws and regulations, including global privacy and data protection requirements.
• Implement and ensure compliance with global privacy laws and data protection requirements (GDPR, CCPA, COPPA).
• Engage with internal and external clients regarding legal and regulatory requirements and enterprise risk management.
• Support negotiations with various stakeholders globally.
• Contribute to the organization’s risk management strategies, focusing on regulatory compliance, cybersecurity, and operational resilience.
• Support intellectual property registrations, renewals, and potential litigation with external counsel.
• Manage external counsel spending and legal budget.
• Travel as required; approximately 25% travel.
• Other responsibilities as assigned.