Assistant General Counsel

At Community Financial System, Inc. (CFSI), we provide friendly, personalized, high-quality financial services and products through our retail division, Community Bank, N.A., which operates more than 200 customer facilities across Upstate New York, Northeastern Pennsylvania, Vermont, and Western Massachusetts. Beyond retail banking, we offer commercial banking, wealth management, investment management, insurance and risk management, and benefit plan administration. We are committed to our employees with competitive compensation, great benefits, and professional development and advancement opportunities.

Responsibilities

• Legal Leadership & Strategy
  • Serve as the chief legal advisor to the CEO, executive team, and Board of Directors.
  • Develop and execute the company's legal strategy in alignment with business objectives.
  • Establish and maintain internal legal policies, processes, and standards.
• ERISA & Retirement Plan Matters
  • Advise on all aspects of the Employee Retirement Income Security Act (ERISA), including plan design, administration, investments, and fiduciary responsibilities.
  • Provide guidance on retirement plan governance, disclosure, and compliance with applicable regulations.
  • Support the development and maintenance of products and services offered under ERISA-regulated structures.
• Collective Investment Trusts (CITs)
  • Provide counsel on the structure, formation, and ongoing operation of Collective Investment Trusts.
  • Ensure CITs comply with applicable banking, securities, and ERISA-related regulations and guidance.
  • Coordinate with internal stakeholders and external service providers to support CIT product offerings.
  • Draft and review operating agreements, member agreements, and related governance documents, including Participation Agreements, Offering Memorandums, and side letters.
• LLC Structures & Corporate Entities
  • Advise on formation, governance, capitalization, and maintenance of LLCs and other corporate entities.
  • Draft and review operating agreements, member agreements, and related governance documents.
  • Ensure ongoing compliance with state and federal requirements for all legal entities.
• Securities Law & Regulatory Compliance
  • Oversee compliance with federal and state securities laws, including disclosure obligations, filings, and transactional matters.
  • Advise on marketing, communications, and distribution activities to ensure adherence to securities regulations.
  • Monitor regulatory developments and recommend appropriate changes to policies and practices.
• Corporate Governance
  • Serve as Secretary (or equivalent) to the Board of Directors, ensuring accurate minutes, records, and corporate documentation.
  • Support Board and committee governance, charters, and policies.
  • Develop and maintain codes of conduct, conflicts of interest policies, and other governance frameworks.
• Contracts & Commercial Transactions
  • Draft, review, and negotiate a wide range of commercial contracts, including vendor agreements, service agreements, NDAs, technology and licensing agreements, Master Services Agreements, and strategic partnership arrangements.
  • Develop standardized templates and playbooks to drive contracting efficiency and consistency.
• Litigation, Investigations & Disputes
  • Oversee litigation, regulatory inquiries, and dispute resolution matters.
  • Manage strategy, case selection, and outcomes in collaboration with internal stakeholders and outside counsel.
  • Implement proactive measures to reduce litigation risk.
• External Counsel Management & Cost Control
  • Select, onboard, and manage relationships with external law firms and other legal service providers.
  • Develop and implement strategies to manage and optimize legal spend, including budgeting, billing guidelines, fee arrangements, and matter staffing models.
  • Allocate work between internal resources and external counsel to ensure efficient use of internal capabilities and external expertise.
  • Regularly review outside counsel performance, cost-effectiveness, and matter outcomes, and adjust panel or preferred firm relationships as needed.
• Risk Management & Compliance
  • Identify, assess, and advise on legal, regulatory, and reputational risks across the business.
  • Collaborate with compliance, risk, finance, operations, and HR to maintain effective control frameworks.
  • Develop and deliver training programs to enhance legal and regulatory awareness throughout the organization.
• Cross-Functional Collaboration
  • Partner with leaders across the organization to support product development, operations, distribution, and strategic initiatives.
  • Provide practical, business-oriented legal advice that enables responsible growth.

Requirements

• J.D. from an accredited law school and active membership in good standing with at least one U.S. state bar.
• Minimum of 10 years of legal experience in a law firm and/or in-house legal department, with significant exposure to financial services, asset management, or a related sector.
• Demonstrated expertise in ERISA, CIT structures, LLCs, and general securities law.
• Proven experience managing external counsel, including cost controls, budgeting, and workload allocation.
• Strong track record of drafting and negotiating complex commercial agreements.
• Exceptional analytical, strategic thinking, and problem-solving skills, with the ability to translate legal requirements into practical business guidance.
• Excellent communication and interpersonal skills, with experience advising executive leadership and boards.
• High ethical standards, sound judgment, and strong business acumen.
• All applicants must be 18 years of age or older.

Preferred Qualifications

• Experience working in or with asset management, retirement services, banking, or other financial institutions.
• Familiarity with related areas such as employment law, privacy/data security, information security, and mergers & acquisitions.
• Experience building or leading an in-house legal function, including implementing processes, tools, and metrics for legal operations.

Benefits

• 11 paid holidays
• Paid vacation
• Medical, Vision & Dental insurance
• 401K with generous match
• Pension
• Tuition Reimbursement
• Banking discounts

Pay

Minimum USD $200,000.00/year. Maximum USD $500,000.00/year.

Physical Requirements

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• While performing the duties of this job, the employee may be required to stand, walk, or sit.
• Use hands and fingers, handle or feel, reach with hands or arms, and speak and hear.
• The employee may occasionally be required to lift and/or move up to 25 pounds.
• Specific vision abilities required by this job include close vision and the ability to focus.