Corporate Counsel and Director of Contracts

Our New Teammate

The Corporate Counsel and Director of Contracts is a senior leadership role reporting directly to the CEO and serving on Skyline’s leadership team. This position owns Skyline’s enterprise legal and contract risk: advising the CEO and leadership team on legal exposure, managing the full contract lifecycle, overseeing subcontractor and vendor risk, and protecting Skyline’s legal and regulatory standing as a state, local, and federal government contractor. The role is exempt, full-time, and remote work eligible.

You can expect to spend your time accomplishing the following:

• 55% of the time on Objective 1: Contract Lifecycle Management
• 20% of the time on Objective 2: Enterprise Legal, Risk & Compliance
• 15% of the time on Objective 3: Vendor & Subcontractor Management
• 10% of the time on Objective 4: Executive Leadership & Governance

Job Responsibilities - What to Expect

• Manage the review and negotiation of contracts and legal agreements.
• Coordinate with third-party legal counsel as needed to ensure legal compliance and resolve contract issues.
• Oversee MBE/VSBE goal compliance for all contracts.
• Manage current contracts for CPI increases and renewals.
• Manage the insurance and bonding programs to support contract requirements.
• Oversee and advise on the change order process.
• Manage contract management team members to ensure their performance and job satisfaction.
• Support the opportunity review process by performing RFP reviews for risk, bonding/insurance compliance and developing Teaming Agreements.
• Support the proposal development process by performing RFP for contract exceptions and completing required forms for submission.
• Support contract aspects of the BD to Delivery process.
• Manage mandatory contract reporting for compliance with revenue reporting and usage fee payment. 
• Advise on organizational conflict of interest (OCI) mitigation across teaming, subcontracting, and proposal pursuits.
• Support and assist internal educational opportunities to improve personnel awareness in handling enterprise legal, contract risk, subcontract risk, and other related matters. 
• Lead SITCH Software license agreement development and conversations from a legal perspective.
• Oversee company corporate legal status and operating agreement.
• Support HR, Cyber and Business Development legal support requests.
• Oversee state licensing requirements.
• Develop and/or maintain legal and contract policy, including delegation of authority, signature authority, organizational conflict of interest, ethics and code of conduct, records retention, and litigation hold.
• Manage litigation, claims, and government disputes (including bid protests) in coordination with outside counsel.
• Serve as primary legal advisor on False Claims Act exposure, including legal review of company representations and attestations to government customers.
• Advise on data privacy and cybersecurity regulatory obligations. During cybersecurity incidents, advise the Incident Commander on privilege, breach notification determinations, and regulatory, client, and insurer disclosure.
• Serve as primary legal advisor on Maryland state and local procurement matters, including COMAR requirements and the bid protest process.
• Provide legal backstop to HR on employment matters and to leadership on corporate governance, entity maintenance, and board-level matters.
• Partner with the Director of GRC on cybersecurity, privacy, and compliance requirements in solicitations, contracts, flow-downs, and third-party assessments. GRC determines technical compliance feasibility; Corporate Counsel owns the contractual position and legal risk.
• Serve as the designated approving authority for all CRM opportunity win closures, reconciling opportunity records against executed contract documentation to verify alignment of value, scope, and terms prior to approval, establishing a critical compliance checkpoint that ensures data integrity and mitigates risk across the sales-to-contract lifecycle.
• Oversee the relationship with subcontractors from a legal and compliance perspective.
• Oversee the creation of NDA, subcontracts and task orders.
• Provide legal, insurance, financial (with finance), and certification risk assessment of each subcontractor. Security and compliance posture assessment is performed by Governance, Risk, and Compliance (GRC).
• Ensure subcontractor insurance compliance.
• Ensure MBE/VSBE certification when partnering.
• Serve as a member of Skyline’s leadership team, advising the CEO and the Executive team on enterprise legal and contract risk.
• Advise the CEO and the Executive team on the development of an enterprise legal and contract risk appetite framework.
• Serve as escalation point for legal, liability, bonding, insurance, and OCI risk in business development go/no-go and proposal risk reviews, in parallel with the GRC escalation point for security and compliance feasibility.
• Prepare legal and risk updates for ownership/board-level discussions as needed.

Your Knowledge & Expertise 

• Bachelor’s degree in business, law or related field
• Master’s or JD preferred.
• Active bar admission in Maryland (or ability to obtain within 6 months), in good standing.
• Proven experience in contract management and negotiations, with a minimum of 10 years in a leadership role. 
• Demonstrated experience serving as primary point of contact with government client legal, procurement, or contracting officer counterparts.
• Strong inclination for Information Technology, Networking, Information Security, and Software-as-a-Service terminology and related legal/contractual considerations.
• In-depth knowledge of contract law, contract drafting, and legal terminology, with the ability to interpret and translate legal/contract nuances and jargon into objective, actionable information for the business.
• In-depth understanding of legal/contractual risk and considerations involved in contracting with State, Local, Federal, Commercial, and Prime contractors to deliver on hardware, software, or service-related contracts.
• Strong understanding of FAR regulations and working knowledge of Maryland state and local procurement regulations (COMAR), including the bid protest process, along with a strong willingness to learn and adapt to other state-specific contracting and procurement requirements as needed.
• Demonstrated ability to identify, assess, and advise on legal, contractual, cybersecurity, privacy, and regulatory risks across government and commercial engagements.
• Familiarity with applicable government contracting and cybersecurity compliance frameworks, including NIST Special Publications, FedRAMP, GovRAMP (f.k.a. StateRAMP), privacy regulations, and related contractual compliance obligations, including ethics and conflicts of interest.
• Ability to identify and handle sensitive and confidential information with discretion.
• Strong leadership and team management skills, with excellent communication, negotiation, and interpersonal skills to support cross-functional collaboration.

Benefits Included:

• Medical Insurance
• Vision Insurance
• Dental Insurance
• FSA Plan
• Paid Time Off
• 401K Retirement Savings Plan
• Training & Tuition Assistance
• Disability & Life Insurance