Corporate Counsel – Director of Contracts

Skyline Technology Solutions

. Serve as a senior leadership team member reporting directly to the CEO .

Posted 10/3/2026full-timeRemote • Maryland • United StatesLead💰 $160,000 - $190,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive expertise in contract management, legal compliance, and risk assessment, particularly in government procurement and cybersecurity regulations. Proven ability to lead legal negotiations and provide strategic legal advice to executive leadership.

Highest-signal resume keywords

Contract ManagementLegal ComplianceRisk AssessmentGovernment ProcurementCybersecurity Regulations

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Contract LawContract DraftingNegotiationLegal TerminologyFAR RegulationsCOMAR RegulationsData PrivacyCybersecurity Risk ManagementInformation Technology LawSoftware-as-a-Service Legal Considerations

Soft Skills

LeadershipCommunicationInterpersonal SkillsTeam ManagementNegotiation Skills

Tools & Technologies

SITCH SoftwareCRM SystemsThird-Party Legal Counsel Coordination

Certifications & Qualifications

Active Bar Admission in MarylandJD Preferred

Industry Keywords

MBE/VSBE ComplianceBid ProtestsGovernment ContractsCorporate GovernanceEntity Maintenance

Tech Stack

Tools & technologies

Cyber Security

About the role

Key responsibilities & impact

Serve as a senior leadership team member reporting directly to the CEO
Advise the CEO and executive team on enterprise legal and contract risk
Manage review and negotiation of contracts and legal agreements
Coordinate with third-party legal counsel on compliance and contract issues
Oversee MBE/VSBE goal compliance, contract renewals, CPI increases, insurance, and bonding programs
Oversee change orders and manage contract management team members
Perform RFP reviews for risk, bonding/insurance compliance, contract exceptions, and required submission forms
Support proposal development and the business-development-to-delivery process
Manage mandatory contract reporting, revenue reporting, and usage fee payments
Advise on organizational conflict of interest mitigation
Lead SITCH Software license agreement development and negotiations
Oversee corporate legal status, operating agreement, state licensing, and legal policies
Support HR, cybersecurity, and business development legal requests
Manage litigation, claims, government disputes, and bid protests with outside counsel
Advise on False Claims Act exposure and government representations
Advise on data privacy and cybersecurity regulatory obligations and incident response disclosures
Serve as primary legal advisor on Maryland state and local procurement matters, including COMAR and bid protests
Provide legal support for employment matters, corporate governance, entity maintenance, and board matters
Partner with the Director of GRC on cybersecurity, privacy, compliance, solicitations, contracts, flow-downs, and third-party assessments
Approve CRM opportunity win closures by reconciling records with executed contract documentation
Oversee subcontractor legal, compliance, insurance, financial, and certification risk assessments
Oversee NDAs, subcontracts, and task orders
Advise leadership on legal and contract risk appetite and prepare legal/risk updates for ownership or board discussions

Requirements

What you’ll need

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
Minimum of 10 years in a leadership role
Proven experience in contract management and negotiations
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
Understanding of legal/contractual risk in State, Local, Federal, Commercial, and Prime contractor engagements involving hardware, software, or service contracts
Strong understanding of FAR regulations
Working knowledge of Maryland state and local procurement regulations (COMAR), including the bid protest process
Ability to identify, assess, and advise on legal, contractual, cybersecurity, privacy, and regulatory risks
Familiarity with NIST Special Publications, FedRAMP, GovRAMP (f.k.a. StateRAMP), privacy regulations, ethics, and conflicts of interest
Ability to handle sensitive and confidential information with discretion
Strong leadership, communication, negotiation, interpersonal, and team management skills

Benefits

Comp & perks

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