Senior Manager, Trust Services

About Workstreet

At Workstreet, we’re on an exciting journey to help businesses scale securely by designing and implementing cutting-edge security and compliance programs. As a fast-growing startup, we specialize in a wide range of frameworks—including SOC 2, ISO 27001, GDPR, CMMC, NIST 800-171, NIST 800-53, and FedRAMP—empowering companies to meet regulatory requirements and enhance their cybersecurity posture from day one.

The Opportunity

We are seeking a highly skilled Sr. Manager, Trust Services to lead a global team responsible for reviewing and managing security questionnaires, contractual security clauses, and compliance documentation for SaaS clients. This role carries executive-level client ownership and demands a leader who can build deep client trust while managing high-complexity engagements with strategic insight and professionalism.

This role bridges cybersecurity, legal, and client engagement — ensuring rapid, accurate, and high-quality turnaround on vendor assessments, NDAs, DPAs, MNDAs, and security-related contract reviews. The ideal candidate will combine deep technical knowledge of security frameworks with strong legal interpretation skills, team leadership experience, and agile delivery expertise. This role requires working US Eastern Time (EST) hours.

What You’ll Do

Client Relationship Management (Primary Focus)

• Own Executive-Level Client Relationships: Serve as the senior point of contact for a portfolio of strategic accounts, building long-term trust and ensuring clients receive an exceptional, high-touch experience at every stage of the engagement.
• Lead and Guide Client Engagements: Provide strategic oversight across multiple trust services engagements, ensuring clients are well-informed, prepared, and confident throughout security reviews, assessments, and contractual negotiations.
• Manage Escalations at the Executive Level: Address complex, high-stakes client concerns with professionalism, urgency, and composure — turning challenging situations into opportunities to reinforce trust and loyalty.
• Be a Strategic Trusted Advisor: Understand the broader business goals of each client and deliver security and compliance guidance that is not just technically sound, but strategically aligned with their objectives.
• Ensure Quality Across All Client Touchpoints: Conduct regular reviews of client communications, deliverables, and quality metrics to maintain consistency and excellence across all engagements.

Team Leadership

• Lead and Develop a High-Performing Team: Supervise and mentor managers, analysts, and reviewers across multiple time zones, fostering a culture of performance, accountability, collaboration, and professional growth.
• Manage Through Managers: Provide leadership and direction to team managers, setting clear expectations, coaching for performance, and ensuring accountability across the full delivery team.
• Drive Resource Strategy: Guide staffing, hiring, and resource allocation to optimize delivery efficiency and support department scalability as the business grows.
• Set and Uphold Standards: Establish and enforce quality benchmarks across the team, ensuring every client-facing output meets Workstreet’s high standards.
• Agile Leadership: Implement agile practices (Scrum or Kanban) to manage workload distribution, track SLAs, and drive continuous improvement through retrospectives and sprint planning.

Trust Services Execution

• Security Questionnaire Review: Oversee the completion, review, and finalization of client and vendor security questionnaires (SIG, CAIQ, or custom formats). Collaborate with SMEs to validate technical and compliance responses.
• Legal Document Review & Redlining: Conduct and manage reviews of NDAs, DPAs, MNDAs, and other contractual security clauses. Collaborate with internal and external legal counsel to redline, comment, and ensure alignment with cybersecurity frameworks and risk posture.
• AI & SME Collaboration: Utilize AI-powered tools to accelerate first-pass reviews and integrate SME feedback to improve accuracy and speed.
• Cross-Functional Collaboration: Partner with Legal, Comp