Senior Manager, Trust Services
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, Compliance, IT, and Sales teams to align responses, ensure contractual compliance, and resolve escalations. Process Improvement: Identify and implement process enhancements, automation opportunities, and playbook updates to increase efficiency and reduce turnaround time. Who You Are Required Demonstrated experience managing client relationships at a senior or executive level — skilled at owning high-complexity accounts, navigating escalations, and delivering a consistently outstanding client experience Exceptional professionalism in all client-facing communication, with outstanding written and verbal English skills 8+ years of experience in cybersecurity, legal security reviews, or vendor risk management 5+ years of proven leadership experience managing distributed or global teams, including direct management of team managers Strong knowledge of SaaS security frameworks (SOC 2, ISO 27001, NIST 800-53, GDPR, HIPAA) Experience with security questionnaires (SIG, CAIQ) and legal document review/redlining Proficiency with collaboration and agile tools (Jira, Slack, Monday.com, ServiceNow, or similar) Strong analytical and problem-solving mindset with exceptional attention to detail Confident communicator capable of bridging legal, compliance, and technical teams Comfortable working across multiple time zones and global cultures Thrives in a fast-paced startup environment
Nice to Have
Certifications: CISSP, CISM, ISO 27001 Lead Auditor, SAFe, Scrum Master, or Kanban Management Professional Experience using AI-assisted review tools (ChatGPT, Drata AI Assist, Vanta, or similar) Background in SaaS environments or vendor risk consulting Experience with platforms such as Drata, Vanta, OneTrust, Secureframe, or ServiceNow VRM Experience with collaboration tools such as Jira, Slack, Microsoft Teams, or Confluence Experience with automation and AI tools such as Power Automate or AI-assisted legal review platforms
What We Offer
Career Development: Clear growth path with mentorship and training opportunities Technical Training: Comprehensive onboarding on security and compliance frameworks Competitive Compensation: Competitive base salary with regular performance reviews, merit-based appraisals, and bonus opportunities Growth Opportunity: Early-stage company with significant room for career advancement Remote-First Culture: Flexibility to work from anywhere while collaborating with a global team
Work Environment
Requirements Reliable high-speed internet connection Quiet, professional home office setup Must be amenable to working US Eastern Time zone hours Fluency in written and verbal English communication skills Workstreet Is An Equal Opportunity Employer As an equal opportunity employer, Workstreet is committed to providing employment opportunities to all individuals. All applicants for positions at Workstreet will be treated without regard to race, color, ethnicity, religion, sex, gender, gender identity and expression, sexual orientation, national origin, disability, age, marital status, veteran status, pregnancy, or any other basis prohibited by applicable law. Employment with Workstreet is contingent upon the successful completion of a background check, which may include verification of employment history, education, and other relevant information, in compliance with applicable laws. Apply To This Job