Senior Manager, Trust Services

Workstreet

3h•Remote

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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.
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.
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.

Benefits

Clear growth path with mentorship and training opportunities
Comprehensive onboarding on security and compliance frameworks
Competitive base salary with regular performance reviews, merit-based appraisals, and bonus opportunities
Early-stage company with significant room for career advancement
Flexibility to work from anywhere while collaborating with a global team

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