Senior Manager, Trust Services

Get to Know the Trust Services Team

In addition to GRC services, we also have a Trust Services team. We move at a fast, focused, and reliable pace - completing deliverables within 1 to 3 business days for customers with 5 clients and customers with 5,000 clients. We work directly with our customers' security and sales points of contact, meaning clarity, teamwork, and problem-solving are at the forefront of everything we do to help our customers drive sales and renewals by using security and compliance as differentiators. If you want to be part of a team that builds the bridge between sales and security, you're in the right place.

The Opportunity

Workstreet is seeking a Senior Manager, Trust Services to lead our global Trust Services organization and the delivery of YAQ (Your Automated Questionnaires), our AI-powered, human-in-the-loop security questionnaire service.

The ideal candidate builds structure in ambiguous, fast-moving environments, adapts quickly when client workflows change overnight, and holds a high bar for accuracy and client experience. This role requires availability primarily during US Eastern Time hours.

This role sits at the intersection of people leadership, client delivery, operations, and product. You'll set and enforce the standards your team works by: how tickets are triaged and prioritized, how AI-generated answers are validated before they reach a customer, how work is QA'd and escalated, and how new clients and new hires get up to speed.

You'll serve as the senior point of contact for strategic accounts and the escalation point when deals are on the line. You'll also be a trusted advisor who helps clients mature their trust programs, not just answer their questionnaires.

What You'll Do

• Lead and develop a global team: Manage a distributed organization of managers, engineers, and analysts across multiple time zones, including hiring, coaching, performance management, and building a bench of leaders who can run accounts independently.
• Own strategic client relationships: Serve as the senior point of contact and escalation path for high-complexity accounts. Set realistic turnaround expectations, coordinate with client security, legal, sales, and engineering stakeholders, and turn high-pressure situations into stronger relationships.
• Advise clients on their trust programs: Help clients strengthen their knowledge bases, trust centers, and due diligence workflows so their security posture becomes a sales accelerator.
• Run client onboarding end to end: Standardize how new clients are launched, from kickoff and knowledge base setup to SLA alignment, intake workflows, and clear ownership between Trust Services, GRC, and the client's own teams.
• Build repeatable team onboarding: Design and run onboarding for new hires, including checklists, shadowing, buddy programs, account-specific playbooks, and YAQ-first training, so new team members ramp quickly and consistently.
• Drive process improvement and operational rigor: Define and document triage, prioritization, QA, and escalation workflows. Formalize SOPs, and move the team from manual handoffs toward automated, measurable processes.
• Champion internal tool adoption and product feedback: Partner with product and engineering on a regular cadence to prioritize reliability, accuracy, and workflow enhancements. Ensure AI-generated responses are validated against approved sources before reaching clients, and gather structured feedback from the team.
• Manage through metrics: Partner with our Program Management team to continuously improve capacity planning, ticket weighting, SLA performance, adoption reporting, and overage tracking. Use that data to allocate accounts, forecast hiring needs, and identify retention and expansion opportunities.

Who You Are

• Senior client relationship leader - bring extensive experience managing executive client relationships, navigating complex accounts, and handling high-stakes escalations with composure.
• Experienced manager of managers - possess 5+ years of experience leading mid-sized teams, including direct experience developing, managing, and holding first-line managers accountable.
• Disciplined operational operator - prove sound judgment under pressure with a bias toward taking immediate ownership and solving issues independently rather than escalating upward.
• High-velocity startup performer - thrive in fast-paced cybersecurity environments, possessing the organizational discipline to manage multiple concurrent compliance programs seamlessly.
• Foundational compliance domain authority - familiar with frameworks across SOC 2, ISO 27001, GDPR, HIPAA, and/or NIST.

What will help you succeed

• Executive-level client presence - experience serving as the senior point of contact for strategic accounts, comfortable leading kickoffs, negotiating realistic timelines with sales and security stakeholders under deal pressure, and resolving escalations in a way that strengthens the relationship.
• Cross-functional translation - the ability to move easily between security, legal, engineering, and sales audiences, turning technical controls and contractual language into clear, accurate answers that unblock deals.
• Advisory exposure - whether you've worked at a consulting company or have worked closely with them throughout the audit process, a background in management consulting, assurance, or advisory practice is helpful.
• Platform automation mastery - practical exposure to configuring and managing automated platforms, especially those related to compliance such as Vanta, Drata, or Secureframe.
• Multi-framework audit expertise - familiarity with risk management frameworks and complex audit methodologies across diverse regulatory standards.

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.

What You'll Need to Thrive

• Excellent written and verbal English communication skills, with the ability to engage confidently with candidates, hiring managers, and business leaders across global teams.
• A reliable, high-speed internet connection and a professional home office environment that supports confidential conversations, virtual interviews, and uninterrupted collaboration.
• Commitment to working a standard schedule of 8:00 AM-5:00 PM U.S. Eastern Time (ET) to effectively collaborate with team members, stakeholders, and cross-functional partners while ensuring timely communication and support.
• Willingness and ability to travel locally for occasional onsite meetings, team gatherings, or business activities as needed.

What we offer

• Career Development: Clear path with mentorship and training opportunities.
• Role-Related Training: Reimbursement for the successful completion of approved training and certification courses relevant to your current role.
• Competitive Compensation: A competitive base salary with regular performance reviews linked to merit-based appraisals and bonus opportunities.

What you'll need to thrive

Hiring and Selection Process

• Candidates must participate in live video interviews throughout the hiring process with camera on (non-negotiable) and be prepared to verify their identity during recruitment and onboarding.
• Employment is contingent upon successful completion of identity verification and background screening, where permitted by law.
• Selected candidates will participate in structured interviews with hiring managers and cross-functional stakeholders to assess role fit, experience, and alignment with Workstreet's operating principles.
• Candidates will receive prompt updates and consistent communication throughout the interview process, ensuring a transparent, smooth, and engaging experience at every step.
• Applicants must be authorized to work in the U.S. without the need for visa sponsorship now or in the future. Workstreet does not provide employment-based visa sponsorship or transfers for this role, including H-1B, L-1, TN, O-1, E-3, H-1B1, F-1 (OPT/CPT), J-1, or any other work-authorized visa category.