Chief of Staff (COS) to the Deputy Chief Information Security Officer (Deputy CISO)

CVS Health•Work At Home-Massachusetts, MA

2d•$175,100 - $334,750

About The Position

The Chief of Staff to the Deputy Chief Information Security Officer (Deputy CISO) is a leadership role responsible for driving execution, alignment, and operational discipline across the cybersecurity organization. Reporting to the Deputy CISO and working closely with the Chief Information Security Officer (CISO), this leader serves as a strategic partner and force multiplier for cybersecurity priorities, ensuring that key programs, budget commitments, strategic initiatives, and executive deliverables are coordinated, measurable, and delivered with impact. This role requires a seasoned, proactive, and highly organized professional who can operate across executive, business, technology, finance, and security teams. The Chief of Staff will help advance the Deputy CISO program by managing critical planning rhythms, supporting cybersecurity strategy, strengthening program governance, coordinating budget and resource planning, and enabling clear communication between the Deputy CISO, CISO, and enterprise stakeholders.

Requirements

10+ years of experience in a fast-paced, complex organizational environment, with at least 3-5 years in a Chief of Staff, strategic operations, or similar high-impact role supporting senior executives.
Demonstrated experience in a large, matrixed organization, preferably within the healthcare or technology sectors.
Strong execution skills: Proven ability to drive complex projects from conception to completion, managing multiple priorities and delivering results under pressure.
Strategic mindset: Ability to understand complex business challenges, connect the dots across various initiatives, and contribute to the development of long-term strategies.
Exceptional written and verbal communication skills, with the ability to articulate complex concepts clearly and concisely1 to diverse audiences, including executive leadership.
Highly proficient in developing compelling presentations and executive-level communications.
Proven ability to interact effectively with all levels of an organization, from individual contributors to the executive suite, with poise, professionalism, and influence.
Strong analytical and problem-solving skills, with a data-driven approach to decision-making.
High degree of discretion and ability to handle confidential information with integrity.
Bachelor’s degree in Business Administration, Information Technology, Cybersecurity, or a related field.

Nice To Haves

Master’s degree in Cybersecurity, Information Security, Information Technology, Business Administration, or a related field preferred.
Experience in cybersecurity, security operations, risk management, or technology leadership support.
Relevant cybersecurity, security program, governance, risk, or project/program management certifications preferred, such as CISSP, CISM, CRISC, CGEIT, PMP, PgMP, or similar credentials.
Experience within a Fortune 100 organization.

Responsibilities

Partner closely with the Deputy CISO to translate cybersecurity strategy into actionable priorities, coordinated plans, and measurable outcomes across the security organization.
Lead cross-functional cyber program governance, ensuring major initiatives, milestones, dependencies, risks, and executive decisions are tracked and driven to completion.
Monitor progress against strategic cybersecurity goals, identify roadblocks, escalate issues appropriately, and proactively recommend solutions to the Deputy CISO and CISO.
Prepare executive-level updates, decision materials, and performance narratives for the Deputy CISO, CISO, and senior leadership forums.
Develop and manage recurring cybersecurity status reports, executive briefings, leadership readouts, and program updates that clearly communicate progress, risks, decisions, and required actions.
Create clear, concise, and audience-appropriate communications for the Deputy CISO and CISO, including talking points, leadership messages, presentation narratives, and enterprise-facing updates.
Establish and maintain the Deputy CISO operating cadence, including leadership meetings, governance forums, business reviews, strategic planning sessions, and executive reporting routines.
Drive alignment across cybersecurity programs to ensure priorities, funding, resourcing, sequencing, and delivery plans support enterprise security strategy and risk reduction objectives.
Collaborate closely with cybersecurity leaders across security operations, governance, risk, compliance, engineering, architecture, identity, threat management, resilience, and related functions to align priorities, resolve dependencies, and advance enterprise cyber objectives.
Streamline and optimize operational processes, communication flows, and decision-making frameworks within the security organization.
Manage and prioritize critical communications, presentations, and deliverables for the Deputy CISO.
Maintain an integrated communications calendar for key cybersecurity deliverables, leadership forums, enterprise updates, board materials, audit responses, and stakeholder engagement milestones.
Support cybersecurity budget planning, resource prioritization, financial governance, and investment tracking to ensure alignment with strategic objectives and enterprise financial commitments.
Partner with finance, procurement, and security leaders to support forecasting, budget reviews, investment cases, vendor spend visibility, and resource allocation decisions.
Develop and maintain mechanisms for tracking cybersecurity program health, including key risks, dependencies, issues, decisions, performance indicators, and executive action items.
Facilitate and prepare for key meetings, including developing agendas, preparing materials, capturing minutes, and ensuring follow-up on action items.
Act as a trusted advisor and central coordination point for the Deputy CISO, while maintaining strong partnership with the CISO and senior cybersecurity leadership team.
Foster strong working relationships with cyber leaders to promote transparency, coordination, accountability, and consistent execution across the cybersecurity leadership team.
Effectively communicate and collaborate with senior leaders across CVS Health, including the executive suite, legal, HR, finance, and other business units.
Serve as a communication bridge between the Deputy CISO, CISO, cybersecurity leadership, business partners, and enabling functions to ensure timely information flow, message consistency, and coordinated follow-up.
Build and maintain strong relationships with internal and external stakeholders to foster collaboration and drive consensus.
Represent the Deputy CISO in selected forums, planning discussions, and stakeholder engagements as needed, ensuring decisions, actions, and follow-through remain aligned with CISO and Deputy CISO priorities.
Attend, lead, and facilitate meetings on behalf of the Deputy CISO as appropriate, representing Deputy CISO priorities, guiding discussion, capturing key decisions, and ensuring timely follow-up on actions and commitments.
Coordinate sensitive, time-critical, or high-visibility cybersecurity matters on behalf of the Deputy CISO, ensuring appropriate stakeholder engagement, escalation, and follow-through.
Conduct research and analysis on industry trends, competitive landscapes, and emerging technologies to inform strategic decisions.
Develop insights and recommendations to support the Deputy CISO in critical decision-making processes.
Prepare comprehensive reports and dashboards to track performance and identify areas for improvement.
Produce dashboards, scorecards, and narrative reports that summarize cybersecurity program performance, budget status, risk posture, delivery progress, and key decisions for executive review.
Identify trends, emerging risks, and operational insights from program data, metrics, audits, assessments, and leadership inputs to inform Deputy CISO and CISO decision-making.
Support preparation for board, executive committee, regulatory, audit, and enterprise risk discussions by consolidating inputs, clarifying messages, and ensuring materials are accurate and actionable.