Executive Assistant-Information Security & Risk Operations

kaishaservice; Georgetown (KY); On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Bonus opportunities

Paid time off

Medical benefits

FSAs/HSAs

14 holidays

401(k)

Tuition reimbursement

Job summary

kaishaservice is seeking an Executive Assistant, Information Security Operations to provide high-impact financial and administrative support to the Information Security and Enterprise Risk teams. You will own the annual budget compilation, deliver monthly budget-to-actual analytics, and produce year-over-year trend reports to inform leadership decisions.

The role also manages renewals and onboarding for cybersecurity MSAs, coordinates with Legal and Procurement, supports TCOR modeling, and helps

Qualifications

• Experience in financial planning, budgeting, and analytics for security operations.
• Experience coordinating monthly variance reviews with cross-functional teams.
• Experience managing cybersecurity MSAs, SOWs, SLAs, and vendor onboarding.
• Familiarity with TCOR, insurance processes, and SOC 2 / ISO 27001 / NIST CSF mappings.
• Strong executive-support skills: calendar management and board materials.

Responsibilities

• Lead annual security budget compilation and analytics.
• Facilitate monthly variance reviews and reforecasts.
• Manage renewals/onboarding for cybersecurity MSAs; coordinate with Legal/Procurement.
• Support TCOR modeling and insurance renewal processes.
• Provide executive calendar management and prep board materials.

Job description

We firmly believe that our employees drive the success of the company! With success in mind as the ultimate goal, we strive to create and provide an environment that offers challenging, stimulating and financially rewarding opportunities. We are looking for The Right One to join our team!

What's In It For You?

• Competitive Salary with Bonus Opportunities
• Paid Time Off
• Comprehensive Medical, Dental and Vision Benefits (Low Premiums!)
• Flexible Spending and Health Savings Accounts
• 14 Paid Company Holidays
• 401(k) with Company Contribution
• Educational Tuition Reimbursement

Summary

The Executive Assistant, Information Security Operations provides high-impact operational, financial, and administrative support to the Information Security and Enterprise Risk teams. This role owns the annual budget compilation process through structured interviews with security leadership, delivers monthly budget-to-actual analytics and year-over-year trending, leads variance review discussions with stakeholders, and proposes next steps grounded in data. The position also manages contract renewals and onboarding for cybersecurity MSAs, coordinates information for corporate insurance renewal programs, handles first-line insurance inquiries and COI distribution, and oversees Total Cost of Risk (TCOR) process management. The role has no independent decision-making authority but is accountable for research, analysis, and well-reasoned recommendations to drive informed decisions.

What You’ll Do

Financial Planning, Budgeting, and Analytics:

Lead the annual security budget compilation process by conducting structured interviews with security management and enterprise risk stakeholders to accurately capture initiatives, run-rate costs, headcount needs, and capital or operating splits. Validate assumptions, timelines, and dependencies; document rationale and risk ranges. Deliver monthly budget-to-actual reporting and analytics. Produce variance analyses (volume, rate, timing, and scope drivers) and year-over-year trending. Create dashboards and executive-ready summaries highlighting key insights, risks, and required actions.

Variance Reviews and Financial Tracking:

Facilitate monthly variance reviews by coordinating agendas, consolidating cross-functional inputs, and leading discussions with management regarding budget variances. Propose corrective actions, re-forecasts, or reprioritization based on data and stakeholder input. Maintain financial calendars, close timelines, and deliverable trackers with Finance. Track savings initiatives (contract consolidations, license optimization, scope right-sizing) and realized benefits.

Contracts, Vendor Management, and Procurement Support:

Fully manage renewals and onboarding workflows for cybersecurity Master Services Agreements (MSAs). Coordinate directly with Legal, Procurement, and Security Subject Matter Experts (SMEs) on contract terms, Statements of Work (SOWs), Service Level Agreements (SLAs), data protection addenda, and risk assessments. Maintain a centralized repository of contract artifacts, expiration dates, and required notice periods. Support the end-to-end vendor lifecycle by intaking requests, assembling due diligence materials, shepherding reviews through approval workflows, and monitoring performance metrics to flag issues. Prepare negotiation packets with spend history, utilization data, benchmarks, and risk considerations.

Risk, Compliance, Insurance, and TCOR Oversight:

Support the corporate insurance renewal process by gathering critical security and risk data for underwriting, including controls, historical incidents, audit results, and overall compliance posture. Coordinate responses to first-line insurance inquiries and manage the distribution of Certificates of Insurance (COIs). Oversee Total Cost of Risk (TCOR) process management by defining core components such as premiums, retentions, claims, incident response, downtime, third-party costs, and mitigation investments. Build and maintain a dynamic TCOR model to report quarterly trends to leadership, partnering with Risk Management to align these insights with budget and vendor decisions. Enable compliance by assisting with evidence collection for audits and assessments - such as SOC 2, ISO 27001, and NIST CSF mapping - while maintaining a calendar for attestations and renewals.

Executive, Operational, and Program Support:

Provide high-level calendar management, meeting coordination, and communications support to security leadership. Prepare executive-ready materials, briefings, Quarterly Business Reviews (QBRs), and board or C-suite packets using clear narratives and clean visuals. Coordinate cross-functional initiatives and track key deliverables using roadmaps, milestones, and risk logs. Standardize and continuously improve operations by creating and updating RACI matrices, Standard Operating Procedures (SOPs), templates, intake forms, and trackers. Safeguard the absolute confidentiality of sensitive security, legal, a