Rob H.

Key Skills

Software

Don't disclose

Top Subject Matter

Cybersecurity governance, risk and compliance

Identity Management/Governance

Cybersecurity Consulting

Top Data Types

Text

Image

Document

Top Task Types

Classification

Question Answering

Segmentation

Freelancer Overview

Senior Manager, IT Governance, Operations & IAM/IGA (Head of Security) at Stride, Inc.. Brings 11+ years of professional experience across legal operations, contract review, compliance, and structured analysis. Core strengths include Don't disclose, Proofpoint, and Azure. Education includes Bachelor of Science, University of Phoenix. AI-training focus includes data types such as Text and labeling workflows including Classification, Question Answering, and Evaluation.

Labeling Experience

Chief Information Security & Transformation Officer at Lee Enterprises

TextQuestion Answering

Founded and led Lee Enterprises’ first security division as CISO, building governance and regulatory teams to achieve SOX and PCI-DSS compliance within six months. Directed work across GRC, incident response, vendor risk management, and security operations while implementing automated tools and playbooks that reduced incident response times. Developed enterprise security awareness and phishing programs, and advised leadership and compliance teams on security incidents, regulatory exposure, and third-party risks. • Produced and maintained risk registers, risk mitigations, and compliance procedures • Managed third-party security compliance through vendor risk assessments and remediation tracking • Used incident guidance and post-incident analysis to inform operational improvements • Led security training outputs intended to change workforce behavior toward phishing

2024 - 2026

Security & Privacy Consultant at Lee Enterprises

TextQuestion Answering

Used NIST Cybersecurity Framework guidance to build and deliver an enterprise cybersecurity strategy and roadmap focused on security maturity and high-risk prioritization. Conducted third-party vendor security posture evaluations using SOC 2 questionnaires and risk assessments to identify gaps and direct remediation. Developed and launched an organization-wide security awareness and training program using interactive modules intended to reduce phishing success. • Completed questionnaire-based vendor risk evaluation outputs • Turned assessed security architecture and controls into actionable prioritization • Delivered security training content via an external training platform • Managed cross-functional security initiatives affecting compliance and risk reduction

2024 - 2024

Senior Manager, IT Governance, Operations & IAM/IGA (Head of Security) at Stride, Inc.

Don't discloseTextClassification

Established and maintained GRC, IAM/IGA, and security governance processes that included creating risk registers, risk mitigations, and security policies aligned to NIST frameworks and audit requirements. Directed vendor risk management via risk-scoring and automated questionnaires, using the outputs to inform remediation actions. Led incident response work in alignment with NIST guidance and performed post-incident analysis to improve future response plans. • Produced classification-style security risk assessments and scoring outputs • Coached teams on remediation planning and audit closure for control gaps • Coordinated third-party compliance checks and tracked remediation status • Governed user access review (UAR) processes for SOX-regulated applications

2021 - 2024

Chief Security & Privacy Officer at eCare21, Inc.

TextClassification

Led security, privacy, and compliance programs across U.S. and international operations, including the creation and maintenance of NIST and ISO 27001-aligned security policies and compliance documentation. Conducted risk assessments and security scans to identify critical vulnerabilities in web applications and collaborated with teams to remediate them. Selected and deployed security products to improve threat detection and designed private cloud and on-prem infrastructure security using Azure and VMware, including automated scanning pipelines with SAST/DAST. • Translated scan findings into vulnerability prioritization and remediation classification • Produced compliance documentation aligned to NIST/ISO 27001 for audits • Managed vendor contracts and security protocols supporting SOX/HIPAA compliance • Supported continuous compliance monitoring through automated security scanning

2020 - 2021

Director of Customer Success, IT & Operations at BluVector

Don't discloseTextSegmentation

Led IT, Security Operations, MSS, and SOC teams supporting a global customer base, focusing on operational incident response improvements and maintaining high service uptime. Developed and oversaw MSS offerings and customer-facing SOC operations, driving process improvements that reduced average incident resolution time. Managed customer relationships that supported long-term engagements and coordinated IT procurement and vendor relationships to ensure delivery of quality services. • Evaluated and improved incident handling processes to reduce resolution time • Supported SOC operations workflows used to assess customer security events • Oversaw service delivery metrics and operational performance targets • Coordinated vendor and operational processes affecting customer security operations

2016 - 2020

Education

Work History