Strategic IT Project Leader with a strong record of delivering complex, high-impact initiatives across fast-paced environments. Skilled in aligning technology solutions with business goals, mitigating risk, and driving cross-functional collaboration. Proven ability to lead diverse teams, manage enterprise-wide deployments, and deliver projects on time and within scope to support organizational growth and operational excellence.
Hi, I’m
Helena Chestnut
IT Leader | Entrepreneur | Mentor
Atlanta,USA
Summary
Skills
- IT Operations & Cloud Management
- Project Leadership & Cross-Team Collaboration
- Healthcare & Education Compliance (HIPAA, SOC 2, FERPA)
- ITSM Process Improvement
- ERP & SaaS Integrations
- Identity & Access Management (SSO, SCIM, Azure AD)
- Competitive Analysis
- Strategic partnerships
- Automation Management
- Adaptability & Resilience
- Mental Agility
Skills
Skills
Cloud & Infrastructure: Azure, AWS, GCP, Cisco Meraki, Palo Alto, Fortinet, SonicWall
Endpoint & System Management: JAMF Pro, Microsoft Intune, ServiceNow, Kanji, CoPilot
Security & Compliance: Okta, Duo, BitDefender, Microsoft Defender, Cisco Umbrella, 1Password Business, HIPAA, ISO 27001, SOC 2, GDPR
SaaS & Productivity: Microsoft 365, Google Workspace, Workday, Salesforce, Atlassian Suite (JIRA, Confluence), Slack, Zoom, Monday.com
Automation & DevOps: Python, GitHub, Bash, Ansible, Power Automate, Tableau
Virtualization & Remote Support: VMWare, Parallels, Microsoft Remote Desktop, TeamViewer
Certification
- Microsoft 365 Certified: Administrator Expert (MS-102)
- Microsoft Certified: Azure Administrator Associate
- Microsoft Certified: Endpoint Administrator Associate
- PMP Certification (In Progress)
- Information Security Certified: ISC2
Overview
10
years of professional experience
1
Certificate
Work History
Greyscale Solutions, LLC
Manager of Business Development
01.2025 - Current
Job overview
- Partnered closely with leadership and client-facing teams to align business and IT strategy, particularly for organizations in healthcare and education.
- Built and coached a business development team with a strong focus on mission-driven clients, including FQHCs and educational, technical institutions.
- Represented the organization at key events, building relationships with potential partners and keeping a pulse on industry needs.
- Mentored junior team members, providing guidance and support to foster professional growth and career advancement within the company.
- Represented company and promoted products at conferences and industry events.
- Developed compelling presentation decks to gain approval for ideas and communicate results.
- Delivered recommendations to long-term accounts to promote brand awareness to key audience.
- Resolved problems with high-profile customers to maintain relationships and increase return customer base.
Fluidra Global
Senior Manager, IT Operations and Help Desk
01.2024 - 08.2024
Job overview
- Directed nationwide IT operations supporting 3,000+ users, including help desk, infrastructure, and endpoint management.
- Aligned IT initiatives with business needs by fostering strong partnerships with HR, Compliance, and department leads.
- Scaled service desk operations through ServiceNow implementation and workflow automation.
- Spearheaded successful rollouts of Microsoft Teams, Zoom Phones, and Workday to enhance communication and HR efficiency.
- Led complex, multi-site technology projects from initiation through completion, meeting critical deadlines and budgets.
- Improved system performance and user experience through continuous evaluation, automation, and standardization.
- Designed and executed training programs to support organization-wide adoption of new technologies.
- Implemented HIPAA-compliant systems and cybersecurity protocols to safeguard sensitive data.
- Developed and maintained disaster recovery and business continuity plans to mitigate operational disruptions.
- Managed departmental budgets, negotiated vendor contracts, and oversaw IT procurement and resource allocation.
CampusWorks, LLC
Director of IT
10.2022 - 06.2023
Job overview
- Took the lead as the organization’s first internal IT leader, building the entire internal IT function from scratch to support a remote, nationwide team.
- Worked closely with the CEO, CFO, and senior leaders to earn SOC 2 Type II certification—ensuring we could support higher ed clients with confidence.
- Rolled out a full-service help desk and endpoint management system, bringing order and visibility to day-to-day support.
- Implemented a project portfolio management (PPM) tool to help managed services teams track their work and tell their success stories more clearly.
- Oversaw a seamless integration between Workday and Salesforce to support HR, finance, and professional services all in one ecosystem.
- Refined employee onboarding by adding automation, documentation, and a human touch—making day one easier for everyone.
- Launched passwordless login and application provisioning to reduce friction and increase security across the board.
- Documented IT services, roles, and responsibilities in a clear, easy-to-understand handbook used across departments.
OneTrust
Associate Director of IT Operations, Americas
10.2019 - 06.2022
Job overview
- Directed nationwide IT operations for 3,000+ users, overseeing help desk, infrastructure, onboarding, and endpoint support.
- Led enterprise rollouts of Microsoft Teams, Zoom Phones, and Workday, enhancing communication and streamlining HR processes.
- Scaled service desk operations by implementing ServiceNow and automating workflows, improving efficiency and user satisfaction.
- Delivered multi-site technology projects on time and within budget, aligning IT strategy with organizational goals.
- Implemented HIPAA-compliant systems and cybersecurity protocols to safeguard data and ensure regulatory compliance.
- Managed IT budgets and vendor relationships, securing cost-effective solutions and driving procurement strategy.
Blink Health
Director, IT, and Workplace Resources
10.2018 - 07.2019
Job overview
Managed by Q, Inc. (WeWork)
Senior Manager, IT
07.2016 - 09.2018
Job overview
Oscar Health
Senior IT Engineer
12.2014 - 03.2016
Job overview
Education
Purdue University (formerly Kaplan University)NEW YORK, NY
Master of Science from Advanced Studies in Network Technology
05.2008
University Overview
HYBRID: NEW YORK, NY & VIRTUAL
Columbia University - Fu Foundation School of EngineeringNEW YORK, NY
Master of Science from Computer Engineering
05.2004
University Overview
Availability
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Timeline
Manager of Business Development
Greyscale Solutions, LLC
01.2025 - Current
Senior Manager, IT Operations and Help Desk
Fluidra Global
01.2024 - 08.2024
Director of IT
CampusWorks, LLC
10.2022 - 06.2023
Associate Director of IT Operations, Americas
OneTrust
10.2019 - 06.2022
Director, IT, and Workplace Resources
Blink Health
10.2018 - 07.2019
Senior Manager, IT
Managed by Q, Inc. (WeWork)
07.2016 - 09.2018
Senior IT Engineer
Oscar Health
12.2014 - 03.2016
Purdue University (formerly Kaplan University)
Master of Science from Advanced Studies in Network Technology
Columbia University - Fu Foundation School of Engineering
Master of Science from Computer Engineering
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