JOB DESCRIPTION

POSITION TITLE

IT Helpdesk Support Specialist

LOCATION

Remote – Dallas, TX or Charleston, SC area

HIRING MANAGER

Hemchand Venigalla

SUNNY

Sunny is changing the world by leveraging digital technologies to help people live healthier lives. Using a digital first strategy, Sunny is helping health plans and employer groups to engage consumers with innovative, integrated health and wealth tools to improve outcomes and drive quantifiable results.

Sunny Payments & Benefits solution helps consumers capitalize on their health benefits by making it easy to spend smarter via directed spend technology for supplemental and specialized benefits. Sunny Rewards, an integrated Reward Dashboard, pairs high-value actions with appropriate financial incentives. Sunny’s simplified consumer experience is designed to maximize rewards, improve health outcomes, and drive quantifiable results.

Sunny’s team of experienced leaders is what truly sets them apart. The elite team represents all corners of the market, ensuring a comprehensive and holistic understanding of the dynamics at play. Drawing from their collective insights, extensive knowledge, and expertise in the field of consumer engagement, the team knows what works and what doesn’t with today’s consumers.

WORKING HERE

Invaluable lessons learned is the genesis of Sunny, which has led to a fine-tuned product-to-market fit that caters to a range of stakeholders in the healthcare space. Whether it’s payers, employers, or individual consumers, Sunny has refined its solutions to meet their unique requirements. Sunny is unmatched in its ability to customize and employ refreshing levels of creativity, adaptability, and inventiveness. This is crucial in an industry where trends and demands change rapidly and calls for a very nimble team.

Sunny is fully committed to revolutionizing consumer engagement. Finally, alignment of valuable actions with financial incentives, a knowledgeable and diverse management team, and a keen understanding of customization and market trends have been brought together to make a significant impact on the way consumers interact with their health and well-being - we hope you consider taking this journey with us!

OPPORTUNITY

This is a remote position; however, candidates must be located in or near Dallas, TX or Charleston, SC. The individual will work remotely but will be expected to come into the local Sunny office periodically, as business needs require.

Sunny Benefits is seeking a motivated and technically skilled IT Helpdesk Support Specialist to join our IT Operations team. In this role, you will serve as the first and second point of contact for all internal technology needs — ensuring our employees have the tools, access, and support they need to stay productive in a fast-paced, compliance-driven environment.

You will play a critical role in managing endpoints, supporting our Microsoft 365 environment, administering Mobile Device Management (MDM) policies, and maintaining hardware across a hybrid workforce. This position requires someone who thrives on solving problems quickly, communicates clearly with non-technical users, and takes pride in keeping our IT environment secure, organized, and running smoothly.

SCOPE OF RESPONSIBILITIES

End User Support:

Serve as the primary point of contact for IT helpdesk tickets via phone, email, and ticketing system (e.g., Jira Service Management)
Provide Tier 1 and Tier 2 support for hardware, software, networking, and access issues
Troubleshoot and resolve issues efficiently, escalating complex problems to senior engineers as needed
Maintain clear communication with end users throughout the support lifecycle and ensure SLA adherence
Document resolutions, create knowledge base articles, and contribute to self-service resources

Microsoft 365 Administration:

Provision and manage Microsoft 365 user accounts, licenses, mailboxes, and distribution groups
Configure and support Outlook, Teams, SharePoint, OneDrive, and other M365 applications
Troubleshoot M365 issues including email delivery, calendar sync, permissions, and conditional access
Assist with M365 policy configuration including retention policies, DLP rules, and MFA enforcement

Mobile Device Management (MDM):

Administer MDM solutions (e.g., Microsoft Intune, Jamf) for enrollment, policy management, and compliance
Manage device lifecycle including provisioning, configuration, and decommissioning of corporate and BYOD devices
Enforce security baselines, encryption, remote wipe, and conditional access policies across device fleets
Support zero-trust and BYOD initiatives in alignment with company security policies

Hardware Support and Asset Management:

Diagnose and resolve hardware issues across laptops, desktops, monitors, and peripherals (Windows & macOS)
Manage IT asset inventory including tracking, procurement coordination, imaging, and disposal
Set up and configure workstations, ensure proper OS and application deployments for new hires
Coordinate with vendors for warranty repairs and hardware replacements

Security and Compliance Support:

Support SOC 2 and HiTrust compliance requirements as they relate to endpoint security and access control
Assist with RBAC enforcement, access reviews, and user lifecycle management (onboarding/offboarding)
Monitor and respond to DLP alerts and assist with security awareness efforts
Follow established ITIL-aligned change management procedures for all changes to IT systems

REQUIRED CANDIDATE QUALIFICATIONS

3+ years of experience in an IT helpdesk or desktop support role supporting 100+ end users
Hands-on experience administering Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive, Intune)
Proficiency with MDM platforms such as Microsoft Intune
Strong hardware troubleshooting skills across Windows 10/11 and macOS environments
Experience managing IT assets and user lifecycle (onboarding/offboarding workflows)
Familiarity with ITIL best practices and ticketing systems (e.g., Jira Service Management, ServiceNow)
Understanding of networking fundamentals: DNS, DHCP, VPN, Wi-Fi troubleshooting
Knowledge of Azure AD (Entra ID) for user and group management
Strong written and verbal communication skills with ability to explain technical concepts clearly to non-technical users

PREFERRED CANDIDATE QUALIFICATIONS

Experience supporting a compliance-sensitive environment (SOC 2, HiTrust, HIPAA, or similar)
Familiarity with Zero Trust security principles, MFA enforcement, and conditional access policies
Experience with DLP configuration and enforcement in M365 Purview or similar platforms
Exposure to cloud environments (AWS, Azure) and understanding of cloud-hosted applications
Experience with scripting for automation (PowerShell for M365/Intune tasks preferred)
Prior experience in a healthcare or fintech company with PHI/PII data sensitivity
Take full ownership of every support interaction — ensuring end users feel heard, supported, and confident in the resolution process while maintaining clear communication and SLA adherence throughout.
Approaches problems with curiosity and patience — taking the time to understand the root cause rather than just applying a quick fix
Demonstrated ability to thrive in a fast-paced, high-growth environment where priorities evolve quickly, processes are continuously refined, and a willingness to step up beyond defined responsibilities is both valued and expected
A continuous learning mindset — open to feedback, eager to grow, and committed to developing both technical and interpersonal skills in a fast-moving environment

COMPENSATION & BENEFITS

Sunny has an ambitious vision to empower people to live healthier and happier lives. We are committed to delivering an outstanding culture and experience for every employee. We offer comprehensive benefits and perks, as well as a high level of flexibility.

As a full-time employee, you can expect:

A competitive compensation package in line with leading technology companies
Flexible PTO with manager approval
Employer sponsored healthcare, dental, vision, short and long term disability, and life insurance opportunities
A company sponsored supplemental benefits plan worth over $1,800 annually in 2024
401k retirement savings plan company matched up to 5%

SUNNY’S COMMITMENTS

Sunny Rewards is an Equal Opportunity Employer. We’re passionately dedicated to providing the ultimate consumer engagement solution, so please send us a note with your comments or questions at info@sunnyrewards.com

Sunny

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IT Helpdesk Support Specialist