Role Description At Privateer IT, we are always looking for talented individuals who thrive on big ideas and bold action. As a seasoned Tier 1 Helpdesk Support Specialist with 1-3 years of experience, you bring a passion for innovation and a commitment to delivering exceptional results. You are driven by outcomes, obsessed with quality, and focused on using innovation as a key driver for client satisfaction and high-performance delivery. Here, you will find the opportunity to grow as a professional in a collaborative, team-oriented environment, where your contributions will have a direct impact on mission-critical projects that make a difference to the citizens we serve. - U.S. Citizenship with the ability to obtain and/or maintain the security clearance level stated below is required for this specific opportunity. Privateer IT, LLC is unable to sponsor at this time. - We strongly encourage Military Veterans and individuals with disabilities to apply! Privateer is seeking an experienced Tier 1 Helpdesk Support Specialist to support the Department of Veterans Affairs (VA). This role provides frontline technical support for an AI-powered clinical intelligence platform supporting the U.S. Department of Veterans Affairs (VA). This position is responsible for delivering high-quality customer service, resolving basic technical issues, and ensuring seamless system access and usability for end users. Qualifications - 1–3 years of helpdesk or technical support experience supporting end users - Active/current VA clearance (required) - Experience using ticketing systems and documenting support interactions - Basic understanding of application troubleshooting and user access management - Strong verbal and written communication skills - Ability to work in a fast-paced, customer-focused environment - High School Diploma or equivalent Requirements - Experience supporting healthcare or clinical systems (nice to have) - Familiarity with AI-based applications or SaaS platforms (nice to have) - Knowledge of VA systems or federal IT environments (nice to have) - IT certifications (e.g., CompTIA A+, ITIL Foundation) are a plus Benefits - May include shift-based schedules to support operational coverage - Remote or onsite work depending on contract requirements - Must adhere to all VA security and compliance standards Physical Requirements - Ability to lift, carry, or move objects up to [specific weight requirement, e.g., 50 lbs]. Requires prolonged standing, walking, or physical activity for extended periods (e.g., up to 8 hours). - Must have the ability to see small details or distinguish colors and communicate clearly in person, via telephone, or during video teleconferences. - Ability to talk, listen, and speak clearly on the phone or in video calls. - Involves performing repetitive tasks, such as typing, data entry, or similar actions. - Requires the ability to kneel, bend, stoop, or squat regularly. Additional Functional Requirements - Ability to safely and successfully perform the essential job functions consistent with the ADA, FMLA, and other federal, state, and local standards, including meeting qualitative and/or quantitative productivity standards. - Ability to maintain regular, punctual attendance in alignment with ADA, FMLA, and other federal, state, and local standards. Accommodation Statement Privateer IT is committed to providing reasonable accommodations to individuals with disabilities, as needed, to ensure equal access to the application and hiring process.

Role Description The Owner Services Specialist serves as a primary point of contact for our homeowners, providing exceptional service and support throughout their partnership with our company. This role requires strong communication skills, attention to detail, and a collaborative mindset. The Owner Services Specialist will assist both new and existing homeowners with questions related to their property, monthly statements, guest updates, and general information about the area. You will work closely with the Reservations, Maintenance, Guest Services, and Housekeeping teams to ensure that each homeowner is informed and confident that their property is being well cared for. Key Responsibilities - Serve as the first point of contact for homeowner inquiries via phone, email, and text, ensuring timely, professional, and courteous responses. - Provide knowledgeable assistance regarding property details, statements, maintenance issues, and company policies. - Support the Owner Services Manager with reporting, data entry, and updates to HOA rules and regulations. - Act as liaison between homeowners and internal departments, including Reservations, Maintenance, Guest Services, and Housekeeping. - Create and manage service or maintenance tasks in company software as needed in response to homeowner or guest concerns. - Review monthly owner statements for accuracy, identifying potential issues such as billing errors or unusually high utility charges. - Assist homeowners with property-related projects such as installations, remodels, deliveries, and special requests. - Partner with the Business Development team to assist with onboarding new properties and ensuring a smooth transition into company management. - Maintain a thorough understanding of company rental inventory, policies, and procedures, as well as local community resources. - Utilize Microsoft Excel, Outlook, and other internal software systems effectively to complete daily tasks. - Perform additional responsibilities as assigned to support the Owner Services department and overall company operations. Qualifications - Strong written and verbal communication skills. - Excellent organizational skills and attention to detail. - Proficient in Microsoft Office (Excel and Outlook) and able to learn new software systems quickly. - Ability to multitask in a fast-paced environment while maintaining a positive and professional demeanor. - Previous experience in property management, hospitality, or customer service preferred. Benefits - Hourly Pay Range: $18 - $21 based on experience - Paid time off such as PTO, sick days, and vacation days - Health insurance - Life insurance - Dental insurance - Vision insurance - Retirement benefits or accounts - Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs - Long term disability insurance - Short term disability insurance Company Description Cape & Coast Premier Properties offers the most extensive collection of luxury beach homes along the Forgotten Coast, from Cape San Blas to St. George Island and Mexico Beach. Focusing on beachfront and private pool properties, we provide world-class guest experiences with upscale amenities, concierge offerings, and white-glove service. - We believe the best vacations take place in strong local communities. - We always aim to create growth and opportunity for our team. - We measure success on the happiness of our guests, team, and the community in which we serve.

• Support the CFO with financial and billing operations • Manage monthly and periodic billings within the Deltek Costpoint system • Submit and track invoices through PIEE/WAWF or other customer-required platforms • Monitor and track DFAS and customer payments to ensure timely receipt • Interface with Government CORs and other points of contact to resolve billing and payment issues • Assist in developing reports related to billing activities, including subcontractor integration • Provide monthly financial reports to Delivery Managers and leadership • Coordinate with Delivery Managers to resolve invoice rejections tied to operational issues • Set up and maintain projects and employee data in Deltek Costpoint per contract requirements • Report on outstanding billings to the CFO on a monthly basis • Manage subcontractor invoicing, including data entry and coordination with the Subcontracts Manager • Serve as a backup for critical finance and accounting functions as needed

Role Description As a Cloud Billing Operations Associate, you will provide support to the cloud billing process, invoicing, suspension, termination, bad debt, and credit card processing. You will manage the support case queue, perform account reconciliations, answer customer cloud billing disputes, address field inquiries, perform ad-hoc reporting for the monthly billing cycle, process Return Authorizations, and participate in cloud billing optimization projects, among other tasks. You will partner closely with customer support and engineering teams. A self-starter, problem solver, meticulous, flexible, and focused on creating an excellent experience for both internal and external customers. To succeed in this position, the Cloud Billing Operations Associate will be both an independent contributor and a team player; and will have a passion for recognizing areas of improvements and implementing change to contribute to enhancements of the overall workflow process. What You Will Be Doing - Supporting cloud billing and invoicing process - Working directly with customers as well as internal customers to understand and resolve their issues via email or sometimes by phone - Managing, prioritizing, and tracking your work in a case management system - Generating reconciliation reports from various platforms - Processing Return Authorizations and Credit Memos in NetSuite - Collaborating with various teams including Support, Legal, OrderOps, Engineering, etc. on advanced billing & contract issues to resolve customer disputes - Working with the Cloud Billing (Eng) Team to review/verify accounts subject to suspension due to nonpayment - Performing light collections for monthly subscribers through a credit card payment platform - Submitting invoices through 3rd party payment platforms as necessary - Submitting evidence for Chargeback disputes through our credit card payment gateway - Understanding the current business systems and workflows to help us make proactive process improvements - Performing root cause analysis and problem solving Qualifications - High level of enthusiasm and pride in your work - Strong ability to learn and see change and challenges as opportunities - Experience in a fast-paced, high-growth, global environment - 3-5 years of professional experience in billing operations or related financial operation - Work hours flexibility: need to work at calendar day 1 at quarter end (even if holiday/weekend) and work US hours for at least day 1-2 of each month - Strong communication skills, both verbal and written - Strong attention-to-detail - Creative problem solving skills - Strong ability to work independently and prioritize in a distributed, dynamic, fast-paced environment - Ability to interact with customers and other teams - Accustomed to working with case management system - Positivity and a love for what you do - Proficiency in MS Excel or Google Spreadsheet - VLOOKUP, pivot tables, analysis - Basic proficiency in SQL/Query language and/or Excel Macros Bonus Points - Understanding of cloud technologies, e.g., AWS, Azure, Google and cloud billing models - Experience with NetSuite, Salesforce, Stripe - Comfort using basic AI tools to increase efficiency and support day-to-day operations Benefits - Competitive pay based on the work you do here and not your previous salary - Health coverage for you and your family in many locations - Ability to craft your calendar with flexible locations and schedules for many roles - Generous number of vacation days each year - We match up to $2000 (or local currency equivalent) for financial donations and service - Up to 40 hours each year to use toward volunteer projects you love - Minimum of 16 weeks of parental leave