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About Us
At Gifthealth, we're revolutionizing the way people experience healthcare by simplifying the process of managing prescriptions and health services. Our mission is to provide a seamless, personalized, and efficient healthcare experience for all our customers. We're a dynamic, innovative, and customer-centric company dedicated to making a positive impact on people's lives.
Position Summary
We are seeking a highly skilled Sr. Five9 Contact Center Engineer to lead the design, implementation, optimization, and support of enterprise cloud contact center solutions. The ideal candidate combines deep technical expertise in Five9 and VoIP technologies with strong consulting, solution architecture, and customer-facing experience.
As a trusted technical advisor, the Sr. Five9 Contact Center Engineer partners with customers, business stakeholders, and cross-functional engineering teams to deliver scalable, highly available contact center solutions that enhance customer experience and operational efficiency. This person serves as a subject matter expert, guiding technical strategy, mentoring engineering teams, and driving successful enterprise implementations from discovery through production.
The ideal Sr. Five9 Contact Center Engineer is equally comfortable designing enterprise contact center architecture that supports 1,000+ users and 25+ programs and consulting directly with executive stakeholders. This person is a strategic thinker and hands-on engineer who enjoys translating customer requests into tangible solutions, communicates confidently with executives and technical teams alike, and is recognized as a trusted advisor capable of leading enterprise contact center transformations.
Key Responsibilities

• Design, architect, implement, and support enterprise Five9 contact center solutions.
• Lead customer discovery sessions to understand business requirements and translate them into scalable technical solutions.
• Configure and deploy Five9 components including routing strategies, IVRs, campaigns, integrations, reporting, and voice infrastructure.
• Design and implement SIP trunk connectivity, carrier integrations, and high-availability voice architectures.
• Troubleshoot complex voice, signaling, network, and application issues across enterprise environments.
• Serve as the technical lead for large-scale deployments, migrations, Proof of Concepts (POCs), and modernization initiatives.
• Provide architecture guidance and technical recommendations while balancing business objectives, timelines, and budget constraints.
• Collaborate with network, security, cloud, infrastructure, development, and customer success teams throughout project lifecycles.
• Create implementation standards, engineering documentation, deployment runbooks, and operational best practices.
• Lead technical knowledge-sharing sessions and establish engineering standards across the organization.
• Identify opportunities to automate operational processes and improve platform scalability, resiliency, and performance.
• Perform root cause analysis for production incidents and implement long-term corrective actions.
• Present technical solutions and architecture recommendations to executive stakeholders, customers, and project leadership.

Qualifications

• Education: Bachelor's degree in Computer Science, Information Technology, Telecommunications, or equivalent professional experience.
• Experience: 8-10+ years of experience designing and supporting enterprise telecommunications or cloud contact center environments, including 5+ years supporting a user base of 1,000+ users across 20+ programs.
• Knowledge, Skills, and Abilities:
  • Extensive hands-on experience administering and implementing Five9 solutions.
  • Strong understanding of SIP signaling, RTP media streams, QoS, DNS, networking, and voice protocols.
  • Experience with enterprise call flow design, IVR development, routing strategies, and omnichannel customer engagement.
  • Experience integrating contact center platforms with CRM, workforce optimization, and third-party business applications.
  • Exceptional troubleshooting and analytical skills across voice, networking, and cloud environments.
  • Excellent written, verbal, and presentation skills with the ability to communicate effectively with both technical and executive audiences.
  • Proven ability to lead complex enterprise implementations while managing multiple priorities.
  • Nice to Have
  • Knowledge of APIs, REST services, webhooks, and integration platforms.
  • Experience developing automation scripts using Python, JavaScript, or PowerShell.
  • Familiarity with cloud platforms such as AWS or Azure.
  • Certifications such as Five9 Certified Engineer, CCNA, CCNP, AWS, Azure, or equivalent contact center certifications.
  • Experience leading consulting engagements or serving as a technical advisor for enterprise customers.

Work Environment

• Location: Hybrid - remote with travel to client sites and offices as needed.
• Schedule: Full-time; occasional after-hours support for production incidents and enterprise go-lives.
• Regular engagement with customers, executive stakeholders, and cross-functional network, security, cloud, infrastructure, and customer success teams throughout project lifecycles.

Key Essential Functions [example below key provision - you may require others]

• Must be able to work at a computer for extended periods, including extended screen time for configuration, troubleshooting, and documentation work.
• Must be able to participate in on-call rotations and respond to production incidents outside of standard business hours as needed.
• Must be able to travel domestically, and occasionally internationally, to customer sites for discovery sessions, implementations, and go-lives.
• Must be able to communicate effectively, verbally and in writing, with both technical teams and executive stakeholders.

Equal Employment Opportunity (EEO) Statement
Gifthealth is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. All employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity, transgender status, national origin, age, disability, veteran status, or any other legally protected status.
We celebrate diversity and are committed to creating an inclusive environment for all employees. If you do not meet every requirement but still feel you would be a great fit for this role, we encourage you to apply!
Disclaimer
This job description is intended to describe the general nature and level of work being performed. It is not intended to be an exhaustive list of all responsibilities, duties, or skills required of personnel. Gifthealth reserves the right to modify job duties or descriptions at any time.
Salary Description
$115,000-130,000