Senior Technical Support Engineer

About Us: Carefeed is an all-in-one operations platform to help senior living and long-term care communities simplify their daily operations. By replacing paperwork, spreadsheets, and disconnected tools with an easy-to-use solution, Carefeed saves time, reduces stress, and ensures residents, families, and staff stay informed and connected. Seamlessly integrating with EHRs and HR systems, Carefeed works alongside the tools providers already use—so they can keep everything running smoothly without extra hassle. With transparent pricing, personalized support, and scalable features, Carefeed serves over 1,600 communities, helping staff spend less time on tedious tasks and more time providing great care, keeping families in the loop, and running their communities with confidence. At Carefeed, we help senior living and long-term care teams lighten their workload, stay organized, and focus on what matters—caring for residents and supporting families. For more information, visit www.carefeed.com.     

About the Role: 

We’re seeking a mission-driven Senior Technical Support Engineer to join our growing team and serve as a key player in our customer experience and technical support. You’ll be the go-to technical expert for complex support cases, working cross-functionally with Product, Engineering, and Client Experience teams to ensure high-quality outcomes and customer satisfaction. This is a high-impact role ideal for someone who thrives on solving complex problems and making a meaningful difference for customers.

Responsibilities: 

• Act as the primary technical contact for escalated support issues, providing hands-on, expert-level troubleshooting and resolution. 
• Analyze, diagnose, and resolve highly complex technical issues related to customer onboarding, product usage, and offboarding 
• Partner with Engineering and Product teams to communicate bugs, suggest enhancements, and ensure timely resolution of customer-reported issues. 
• Create and maintain technical documentation and best practice guides to empower customers and internal teams. 
• Communicate effectively with customers through email, phone, and remote sessions to deliver world-class technical support. 

Skills:

• Proficiency working across macOS, Windows, and common SaaS platforms, including Microsoft 365, Google Workspace, Slack, and Zoom. 
• Hands-on experience with endpoint management tools (e.g., Jamf, JumpCloud) and support ticketing systems like Jira. 
• Solid understanding of networking fundamentals, including Wi-Fi diagnostics, VPN configuration, and basic firewall troubleshooting. 
• Strong interpersonal skills with the ability to clearly convey technical information to both technical and non-technical audiences. 
• Highly detail-oriented and capable of managing multiple priorities in a dynamic, fast-paced environment. 
• A proactive, service-driven approach with a strong sense of ownership in problem resolution. 
• Skilled in identifying root causes, synthesizing data, and applying structured thinking to resolve complex technical issues. 
• Familiarity with IT security best practices; experience with HIPAA or similar compliance frameworks is a plus. 
• Expertise in diagnosing and resolving issues in complex systems, including experience with: 
  • Operating Systems: Windows, Linux/Unix 
  • Networking: TCP/IP, DNS, firewalls, VPNs 
  • Databases: SQL/MySQL/PostgreSQL 
  • Cloud Platforms: AWS (preferred) 

Qualifications: 

• 5+ years in technical support or customer success engineering, with at least 2 years in a senior or escalation-level role. 
• Experience in a startup environment or healthcare industry is a plus. 
• Proven track record of providing excellent customer service and handling challenging customer situations with professionalism. 
• Familiarity with ITIL processes and service management tools (e.g., Jira, Intercom, etc.). 
• Bachelor's degree in computer science, Information Technology, or related field, or equivalent practical experience. 
• Experience working in SaaS or enterprise software environments. 

Work Location: Chicago, IL (Hybrid) 

What You’ll Love:  

• Join a fast-growing startup making a real impact in the lives of senior care providers and their communities 
• Comprehensive medical, dental, and vision insurance to support your health and well-being 
• 401(k) plan to help you plan for the future 
• Paid vacation, sick time, and company-paid holidays to support work-life balance 
• A culture that values growth and development, with opportunities to grow your career as we scale 

Carefeed provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.