📍 Job Overview

Job Title: Senior Systems Engineer - Observability/Windows
Company: Clear Capital | CubiCasa
Location: Remote - US
Job Type: Full-Time
Category: DevOps Engineer, System Administrator
Date Posted: 2025-07-21
Experience Level: 5-10 years
Remote Status: Remote

🚀 Role Summary

Key Responsibilities: Own and innovate monitoring and observability solutions across a hybrid cloud environment. Troubleshoot complex problems and partner with development teams to build new solutions.
Key Skills: Monitoring, log aggregation, Windows Server, Active Directory, enterprise virtualization, NAS/SAN storage, CI/CD practices, Python, PowerShell, automation, public cloud, infrastructure as code.

💻 Primary Responsibilities

Monitoring & Observability: Design, maintain, and operate monitoring solutions to ensure organization-wide visibility. Grow and maintain infrastructure from bare metal to hypervisors, VMs to containers within state-of-the-art datacenters.
Troubleshooting & Problem-Solving: Troubleshoot complex problems to root cause across technology stacks and teams. Modernize administrative practices and partner with development teams to build new solutions from proof of concept to production.
Collaboration & Communication: Work closely with software development teams to build highly scalable, secure, and always-available solutions. Contribute to an engineering culture and mindset.

🎓 Skills & Qualifications

Education: Bachelor's degree in Computer Science, Engineering, or a related field. Relevant experience may be considered in lieu of a degree.

Experience: 5+ years in a Senior Systems Engineer role in a diverse enterprise environment.

Required Skills:

Strong operational monitoring experience with hybrid cloud, building alerting, and dashboards for organization-wide visibility.
Strong understanding of SLA's and solutions to measure, monitor, and report on the health, performance, and reliability of systems and applications.
Industry certification for core discipline (e.g., MCSE, RHCE, Linux+, NCDA, VCP).
Technical Proficiencies:
- Monitoring: Nagios, Prometheus, Grafana, ELK Stack, Datadog, or similar.
- Log aggregation, analysis, and management of logging systems.
- Windows Server and Active Directory.
- Enterprise virtualization environments (VMware, HyperV).
- Enterprise NAS/SAN Storage: iSCSI, NFS, CIFS (NetApp).
- CI/CD practices, SDLC toolsets; specifically Git, Jenkins, Bitbucket, VSCode.
- Python, PowerShell, and other scripting.

Preferred Skills:

Automation/orchestration tools (e.g., Ansible, Puppet, Chef).
Public cloud experience (e.g., AWS, Azure, Google Cloud).
Infrastructure as code (e.g., Terraform, CloudFormation).
Endless curiosity and a passion for learning new technologies.

📊 Web Portfolio & Project Requirements

Portfolio Essentials:
- Demonstrate your monitoring and observability solutions, including alerting and dashboard examples.
- Showcase your troubleshooting skills with case studies or examples of complex problems you've solved.
- Highlight your collaboration and communication skills with examples of projects where you've worked closely with development teams.
Technical Documentation:
- Provide documentation on your monitoring and observability solutions, including architecture, configuration, and best practices.
- Include examples of your scripting and automation work, demonstrating your proficiency in Python, PowerShell, or other relevant languages.

💵 Compensation & Benefits

Salary Range: $120,000 - $155,000 annually, depending on location, experience, and qualifications.

Benefits:

Comprehensive medical, dental, and company-paid vision insurance.
401(k) retirement plan with employer match.
Voluntary life and AD&D insurance options.
Paid time off (PTO) and paid holidays.
Employee assistance and wellness programs.
Company-paid short-term disability coverage.
Company contributions to health savings funds (with participation in the high-deductible health plan).
Company-paid access to Galileo for virtual primary care and Rula for virtual mental health resources.
Career and skill development resources.
A mission-driven environment where your work makes a measurable impact on the real estate industry.

🎯 Team & Company Context

Company Culture:

Industry: Real estate technology.
Company Size: Medium to large (200-500 employees).
Founded: 1999.
Team Structure: The IT Operations team works closely with software development teams to build and maintain highly scalable, secure, and always-available solutions.
Development Methodology: Agile/Scrum methodologies and continuous integration/continuous deployment (CI/CD) pipelines.
Company Website: clearcapital.com

Career & Growth Analysis:

Web Technology Career Level: Senior Systems Engineer, focusing on monitoring and observability in a hybrid cloud environment.
Reporting Structure: Reports directly to the IT Operations Manager.
Technical Impact: Responsible for ensuring the health, performance, and reliability of systems and applications across the organization.

Growth Opportunities:

Technical Growth: Expand your skills in monitoring, observability, and automation tools. Contribute to the modernization of administrative practices and infrastructure.
Leadership Growth: Develop your leadership skills by mentoring junior team members and collaborating with cross-functional teams.
Architecture Impact: Influence the architecture and design of monitoring and observability solutions, ensuring they meet the needs of the organization.

🌐 Work Environment

Office Type: Remote work environment with occasional on-site meetings or training sessions.

Office Location(s): Remote - US (timezone: America/Chicago).

Workspace Context:

Remote Work: Work from home or a remote location, with a dedicated workspace and reliable internet connection.
Collaboration Tools: Utilize collaboration tools such as Slack, Microsoft Teams, or Google Workspace for communication and project management.
Hardware & Software: Use company-provided hardware and software, including laptops, monitors, and relevant software licenses.

Work Schedule: Full-time, with a flexible work schedule that may include occasional on-call duties or after-hours support.

📄 Application & Technical Interview Process

Interview Process:

Step 1 - Phone/Video Screen: A brief conversation to discuss your experience, qualifications, and career goals.
Step 2 - Technical Assessment: A hands-on assessment or take-home project to evaluate your technical skills in monitoring, troubleshooting, and scripting.
Step 3 - On-site/Video Interview: A deeper dive into your technical expertise, problem-solving skills, and cultural fit with the team.
Step 4 - Final Decision: The hiring team will make a final decision based on your technical skills, cultural fit, and alignment with the company's values.

Portfolio Review Tips:

Tip 1: Highlight your monitoring and observability solutions, including alerting and dashboard examples.
Tip 2: Showcase your troubleshooting skills with case studies or examples of complex problems you've solved.
Tip 3: Demonstrate your collaboration and communication skills with examples of projects where you've worked closely with development teams.

Technical Challenge Preparation:

Tip 1: Brush up on your monitoring and troubleshooting skills, focusing on hybrid cloud environments.
Tip 2: Familiarize yourself with the company's tech stack and be prepared to discuss your experience with relevant tools and technologies.
Tip 3: Practice your problem-solving skills and be ready to explain your thought process and decision-making during the interview.

ATS Keywords: (Organized by category)

Monitoring: Nagios, Prometheus, Grafana, ELK Stack, Datadog, Zabbix, New Relic, AppDynamics.
Log Aggregation: ELK Stack, Logstash, Kibana, Elasticsearch, Splunk, Graylog.
Windows Server: Active Directory, Group Policy, PowerShell, Windows Server 2016, Windows Server 2019.
Enterprise Virtualization: VMware, HyperV, vSphere, ESXi, vCenter, Hyper-V Manager.
NAS/SAN Storage: NetApp, EMC, Dell EMC, HPE, QNAP, Synology.
CI/CD Practices: Git, Jenkins, Bitbucket, VSCode, GitLab, CircleCI, Travis CI.
Scripting: Python, PowerShell, Bash, Ansible, Puppet, Chef, Terraform, CloudFormation.
Soft Skills: Problem-solving, troubleshooting, communication, collaboration, teamwork, leadership.
Industry Terms: Hybrid cloud, multi-cloud, on-premises, cloud migration, infrastructure as code, IT operations, DevOps.

🛠 Technology Stack & Web Infrastructure

Monitoring & Observability:

Nagios, Prometheus, Grafana, ELK Stack, Datadog, or similar.

Log Aggregation:

ELK Stack (Elasticsearch, Logstash, Kibana), Splunk, Graylog, or similar.

Windows Server & Active Directory:

Windows Server 2016, Windows Server 2019, Active Directory, Group Policy, PowerShell.

Enterprise Virtualization:

VMware (vSphere, ESXi, vCenter), HyperV, Hyper-V Manager.

NAS/SAN Storage:

NetApp, EMC, Dell EMC, HPE, QNAP, Synology, or similar.

CI/CD Practices & Tools:

Git, Jenkins, Bitbucket, VSCode, GitLab, CircleCI, Travis CI, or similar.

Scripting & Automation:

Python, PowerShell, Bash, Ansible, Puppet, Chef, Terraform, CloudFormation, or similar.

👥 Team Culture & Values

Clear Capital Values:

Wherever it Leads, Whatever it Takes®: No matter how remote, complex, or unexpected, our commitment never wavers.
Hire NICE people: Skills can be taught, but character shines through. We seek those who bring integrity, kindness, and grit.
Lift others up: We lead with empathy and strive to improve the lives of those around us.
Sweat the details: Excellence lives in the little things. Getting it just so is how we make a big impact.
Raise the bar: We don't settle for industry standards; we redefine them.

Collaboration Style:

Cross-functional Integration: Work closely with software development teams to build highly scalable, secure, and always-available solutions.
Code Review Culture: Collaborate with team members to review and improve code, scripts, and configurations.
Knowledge Sharing: Share your expertise and learn from others to continuously improve your skills and the team's collective knowledge.

⚡ Challenges & Growth Opportunities

Technical Challenges:

Challenge 1: Design, implement, and maintain monitoring and observability solutions across a hybrid cloud environment.
Challenge 2: Troubleshoot complex problems and identify root causes across diverse technology stacks and teams.
Challenge 3: Modernize administrative practices and contribute to the modernization of infrastructure.
Challenge 4: Collaborate with development teams to build new solutions from proof of concept to production.

Learning & Development Opportunities:

Opportunity 1: Expand your skills in monitoring, observability, and automation tools.
Opportunity 2: Contribute to the modernization of administrative practices and infrastructure.
Opportunity 3: Develop your leadership skills by mentoring junior team members and collaborating with cross-functional teams.
Opportunity 4: Influence the architecture and design of monitoring and observability solutions, ensuring they meet the needs of the organization.

💡 Interview Preparation

Technical Questions:

Question 1: Describe your experience with monitoring and observability tools. How have you used them to ensure organization-wide visibility and maintain system health?
Question 2: Walk us through a complex problem you've troubleshot in the past. What steps did you take to identify the root cause, and what was the outcome?
Question 3: How do you approach automating repetitive tasks or improving existing processes? Can you provide an example from your previous experience?

Company & Culture Questions:

Question 1: How do you stay up-to-date with the latest trends and best practices in monitoring and observability? Can you share an example of a new tool or technique you've recently explored?
Question 2: Describe your experience working with development teams. How have you collaborated to build new solutions from proof of concept to production?
Question 3: How do you prioritize and manage your workload when facing multiple projects or deadlines? Can you provide an example from your previous experience?

Portfolio Presentation Strategy:

Strategy 1: Highlight your monitoring and observability solutions, including alerting and dashboard examples.
Strategy 2: Showcase your troubleshooting skills with case studies or examples of complex problems you've solved.
Strategy 3: Demonstrate your collaboration and communication skills with examples of projects where you've worked closely with development teams.

📌 Application Steps

To apply for this Senior Systems Engineer - Observability/Windows position:

Submit your application through the application link provided.
Customize your resume and portfolio to highlight your relevant experience and skills in monitoring, troubleshooting, and scripting.
Prepare for the technical assessment by brushing up on your monitoring and troublesability skills, and familiarizing yourself with the company's tech stack.
Research the company and its values to ensure a strong cultural fit and alignment with your career goals.
Practice your problem-solving skills and be ready to explain your thought process and decision-making during the interview.

Content Guidelines (IMPORTANT: Do not include this in the output)

Web Technology-Specific Focus:

Tailor every section specifically to DevOps, system administration, and web infrastructure roles.
Include web technology methodologies, responsive design principles, and server management practices.
Emphasize web portfolio requirements, live project demonstrations, and user experience considerations.
Address web technology career progression, emerging technology adoption, and technical specialization.

Quality Standards:

Ensure no content overlap between sections; each section must contain unique information.
Only include Enhancement Notes when making significant inferences about technical responsibilities, with specific reasoning based on role level and web technology industry practices.
Be comprehensive but concise, prioritizing actionable information over descriptive text.
Strategically distribute web technology and server administration-related keywords throughout all sections naturally.
Provide realistic salary ranges based on location, experience level, and web technology specialization.

Industry Expertise:

Include specific web technologies, frameworks, server platforms, and infrastructure tools relevant to the role.
Address web technology career progression paths and technical leadership opportunities in web teams.
Provide tactical advice for web portfolio development, live demonstrations, and project case studies.
Include web technology-specific interview preparation and coding challenge guidance.
Emphasize responsive design, performance optimization, accessibility standards, and user experience principles.

Professional Standards:

Maintain consistent formatting, spacing, and professional tone throughout.
Use web technology and server administration industry terminology appropriately and accurately.
Include comprehensive benefits and growth opportunities relevant to web technology professionals.
Provide actionable insights that give web technology professionals a competitive advantage.
Focus on web technology team culture, cross-functional collaboration, and user impact measurement.

Technical Focus & Portfolio Emphasis:

Emphasize web technology best practices, responsive design principles, and performance optimization.
Include specific portfolio requirements tailored to the web technology discipline and role level.
Address browser compatibility, accessibility standards, and user experience design principles.
Focus on problem-solving methods, performance optimization, and scalable web architecture.
Include technical presentation skills and stakeholder communication for web projects.

Avoid:

Generic business jargon not relevant to web technology roles.
Placeholder text or incomplete sections.
Repetitive content across different sections.
Non-web technology terminology unless relevant to the specific role.
Marketing language unrelated to web technology, server administration, or user experience.

Generate comprehensive, web technology-focused content that serves as a valuable resource for web developers, server administrators, and infrastructure professionals evaluating career opportunities and preparing for technical interviews in the web technology industry.

Senior Systems Engineer - Observability/Windows