DevOps Engineer (Growth Path to Team Lead)

Important: This position is open only to candidates who currently reside in one of the following US locations: Oregon, Washington, California, Connecticut, Arizona, Minnesota, Michigan, Nevada, Louisiana, Texas, North Carolina, Virginia, or D.C. This is ahard requirementfor employment. Applications from outside these locations will not be considered. --------------------------------------------------------------------------------- About Castle Rock Associates Castle Rock Associates is an industry leader in developing software for transportation agencies across North America and Europe. Our software includes real-time websites, mobile apps, and phone systems that deliver real-time, human-centered 511 traveler information to the public and other agencies—including unplanned road closures, long-term work zone reports, winter road condition updates, live camera feeds, snowplow locations, and more. We’ve been in this industry for over 40 years, but we’ve remained a small (~30 people), focused, and highly productive team with a suite of successful products that we continue to grow and develop with our clients. At the heart of our business is our 24/7/365 DevOps support team. This team deploys, maintains, and monitors our systems in the Amazon Web Services (AWS) cloud, ensuring they run reliably around the clock. An on-call rotation is in place to address technical issues as they arise. Our clients consistently tell us our customer service is unmatched in the industry. The Opportunity We’re looking for a hands-on DevOps Engineer who is eager to deepen their technical expertise while building the leadership skills to one day lead or manage our DevOps team. This is a technical role from day one — you’ll work directly in AWS, deploy and maintain services, and help solve challenging problems — but you’ll also receive mentorship from our CTO and senior engineers to prepare you for increasing leadership responsibilities. If you thrive on variety, enjoy working on a small but mighty team, and want to grow into a technical leadership role without giving up hands-on work, this is the place for you. Why This Role Is Great for You • You’re ambitious but still building experience— this role lets you keep sharpening your technical skills while learning leadership in a safe, supportive environment. • You like wearing many hats— you’ll work across AWS, automation, deployments, troubleshooting, and even client interactions. • You want clear growth steps— you’ll start with technical ownership, progress to small project leadership, and ultimately have the opportunity to run the DevOps team. • You’ll get mentorship from the top— direct guidance from our CTO and collaboration with senior engineers. • You’ll see your impact every day— in a small team, your work directly influences uptime, client satisfaction, and product success. What You’ll Do Now • Collaborate with the CTO and DevOps team to support deployments, monitoring, and maintenance of our AWS-based systems. • Participate in sprint planning and team discussions to learn how priorities are set and managed. • Deploy and verify software updates across Java, Node.js, and other platforms. • Triage and troubleshoot software and network issues. • Automate processes to make operations faster and more reliable. • Help design and implement system monitoring solutions. • Manage and configure network infrastructure and software. • Join the on-call rotation to provide 24/7 technical support (with guidance from senior team members). • Provide internal technical support across the company. How You’ll Grow • Gradually take on more responsibility for setting team priorities and guiding day-to-day operations. • Lead small projects or initiatives to practice coordination and accountability. • Mentor newer team members as you develop your leadership style. • Eventually step into the Team Lead role, managing DevOps resources and priorities while continuing hands-on work. What We’re Looking For Must-Have Skills • 2+ years of experience managing and troubleshooting distributed software systems and web applications, preferably in AWS. • Solid AWS knowledge (EC2, RDS, Route53, Lambda, CloudFormation, S3). • Strong scripting skills for automation. • Experience deploying Java web applications. • Familiarity with PostgreSQL and basic database management. • Git experience. • Comfort in both Linux and Windows environments Nice-to-Have Skills • Terraform, Ansible, or similar automation tools. • Programming experience in Java, JavaScript, Python, or similar. • Exposure to staging/production environment support. • AWS SDKs and CLI Personal Qualities • Eagerness to learn and grow into a leadership role. • Exceptional communication skills — able to explain technical concepts clearly. • Dependable and reliable, especially in a support rotation. • A “yes, and?” mindset — collaborative, problem-solving oriented. Compensation & Benefits • Salary range: $90,000 – $100,000, depending on experience. • Company-paid medical, dental, and vision for employees and family members • 401K with employer match • Life insurance policy • Short-term and long-term disability coverage • Paid holidays and generous vacation/sick leave • Flexible work environment and opportunities for growth To apply, please submit a resume and cover letter and carefully answer all of the questions we have posted on the job listing. We’re excited to meet you! Job Type: Full-time Pay: $90,000.00 - $100,000.00 per year Benefits: • 401(k) • 401(k) matching • Dental insurance • Flexible schedule • Health insurance • Life insurance • Paid time off • Parental leave • Vision insurance Application Question(s): • Do you currently reside in one of these US locations? • Oregon • Washington • California • Connecticut • Arizona • Minnesota • Michigan • Nevada • Louisiana • Texas • North Carolina • Virginia • District of Columbia • Write 1 -2 paragraphs explaining why you are a good fit for this role, emphasizing not your technical skills but your background in either being a team lead or aspiring to be a team lead. Experience: • AWS Deployment: 2 years (Required) Language: • English (Required) Work Location: Remote