Senior DevOps Engineer, TechOps

At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products.

We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact.

What You'll Get to Do:

• Manage endpoint device systems across MacOS and Windows platforms in a fast-paced environment
• Support the entire user lifecycle including onboarding.
• Support and contribute to TechOps initiatives within including SSO, Endpoint Protection and Fleet management.
• Collaborate with the DevOps team to maintain security, scalability, and reliability of cloud infrastructure
• Develop and maintain Python scripts to automate routine tasks
• Assist with monitoring systems, alert management, and incident response procedures
• Serve as the primary point of contact for user support, troubleshooting hardware and software issues for the team.
• Contribute to documentation of IT and DevOps processes, policies, and procedures
• Help drive the technology architecture to support Roofr's next stage of growth

What You'll Bring to the Role:

• 5+ years of experience in IT systems administration or similar technical role
• Strong communication skills and ability to work across the organization
• Strong proficiency with MacOS and Windows endpoint management including packaging, patch management and remote provisioning.
• Hands-on experience with MDM solutions, preferably Rippling
• Experience administering GSuite including setting up SSO / SCIM integrations
• Working knowledge of cloud infrastructure and containers
• Proficiency in Bash, Powershell and Python scripting for automation and system integration
• Understanding of version control systems (Git) and collaborative workflows
• Understands the challenges and priorities of an early-stage fully remote company
• Proven experience planning and executing the technical logistics for on-site company events, including all-hands meetings and multi-day retreats.

Bonus Points For

• Experience with configuration management tools (Terraform, Ansible, Chef, Puppet)
• Experience with API integrations and automation workflows

🏠 What we offer:

When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career:

🏝️ Vacation/Paid Time Off:

• 1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2!
• 1 Friday off per month (we call those our laundry days!)
• Company wide paid shutdown for the week between Christmas and New Years
• Flexible time off
• 80% employer paid benefits
• RRSP/401k match
• Generous Parental Leave policy

🤝 Perks:

• We host 2 retreats per year and great team building activities
• Ample learning and development opportunities to continue growing your career
• Home office setup stipend
• Internet and phone allowance
• Remote first culture
• Weekly Friday paydays!

Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.

IMPORTANT NOTICE: Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site (https://boards.greenhouse.io/roofr). Please be cautious of job offers that come from non-company email addresses (@roofr.com), instant messaging platforms, or unsolicited calls.