Pirates Wanted: Senior IT Systems Engineer

Every ecommerce business deserves the cheapest shipping rates. That’s why Pirate Ship’s simple shipping software levels the playing field for small businesses, giving them free access to the deepest shipping discounts with no fees or hidden costs. We’re currently on the lookout for exceptional pirates to join our crew as an Senior IT Systems Engineer otherwise known as a Sail Master to us here at Pirate Ship.

Pirate Ship is a remote-first company, and like any jolly crew of pirates we operate in a casual and creative atmosphere, where everyone’s ideas are welcome and having fun is encouraged. We offer competitive pay, exceptional benefits, and the opportunity to tell people you’re a pirate when they ask what you do. As Steve Jobs said, “It’s more fun to be a pirate than to join the navy!”

Responsibilities:

1. Chart a course- Infrastructure Management & Architecture: Design, implement, and maintain enterprise-level IT infrastructure. Lead architecture decisions for scalable, secure, and high-availability systems that support business operations and growth objectives.
2. Balanced buccaneering- System Administration & Operations: Oversee day-to-day operation and integrations of critical systems in a mostly macOS environment using standard enterprise services such as Google Workspaces, Slack, Notion, Asana, and other cloud-based platforms.
3. Batten down the hatches- Security & Compliance: Assist in the implementation and maintenance of standard security protocols, access controls, and compliance frameworks to protect organizational data and systems. Conduct regular security assessments alongside our Security team partners, and coordinate incident response activities while ensuring adherence to industry standards such as SOC2, ISO 27001, GDPR, etc.
4. Aft rigging- Automation & Process Improvement: Develop and implement automation inline with business objectives to improve efficiency and end-user experience. Identify process inefficiencies and create standardized procedures to improve operational reliability and reduce manual intervention.
5. Support your crew- Ticketing & Support: Assist in the management of IT support ticket backlog efficiently while delivering exceptional customer service and technical solutions to end users across the organization.Ride the seas of change: You’re comfortable in a remote environment where there’s lots of change.
6. Sail from your port o’ call: You’re able to work from home and connect with your crewmates throughout the day over chat, voice, and video through company provided equipment. Quarterly in-person meetings at varied locations.
7. Hoist the Jolly Roger: Share your experience, expertise and interest with the crew to enhance our fun and progressive culture.

Requirements/Minimum Qualifications:

1. 5+ years of enterprise IT systems engineering experience.
2. Deep experience with Mobile Device Management (MDM) solutions like Jamf Pro, Microsoft Intune, or Kandji (Rippling experience a major plus).
3. Advanced proficiency with Apple Business Manager (ABM).
4. Expertise in macOS zero-touch imaging, deployment, and automated provisioning workflows.
5. Extensive experience with major cloud providers (AWS, Azure, Google Cloud Platform).
6. Experience in configuration profiles creation and deployment for security policies, network settings, and application management.
7. Cloud identity and access management (IAM) implementation and governance.
8. Experience in Single Sign-On (SSO) implementation with SAML, OAuth, etc..
9. Basic understanding of compliance frameworks (SOC 2, ISO 27001, GDPR).
10. Project management skills using standard tools (Asana, Jira, etc.)
11. Experience in maintaining a ticket backlog and stepping in to assist, and oftentimes own, end-user support tickets.
12. Strong troubleshooting and problem-solving abilities, with a major emphasis on customer service and experience.
13. Excellent documentation and communication skills.
14. Experience mentoring junior team members.

Bonus Points For/Preferred Qualifications:

1. YARRrrr! The ability to speak like a pirate!
2. Rippling IT administration experience preferred, not required.

Compensation & Benefits:

1. Compensation - The pay range for this role is $115,000-$125,000 yearly USD plus a performance based bonus.
2. Vacation Time - We offer 144 hours of accrued vacation time to start to keep our pirates rested & rejuvenated!
3. Paid Holidays - 12 paid holidays per year.
4. Paid Sick Time - 80 hours annually.
5. Medical Insurance - 100% covered for Pirates by the company and kicks in the first of the month after enrollment. If you want to add any dependents (spouse, partner or children), they’ll be 50% covered.
6. Dental and Vision - 100% covered for Pirates and 50% covered for dependents.
7. 401(K) - We offer a Traditional 401(K) and a Roth 401(K), and pirates who contribute 1-3% of their annual salary get matched 100% by the company.
8. Parental Leave - Full 12 weeks for parents for the birth, adoption, or foster placement of a child.
9. Home Office Reimbursement - We provide a one-time home office reimbursement of up to $1,500 to purchase an ergonomic desk and chair.
10. Other Stipends for Remote Individuals - Wifi & snacks, we’ve got y’er back!
11. Virtual Tacos for ARRrrrsome Rewards- “Hey Taco!” is our employee recognition program where you can give and receive virtual "Tacos" which can be redeemed for rewards.

We Sail Under Our Three Pirate Codes:

1. People Over Plunder - Screwing people over is a game for lily-livered landlubbers! We believe that doing what’s right is the tide that raises every ship, including ours.
2. Clarity, Not Confusion - Confusion is tyranny. Clarity is freedom. We strive to make things easy to understand and tackle real needs for our customers.
3. Play or Perish - A life without laughter isn’t worth living. Why should that be any different in business?

Our Values Reflect Who We ARRrrr:

1. Be Fair - Accessible to everyone, so no one’s left out.
2. Be Nice - Empathy, humanity, and humor go a long way.
3. Be Real - Be reliable and back up the pirate talk.

We work to ensure our company is a safe and supportive environment for everyone. As our crew continues to grow rapidly, we want to do all we can to create an environment where everyone can feel included.

How we do this:

1. We pay well and offer world-class health benefits so you can focus on being a balanced pirate!
2. No degree? No problem. We value experience of all kinds!
3. The crew helps select nonprofits for our quarterly donation program.
4. We don’t shy away from hard conversations. Building a better world takes constant feedback, conversations and hard work!
5. We do engagement surveys twice a year to constantly iterate our policies and procedures.
6. We acknowledge the identities and experiences of everyone.

Pirate Ship is committed to provide equal employment opportunity (EEO) and equal pay to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law. Pirate Ship will provide reasonable accommodations for qualified individuals with disabilities as needed.

Before candidates officially set sail with Pirate Ship, we do conduct a post-offer, pre-employment background check. But don’t worry, Pirate Ship is all about second chances! We proudly consider qualified applicants with prior arrest or conviction records. Our commitment to building a diverse and talented crew means that we look at the whole person, not just their past, and we do so in line with local, state, and federal laws. So, whether you're a first-time sailor or have a bit of history, we’re excited to explore the possibility of you joining our crew!

We welcome feedback for making our company a lighthouse in the industry.

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