Head of IT

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

As Sentry’s Head of IT, you will design, build, and manage our growing SaaS technology ecosystem—ensuring its availability, reliability, and security for a global workforce. Partnering closely with our leaders, you will define priorities and implement innovative solutions across our tools, systems, networks, and technical support, while championing IT security and delivering an exceptional experience for all Sentaurs. As a people leader, you’ll coach, support, and inspire your team to deliver their best work.

• Bring deep, practical experience in IT operations, networking, IAM, enterprise AI, and endpoint management, with a proven track record of delivering results in complex, fast-paced environments.

• Define, prioritize, and execute IT initiatives that improve collaboration, cost-effectiveness, compliance, and security at enterprise scale.

• Design and scale IT Operations and Corporate Infrastructure to support a growing, hybrid workforce, ensuring high availability and performance of critical systems.

• Partner closely with the Security organization to design, deploy, and operate robust IT security solutions, ensuring the protection of corporate infrastructure and data.

• Manage vendor relationships and identify opportunities to optimize costs through efficient internal operations, rationalized investments, and business enablement.

• Consult with stakeholders across the organization to identify business and technology needs, translating them into actionable IT strategies.

• Partner with Workplace teammates and lead office build outs as the company expands operations.

• Monitor and optimize the delivery and operation of IT services, proactively identifying and resolving issues to maintain seamless business operations.

• Provide regular metrics and KPIs to gauge the effectiveness of service delivery and inform decision-making.

• Offer direction, guidance, and training to global IT staff, fostering a culture of learning and growth.

• Deploy and manage solutions across offices in multiple timezones and countries.

• 7+ years of experience working in IT operations, overseeing high-impact projects. Bachelor's degree in computer science (or a related field) or equivalent work experience.

• 3+ years of people management experience leading multiple technical teams, distributed across multiple geographies.

• Expert-level understanding of computer systems, network and systems administration, identity systems, and telecommunications systems.

• Excellent communication, leadership, decision-making, and project management skills.

• Proven experience in operating and managing security, automation technology, and automation programs. Including experience in configuring, deploying, and leading:

  • Cloud-based enterprise identity management including Okta, SSO, SAML, etc.

  • Cloud enterprise services such as Google Workspaces, Slack, Microsoft 365, Linear, etc.

  • Configuration management systems, such as Kandji.

  • IT assets including endpoints, office networking, and A/V conferencing systems.

• Experience working on the IT aspect of common compliance frameworks, such as SOC2, ISO27001, and others.

• You have worked in a fast-paced, high-growth startup environment.

• Experience using infrastructure as code tools, such as Terraform.

• Experience implementing best practices in data governance.

• Knowledge and experience in information security and security engineering is a plus.

Not sure if you meet 100% of the qualifications? We encourage you to apply anyway. We're interested in people are excited about this opportunity and eager to grow.

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $200,000 to $250,000. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

If you need assistance or an accommodation due to a disability, you may contact us at [email protected].

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