About Gladly

Gladly, the customer-centered, AI-powered customer support platform is built around people, not tickets. Unlike traditional ticket-based customer support solutions, our software helps brands deliver radically personal service at scale by integrating every channel—voice, email, SMS, chat, social messaging, and self-service—into a single, lifelong conversation stream. Companies like Allbirds, Bombas, Crate & Barrel, and Warby Parker use Gladly to create exceptional customer experiences, transforming everyday customer interactions into lasting connections. 

Gladly is a fully distributed company that embraces remote work and believes in flexibility, innovation, and inclusivity. We foster a collaborative, inclusive culture that prioritizes growth, DEIB, and meaningful connections. At Gladly, people are at the heart of everything we do.

The Opportunity

As Gladly’s Manager, IT, you’ll play a vital role in shaping and managing our IT operations, supporting a 100% remote workforce while driving innovation and scalability. You will design and implement strategies that enhance security, efficiency, and productivity, ensuring employees are equipped with the tools and systems they need to thrive. This role is perfect for a tech-savvy leader who excels at fostering collaboration, driving process improvements, and ensuring the seamless delivery of IT solutions that empower both employees and customers.

What You’ll Do

Strategic Leadership

• Create and execute an IT roadmap that aligns with Gladly’s remote-first vision and business goals.
• Foster and approach IT initiatives and operations with a culture of innovation.
• Partner with senior leadership to ensure IT initiatives drive operational success.

IT Operations and Systems

• Manage the implementation, optimization, and maintenance of IT tools, systems, and infrastructure.
• Oversee onboarding and offboarding processes to ensure efficiency and security.
• Negotiate contracts, service-level agreements (SLAs), and pricing with vendors to ensure optimal value and cost-efficiency in alignment with organizational objectives.

Cybersecurity and Compliance

• Lead efforts to maintain and improve cybersecurity protocols, protecting company data and ensuring compliance.
• Stay ahead of emerging trends in IT security, implementing best practices to mitigate risks.

Process Improvement and Innovation

• Continuously evaluate IT processes and tools, driving improvements that enhance productivity.
• Integrate new technologies to create better employee experiences and operational outcomes.
• Act as a technical advisor to teams, offering insights and support on key initiatives.

What We’re Looking For

• 5+ years of IT experience, with at least 1 years in a leadership or management role.
• Proven success managing IT systems in remote-first or hybrid environments.
• Strong understanding of cybersecurity standards, compliance, and risk management.
• Experience with JAMF, OKTA, 1Password, SaaS tools, cloud platforms, and complex system integrations.
• Demonstrated ability to lead cross-functional projects and manage competing priorities.
• Excellent communication, collaboration, and problem-solving skills.
• Bachelor’s degree in IT, Computer Science, or a related field (or equivalent experience).

Compensation

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The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Glady’s bonus plan for eligible roles. In addition to cash compensation, all Gladly's employees are eligible to participate in Gladly's equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job-related reasons.