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.
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 year 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).
At Gladly, we’re not just building software—we’re transforming an industry. We take a people-first approach, both in our product and our culture. When you join us, you’ll enjoy:
- Competitive salaries, stock options, and comprehensive benefits
- Generous paid time off, parental leave, and home office stipends
- A fully remote work environment with opportunities for in-person team gatherings
- A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer-first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.
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What We Do
Uniquely powered by Customer AI, Gladly is the only CX platform that puts the customer —not tickets —at the center of every conversation. Trusted by the world’s most customer-centric brands, including Crate & Barrel, Ulta Beauty, and Tumi, Gladly delivers radically efficient and radically personal experiences.
Gladly was built for B2C leaders who refuse to compromise on operational efficiency or experience. With Gladly, every conversation feels uniquely tailored and instantly responsive, emotionally intelligent and operationally precise, deeply personal and effortlessly scalable. At the heart of our simply powerful platform is Gladly Customer AI —uniquely designed to maintain a single, continuous conversation across all channels while striking the perfect balance of technology and human connection.
Gladly is loved and trusted by hundreds of world-class brands to deliver award-winning experiences and drive serious results —240 million conversations powered by Gladly Customer AI, $510M cumulative cost savings across brands using Gladly, and a 65% increase in CSAT scores.
Customer experience isn’t broken—it’s just built on the wrong foundation. Gladly reimagines CX with AI that gets it right.
Why Work With Us
Putting people first is kind of our thing. Not only is it at the core of our product, but shapes our overall culture at Gladly—from our approach to hiring, to our benefits, and how we think about our place in the community.
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