Top Benefits
About the role
Who you are
- You are a "Tinkerer-in-Chief": You love leadership, but you miss the thrill of fixing a broken build or finding a needle-in-a-haystack bug
- You lead by doing: You believe the best way to earn a team's respect is to be the person they turn to when they are technically stuck
- You are obsessed with "The Why": You don't just want your team to close tickets; you want them to understand the underlying architecture of why the error happened
- You thrive in the deep end: You are comfortable reading stack traces in languages you might not write fluently, and you can explain complex technical concepts to both junior devs and CTOs
- 8+ years of total experience in technical support, software engineering, or sales engineering
- 2+ years of people management or team lead experience, with a track record of hiring and mentoring technical talent
- Deep Technical Proficiency: You must be able to read and debug code. Experience with Python, JavaScript, or other languages is required. You should be comfortable opening a browser console or a terminal to reproduce an issue
- Modern Stack Knowledge: Strong understanding of the modern dev landscape (CI/CD, APIs, Microservices, Frontend vs. Backend, Observability)
- Hands-On Philosophy: A willingness to roll up your sleeves and work tickets. If you are looking to move away from technical work entirely, this is not the role for you
- Previous experience working as a Software Engineer or in a DevOps role
- Active contributions to Open Source projects (please share your GitHub!)
- Experience implementing Support tools or workflows (Zendesk, JIRA, Linear)
What the job involves
- At Sentry, our customers are software developers
- Solving their problems is complex, technical, and requires deep code literacy
- We don't believe in "managers who don't know the product." We are looking for a Technical Support Manager who leads from the front lines
- You will lead a team of high-performing Support Engineers, but you won't be managing from an ivory tower
- You will be a "Player-Coach" - spending a significant portion of your week in the queue, handling the most complex technical escalations, debugging code in open-source repos, chatting with engineers at Discord, and acting as the primary Subject Matter Expert (SME) for your team
- You are a former engineer or high-level support architect who loves the technical hunt but is ready to force-multiply that passion by mentoring a team
- You will drive success not just by tracking metrics, but by showing your team how to solve the unsolvable
- Be the Technical SME: Serve as the ultimate escalation point for complex questions regarding Sentry’s SDKs, trace propagation, and more
- Active Queue Participation: Dedicate a portion of your week to answering inbound support requests, keeping your product knowledge sharp and setting the standard for quality
- Triage & Debug: Triage, reproduce, and report complex product bugs. You will be expected to read source code to distinguish between a user error and a true platform bug before escalating to Engineering
- Community Engagement: Engage directly with users in our public channels (Discord, GitHub) to solve problems and represent the Sentry brand technically
- Develop the Team: Conduct code reviews on ticket responses, provide deep technical feedback, and mentor engineers on debugging strategies and software fundamentals
- Drive Performance: Own your team’s core metrics (CSAT, Response Time, Resolution Time) and workload balancing
- Shape the Knowledge Base: Not only write articles yourself but curate the team's output to ensure our internal guides and customer-facing docs are technically accurate and up-to-date
- Incident Command: Participate in the on-call rotation for high-severity issues and act as the Incident Commander for support during critical outages
Benefits
- Competitive Compensation + Equity
- 401k Plan
- Medical, Dental, Vision Insurance
- Commuter Stipend
- Professional Development Stipend
- Health & Wellness Benefits
- Charitable Matching Program
- Flexible PTO
- Paid Parental Leave
About Sentry
Your business. Your employees. Your peace of mind. At Sentry, we understand what matters most to you. Because we've spent the last 120 years building trust with our customers—one conversation at a time. We got our start in 1904, when members of the Wisconsin Retail Hardware Association formed their own insurance company. Our dedication to personalized service—and to honoring our Midwestern roots—has helped make Sentry part of one of the largest and most financially secure mutual insurance groups in the United States. Our customers work in a wide range of industries, including transportation, manufacturing, metalworking, construction, auto dealerships, and more. Many of them have been with us for decades. From 401(k) plans and general liability, to commercial property and workers’ compensation, we offer solutions that can help protect your business and your employees. We are headquartered in Stevens Point, Wisconsin, and have offices located across the United States. With more than $25 billion in assets, an $8 billion* policyholder surplus, and an A+ (superior) rating from AM Best,** the industry’s leading rating authority, we can help provide you peace of mind. To learn more about us, the industries we serve, and the products we offer, visit sentry.com. The content provided here is for informational purposes only: https://www.sentry.com/footer/legal-disclaimer. *Assets and policyholder surplus are as of December 31, 2023, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. https://www.sentry.com/-/media/sentry-insurance/home/about-us/annual-report-2023/2023-sentry-year-in-review.ashx **Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.
Top Benefits
About the role
Who you are
- You are a "Tinkerer-in-Chief": You love leadership, but you miss the thrill of fixing a broken build or finding a needle-in-a-haystack bug
- You lead by doing: You believe the best way to earn a team's respect is to be the person they turn to when they are technically stuck
- You are obsessed with "The Why": You don't just want your team to close tickets; you want them to understand the underlying architecture of why the error happened
- You thrive in the deep end: You are comfortable reading stack traces in languages you might not write fluently, and you can explain complex technical concepts to both junior devs and CTOs
- 8+ years of total experience in technical support, software engineering, or sales engineering
- 2+ years of people management or team lead experience, with a track record of hiring and mentoring technical talent
- Deep Technical Proficiency: You must be able to read and debug code. Experience with Python, JavaScript, or other languages is required. You should be comfortable opening a browser console or a terminal to reproduce an issue
- Modern Stack Knowledge: Strong understanding of the modern dev landscape (CI/CD, APIs, Microservices, Frontend vs. Backend, Observability)
- Hands-On Philosophy: A willingness to roll up your sleeves and work tickets. If you are looking to move away from technical work entirely, this is not the role for you
- Previous experience working as a Software Engineer or in a DevOps role
- Active contributions to Open Source projects (please share your GitHub!)
- Experience implementing Support tools or workflows (Zendesk, JIRA, Linear)
What the job involves
- At Sentry, our customers are software developers
- Solving their problems is complex, technical, and requires deep code literacy
- We don't believe in "managers who don't know the product." We are looking for a Technical Support Manager who leads from the front lines
- You will lead a team of high-performing Support Engineers, but you won't be managing from an ivory tower
- You will be a "Player-Coach" - spending a significant portion of your week in the queue, handling the most complex technical escalations, debugging code in open-source repos, chatting with engineers at Discord, and acting as the primary Subject Matter Expert (SME) for your team
- You are a former engineer or high-level support architect who loves the technical hunt but is ready to force-multiply that passion by mentoring a team
- You will drive success not just by tracking metrics, but by showing your team how to solve the unsolvable
- Be the Technical SME: Serve as the ultimate escalation point for complex questions regarding Sentry’s SDKs, trace propagation, and more
- Active Queue Participation: Dedicate a portion of your week to answering inbound support requests, keeping your product knowledge sharp and setting the standard for quality
- Triage & Debug: Triage, reproduce, and report complex product bugs. You will be expected to read source code to distinguish between a user error and a true platform bug before escalating to Engineering
- Community Engagement: Engage directly with users in our public channels (Discord, GitHub) to solve problems and represent the Sentry brand technically
- Develop the Team: Conduct code reviews on ticket responses, provide deep technical feedback, and mentor engineers on debugging strategies and software fundamentals
- Drive Performance: Own your team’s core metrics (CSAT, Response Time, Resolution Time) and workload balancing
- Shape the Knowledge Base: Not only write articles yourself but curate the team's output to ensure our internal guides and customer-facing docs are technically accurate and up-to-date
- Incident Command: Participate in the on-call rotation for high-severity issues and act as the Incident Commander for support during critical outages
Benefits
- Competitive Compensation + Equity
- 401k Plan
- Medical, Dental, Vision Insurance
- Commuter Stipend
- Professional Development Stipend
- Health & Wellness Benefits
- Charitable Matching Program
- Flexible PTO
- Paid Parental Leave
About Sentry
Your business. Your employees. Your peace of mind. At Sentry, we understand what matters most to you. Because we've spent the last 120 years building trust with our customers—one conversation at a time. We got our start in 1904, when members of the Wisconsin Retail Hardware Association formed their own insurance company. Our dedication to personalized service—and to honoring our Midwestern roots—has helped make Sentry part of one of the largest and most financially secure mutual insurance groups in the United States. Our customers work in a wide range of industries, including transportation, manufacturing, metalworking, construction, auto dealerships, and more. Many of them have been with us for decades. From 401(k) plans and general liability, to commercial property and workers’ compensation, we offer solutions that can help protect your business and your employees. We are headquartered in Stevens Point, Wisconsin, and have offices located across the United States. With more than $25 billion in assets, an $8 billion* policyholder surplus, and an A+ (superior) rating from AM Best,** the industry’s leading rating authority, we can help provide you peace of mind. To learn more about us, the industries we serve, and the products we offer, visit sentry.com. The content provided here is for informational purposes only: https://www.sentry.com/footer/legal-disclaimer. *Assets and policyholder surplus are as of December 31, 2023, and represent the aggregate total for all members of the Sentry Insurance Group and are not reflective of any individual underwriting company. https://www.sentry.com/-/media/sentry-insurance/home/about-us/annual-report-2023/2023-sentry-year-in-review.ashx **Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. For details about AM Best’s rating scale, see ambest.com/ratings/guide.pdf.