As a Tier 2 Customer Support Engineering specializing in Windows and Active Directory, you serve as subject matter expert bridging deep technical troubleshooting and executive-level customer communication. In this role, you will solve high-complexity identity and directory integration escalations that directly impact enterprise customers' core IT infrastructure. We are seeking an engineer who is eager to expand their impact by learning to support broader platform capabilities, including RADIUS, SSO/SMAL/SCIM, and our cutting-edge AI features.
Roles and Responsibilities :
Serve as a senior technical point of contact for executive, VIP, and C-suite stakeholders, driving clear and transparent communication throughout high-pressure incidents and complex customer escalations.
Manage large-scale commercial and enterprise customer relationships by providing high-level technical guidance to senior leaders and engineers, ensuring complex issues are understood and addressed at a business-impact level.
Provide technical support, troubleshooting, and issue resolution to our customers via email, telephone, chat, or remote web session, applying deep technical analysis to complex Windows and Active Directory integration challenges.
Manage a queue of support tickets for high-priority and complex technical issues, leveraging evidence-based troubleshooting—such as log analysis (XPath, event logs), network traces (Wireshark, pktmon), and memory dumps—to identify root causes beyond surface-level symptoms.
Reproduce issues in-house through structured testing and variable isolation to prove technical theories, ensuring fixes are robust and not reliant on temporary workarounds.
Collaborate with peers, escalation points, and internal engineering teams to provide clear, high-quality escalations. Ensure every escalation is backed by a defensible technical diagnosis based on captured evidence and thorough preliminary research.
Collaborate with Product and Learning teams to ensure customer education programs are accurate and up to date, providing technical feedback based on recurring troubleshooting trends.
Maintain a deep technical understanding of the entire JumpCloud Platform and its integration with Windows/AD environments.
Collaborate with Account Managers, Customer Success Managers, and Implementation Engineers to ensure the success of our new customers as they transition into the day-to-day use of our product.
Develop and maintain internal knowledge base articles to increase shared knowledge among the entire support engineering team, specifically focusing on documenting complex troubleshooting methodologies and "how-to" guides for advanced diagnostic tools.
Collaborate with peers on projects aimed at improving the customer and support engineer experiences by optimizing diagnostic workflows and internal tooling.
On-call rotation required. Duties include monitoring of status updates and external customer responses to incoming cases during outages, maintaining clear communication with stakeholders throughout the incident lifecycle.
What You Bring :
Experience: 7+ years in a technical, customer-facing SaaS environment, with 2–3+ years of specific experience handling mission-critical technical escalations.
Executive & VIP Engagement: Proven ability to partner with senior leaders, executives, and internal engineers. You excel at synthesizing complex technical root causes—such as authentication failures or GPO conflicts—into clear, business-impact communication for non-technical stakeholders (CIOs/CISOs).
Windows & AD Expertise: Deep proficiency in the Windows platform (Registry, PowerShell, Credential Manager, Event Logging) and Active Directory. You are comfortable utilizing advanced diagnostic tools (Sysinternals, Wireshark, XPath) and have a strong desire to expand into new technologies like RADIUS, SSO, and AI features.
Evidence-Based Troubleshooting: A methodical, systematic approach to resolution. You isolate variables and replicate edge cases to build defensible diagnoses, ensuring permanent solutions rather than relying on workarounds.
Soft Skills & Mentorship: A teaching instinct. You mentor peers, document complex workflows for the broader team, and exercise excellent judgment when setting escalation boundaries—ensuring customers feel supported even when a direct fix is outside of scope.
#LI-JR1
Skills Required
- 7+ years of experience in a technical, customer-facing SaaS environment
- 2–3+ years handling mission-critical technical escalations
- Experience partnering with senior leaders, executives, and internal engineers
- Deep proficiency with Windows, including Registry, PowerShell, Credential Manager, and Event Logging
- Deep expertise in Active Directory
- Experience with Sysinternals, Wireshark, XPath, and advanced diagnostic tools
- Evidence-based, systematic troubleshooting and issue reproduction experience
- Excellent executive-level written and verbal communication skills
- Mentorship and technical documentation experience
- Fluent English communication skills
- Ability to work remotely from and be authorized to work in Mexico
- Availability to participate in an on-call rotation
- Willingness to expand expertise into RADIUS, SSO, SCIM, and AI features
What the Team is Saying
JumpCloud Compensation & Benefits Highlights
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Healthcare Strength — Day-one medical, dental, and vision in the U.S., with HSA options and employer contributions, are complemented by no-cost EAP support and mental-health coverage. Expanded medical travel coverage is also highlighted when in-network care is not available nearby.
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Retirement Support — A U.S. 401(k) with employer matching (50% up to 6% per Built In) anchors the retirement offering. Access to a personal financial consultant at no cost provides additional planning support.
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Leave & Time Off Breadth — Flexible/unlimited PTO is emphasized alongside paid sick days, paid holidays, and wellness days. Parental and family medical leave are also highlighted.
JumpCloud Insights
What We Do
JumpCloud’s mission is to Make Work Happen®, providing simple, secure access to an organization’s technology resources from any device, or any location. The JumpCloud Open Directory Platform gives IT, security operations, and DevOps a single, cloud-based solution to control and manage employee identities and their devices, and apply conditional access controls based on Zero Trust principals. Since launching in 2012, our global user base has grown to more than 150,000 organizations, with more than 5,000 paying customers including Cars.com, GoFundMe, Grab, ClassPass, Uplight and Peloton. JumpCloud has raised over $400M from world-class investors including Sapphire Ventures, General Atlantic, Sands Capital, Atlassian, and CrowdStrike. Our teams are growing fast, too, and we're looking for talent across engineering, sales, customer success, marketing, product management, and more. Join our team of dedicated, passionate, and creative people who are eager to change the IT industry forever. We live by our core values which are: Build Connections Think Big 1% Better Every Day
Why Work With Us
We offer an incredible opportunity to see your impact. Each team member gets an up close personal view and education into building a fast growing startup. We are transparent about what we are doing, how we are doing it, and the decisions that we are making. There is opportunity to progress and flexibility to find unique approaches to our business
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JumpCloud Offices
Remote Workspace
Employees work remotely.
JumpCloud is committed to being remote-first across the world. We have team members in most U.S. states and in 14 countries.
