Senior Technical Support Specialist

Bigbear.ai•UNAVAILABLE, UNAVAILABLE

1d•Remote

About The Position

Ask Sage, a BigBear.ai company, is the leading Generative AI platform that augments the velocity of government and commercial teams with dozens of use cases, from coding to cybersecurity to acquisition to data analysis and beyond. Our secure platform delivers cutting-edge technology that enables teams to focus on strategic initiatives while we take care of the heavy lifting. We are seeking a Senior Technical Support Specialist to serve as a team lead and support the customers behind our revolutionary platform.

Requirements

Four years of combined experience in technical support, IT service desk, or customer support engineering, preferably in a SaaS or technology company.
Experience resolving complex technical escalations, conducting root cause analysis, and coordinating with engineering.
Strong knowledge of Active Directory, Microsoft Entra ID (Azure AD), Microsoft 365, and identity and access administration.
Experience creating knowledge articles, runbooks, or support documentation and implementing standards that improved service-level performance.
Proficiency with ServiceNow or equivalent ticketing systems, knowledge platforms, and reporting tools.
Excellent written and verbal communication skills, including explaining technical concepts to non-technical users.
Ability to work with general direction, exercise judgment under pressure, and mentor peers in a fully remote environment.
Eligibility to obtain and maintain a DoD clearance.

Nice To Haves

Six or more years of relevant technical support experience.
Experience as a senior support specialist, escalation engineer, or team lead in a SaaS environment.
Experience supporting generative AI, machine learning, or large language model platforms.
Experience supporting federal, DoD, or public-sector customers in FedRAMP High or DoD IL5 environments.
Measurable success improving processes, automation, self-service, training, onboarding, or vendor and license management.
ITIL Foundation, HDI Support Center Team Lead, CompTIA A+, Network+, Security+, or similar certification.

Responsibilities

Serve as the primary escalation point for complex, ambiguous, and high-visibility customer issues, determining diagnostic approaches and driving cases through resolution.
Diagnose platform issues involving authentication, security configuration, account provisioning, access entitlements, verification and notification workflows, integrations, and generative AI features.
Lead root cause analysis for recurring or systemic issues and partner with engineering to implement permanent fixes.
Support incident response by tracking customer impact, maintaining accurate records, and communicating timely status updates.
Maintain deep knowledge of Ask Sage features, configurations, integrations, limitations, releases, and support requirements.
Apply expertise in Microsoft Entra ID (Azure AD), Active Directory, single sign-on, and multi-factor authentication.
Own support knowledge management, including content standards, accuracy audits, gap analysis, and retirement of outdated material.
Create and maintain internal runbooks, troubleshooting playbooks, escalation procedures, customer FAQs, and self-service guides.
Establish case documentation standards supporting auditability and reporting in FedRAMP High and DoD IL5 accredited environments.
Define and improve support workflows, severity levels, escalation paths, and service-level targets.
Optimize ticketing, queue routing, templates, automation, and self-service strategies, measuring their impact on ticket volume and resolution time.
Partner with engineering, product management, security, compliance, vendors, and third-party providers to resolve technical issues and improve support delivery.
Translate recurring customer concerns and case trends into evidence-based recommendations for product, training, documentation, tooling, and process improvements.
Represent the customer and support function during release planning and readiness reviews.
Build and analyze support metrics, including ticket volume, first-contact resolution, resolution time, backlog health, and customer sentiment; communicate findings to management.
Coordinate ticket triage, workload distribution, and coverage across a small team.
Mentor specialists through troubleshooting, case reviews, knowledge sharing, onboarding, and training; identify skill gaps and development needs for leadership.