Job Description

Company Description

SquareTrade, Inc. d/b/a Allstate Protection Plans (“SquareTrade”) is one of the fastest-growing companies in its industry. We’re transforming a $30B market through service innovation and an unwavering focus on customer satisfaction. Our partners include some of the world’s most recognized retailers and carriers—Walmart, Target, Amazon, Costco, and The Home Depot, to name a few. We consistently earn industry awards, have tens of thousands of 5-star reviews, and we’re just getting started.

As part of the Allstate family, SquareTrade has headquarters in the Bay Area and London, and we’re expanding rapidly across Europe and Asia Pacific, including Japan, Australia, Korea, and Thailand.

Job Description

The SquareTrade Cloud L2 Technician provides advanced email- and phone-based break/fix and cloud remediation support for SquareTrade’s cloud support clients, including Microsoft cloud solutions sold through partner Cloud Solution Provider (CSP) programs. This role owns escalations from Cloud L1 and manages vendor support cases, including Microsoft cases through Partner Center, on the customer’s behalf. The ideal candidate has deep, hands-on Microsoft 365, Entra ID, and Intune troubleshooting experience.

This is a client-facing role focused on resolving complex and high-impact issues for SquareTrade clients, while keeping our support team as the customer’s single point of contact through resolution. The role also supports Cloud L1 technicians in their professional and technical development through ongoing mentoring and guidance.

The individual in this role will work across the Microsoft Modern Workplace stack, including Exchange Online and mail flow, Microsoft Teams, SharePoint Online, OneDrive, Microsoft Entra ID (Conditional Access, MFA, Entra Connect, and hybrid identity), Microsoft Intune and Autopilot, Microsoft Defender, Microsoft Purview, Microsoft 365 Copilot, and other emerging virtualization and cloud-based technologies brought into scope, such as Dynamics 365 Business Central and Windows 365. Strong familiarity with hybrid Exchange and hybrid identity environments is a plus.

The person in this role will be responsible for the following activities:

• Provide live assistance to Cloud L1 technicians in the Cloud Escalations room and take ownership of escalated cases when needed
• Provide advanced break/fix and cloud remediation support for Microsoft 365 services, including Exchange Online, Teams, SharePoint, OneDrive, Entra ID, Intune, Defender, Purview, and Copilot
• Open, monitor, and drive Microsoft support cases through Partner Center on the customer’s behalf, remaining the primary point of contact until resolution, and escalate stalled cases through management
• Review and approve Cloud L1 requests to open Microsoft tickets, and take ownership of all Severity A issues
• Troubleshoot GDAP relationships, delegated access, and Conditional Access policies that affect partner access to customer tenants
• Provide best-effort root cause analysis using available logs, traces, and service health data
• Isolate issues involving third-party products (mail gateways, MDM, add-ins) and hybrid environments that affect the Microsoft 365 tenant, and refer customers to the appropriate vendor or team
• Apply CSP scope boundaries consistently, routing out-of-scope requests (such as Azure, licensing, provisioning, and on-premises-only issues) to the correct team
• Achieve and maintain a high level of customer satisfaction and contribute to the team’s CSAT, NPS, and quality goals
• Use Salesforce as the system of record: document all troubleshooting, customer communication, and Microsoft case updates in the ticket, and track work time and activities for management
• Identify customer needs beyond break/fix scope (implementation, configuration, training, or advisory work) that come to light during case work, and route them to the appropriate account team
• Remain up to date on the latest Microsoft 365, Entra ID, Intune, and Copilot technologies, tools, and capabilities
• Research and train on emerging Microsoft cloud technologies, and pursue relevant Microsoft certifications
• Assist in developing functional designs, processes, training, and definition of support procedures as requested
• Help develop and refine runbooks, knowledge articles, and best-practice documentation for Microsoft 365, identity, security, and CSP support processes

On an as needed basis:

• Support new-product readiness (for example, Dynamics 365 Business Central Tier 2 support and Copilot agents) by testing, documenting scope, and training other technicians
• Support the team’s work with Microsoft, partner account teams, and third-party vendors to deliver exceptional value to our clients

Qualifications

• Customer satisfaction as a priority within the scope of work outlined by SquareTrade and our clients
• Ability to work with and understand the levels of technical expertise they will interact with
• Ability to manage and document time and activity without immediate supervision
• Ability to work independently and manage multiple tasks and case assignments
• 3+ years of relevant professional experience in a Microsoft 365 or cloud support environment
• 3+ years of client facing technical experience
• Ability and discipline to work in a fast paced and organizationally complex environment
• Able to effectively adapt to rapidly changing technology to lead and manage workflow
• Strong knowledge of Microsoft 365 administration and troubleshooting, including Exchange Online, Teams, SharePoint, and OneDrive
• Technical proficiency including strong troubleshooting and problem-solving skills
• Experience identifying and reporting on gaps in peer skillsets
• Ability to assist with documenting skill requirements and required certifications for roles/positions
• Knowledge of governance and security best practices and experience applying these to solve client problems
• Strong working knowledge of Microsoft Entra ID, Conditional Access, MFA, Entra Connect, and Microsoft Intune
• Experience with Microsoft Partner Center, CSP/NCE, and GDAP preferred, or the ability to learn quickly
• Working knowledge of Active Directory, hybrid identity, domain management, permissions, and public DNS (MX, SPF, DKIM, DMARC)

Additional Information

At SquareTrade you'll have access to:

• Medical, dental and vision coverage with network optionality and the ability to contribute to a savings account (HSA or FSA)
• Up to 4% company match into 401(k) and contributions into your company-sponsored pension
• $75/month budget to help prioritize your physical wellbeing
• $80/month stipend to subsidize connectivity costs
• Mental health resources including free 1:1 therapy, coaching sessions and digital resources
• Supportive leave policies
• Generous PTO Policy in addition to 9 Company Holidays
• Tuition reimbursement up to $5,250 per year to further your personal educational advancement desires
• Hybrid work arrangements with regular investment in gatherings/offsites to spend time together as team
• Various corporate perks and discounts

SquareTrade estimates the possible base compensation for this role, if hired in the U.S, to be in the range: $23-$31 hourly

SquareTrade/Allstate Protection Plans generally does not sponsor individuals for employment-based visas for this position.

The candidate(s) offered this position will be required to submit to a background investigation.

Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.

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SquareTrade is proud to be an Equal Employment Opportunity employer. We are committed to creating an inclusive work environment for all employees. We celebrate diversity and encourage applications from all qualified individuals regardless of race, religion, color, national origin, sex, gender identity, gender expression, sexual orientation, age, marital status, veteran status, or ability status. It is the Company’s policy to employ the best qualified individuals available for all jobs. Therefore, any discriminatory action taken on account of an employee’s ancestry, age, color, disability, genetic information, gender, gender identity, gender expression, sexual and reproductive health decision, marital status, medical condition, military or veteran status, national origin, race (include traits historically associated with race, including, but not limited to, hair texture and protective hairstyles), religion (including religious dress), sex, or sexual orientation that adversely affects an employee's terms or conditions of employment is prohibited. This policy applies to all aspects of the employment relationship, including, but not limited to, hiring, training, salary administration, promotion, job assignment, benefits, discipline, and separation of employment.

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