What not to tell your employer.

• Preventing anything too revealing.
• REAL why your reason. NO TECH HUB.

SHOW PASSION* “I’m the right candidate for this role for three main reasons.

First, I bring over 15 years of hands-on experience running Microsoft 365 and messaging in highly regulated environments – mainly financial institutions and PCI-regulated industries. I’m very comfortable working under regulatory pressure, with auditors looking over our shoulders, and making sure controls are actually implemented, not just documented.

Second, I can add value very quickly. On day one, I can start learning your environment, and by the end of the first week I can begin delivering real output. In previous M&A projects, I’ve come in, run a full gap analysis on the M365 tenant and the surrounding security stack, identified misconfigurations, and started closing critical gaps while in parallel building a longer-term roadmap. I’m used to reviewing security posture, plugging the biggest holes first, and then coming back with a structured roadmap.

Third, I’ve literally worked my way up from the trenches, so I understand the full stack end-to-end. As a lead engineer, my day involved juggling 10 integration projects while handling day-to-day operations. During the pandemic, I spent weeks working around the clock supporting SBA loan forgiveness and PPP workloads – keeping email, collaboration, and remote access stable while volumes spiked. I’ve participated in every biannual DR exercise, and I’m often the person the CIO, CISO, and operations teams call when there’s a major M365 incident. I know how to stay calm, troubleshoot under pressure, communicate clearly, and get services back to green.

Im confident I can ramp up quickly at lendingclub and you will not regret hiring me; my history and actions speaks for itself.

Summarize your resume.

Well as you can see from my resume - Summarize your resume (oldest to most recent)

Communicate how you are the person for the job. How you meet all your qualifications.

Small percentage, and what you can recall your

And that's what bring me here today and why I'm excited about this opportunity.

*What are you working on* Reveal your flaws.

From all the people you interview you should hire me.

Think of the question as a trade Off.

- I'm not the fastest worker / but what work I do submit is accurate and is meant to be a reference for others to use for future references will be . what extra time i do does not cause any issues (mitigation) i always make sure i clarify what time frame is good and if it works well.

In a recent merger and acquisition, I took time to chronically identify records and archives during the company's adoption of different products. For example, on-premises data is held on tape, and to break it down on how its processed, in what year, and how destruction occurs paints a complete picture. It also provides a guide for legal and compliance to identify where these artifacts reside and if they still exist.

1. I would need additional details? Feel for the culture.
2. Approved position > What range > That would work well for me.
3. No Range > Between 100-170 year.

https://lendingclub.wd1.myworkdayjobs.com/en-US/External/job/Sr-Microsoft-M365-Engineer_R0007146

Administer and optimize:

Exchange Online

SharePoint

OneDrive

Microsoft Entra ID (Azure AD)

Intune

Define and enforce messaging and collaboration architecture best practices

Plan and document technical changes (change control, design docs, runbooks)

Review and maintain scheduled tasks and jobs related to M365

Work with cross-functional teams to translate business needs into secure, scalable solutions

Oversee application registration and lifecycle management in Entra ID

Manage access controls (permissions, app roles, consent)

Implement governance for apps integrated with Entra ID

Ensure secure SSO and identity flows for internal and third-party apps

Manage company email domains and DNS records:

SPF

DKIM

DMARC

Configure and operate Proofpoint and M365 transport rules

Manage routing, relays, and connectors for internal/external mail flows

Proactively monitor mail flow and investigate delivery and spam/phish issues

Troubleshoot:

Send/receive failures

Message tracking

Relays and connectivity to messaging systems

Implement and maintain organization-wide mail policies, rules, and aliases

Automate repetitive M365 tasks with PowerShell

Develop and maintain:

Automation scripts

Scheduled O365 jobs

Reporting and inventory scripts

Build proactive tools and monitoring to detect and resolve issues early

Standardize admin workflows through reusable functions and modules

Oversee Copilot for M365 configuration and rollout

Define secure guardrails for:

Copilot Studio

Power Automate and end-user automation

Balance enablement vs. data protection (access scopes, data boundaries)

Provide end-user training and guidance for safe and effective use of AI and low-code tools

Act as Tier 3/4 escalation for complex M365 and messaging issues

Partner with the Service Desk to:

Resolve advanced issues

Create SOPs and runbooks for common tickets

Review and communicate about global outages:

Impact

Status

Remediation steps

Participate in on-call rotations and off-hours support as needed

Ensure consistent operational excellence across the M365 environment

Partner with Legal and Compliance on:

Email retention and archival policies

Data governance and classification

Execute and manage legal holds and ensure data integrity

Support eDiscovery workflows across Exchange, SharePoint, and OneDrive

Maintain strong cloud security and compliance posture across M365 services

Align platform configuration with regulatory and audit requirements

Support end users on:

Microsoft 365 apps

Windows and macOS environments

Collaboration tools (Zoom, Atlassian, Slack)

Demonstrate a customer-first support mindset

Improve end-user experience and productivity through configuration, policies, and guidance

Collaborate with teams in a hybrid work environment (onsite and remote)

Apply core networking knowledge:

DNS

DHCP

HTTP

SSL/TLS

TCP/IP

Understand identity and access flows affecting M365

Support:

Device imaging

Software deployment

Remote support solutions

Diagnose issues across client, network, and cloud layers

Experience:

6+ years supporting Microsoft 365 and Exchange environments

Bonus: 3+ years in highly regulated industries

Legacy Exchange Server experience (on-prem)

Skills:

Strong PowerShell and automation

Documentation, organization, and communication

Vendor and partner management (bonus)

Ability to quickly learn and integrate new tools into M365

Work model:

Hybrid (San Francisco or Lehi), in-office Tue–Thu

Flexible across time zones (HQ in Pacific Time)

Willing to participate in 24/7 on-call as needed

Certifications (bonus):

M365 / security-related certs

CompTIA / PMP / similar (project and best-practice alignment)

As part of our organization's rollout of Microsoft Copilot, we are implementing a set of structured guardrails to ensure responsible AI usage, data governance, and compliance with industry and internal standards. This page outlines the technical, administrative, and user-level controls being applied.

Copilot is a powerful generative AI tool designed to enhance productivity across the Microsoft 365 suite. To maximize its value while minimizing risk, guardrails have been established to:

• Prevent unauthorized data exposure
• Maintain compliance with internal and external regulations
• Ensure responsible and ethical AI usage
• Protect against misuse or prompt injection

These guardrails align with Microsoft’s Responsible AI framework and our internal IT security policies.

• Copilot access is scoped using Entra ID (Azure AD) group memberships.
• Only licensed and security-cleared users are granted access.
• Multi-Factor Authentication (MFA) is enforced for all Copilot users.
• Conditional Access policies apply to manage risk-based access.

• Copilot is restricted to accessing only authorized Microsoft 365 data repositories (SharePoint Online, OneDrive, Teams).
• Sensitivity labels and Microsoft Purview DLP policies are used to limit access to classified or high-risk data.
• Data classification and label inheritance are enforced at the file and container level.

• Prompt best practices training is provided to all users.
• Prompts are monitored for malicious intent, sensitive content, or misuse.
• Guardrails are configured within Copilot Studio for custom Copilot applications, limiting scope and context access.

• Microsoft 365 unified audit logs are enabled to track Copilot interactions.
• Defender for Cloud Apps is used to monitor for abnormal or noncompliant behavior.
• Alerts are integrated into our SIEM for incident response and anomaly detection.

• Required onboarding covers:
  • Understanding what Copilot can/can’t access
  • Safe prompt writing and reviewing AI-generated output
  • Data sensitivity and acceptable use
• A Copilot-specific Acceptable Use Policy (AUP) is included in onboarding materials.
• Periodic reminders and updates are issued via email and the company intranet.

Copilot is here to support your daily work—but just like any AI tool, it must be used responsibly. Our guardrails ensure Copilot can only access data you're already authorized to see. Never input sensitive personal or client data into prompts. Always review Copilot responses critically and consult the Copilot Usage Guide if you're unsure.

If you have questions, reach out to the IT Compliance team at itcompliance@example.com.

• Microsoft Copilot Documentation
• Microsoft Responsible AI Principles
• Acceptable Use Policy
• Copilot User Quick Start Guide

• IT Security
• Microsoft 365 Engineering
• Compliance & Risk Management