Summary This is a hands-on technical IT position, not a customer service or call center role. You will resolve escalated tickets, support infrastructure projects, and configure MSP tooling daily. If you are not comfortable working inside Microsoft 365, servers, and networks, this is not the right fit. Who this role is for: an experienced L2 technician with 3–7 years of hands-on MSP experience who wants more responsibility than their current seat offers. You're doing escalation work today, you're good at it, and you're ready to prove you can run a service desk — not someone 20 years in looking to coast, and not an L1 looking to skip a step. About Us We are a growing Managed Service Provider (MSP) serving engineering firms. We run a modern MSP stack and a 24/7/365 L1 help desk. We need a strong L2 to serve as our primary escalation point — and to grow into our Service Desk Lead role as we scale. The Role Type: Contract to hire. High performers grow into a permanent Service Desk Lead position — this is a real path, not a teaser. Hours: This is a full-time, 40-hour-per-week commitment with set daily working hours during EST (Eastern Time, US). Both are non-negotiable due to our response time commitments — this is not a side gig you can run alongside another job. Start: As soon as possible. Interviews: You will interview with the President and CTO before any commitment is made. What You Will Do Primary escalation point for our 24/7/365 help desk: Take escalations from the L1 help desk and drive them to resolution Communicate clearly with customers by phone and email Provide recommended solutions and root cause analysis Document SOPs for recurring issues Hit our KPIs consistently (see below) Support the CTO on project delivery: Email migrations Server migrations SharePoint migration and development Infrastructure and network upgrades Client assessments Support the CTO on new client onboardings: Install our core stack: RMM/PSA, EDR/MDR, IT documentation platform, M365/Google Workspace, backup and BCDR, email security, remote access, security awareness training, password management, DNS and web security, M365 management tooling Configure the stack per client needs Identify onboarding roadblocks and communicate recommended next steps Validate completeness with reporting Bonus (not required): Technical support experience with engineering applications like Revit, AutoCAD, or Bluebeam. Who You Are Currently doing L2 work at an MSP (or just left one). 3–7 years of hands-on experience resolving escalated tickets across Microsoft 365, Windows Server, and networking. We will train you on our specific stack, but not on the fundamentals. Available for 40 hours a week, now. If you're currently full-time somewhere else, tell us your transition plan in your application. Highly motivated. This is our #1 criteria. We want someone hungry to take on more responsibility over time, including leading the entire service desk as we grow. If you want a role that's bigger than the one you have now, this is it. Highly flexible. The role mixes escalation work, project support, and onboarding. We are a startup environment, so no task is above or beneath anyone on the team. Independent. We will train you on our stack, but you need to be assertive enough to lead from there. A documenter. You must be willing to write down ticket resolution steps and SOPs. A clear communicator. Strong spoken and written English. You will be on the phone and in email with customers daily. KPIs You Will Own Initial customer response time: ~30 minutes Follow-on customer response times: ~30 minutes CSAT via customer satisfaction surveys (currently at 100%) Supporting the CTO in completing client onboardings within 30 days and delivering projects on schedule

We are looking for an experienced IT infrastructure engineer to implement an existing IT/security architecture plan for a small technology organization. The target design has already been defined. We need someone who can come in, validate the implementation approach, configure the required systems, test the environment, and document the completed setup. Ideal Experience: - Microsoft Entra ID/Microsoft 365 - SSO, SAML, SCIM, MFA, and role/group-based access - Microsoft Intune/device compliance - AWS identity and access management - Device management and access policies - Secure access to private cloud resources - Developer and collaboration platforms - Credentials management When applying, please describe 1-2 similar environments you have personally implemented, which portions you handled directly, and your availability to begin.

## Overview Friendly Solutions is a managed IT services provider supporting small and mid-size businesses across legal, financial, healthcare, construction, manufacturing, and other industries. This role delivers remote technical support across all areas of SMB IT infrastructure. The ideal candidate is a resourceful generalist capable of independent problem-solving across diverse client environments. --- ## Responsibilities **Desktop, Email & Application Support** - Microsoft 365 administration across multiple tenants (Outlook, OneDrive, Teams, mail flow) - Windows workstation and laptop deployment, configuration, and remote troubleshooting - User onboarding and offboarding (accounts, email, permissions, MFA, licenses) - Email migration, spam filtering (SpamTitan), and phishing response - Industry-specific business application support **Infrastructure & Security** - Active Directory, Group Policy, DNS, and DHCP management - Security incident response and access control enforcement - Multi-factor authentication (Duo Security) and endpoint protection (ESET) management - Firewall, switch, and wireless access point configuration - VPN setup and maintenance with MFA integration - Server and backup administration (Acronis, Veeam) --- ## Qualifications **Required:** - Windows 10/11 administration - Microsoft 365 multi-tenant administration - Windows Active Directory and Group Policy - Networking fundamentals (TCP/IP, DNS, DHCP, VPN) - Remote troubleshooting tools (ScreenConnect, RDP, or equivalent) - Strong communication skills in English and Polish - Ability to manage multiple priorities independently **Preferred:** - Firewall configuration (/pfSense) - Backup solutions (Veeam) - Duo Security - Industry-specific software experience - CompTIA A+/Network+/Security+, Microsoft 365 certifications, or CCNA

Summary Craig Group is seeking a knowledgeable, proactive IT & Google Workspace Consultant to support and optimize our technology environment. This is a hands-on contractor role for someone who enjoys solving problems, recommending practical solutions, and helping a remote team work efficiently through well-managed systems. This is an excellent opportunity for an experienced IT professional looking for flexible, ongoing consulting work with a growing, technology-enabled consulting firm. Responsibilities - Own the maintenance of Google Workspace - Advise on IT setup and best practices - Problem-solve solutions as they arise regarding team collaboration and system use - Ongoing IT needs Position Details - 1099 independent contractor - Approximately 2 hours per week (with occasional flexibility as needed) - 100% remote (work from home) - Preferred start date: ASAP About Craig Group Craig Group is an operator-led go-to-market strategy and execution partner for private equity and PE-backed lower- to middle-market portfolio companies. We are technology-enabled and AI-supported, built to accelerate organic growth within the realities of a hold period. We work with management teams and operating partners to identify the highest-value segments, clarify ICP and messaging, and build a repeatable revenue engine across marketing, sales, and customer expansion, then implement the plan, so results show up in pipeline quality, win rate, deal size, recurring revenue, profitability, and EBITDA.

We are seeking an experienced MSP engineer or technical consultant to support the integration of newly acquired managed service providers into our operating environment. This is a project-based contract role with engagements typically lasting 60 to 90 days. Successful candidates may be invited to participate in future acquisition integration projects on an ongoing basis. About the Role Your primary responsibility will be to review, validate, and standardize technical documentation from acquired MSPs and client environments. You will work closely with our internal Integration and Service Operations teams to bring documentation, asset records, network diagrams, vendor information, and operational procedures into alignment with our standards. This role is ideal for a former MSP Systems Administrator, Senior Engineer, Service Manager, or Technical Consultant who enjoys discovery, documentation, and process improvement. Responsibilities • Review existing MSP documentation for completeness and accuracy • Conduct interviews with technical staff and key stakeholders to gather missing information • Audit Microsoft 365, Azure, networking, security, backup, and endpoint management environments • Update and standardize documentation according to established SOPs and templates • Create or update network diagrams, asset inventories, vendor records, credential records, and support procedures • Identify documentation gaps, technical debt, and operational risks • Produce final documentation packages and handoff materials for operational teams • Participate in integration meetings and status updates as needed Required Experience • 2+ years working within a Managed Service Provider (MSP) • Strong understanding of Microsoft 365 and Azure environments • Experience documenting networks, systems, and operational procedures • Ability to work independently with minimal supervision • Strong written communication and organizational skills Preferred Experience • ITGlue, Liongard, ConnectWise Manage, Autotask, Datto RMM and similar platforms • MSP acquisition or integration experience • Network infrastructure documentation • Cybersecurity, data backup, and compliance documentation • Multi-site client environments Engagement Details • Contract / project-based • Typical engagements range from 60 to 90 days • Flexible hours • Remote work • U.S.-based preferred, but highly qualified international candidates will be considered • Potential for recurring opportunities throughout the year Please provide: - Summary of your MSP experience - Documentation platforms you have used (IT Glue, Hudu, etc.) - Examples of documentation projects you have completed - Experience supporting MSP mergers, acquisitions, or large clients

We need an expert to configure and integrate OneDesk on-prem with our existing systems. The work includes setting up the on-prem environment, connecting it to our current infrastructure, and ensuring smooth operation after deployment. You should be able to handle configuration tasks, troubleshoot issues, and support the transition from our current setup. Experience with similar on-prem deployments and integration projects is important. This is a part-time engagement for a small project with a clear scope. Specific items include: -Email & OAuth2 configuration with Google Workspace -domain setup & TLS certificate configuration -Automate TLS certificate renewals -EC2 linux instance hardening -AWS S3 integration -Postgres database backup and restoration testing -Troubleshooting linux performance issues

About Us We're a multi-site behavioral health services company operating clinics in California and Georgia, with approximately 60 employees across five locations. We issue company-owned laptops and iPads to clinical and administrative staff. Our environment: Google Workspace Business Plus for email, identity, and file storage. Our fleet is roughly 3 Windows laptops, 20 MacBooks, and 8 iPads. Because we operate in healthcare, our devices may touch protected health information (PHI), so HIPAA-appropriate safeguards are a requirement, not a nice-to-have. The Problem We are paying for Google Workspace Business Plus, which includes advanced endpoint management — and none of it is configured. There is no enrollment process, no enforced passcodes or disk encryption, no app control, no remote wipe capability, and no reliable visibility into who has which device or what's installed on it. Devices are handed out and tracked informally. We want this built out properly, once, using what we already own wherever possible, with documentation clear enough that our operations and HR staff can maintain it in-house afterward. Scope of Work 1. Assessment and gap analysis Inventory our existing devices and audit our current Google Admin console endpoint management configuration Tell us specifically what Business Plus covers for each device type — Windows, macOS, iPadOS — and what it does not Verify all device-using staff hold Business Plus licenses, since endpoint policies are licensed per user Recommend what, if anything, we need to buy on top of Google to close the remaining gaps, with cost per device or per user. We expect the honest answer may involve a dedicated Apple MDM and an endpoint protection product; make the case either way Confirm Business Associate Agreement coverage for anything you recommend, and verify our Google Workspace BAA has been accepted in our Admin console 2. Google Workspace build-out Configure Google Admin console endpoint management: organizational units by role and location, device approval workflow, and context-aware access where appropriate Enable advanced mobile management and configure the Apple push certificate for our iPads Configure Windows device management and BitLocker policy Set up Apple Business Manager so our iPads can be supervised and future purchases enroll automatically Stand up any supplemental MDM or security tooling identified in step 1, with identity anchored to our Google accounts — we do not want a second directory to maintain 3. Security baseline Enforce disk encryption on laptops (BitLocker on Windows, FileVault on Mac) and confirm encryption is actually active on each machine, not merely configured in a console Enforce device passcodes and screen-lock timeouts across all device types Configure remote lock and full remote wipe Deploy endpoint protection / antivirus Application allow/block controls and restrictions on personal cloud storage or unapproved apps OS patch and update enforcement 4. Application deployment Package and push our standard app set to the correct device groups (list provided after hire; includes clinical data collection and productivity applications) 5. Enrollment of the existing fleet Enroll our currently deployed devices Identify which devices require a wipe and reset to enroll properly, and propose a sequencing plan that minimizes disruption to clinic operations across two time zones 6. Monitoring and reporting Compliance dashboard and alerting for out-of-policy devices Asset inventory report we can reconcile against our HR records 7. Policy, documentation, and handoff Written device use / acceptable use policy suitable for inclusion in our employee handbook Device assignment and return acknowledgment form Standard operating procedures for: issuing a new device, onboarding a new hire, offboarding a departing employee including remote wipe, and responding to a lost or stolen device Live training session (recorded) for our operations and HR staff so we can administer this going forward without ongoing contractor support Deliverables Fully configured endpoint management environment with all existing devices enrolled and reporting compliant Documented security baseline and configuration profiles Written device policy plus assignment and return forms Admin SOP runbook Recorded training session and 30 days of post-launch support for questions Required Experience Hands-on MDM/UEM deployments for small to mid-size organizations — tell us how many and on which platforms Direct, current experience configuring Google Workspace endpoint management on Business Plus, including its real limitations Integrating a third-party MDM with Google Workspace as the identity provider Both Apple (macOS/iPadOS) and Windows management Apple Business Manager and Automated Device Enrollment Windows encryption and update enforcement in a Google-identity environment, not Microsoft 365 Experience with HIPAA-regulated or otherwise compliance-sensitive environments Clear written communication — we need documentation a non-technical operations manager can actually follow Nice to Have Prior work with healthcare, behavioral health, or multi-site clinical organizations Familiarity with BambooHR for reconciling device assignment against employee records Multi-state operations experience Engagement Details Type: Fixed-price with milestones preferred; open to hourly for the right candidate Timeline: Kickoff within two weeks, initial rollout complete within [4–6] weeks Availability: Some work must align with U.S. Pacific and Eastern business hours to coordinate with clinic staff Please Include in Your Proposal What can we accomplish using only what Business Plus already includes, and where will we genuinely need to add tooling? What are the top three things Google Workspace endpoint management cannot do that we should be aware of? How would you handle our MacBooks specifically? Two or three comparable projects you've completed, with device counts and platforms Any additional per-device or per-user monthly cost your approach would introduce Your fixed-price quote and proposed milestones Your experience with HIPAA safeguards as they apply to endpoint devices Start your proposal with the word "ENROLLED" so we know you read the full posting.

We are seeking an IT support specialist to assist with MS 365, HIPAA compliance, and computer software management in a healthcare environment. The role involves working on Macs and ensuring seamless IT operations. The ideal candidate will have experience in technical support and customer service, with a focus on healthcare IT solutions. Must be fully-proficient and certified in MS 365, one-drive, Sharepoint and all aspects of connectivity between server, in-house computers and mobile phones

Need a Microsoft Infrastructure & Migration Engineer to lead identity and email modernization projects for our enterprise clients. In this role, you will be responsible for designing and executing cloud migration strategies—specifically migrating legacy local Active Directory and personal/standalone account environments to modern Microsoft Entra ID (formerly Azure AD), as well as transitioning legacy email systems and Outlook environments to Microsoft 365 (M365)

We are a financial services company looking for an IT specialist to help us make sure we have archiving set up in our Microsoft Business 365 Standard ecosystem. We have to have this for compliance with SEC 17a-4 and want to ensure our Teams, Email, and our VoIP phone system are journaled to the archiving. Overall would appreciate any insight to general security of our SharePoint system too. If replying to this post, please don't just paste a generic cover letter - I'll ignore your response. Leave me your first embarrassing email address handle (not the @domain, for security and Upwork compliance) to prove you read this and some fun! Thanks.