I am a GS-13 federal employee (age 62, approaching retirement eligibility) and the sole owner of an active Virginia S-Corporation holding a federal government contract. I am also a practicing fine artist with emerging institutional income and an active residential property held in an LLC. I need a seasoned Certified Financial Planner or CPA-level tax strategist who can look across all of my income streams simultaneously and architect a cohesive, integrated strategy — not manage a single piece of the puzzle. My situation is genuinely multi-layered and requires someone comfortable holding complexity: • Federal retirement: FERS pension, TSP rollover strategy, Social Security (age 62 claim, WEP/GPO resolved under Social Security Fairness Act), and OPM coordination • S-Corporation: Active federal contract income flowing through an S-Corp (Form 1120-S filed annually); need ongoing officer compensation optimization, QBI deduction maximization, retirement vehicle strategy (prior SEP rolled into TSP; no Solo 401(k) currently established), Section 179 planning, and accountable plan documentation • Real estate: Residential condo held in an LLC, currently evaluating mortgage recast, rental conversion, depreciation strategy, and Real Estate Professional Status (REPS) — specifically whether REPS is defensible and beneficial given anticipated post-retirement income structure • Tax liability reduction: I need specific, executable strategies — not general guidance — covering the transition years between active federal employment and full retirement, when S-Corp income, pension, Social Security, and rental income all overlap • Future income: Emerging fine art income (institutional commissions, auction houses) that will eventually need its own tax treatment and estate integration • Ongoing continuity: I want someone who can work with my existing CPA (tax filing) and estate attorney without duplicating effort, taking a CFP-level planning role that neither currently fills WHAT I AM NOT LOOKING FOR • General financial wellness coaches • Advisors who only manage investment portfolios and collect AUM fees • Anyone who will redirect me back to a generalist or suggest I "talk to a CPA" — I have one • Template advice that does not engage with federal employee benefit structures specifically IDEAL BACKGROUND • CFP credential strongly preferred; CPA with retirement planning depth considered • Demonstrated experience with federal employee retirement (FERS, CSRS, TSP, OPM processes) • Hands-on S-Corporation tax strategy experience (not just bookkeeping) • Familiarity with real estate professional status (REPS) qualification and documentation • Ability to model multi-income-stream scenarios across a 3–5 year retirement transition horizon • Estate-aware thinking (LLC, S-Corp, and estate attorney already engaged) • Comfortable working alongside existing advisors as a planning coordinator, not a replacement • Patient, clear communicator — able to explain complex strategies in plain language and take time to ensure full understanding before moving to execution SCOPE OF ENGAGEMENT Phase 1 Review of existing financial documents, retirement projections, S-Corp structure, and real estate scenarios. Produce a prioritized tax reduction and retirement income strategy document with specific, actionable recommendations. Phase 2 (Ongoing — as needed): Quarterly check-ins, year-end tax planning coordination, S-Corp officer comp and distribution review, and as-needed consulting on real estate and art income decisions. BUDGET Open to discussion. Prefer hourly for Phase 1 with potential to establish a retainer for ongoing advisory. Please provide your hourly rate with your application. HOW TO APPLY Please respond with: 1. Your credential(s) and relevant specializations 2. A brief description of 1–2 engagements where you navigated a similar multi-stream situation (federal employee + small business, or federal employee + real estate) 3. Your approach to working alongside an existing CPA and estate attorney 4. Your hourly rate Applicants who send generic proposals without addressing the specifics above will not be considered. This is a U.S.-based engagement. Candidate must have working knowledge of U.S. federal employee benefits, IRS S-Corporation rules, and Virginia/Maryland/DC tax environment preferred.

We require a US Tax professional (CPA, EA, or tax preparer) for handling taxes for our company. Kindly quote your total fixed price for your service proposal. About the Company: Wyoming multi-member LLC (with 2 members, 50% each) Started on December 4, 2025 - so the year 2025 is a 4-week year No operations at all during 2025 - hence no income, no expense, no bank transaction, no US employee Both partners are non-US persons (i.e., non-residents, no SSN, residing outside of the USA) Extension has been filed successfully - 1065 extension to September 15, 2026 EIN number already has been issued Company continues its business operations in 2026 Scope of work: Preparation and e-filing of the 2025 Form 1065 (zero-activity short year) and preparation of Schedule K-1 for each member prior to 9/15/2026 Recommend whether Schedules K-2/K-3 are needed in the case of zero-activity year (preparation of the said schedules in case if yes) ITIN applications (Form W-7) for both of the members, since we are outside the US territory, could you advise whether you are a Certifying Acceptance Agent (CAA) yourself or you cooperate with such CAAs? Is there any possibility of conducting the passport verification through video conference or any other documents would be necessary to provide? Recommend whether any of the members is subject to file the 2025 Form 1040-NR due to zero activity Please indicate in your proposal: Total fixed price in detail: (a) Form 1065 with K-1s; (b) ITIN services per person; (c) 1040-NR if necessary; Whether you are a CAA or you have any procedure for obtaining ITINs for clients outside the US Experience working with foreign owned US LLCs (mandatory item); Timeline for each task. Future considerations, this is an undertaking from our side: In case there are no issues with the preparation of 2025 filing (the filing is done properly, in a timely manner, and with proper communication), then we will receive 2026 tax year filing as well. As the business will be operating in 2026, this would be more substantial, ongoing engagement (Form 1065, K-1s, etc.). We are searching for a tax advisor for the long term, not for the short run. If you have an annual compliance package for foreign-owned LLC, please include it in your proposal.

We’re a growing, multi-location tax & accounting firm headquartered in Basalt, Colorado. We need an experienced HR consultant to audit our inherited employee handbook, tell us what we don’t know we’re missing, and rebuild it for the states we actually operate in today — with California in the mix. The backstory: our current handbook came to us through our first acquisition. It was originally drafted by an Oregon labor attorney when the firm was Oregon-based. Since then we’ve moved our center of gravity to Colorado, expanded across multiple states, and added a tax practice that carries heavier federal compliance exposure. The handbook still carries Oregon-specific language and has essentially no California content. This is a gap analysis and modernization job — not a proofread. Our current footprint: • Colorado — 2 employees (operational center of gravity) with another starting July 6 • California — 1 new hire starting July 6 • Michigan — 1 new hire starting July 6 • Pennsylvania — 1 employee • North Carolina — 1 employee departing imminently (likely coming off the list) • One additional hire is being recruited; their state is not yet known, so the handbook needs to flex as the footprint moves. The work is scoped in two waves: Wave 1 — hard deadline Thursday, July 2 (evening). A prioritized gap-analysis memo (what’s out of date, what’s missing, what’s a live risk vs. a wording fix, and what needs licensed counsel) plus a clean “day-one packet” of the core policies our new California and Michigan hires must receive and acknowledge on July 6. Wave 2 — follow-on. The deeper state-by-state rewrite, state addenda, full Oregon cleanup, brand-voice integration, and alignment with our data-security obligations. Two things make this firm-specific: • Privacy & data security. As a tax firm we have FTC Safeguards Rule and IRS data-security obligations and an existing draft WISP/incident-response plan. We need the handbook validated against those obligations (confidentiality, acceptable use, remote-work security) and we need you to independently flag where it’s silent on what a tax/accounting firm should address. • Brand alignment. The handbook should reflect our mission, vision, and values. These exist in rough form and we’ll share them in a short intake call — expect to sharpen our voice with us, not inherit polished source material. Honesty about the consultant-vs-attorney line. We are not asking you to “certify” legal compliance, and we don’t want anyone who claims they can. We want a strong consultant who can do a real gap analysis, write compliant policy language, and clearly flag anything that needs a licensed employment attorney in a given state. We are separately retaining California counsel for the load-bearing calls; you’d draft your best version and coordinate with them on the items that carry real risk. You’re a strong fit if you have: • Hands-on experience building or rebuilding multi-state employee handbooks, including California (this is a hard requirement, not a bonus). • Working fluency in the consultant-vs-attorney line — you know what you can responsibly deliver and what you escalate. • Bonus: experience with professional-services or accounting/financial firms and their data-security obligations (GLBA / FTC Safeguards / IRS WISP). • Availability to deliver a Wave-1 product by Thursday, July 2, with an intake call in the next day or two. To apply, please answer in your proposal (generic proposals will be passed over): Q1. Describe a multi-state handbook you rebuilt that included California. What specific California provisions did you have to add or change? Q2. How do you decide what you’ll draft yourself versus what you flag for licensed counsel? Give a real example. Q3. Have you worked with firms that have data-security obligations (GLBA / FTC Safeguards / IRS WISP)? What did you do? Q4. Given an Oregon-coded inherited handbook and CA + MI hires starting in days, what would you prioritize in the first five days? Q5. Confirm you can deliver a Wave-1 product by Thursday, July 2, and that you’re available for an intake call in the next 48 hours.

The Background - I have a legal malpractice lawsuit in Massachusetts. After my trial against my business partner in 2004, Norfolk Superior court. The horrible representation I received led to me losing all of my assets and money which was $800k.I did win $242k, but I was traumatized. My attorney lied to me on several points starting with omitting the appeals process and telling me I would receive my settlement shortly after the trial. At trial my attorney did not try to expose the "Misrepresentation" He left out the most critical evidence and testimony, everything that would prove "Intentional Misrepresentation." My attorney had medical and psychological evidence but failed to be aware that he would need expert witnesses. He dropped the" Emotional Distress" claim. I was in a state of exhaustion and did not comprehend his negligence's. I was unable to work for four years going into the trial and he was unaware I could claim "Lost Income." I leveraged everything I had to make it to trial only to be told after the trial of the appeals process and that they do not handle appeals or make appellant recommendations. I was already exhausted before the trial and traumatized by the settlement outcome. I was never able to maintain any employment after that. I had sold my insurance agency for $ 500k, that money was gone and I leveraged all $ 360k of my home's equity and that was gone. I expected to win and replenish everything shortly after the trial, which I immediately realized was not going to happen. I sold my house and walked away with nothing. I developed chronic fatigue syndrome (ME/CFS) a few months later, leaving me bedridden for 18 years with severe exhaustion, cognitive impairments and physical maladies. I was never to work again. The law firm owner realized all of the negligence's that occurred. and there were significant others I'm not mentioning. He and my attorney conspired to fraudulently conceal the negligence's. First, they told me multiple times that they did the best they could, and nothing was overlooked. Second, I had another trial six months later. My attorney filed it incorrectly in Superior Court when it belonged in Civil Court. I waited three years. I had purchased a used vehicle from a used car brokerage, and the engine blew up because the brokerage firm put a new radiator thermostat in upside down. I had a BMW mechanic testify in court that it was placed upside down. The Defense called a recess and began making low ball offers which I refused. My same attorney stepped in and demanded I take the offer which 50% less than what my damages with accrued interest was worth and also throwing away very likely treble damages. My attorney sad I owed his law firm money from the first trial, and he would walk out if I didn't settle now. I felt lost, confused and suffering from exhaustion. I agreed. Seventeen months after the first trial I was called into my attorney's office under false pretenses. I was blindsided by the law firm owner who immediately started yelling at me to change my appellant attorney. When I said no, he offered to pay the retainer fee of $ 2,500 if I changed appellant attorneys. I eventually walked out without agreeing. The owner and my attorney were trying to keep the evidence and testimony that wasn't given at the original trial a secret, which would expose the negligence's. i never told my appellant attorney of any mishandling or the meeting i had with my attorneys to try and persuade me to change appellant attorneys. I never questioned my attorneys at the meeting about any mishandling. I just left my appellant attorney to deal with the transcript. I was suffering with exhaustion, multiple cognitive impairments and over 20 physical maladies. Two years later, as the transcript was nearly completed. I received two letters from the law firm, again reminding me of their "offer." Their fraudulent concealments were obvious to the average person as well as the original negligence's at both trials. But I was suffering from chronic fatigue syndrome, (CFS or ME/CFS) a rare incurable disease. it took seven years to find a specialist to diagnose the disease there is no biological tests for it. The only way to identify it was by asking the appropriate questions. I was told that there is no need for follow up appointments, so I do not have any medical evidence other than a letter from my ME/CFS specialist. I tried acupuncture for three yrs. which helped my physical pain but without any cognitive improvements. I have a letter form the acupuncturist and her observations, though it is not certified. The disease left me bedridden with 30 symptoms, severe exhaustion, mental and physical ailments for 18 years. I made a recovery in 2023 thanks to an unexpected positive reaction to the covid 19 vaccine. I finally was having some clarity. Through the years I tried talking to attorneys but because of the ME/CFS and trauma I could not communicate. I just said I sued my business partner, won, but lost everything. The phone calls ended in less than five minutes because I could not answer their questions. i had no idea that there was any mishandling, it just didn't seem right I should lose everything and not understanding why. My ME/CFS disease prohibited me from understanding what mishandling had occurred or expressing my thoughts to other attorneys. How could I sue for legal malpractice if I didn't know what negligence's occurred and couldn't talk about the trial. Just making phone calls It should be clear that had I been able to communicate it would have ended with my attorney or any attorney representing me in a legal malpractice lawsuit. There were enough negligence's, professional misconduct and fraudulent concealment to merit a legal malpractice lawsuit. Where is the proof that I was able to communicate with any attorney. Where is the lawsuit, where is the complaint to the Bar of Board of Overseers. The Defense and the Court used that against me., even though I clearly stated I was unable to communicate with my appellant attorney or any other attorney. For the same reason I could not communicate with other attorneys. Since I failed in the past, I filed my own legal malpractice lawsuit, pro se. To toll time, I filed under "Incapacitation due to mental illness" which failed because the court stated that because I had tried contacting attorneys over 18 years, this clearly indicating I was aware of my lawyers failing him. Not because of my disability. It was my disability that prevented me from communicating. The Defense and court ignored the letter from my ME/CFS specialist stating that I could not pursue my lawsuit against my attorney because. of my ME/CFS. Unfortunately, it was a poor choice of words. I was not pursuing a lawsuit I had not identified any mishandlings. I was trying to communicate the events of the trial and if there were any mishandlings I would see what should be done. But I never communicated the events. I hope there is a distinction. It was the trauma and ME/CFS ailments that kept me from identifying the negligence's and communicating with my own appellant attorney and other attorneys. I supplied the court with my ME/ CFS specialist, letter, articles on the disease and two affidavits from witnesses. I appeared in Court on October 4, 2024, when the Judge denied me a trial. I asked the Judge if I could file under fraudulent concealment. He said he would allow me time. but I never received any notice of expiration. I wasn't anticipating any problem with time. I learned a few days later that my stepmother had aggressive cancer. I tried balancing her needs with filing a new complaint, but I could not do both. I gave my stepmother my attention, figuring to return to the Fraudulent Concealment" complaint after the funeral and grieving. She died three months later, January 2025. I did not expect was that all the emotion from the loss and the stress of waiting to file my complaint, I did not expect a relapse of my ME/CFS. I was bedridden again for nearly a year. I called the court several times to find out of the expiration date, but they said there was none on record. In August 2025 I contacted the Defense who told me the case was closed but without prejudice. I finished the complaint identifying 5 fraudulent concealment acts. I supplied the court with the death certificate an affidavit from my roommate explaining my relapse of ME/CFS and apologies. The court sent me a 4+ page letter denying me a trial stating that notwithstanding my professed disability made clear that I fully appreciated the nature of my legal tights and the consequences of his acts and failure to act. That my 19-year quest to speak with malpractice attorneys about pursing a claim seeking to explain his reason for suspecting legal malpractice" makes crystal clear that the governing statues of limitations dd not run against Plaintiff's malpractice claims because I suffered a disability that compromised my capacity to appreciate and prosecute my legal rights.my legal rights to run against Plaintiff's malpractice claims because I was suffering from a disability that compromised his capacity to appreciate and prosecute his legal rights. The court listed Petersen v Time Inc. and other precedents. Fraudulent Concealment was not included as a denial. The court pointed out that I was untimely. stating that I was readdressing my ME/CFS and that it took my 17 months from the first denial to respond which was 5 months after the statute of limitations and the i used Rule 60 which was the wrong vehicle. I have less than 20 days to provide an argument. I had withheld twelve years of psychiatrist notes but in reading them I did mention suing my attorneys and my psychiatrist assessment of my cognitive abilities does not align. The only other evidence that I have and did not present was an MRI of my brain which shows elevated levels of Foci, which is not uncommon in ME/CFS. The Foci causes cognitive impairment. In 2023 I made great cognitive improvements thanks to the Covid 19 vaccines. In all these years I never spoke of the trial that caused all of this because I never overcame the trauma and the CFS until the Covid 19 vaccines. My needs - I am placed in a difficult situation. I am looking for an attorney or someone who understand my problems and file a convincing motion for reconsideration in a very short time. Someone who can so the research to find exceptions to the law and file a response that will get an approval from the court to proceed to trial. If I can get the approval for a trial, I can also file a complaint with the Bar of Board Overseers and look for an attorney who can represent me. Unfortunately, time is a serious factor. The horrible representation is obvious, and the fraudulent concealment is obvious, but I don't think I have to prove that now, it's getting the trial. approval. I am open to this being an hourly or set price.

## 1) Tier 2/3 MSP Engineer – As Needed **Title:** Tier 2/3 MSP Engineer – As Needed | Microsoft 365, Windows, Networking, SMB Support We’re a growing MSP building a bench of reliable contractors we can use for **as-needed project work, escalations, overflow support, and client onboarding tasks**. Most of our clients are **small to mid-sized businesses**, with a strong focus on **professional services firms** such as CPA/accounting, architecture, engineering, and similar organizations. We are looking for a **Tier 2/3 MSP Engineer** who is comfortable jumping into a client environment, troubleshooting issues, handling escalations, and supporting projects when needed. This is **not a full-time role**. We are looking to build a relationship with someone we can use on a recurring **contract / as-needed basis** as work comes up. ### Typical work may include: * Tier 2/3 escalation support for SMB clients * Microsoft 365 administration and troubleshooting * Exchange Online, Entra ID / Azure AD, MFA, shared mailbox, permissions, and user issues * Windows workstation and Windows Server troubleshooting * Basic to intermediate networking support including VPN, firewall, switch, and wireless troubleshooting * SharePoint / OneDrive support and occasional migration assistance * Client onboarding tasks, documentation cleanup, and project support * Working alongside onsite technicians or other contractors when needed ### Ideal experience: * Prior experience working for or alongside an **MSP** * Strong experience supporting **SMB environments** rather than only large enterprise * Comfortable working across multiple client environments * Hands-on experience with **Microsoft 365**, **Windows Server**, **Entra ID**, **Exchange Online**, **SharePoint**, and general endpoint / user support * Solid troubleshooting ability across Microsoft, networking, and general infrastructure issues * Able to communicate clearly and document work professionally ### Nice to have: * Experience with RMM / PSA platforms * Familiarity with environments in the **10–100 user range** * Experience with client onboarding, migrations, or remediation projects * Ability to assist after-hours for planned cutovers or urgent issues when needed ### Engagement structure: We are specifically looking for someone open to: * **As-needed / project-based work** * Escalations that may come up periodically rather than every week * Short projects ranging from a few hours to several days * Occasional after-hours support for cutovers or urgent issues ### When applying, please include: 1. A brief overview of your MSP and SMB support experience 2. The Microsoft / server / networking areas you are strongest in 3. Whether you are comfortable supporting multiple client environments 4. What your availability typically looks like for project-based or urgent work 5. Whether you’re open to coordinating via **Slack or Microsoft Teams** if we’re a fit

Overview: We are a growing Managed IT Services Provider (MSP) based in the Pittsburgh, PA area looking for a reliable and sharp Level 1 IT Support Technician to assist with day-to-day support operations. This role is critical to our growth. We need someone who can handle frontline support efficiently, communicate clearly with clients, and escalate issues appropriately. If you are proactive, organized, and take ownership of your work—we want to work with you. ⸻ Responsibilities: • Provide Level 1 remote support for end users (Windows, basic Mac support) • Handle ticket intake, triage, and resolution through our ticketing system • Troubleshoot common issues: • Password resets • Microsoft 365 (Outlook, Teams, OneDrive) • Printer issues • Basic networking (connectivity, WiFi troubleshooting) • Install and configure software applications • Assist with onboarding/offboarding users • Document issues, resolutions, and client environments • Escalate complex issues to Level 2/3 as needed • Follow SOPs and contribute to improving documentation ⸻ Required Skills: • Strong communication skills (clear written and spoken English) • Experience with: • Microsoft 365 Admin Center • Windows 10/11 support • Basic networking (IP, DNS, DHCP fundamentals) • Ability to follow processes and stay organized • Reliable internet connection and availability during business hours ⸻ Preferred (Nice to Have): • MSP experience (this is a big plus) • Familiarity with RMM tools (Datto, Ninja, Kaseya, etc.) • Experience with ticketing systems (Zoho Desk, Jira, etc.) • Basic understanding of cybersecurity best practices • Experience with Apple/Mac environments ⸻ Work Expectations: • Availability during Eastern Time business hours (9 AM – 5 PM) • Daily communication and updates on tickets • Ability to follow defined processes and checklists • Willingness to learn and improve continuously ⸻ How to Apply: Please include: 1. A brief summary of your experience with IT support 2. Your experience working in an MSP (if any) 3. Tools and platforms you’ve used 4. Your availability (hours per day/week) 5. Example of a common issue you’ve resolved and how you handled it ⸻ Important: We are looking for someone long-term. Reliability, communication, and ownership matter more than just technical skill. If you are someone who takes pride in doing things the right way and wants to grow with a company—this is a great opportunity.

We're an early-stage startup building an exciting new IT support platform for small businesses. We’re looking for experienced IT support professionals who care as much about how they interact with people as what they fix. We're looking for independent, critical thinkers, so please do not waste either your or my time with a reply that is LLM-generated. It will be immediately discarded without further consideration. The Role You’ll work as an independent contractor, accepting support jobs through our in-house dispatching system. You'll effectively set your own hours, accepting only those jobs that work with your schedule. Initially, support may involve more direct customer interaction (live sessions, screen sharing), with the expectation that over time, more issues may become asynchronous as our software matures. This is a startup, so details will evolve as we learn. We’re upfront about that and value technicians who can work comfortably in a system that’s improving in real time. ⸻ What You’ll Help With (Examples) Typical issues include the kinds of problems MSP technicians see every day, such as: • Microsoft 365 issues (Outlook, OneDrive sync, licensing, account access) • Wi-Fi or basic network troubleshooting • Printer setup and connectivity issues • Performance issues, disk space cleanup, basic security concerns • Helping non-technical users understand what’s going on and what to do next Technical competence matters, but calm, clear, human communication matters even more, especially early on. ⸻ What We’re Looking For Required • 3–5+ years of IT support / helpdesk experience (MSP experience strongly preferred) • Excellent people skills: patient, clear, and comfortable interacting directly with end users • Strong written and spoken communication • Ability to explain your troubleshooting approach step-by-step • Good listener; customers shouldn’t need to repeat themselves • Reliable and punctual when you accept a support session • Comfortable following structured support flows and documenting outcomes • US-based with native-level English fluency Strongly Preferred • Willingness to offer candid, constructive feedback to improve our processes • Interest in contributing to troubleshooting documentation (what worked, what didn’t) • Located in or near Austin or NYC (optional; may enable on-site work in the future) ⸻ Flexibility, Pay & Structure • Contractor role • You choose when to accept jobs • Compensation will start hourly while we establish baselines and gather data No guaranteed hours initially, so this opportunity is best suited for experienced technicians who may already have a roster of their own clients and are looking for interesting, additional work. ⸻ Trial Process (Paid) Shortlisted candidates will complete a paid live trial: • A realistic support scenario • Live interaction and troubleshooting • Focused on communication, judgment, and problem-solving, not speed or memorization This helps ensure a good mutual fit before ongoing work. ⸻ Who This Is Not For • Entry-level or script-only support roles • High-volume, low-touch ticket grinding • Technicians who dislike customer interaction or documentation • Anyone uncomfortable with evolving systems in an early-stage product To confirm you read the full post, please include the phrase “clear communication” somewhere in your application. ⸻ How to Apply Please include: 1. A brief summary of your IT support experience (especially MSP work) 2. One example of a support issue where communication with the user mattered as much as the fix 3. Your typical availability (roughly) 4. (Optional) What you think most IT support systems get wrong today

Systems Administrator – Opportunity Overview Position Summary A family-owned organization is seeking a well-rounded Systems Administrator (“jack of all trades”) to support and modernize their IT environment. This role will report directly to the CFO (and potentially COO) and will play a key role in cloud migration, infrastructure optimization, and application support. --- Work Environment & Schedule • Work Model: Hybrid (open to flexibility) • Office Hours: Office opens at 6:00 AM • Core Schedule: 8:00 AM – 5:00 PM CST • After-Hours Expectation: • Occasional support needed for dispatch later in the day • Potential Saturday morning availability --- Team Structure • Team expansion to 2 IT hires total: • Systems Administrator (this role) • IT Support resource (reports/supports Sys Admin) --- Key Responsibilities • Serve as a generalist across infrastructure and systems • Support cloud migration initiatives and environment optimization • Assist with transition away from on-prem data center • Improve security posture and disaster recovery capabilities • Manage application transitions (moving to new systems) • Provide web application support • Includes understanding an internally developed driver application (being phased out) • Troubleshoot and resolve time zone and system update issues • Example: MST vs EST discrepancies affecting driver reporting • Collaborate with operations/dispatch on system-related issues • Identify gaps and implement improvements via scripting and automation --- Technical Requirements • Strong experience with: • Microsoft ecosystem (core focus) • Azure • Microsoft 365 • Active Directory (AD) • SQL • Cloud Migration • Experience working across split or hybrid environments • Exposure to: • Web application support • Infrastructure modernization • Ability to: • Script and automate processes (PowerShell or similar) • Analyze and troubleshoot complex system issues --- Key Initiatives / Projects • Ongoing cloud migration strategy (splitting workloads across environments) • Transitioning to a new application ecosystem • Eliminating legacy data center infrastructure • Enhancing security and disaster recovery frameworks • Addressing time zone discrepancies impacting operations • Evaluating and improving existing scripting/automation gaps --- Candidate Profile • True “jack of all trades” with broad IT systems experience • Comfortable operating in a lean IT team • Strong communication skills to work with business leadership (CFO/COO) • Ability to support both strategic initiatives and daily operations • Experience in logistics, dispatch, or driver-based systems is a plus --- Certifications / Education • Verification required for: • CompTIA certifications (or equivalent foundational certifications) • Relevant education and technical credentials --- Interview Process • Initial screening: Scheduled for first week of July --- Additional Notes • Environment includes dispatch operations across multiple time zones • Systems may require tuning to ensure accurate reporting across MST/EST • Vendor/OEM involvement may be part of troubleshooting efforts

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

## 3) M365 / Azure / AWS / Security Contractor – As Needed **Title:** M365 / Azure / AWS / Security Contractor – As Needed | MSP Projects, Hardening, Cloud, Remediation We’re a growing MSP building a bench of trusted contractors we can use for **as-needed Microsoft 365, Azure, AWS, and security-related projects** across our SMB client base. Our clients are primarily **small to mid-sized professional services firms**, and we’re looking for someone who can step in for cloud, security, and higher-level technical work when needed. This is **not a full-time role**. We’re looking for a contractor we can use for **short-term projects, escalations, hardening work, migrations, remediation, and occasional client-specific needs** as they arise. ### Typical work may include: * Microsoft 365 administration, cleanup, remediation, and best-practice improvements * Entra ID / Azure AD, MFA, Conditional Access, identity and access configuration * Exchange Online, SharePoint, OneDrive, and Intune-related support or project work * Azure infrastructure support, tenant cleanup, cloud migrations, and troubleshooting * AWS support for SMB environments including areas such as IAM, EC2, VPC, permissions, and cloud troubleshooting * Security hardening, remediation, post-incident cleanup support, and general security improvement projects * Reviewing client environments and providing technical recommendations, findings, and implementation support ### We’re particularly interested in contractors with experience in some combination of: * **Microsoft 365 / Exchange Online / SharePoint / OneDrive** * **Entra ID / Azure AD / Conditional Access / Intune** * **Azure** * **AWS** * **Microsoft Defender / M365 security hardening** * General security remediation, incident cleanup support, or cloud security improvement work ### Ideal experience: * Prior experience supporting **SMB environments** or working in an **MSP / multi-client environment** * Ability to work independently, document findings clearly, and communicate at a professional level * Comfortable stepping into projects that may last anywhere from a few hours to several days * Comfortable supporting environments in the **10–100 user range** * Able to work with a small MSP team and provide strong technical guidance where needed ### Engagement structure: We are specifically looking for someone open to: * **As-needed / project-based work** * Cloud, Microsoft 365, Azure, AWS, and security-related projects that may come up periodically rather than on a fixed weekly schedule * Remediation, hardening, migration, or escalation work as needed * Occasional after-hours work for planned cutovers, urgent remediation, or project deadlines ### When applying, please include: 1. Which of the following you work in most often: **Microsoft 365, Azure, AWS, security / hardening / remediation** 2. Whether you’ve worked with MSPs or supported multiple SMB client environments 3. The types of projects you’re strongest in today 4. Your availability for short-term project work or urgent escalations 5. Whether you’re comfortable coordinating over **Slack or Microsoft Teams** if we’re a fit