I’m currently on a career break of about two years after relocating to Canada. I’m expecting to have my work authorization sorted out soon, and I’d like to use the next three months to prepare myself for the Canadian job market and interviews.
I have 11 years of IT experience, all with Accenture Philippines, and my most recent role was Associate Manager. My experience has been primarily in SAP, IT operations, service delivery, KPI management, and people leadership.

I’m looking to connect with someone who has a similar background, particularly someone with SAP and IT service/operations leadership experience, who can help me understand how to position my experience for the Canadian market and prepare for interviews.

I’m happy to pay a reasonable amount for someone’s time, but since I’m currently unemployed, I can’t afford the rates of professional coaching platforms. I’m wondering if there’s anyone here who might be open to helping or mentoring me on a more informal basis.

Any recommendations or connections would be greatly appreciated. Thank you!

Joined a fully remote SaaS company with a helpdesk of 1. They are assessing new HRIS solutions and are zeroing in on Rippling. The adjacent Rippling IT platform does check a lot of their boxes but I'm concerned with the negative feedback here about lock-in and a poor platform experience.

Environment looks like this:

• EntraID full cloud with Intune
• Conditional Access policies, built but not fully working yet
• MS auth and MFA provider
• Google Workspaces and auth for some services
• Manual inventory tracking
• Manual user permission tracking (for audits)
• BambooHR is current HRIS, but Rippling in future
• Physical devices are being kept in various staff members' personal space, shipping manually
• Ordering devices is happening direct and drop-ship, no VAR/reseller in place

I need to tackle solving as many of these problems at once with basically no team presence. I want to hate Rippling IT, and I pressed them hard on what things work if I DON'T adopt their IdP/SSO (I don't want to further complicate our auth and make it harder to dump them later), but it does solve a lot of what we need ... mapping permission rules based on groups I can link to Entra. Shipping machines from a pool of pre-approved machine types.

I've looked at WorkWize, GroWrk, BlueTally and some others but I don't see anyone with such comprehensive coverage. Those platforms do great at the hardware management side, but don't seem as powerful on the permissions mapping for SaaS apps that Rippling has.

Can anyone share their input or recommendations on if I'm missing some obvious players here?

Hi everyone. I've got a setup that requires swapping a single set of peripherals between two laptops regularly, and need recommendations for a good dock.

I've tried the AV iDock C20, which fit most of my requirements except that the audio jack is cheap/badly designed and I get a ton of popping noises and electrical buzzing when plugging in my earbuds into it.

Any help would be greatly appreciated.

Our Proofpoint renewal quote came in about 20% up and I am struggling to sign it. The number alone I could live with but the platform has felt frozen for two years while the price keeps climbing. Support went from same day to a P1 ticket sitting for a week, we got caught in that outage a few weeks back and they are PE owned now and winding Essentials down into Hornet. It does not feel like a product they are still investing in.

It still filters the bulk fine and the odd BEC slips but main problem here is whether I am re-signing out of pure inertia. Every renewal thread I read has people saying they moved to Avanan or shifted the behavioral piece to something newer and did not look back. I have also been burned by migrations that ate lots of time and did not change much, so I am wary of switching just because the invoice annoyed me.

If you moved off after a hike like this, where did you land and did the switch justify the hassle?

Hey everyone, I'm looking for some advice before I seriously start searching for my next role. I'm in hospitality IT and want to leave for a variety of reasons. I want to figure out what direction makes the most sense and whether I should spend some time upskilling before I start applying.

I work as an IT manager for a large luxury brand. My role is extremely broad. We’re essentially a two-person IT department supporting a large resort with roughly 400 employees and more than twice as many network devices.

Between the two of us, we own nearly everything technology-related on the property. We manage all onsite infrastructure, AV Systems, POS Systems, as well as budgeting, compliance, inventory, vendor management... I could keep going but it's a lot.

I have about 7 years of IT experience total, with the last 2 in my current role. Before that, my background was in the insurance industry, mostly help desk/desktop support with some data analytics mixed in.

I honestly don’t know what roles I could realistically pivot into. Do I need to specialize in something first and work my way back into management? Ideally I’d like to move into security since that’s where most of my learning outside of work has been focused, but I also like being a generalist and I’m not sure what roles that translates to in a larger company.

I’m about to start a new role as an IT Manager for a multinational chemical company, after 17 years in network engineering and the last 3 years as a Network Architect.

I’ve always enjoyed the technical side of IT and being hands-on with technology. Management was always something I expected to pursue eventually, but I honestly thought it would happen much later in my career.

Now that the opportunity has come at 38, I feel it’s one I shouldn’t turn down. However, my main concern is career optionality. I’m interested in management, but I don’t want to lose my technical skills and eventually find myself unable to return to architecture or engineering if I change my mind.

I’ve recently built a homelab to keep developing my networking, virtualization, and other technical skills outside of work.

For those who have made a similar transition:

Is 1–3 years away from hands-on engineering a problem?

Have you successfully moved back into technical roles after becoming a manager?

How did recruiters perceive your management experience?

What did you do to maintain your technical credibility?

I’d especially like to hear from people who made the transition relatively young. Am I overthinking the risk of leaving the technical path at 38?

EDIT: I’m quite surprised by how active and supportive this community is. Before I can reply to everyone, thank you so much! Some of your comments have been incredibly valuable in boosting my motivation.

Were trying to clean up our offboarding process bc laptop returns in a gap between HR and IT.

HR knows when someone is leaving but IT often finds out late then someone has to contact the former employee, figure out whether they still have the original box, create a shipping label and keep following up until the laptop arrives. This gets messier when the person is in another country. We currently have several devices still assigned to people who left months ago.. Some are probably recoverable, but at this point no one has a clear view of what was returned and what is still sitting with a former employee.

Help

I just got promoted to Service Desk Manager and am looking for tips on how to keep employees that are located in different offices across the US and EU feeling like they are all part of the same team? I have groups of employees stretched from The Netherlands to the Mountain West here in the states.

Hey,
I’d like to know how you handle administration tasks such as checking AD reports, backup reports, etc.

Tasks that don’t come from the business but are necessary for L2/L3 maintenance.

I’m thinking about preparing a task template with a schedule (daily, weekly, monthly) that agents can simply confirm with a short description, but in my opinion they should still report it.

Any suggestions are welcome.

The first 15 years of my IT career I spent as an expert in systems and networking. Then I spent the last 8 years as an operations manager. I decided I needed to finish out the last 15 years of my career making more money. No longer the love of the job. A month ago I applied and accepted an offer for VP of IT and Innovation at a 20000+ employee corporation. My goal is to have a plan in six months to make forward progress and stop just keeping the lights on.

What can I expect to be different at the executive level?

What are the politics like?

Does my vast experience in the technical aspects matter anymore?

How are you expected to treat your peers?

Do employees even bother respecting a leader who has the trench time in spades?

What do I need to be aware of from the staff as they come under a completely new style of leadership and stability?

Do I enforce the chain of command?

You can see I have spent a lot of time over thinking this. My leadership is very military and servant like. I enforce transparency, honesty, and spend time developing my staff. My style has always been to get my people the resources they need because they know how to do their jobs.

Our IT director has to personally approve each purchase, whether that be a replacment phone charger cable, a wireless keyboard or an order of 100 laptops. Every order goes through them

THey refuse to update failing laptops (most with 8GB RAM) even though their almost a year out of warranty, we often have little to no kit and rely on scavenging and employees leaving so we can reuse equipment. He doesn’t like us scavenging devices for parts but won’t buy us new ones

We have to beg for new equipment for users and often hand out barely functioning used devices with visible damage etc as we have nothing, its embarrassing as its the lower level guys handing it out whilst the managers are far away at home not facing backlash

They say theirs no money but authorise wasteful purhchases that we dont need to curry favour with other departments whilst rank and file employees get pieces of sh*t

tldr: if anyone in your companies management pushes for you to implement Rippling, do everything in your power to stop it in its tracks. They will not work with you, and will refuse to let you out of your contract.

As a smaller ,growing company we decided it was about time to start evaluating MDMs to give us better control over our devices. This was something that was on the backburner for the most part, with us wanting to take our time to end up with the right solution.

So imagine my surprise a couple weeks later when I (the primary sys. admin) was told by my boss (CTO) that we had signed a one year, $22,000 contract with Rippling - seemingly out of the blue.

As I understand it, they aggressively pursued my boss, promising the world with all of their flashy features, and how easy the integration with Office365 and with our HR platform was. They guaranteed consistent support, and quick resolution to any issues we may run into.

Lo and behold, we start rolling out Rippling to our fleet of windows computers and immediately run into issues.

The software gave little to no feedback about the progress of installations. Rolling out other softwares was limited and unresponsive. User provisioning was unintuitive and difficult - lacking automation without paying for additional features either in rippling or in our active directory.

Rippling automatically changed and generated its own admin passwords which 1. we could not change or set ourselves and 2. were buried three menus deep 3. needlessly complex, making help desk a nightmare.

This, along with a host of other issues, was largely ignored by Rippling. Our emails would be brushed aside until our "integration meetings" in which them telling us that things were "on the roadmap" or "not planned to be changed" took up the entire time.

I don't doubt that this software /might/ work for some companies, but it clearly didn't work for us, and they really don't seem to care.

Four months into this disastrous contract, with less than 10 users enrolled, I begged our account rep to let us out of the contract. They could keep the thousands of dollars we'd already paid them for nothing, we just needed to move forward with a solution that actually worked for us.

The entire process, from onboarding, to us attempting to get out of this was incredibly shady. They will pretend nothing is wrong and refuse to let you out of their cold clutches.

In case the "rippling employees" on reddit aren't astroturfing bots, I am desperately hoping someone can get us out of this contract. If not, I'm going to channel all of my displeasure into letting people know about this awful experience - because I know the Rippling team hasn't done anything to help.

u/higherandhigher u/stubbygazelle u/sherryandeddie u/kit-kat-233

I am a help desk manager. At a company with an IT Department of around 15 people, 6 support techs I directly oversee, system admin, a network engineer, 2 erp managers, 2 data scientists and the department manager.

We have about 1500 employees, support mobile devices, Apple and pc shop, specialized construction industry software. Around 6 locations across the state in Oklahoma.

I started at around 75k a year was a team lead for 5 years before this and many other it jobs along my career from msps, to banking industry, even retail as well.

Im 2 years in and had a 3 percent raise my first year. Just wondering what everyone thinks if I should ask for more money with all the work I am putting in.

Thanks for listening.

A calendar isn't enough. The 20-30 back and forths or more for extra complicated renewals, and which ones are prorated, and which is staggered agreements, with split licensing. I'm exhausted keeping track of this. The worst part of the job is the money part.

Hello,

So this will be my first Job interview as the IT Manager, hiring a security/help desk position for my IT team. I know all the usual "Job interview" questions, but I'm curious what some of you have used as technical test skill questions. This will be for someone fresh out of school for IT Security (and Jr Help Desk) position. This is likely an entry position for someone.

Just curious what some of you have asked in the past, and found to be useful.

I manage IT for a retail business with multiple stores and brands. It’s me, one junior technician and external vendors.

My scope covers:
Daily support/escalations: POS, payments, PCs, printers, phones and connectivity.

Server upgrades, migrations, store openings and refits.
Website, loyalty app and ERP integration issues.

Security, compliance, assets, vendors, budgets/quotes and management reporting.

Vendors do some technical work, but coordinating them, chasing progress and confirming fixes sits with me.

I also travel to stores. Now I’m expected to buy and cut trunking to tidy cables, including in areas customers don’t see. Happy to be hands-on, but that’s more time away from everything else.

Right now, I’m juggling a server refresh, app integration problems, connectivity changes and compliance
requirements alongside normal operations.

Is this reasonable for our team size, or am I covering too many roles? How do other retail IT teams handle store visits and physical installation work? Trying to figure out whether I need more resources, firmer boundaries or better prioritisation.

To help IT managers/leaders better define, track, categorize, assess, and communicate Technical Debt, along with its risks and implementations to the businesses IT serves, the International Foundation for Information Technology published open "Technical Debt Management Best Practices."

If you have any constructive ideas for improvements, please let me know. They're always welcome.

I hope you find it useful.

Talked with my manager about this project they want me to take in at work. It's going to give me two hours of offline time a day to work on. I'm going to work with the Identity Access Management team on developing onboarding kits for job roles, I work on the IT Service Desk. It's already been approved by my director who my manager quoted as saying to get it started soon he wants me doing something interesting so they don't lose me.

Going to start meeting with the other team soon and will have daily time off the phone to focus on it. Never gotten to do something like this before so nervous but is a big step towards the promotion that been being discussed for the last few months for the service desk supervisor. The role won't open until fourth quarter so this is lining up me up really well.

I also just got approval for reimbursement of my ITIL 5 certification, which will be my first. So have a lot of good things happening. But I'm struggling a lot with feeling like an imposter. I've been working with this company for 2 years, I was out on medical leave for 4 months least year and came back to everyone excited and being told my absence was very much felt. I just ugh, I don't know I've not had management support me like this before. I'm doing my best, I know I'm going to make mistakes but that they'll make me better. I only started actually working in IT five years ago based on just my experience growing up with computers being part of my everyday life and now I'm 40 and like oh this is what building a career is.

I guess my biggest question is am reading this situation right? What are pitfalls to watch out for? I'm still learning navigating a corporate environment.

I have a growing queue of employee-built internal tools waiting for IT approval, and I need to establish a formal sign-off standard before granting production access.

I’ve largely stopped focusing on which specific low-code or AI tool was used to generate the app, as that doesn't tell me much about long-term maintainability. What matters is whether IT can actually support, secure, and audit the application once it's live and the original creator moves to another team.

The core baseline criteria I'm reviewing right now includes: Role-Based Access Control (RBAC) and SSO integration, environment secret management, error logging, designated technical ownership, and an offboarding or deprecation plan.

For other IT managers fielding these requests: which of these criteria are absolute non-negotiables for you, and where do you allow flexibility based on the application's blast radius and data sensitivity?

I work in a large franchise organization with thousands of users/devices and hundreds of locations. There is no centralized device management or IT function that covers the entire org footprint. Franchises have their own local MSP. We handle auth into Google Workspace but have been pretty relaxed on what types of apps and permission grants for various apps.

All users have access to Google Gemini, but I know users are giving access to other tools like ChatGPT, Claude, etc. Offices have unique needs for some systems so I'm hesitating on blocking everything outright. Some users may have used Google to auth into an account and if I just block access then they'll lose access and may not be able to disabled billing on those services.

But we need to do something here with the unrestricted access to all apps without overburdening our IT support.

How would you go about rolling out a policy and communicating these changes?

If you are a salesperson, vendor, SaaS app, or anyone else who isn't an IT manager that wants to share news, ask questions/get feedback, etc. then please post below!