MSP Automator reviews us

MSP Automator took a deep dive into going with live with B365.“We have breathing room. We have time to do other stuff for once.”

Review: Benchmark 365 Proves Ethical Outsourcing Requires No Compromise


Written by CEEJ on July 28, 2022 at 10:04 pm Source:


If you’ve been ’round these parts any length of time you’ll know that I don’t make a habit out of heaping undeserved praise upon vendors. Most of them deserve nothing but our contempt for doing things like making us sit through hour-long Zoom demos with salesbots to get quotes and making LOB apps that require local admin for all users. Honorable mention to Kaseya who has once again managed to live up to their reputation as the “SaaS Antichrist” by decimating Datto in record time. It doesn’t have to be this way. Vendors don’t have to be predatory snake-oil salesmen fueled by VC money and with a prime directive of extracting every possible cent from any customer they encounter. Employers don’t need to compromise benefits and staff morale to make ends meet. There are better ways. Benchmark 365 is one of those better ways.

*Disclaimer: I don’t take money or incentives from vendors to write these reviews and I don’t monetizethis website because I feel it would compromise my neutrality and credibility. I share information and opinions with the community so they can make informed decisions in their own businesses, because people deserve to hear things from people who aren’t being paid to say them once in a while. In that same vein, my opinions don’t reflect those of my employer or any company I roast, and anything I post is solely my own and in “good” faith. Anything posted on this site that could be construed as inflammatory, defamatory, or rude should be considered satire. For instance: “Kaseya executives feast on the flesh of executives they conquer” is clearly inflammatory and maybe even a bit defamatory, regardless of it actually being 100% true. So, you know, like, your mileage may vary and stuff.


Outsourcing doesn’t have to be a naughty eleven-letter word. It doesn’t have to invoke fear in the minds of employees and people don’t need to be scared for their jobs when they hear you’re bringing an outsourced provider in. If you go into an engagement with a company like Benchmark or one of their competitors with the intention of outsourcing your entire staff overseas and firing your full time staff, you are a dick and this post is not for you. There may be no ethical consumption under capitalism but you don’t need to expedite our demise.

We started our outsourcing journey for three reasons:

  1. Coping with loss of multiple staff on vacation, PTO, or sick time on some days was stressful on ticket counts and resolution times. Having a buffer or crutch to lean on during either busy days or days we have staff out would prevent service quality from suffering.
  2. We’ve been working with Sea Level for almost a year (review to come someday, highly recommend will do for now) and our processes are starting to produce actionable data about where we can improve metrics. Likewise our documentation and processes are now capable of easily sustaining outsourced augmented staffing. “Inspect what you expect” is the best and most obnoxious advice I’ve had drilled into my head from this experience. A moderate time investment to fully standardize your stack and documentation across clients is worth 10,000X the cost.
  3. Quality of life for our current staff. Being on call sucks and as we add clients willing to pay for overnight support, it isn’t fair to expect our staff to wake up at 2 AM for someones stupid fucking printer, even with the overtime pay. (Nothing you are printing at 2 AM can be that important or worth the OT. Nothing.) We wanted to offer consistent support 24/7 without burdening on-call engineers.

My boss is a really great guy. I was lucky to find a unicorn MSP and they were lucky to find a (sassy and somewhat abrasive) unicorn engineer in me. He prides himself on the service we provide and he was skeptical that any kind of outsourcing partner anywhere could really do what we do as well as we do. Fair assessment, to be honest. The contenders so far were hilariously lackluster.

If I think back to it now, outsourcing was a naughty eleven letter word here because we thought about it all wrong. We thought it was an all or nothing: send all your tickets to an overseas call center and ride it out until your clients mutiny or you hire your way out of it. We didn’t realize the smart way to do it is to augment your current staff. We didn’t realize there was a company willing to grow into a partnership and fill those gaps without crossing over into making someone redundant. We were playing a zero sum game with ourselves and we didn’t need to be. You can ethically augment your MSP with outsourced staff without pissing anyone off or going broke. But you need to be properly positioned to do so.


Vendor pitch meetings really piss me off. Like, several hours in advance. Knowing I’m going to lose an hour of good engineering listening to a sales drone promise me their SaaS product will solve all my problems physically pains me. This is relevant because I normally start any vendor call on the offensive to try to root out the bullshitters early and shut them down. There’s nothing worse than getting 45 minutes into a demo to find out there’s a deal-breaker. Fuck that. I had gone through several other outsourcing vendor meetings and walked away from every single one feeling scummy. Then I got to the last vendor on my list, Benchmark 365.

James, the CEO, and our would-be account manager, Rosie, responded to our initial inquiry within a day and unlike other vendors we spoke to, they weren’t interested in getting us on a call until they did some homework and vetted some simple financials and other metrics from our end. If this is where you’re saying out loud to yourself “why do they need my financials?! I’m not telling them that stuff!” – shut up. No, really, shut up. This makes a lot of sense from their end and shows a methodical and calculated approach to their partnerships. Benchmark doesn’t lock you into an agreement. Being a month-to-month expense for an MSP and with a considerable initial turn up investment from their end to train staff for your environments, it absolutely makes sense to screen for the bullshit break-fixers who are barely treading water and trying to throw a Hail Mary by hiring outsourced help. No need to tie yourself to a sinking ship and cultivate potential animosity. Self preservation is a trait of the intelligent. Besides, they’re not asking for audited financials. It’s more of a quick back-of-thenapkin- math web form. Once we turned our info-gathering form in we had a call set up within a couple days. Pretty decent turnaround for a business primarily operating on the opposite side of the planet.

I want to stress that my expectations were very low and I was initially a bit put off about this screening. After going through a call with a competitor that I won’t name but is one of the bigger players in this market that was less of a presentation and more of a used-car-salesman type trying his hardest to make their model sound as exploitative and unethical as possible, my experience with Benchmark 365 was the exact opposite and a huge boost to my faith in the human race.

If you meet James you’ll immediately notice he’s not your typical sales type. In fact, I didn’t feel like he was selling me anything the entire call. I actually kind of felt like he was trying to talk me out of it. James strikes me as a guy who has been victimized by a bunch of dickhead MSP owners with unrealistic expectations in the past and wants to under-promise and over-deliver. He was extremely transparent and upfront from the start that this is a process that requires engagement from both sides. You get out of it what you put into it in terms of documentation, communication, training, system stability, etc. This is not a ripcord you pull in emergency to keep from flying your business into a mountain, this is a planned flight path around the mountain with someone you know and trust in the co-pilot seat. While it was mentioned that some MSPs have been successful offloading their entire support workload to Benchmark, that isn’t their ideal situation and definitely wasn’t ours. James said the sweet spot for most successful clients is offloading about 20% of their ticket volume to Benchmark after a pilot and ramp up period. Three plans are available offering a few different blocks of tickets, and you can buy additional if needed, all month to month. I won’t share pricing, other than to say it’s more than reasonable and considerably less than a FTE. No lock-in agreements and the ability to scale up or down infinitely with 30 days notice are other huge benefits Benchmark has that no one else does. Their primary call center is in the Philippines where most of the population speaks fluent English.

Their presentation was excellent, by the way. If you sit through it you’ll probably notice like I did that this is a program designed by someone who runs an MSP and understands exactly the things that make MSP owners and managers suffer. Ticket surges, covering PTO and vacations, staffing and hiring concerns are all real as we stare down the barrel of a recession. The clearly outlined expectations, costs, expertly crafted onboarding timeline, and thorough FAQs you receive after the meeting paint a picture of a company who has seen some shit and are a bunch of battle hardened badasses who absolutely know you will try to blame your failure on them and will not be taking any of that shit from you.

Love it. Sign me up.


Is it wrong to say I anticipated a massive shitshow? I hope not, because I was pleasantly surprised and how much of a shitshow it was *not*.

The standard timeline is a 14 day ramp up period where you set up integrations, train relevant employees, share documentation and accounts, and do technical deep dives with their trainers who go back and train the helpdesk staff. They want to start taking tickets/calls on day 14. This seemed laughably short to me. 14 days to learn ALL OF THIS *gestures obscurely at ITGlue*?! Blasphemy. No systems of mine are so trivial to be decoded in 14 days.

Yeah so they did it in like 8 days. Spoiler alert, this is the first of many defeats on this topic for my pride. My ego may not survive the rest of this review.

They set up a local phone number we can route calls to and claim most are answered in 2 rings or less (a claim I will confirm is true so far). We had a technical deep dive session for two hours with a trainer who was very unimpressed with my life’s masterpiece. Not unimpressed like he wasn’t interested, but unimpressed like he was used to dealing with much more complicated stuff than this.

That’s when I came to the realization that in the same way MSP helpdesks nurture excellent IT generalists, working for many MSPs at once makes you some kind of goddamn helpdesk supersoldier or something, I don’t know. I feel small, hold me :(.

This entire onboarding process was so painless I was experiencing a feeling known by non-IT folk as “cautious optimism,” a refreshing change from the normal existential dread.


Go live day for me was a little anxiety-inducing. I had a lot of personal credibility riding on this with my boss. The thought of this spiraling out of control into a shitshow he’d have to explain to clients was one I couldn’t really stomach. If you’ve made it this far you can probably guess that I am still gainfully employed (for now at least) and we didn’t have the world-ending meltdown I expected. It was actually pretty boring. We sent them tickets and they crushed them. Like, absolutely and totally in every way. I actually got frustrated at one point that they were so good at fixing stuff that isn’t explicitly documented or covered in training that I started sending some curveballs. A weird Egnyte configuration here, complicated nested file permissions there, approval required here. Crushed. Every single one. Barely any questions and no escalations back. And their ticket notes/documentation? Fucking exceptional. Better than mine even.


Communication is key, blindly firing a ticket for an undocumented procedure may or may not result in a question. Sending a ticket over and following it up with a note in their SmartDesk web console (where you can real time chat with the entire team assigned to your account including dispatch/technicians) will result in a successfully closed ticket 100% of the time. This is where a little bit of time investment from a service manager brings exponential gains in efficiency and ticket metrics.

Having good basic documentation for things (onboarding, offboarding, stack definition, network diagram, and a document for anything niche or specific) in ITGlue paid off big time. Where they ask questions and identify gaps in the documentation, we fill the gaps and update it. The added benefit of this can’t be overstated. It’s a forced documentation churn that you wouldn’t normally have. It’s another set of eyes finding the missing pieces of the puzzle so you can fill them in. We never get asked the same question twice and information is distributed quickly among the Benchmark team.

After hours support is excellent. Clients love getting help whenever they need it, and on-call engineers only need to be paged for serious escalations. Something that happens very infrequently, I will add. Not coming in to a full front desk queue in the morning is liberating.

We have breathing room. We have time to do other stuff for once.


I’ll take a cheap shot in the spirit of the moment though – their SmartDesk portal (which is their homebrew helpdesk interface) leaves a little to be desired. It has some bugs that aren’t world ending, mostly cosmetic and occasionally a bit funny. There’s one particularly unsettling waterfall chart on the dashboard that is as indecipherable as it is beautiful.

Whatever the fuck this means

Not to fear, while Benchmark is vendor/PSA agnostic they can integrate at least at a basic level with most everything out there. We’ve got it working with HaloPSA in an efficient way. If you prefer to use their SmartDesk product instead of your own ticketing or PSA you can totally do that too.


There are not a lot of vendors where you can say “I am getting every penny of value out of this and it is absolutely worth what I’m paying for it.” You can do that with Benchmark. If you have the wherewithal and discipline to take on a serious partnership with Benchmark, you can recession-proof your MSP and it can be a win for everyone involved. Scaling can become painless and efficient and you can go after bigger clients and spend more time focusing on important stuff instead of putting out helpdesk fires.

If you’re a lazy dickhead who wants to buy your way out of any kind of work, this isn’t the vendor for you.

James and his staff are exceptional. They are the real deal. They are talented and kind individuals who do an excellent job and have strong technical competencies. We don’t feel like we’re outsourcing or augmenting. We just feel like part of our team is on the other side of the world in a different office. In the post-COVID remote workplace, why does it matter where you are in the world if you’re delivering world class support?


Other Case Studies

qt=q_95 1

Retooling for success

Working with B365 has been a very positive experience and helped with both our growth strategy and focusing more on our delivery.

Atlas-IT-Consultancy-Central-Coast 1

Peace of Mind 24/7

The goal for me personally is to be doing less technical stuff so that I can spend more time finding new clients.

image 7

Taking control

The feedback from clients is that the B365 is really friendly, highly professional, responsive and eager to please.