Meet the author: Gene Reich is the CEO and Co-Founder of Traceless, an AI-powered business communications cybersecurity company that protects organizations against social engineering, AI-driven voice attacks, identity fraud, and data exfiltration. Traceless secures the human layer of enterprise security — the phone calls, chats, emails, and tickets where most breaches actually begin — through three core capabilities:
Traceless integrates natively into the tools teams already use — including Slack, Microsoft Teams, ConnectWise, ServiceNow, Okta, and 15+ other platforms — with no disruption to existing workflows, trusted by enterprises across healthcare, financial services, managed IT, and more.
Before founding Traceless, Gene spent two decades building POINT into a nationally recognized Apple managed service provider — giving him a frontline perspective on the security gaps businesses face every day. He has also served on the Apple Consultants Network Advisory Council and the ConnectWise Cyber Security Advisory Council.
Outside of work, Gene is a dedicated family man who enjoys growing vegetables and spending time with his wife and three children.
In a recent webinar, I sat down with Connor Swalm from Phin Security to talk about what managed service providers should actually look for when evaluating vendors and the red flags that should make you run the other direction.
Here are the biggest takeaways.
My friendship with Connor actually started the way many MSP/vendor relationships do: at a conference.
Except instead of polished corporate branding and identical polo shirts, we bonded over purple life jackets, tie-dye tracksuits, and tequila shots at a booth.
As ridiculous as that sounds, it revealed something important: Authenticity matters. You don’t just buy software. You buy relationships.
If a vendor feels fake, overly polished, or focused entirely on quotas instead of helping your MSP succeed, that becomes obvious very quickly. The best vendors show up as real people first, not just sales organizations chasing badge scans. And yes, badge scanning came up.
Connor shared a story about a vendor employee aggressively scanning badges at an after-hours event just to hit a quota. No conversations or relationship-building. Just a goal to hit an essentially meaningless number. That interaction became an instant lesson in what not to do, because when vendors start treating MSPs like CRM entries instead of partners, trust disappears immediately.
Trade shows are designed to excite you, but it’s easy to confuse excitement with necessity.
A lot of MSPs come home from conferences convinced they need a shiny new platform immediately. But once the day-to-day fires start again, those tools often sit unimplemented for months.
The solution?
Before you ever step onto the trade show floor, define:
Without that framework, it’s easy to get swept into a great sales pitch and lose sight of what your MSP actually needs.
Good vendors don’t blindly say yes to everything, but great vendors do make customers feel heard.
Vendors should regularly reach out to MSPs who submit feature requests to understand:
That level of engagement matters.
MSPs want vendors who understand the realities of their business — especially when their own customers are depending on them.
A “simple” issue like a broken printer might actually be mission-critical for a small business client. Vendors who dismiss problems because they seem minor often miss the bigger operational impact.
One major red flag with managed service provider software? No trial.
If a vendor expects you to sign a long-term agreement before you can even determine whether the product works for your environment, that should raise immediate concerns. Trials create trust and they allow you to:
And honestly, trials benefit vendors too. The best partnerships happen when both sides know the fit is right.
A major aspect to keep in mind when searching for a vendor is how their contracts are structured:
Contract structure tells you a lot about a vendor’s priorities. Are they trying to maximize long-term partner success? Or maximize short-term revenue extraction?
That’s not to say all annual agreements are bad.
In some cases, annual contracts can actually benefit MSPs:
The real issue isn’t contract length. It’s whether the vendor relationship is built on mutual value
Not to mention, you should always have a lawyer review your vendor agreements. Spending a few hundred dollars upfront can save you tens of thousands later.
AI has entered the chat — specifically around data handling and transparency.
More MSPs are starting to ask vendors:
These questions are becoming especially important in regulated industries like healthcare and finance. AI isn’t “bad”, but transparency matters.
Vendors should clearly explain:
If vendors can’t answer those questions clearly, you should proceed with caution.
SOC 2 is a must, but it doesn’t automatically mean a vendor is secure. It simply means the vendor follows the processes they claim to follow.
MSPs still need to evaluate:
A certificate alone shouldn’t replace due diligence.
One of the final points from the webinar centered around community.
The MSP industry is unique because peer groups, referrals, and shared experiences heavily influence buying decisions, which is really a good thing.
The best vendor relationships rarely start with:
“Here’s our pricing sheet.”
They usually start with:
“These people actually understand how we operate.”
Whether through peer recommendations, community engagement, or simply authentic conversations, MSPs tend to gravitate toward vendors who genuinely want to help them succeed, because you can only trust a product as much as you trust the people providing it.
The vendor dating game is only getting more complicated. More vendors are entering the MSP space every year, AI is accelerating product development, marketing is louder than ever, and conferences can feel like a nonstop stream of promises.
The MSPs that avoid getting burned are usually the ones that:
Or as Connor put it during the webinar:
“Treat people the way you want to be treated… and put your shopping cart away.”
Honestly? That’s probably good advice for vendor relationships, too.