An honest review of Pylon for B2B customer support

Picking a new customer support platform is a pretty huge decision. In B2B, it’s even trickier because you’re juggling long-term relationships and chats across a dozen different channels. For what feels like forever, the big names like Zendesk or Intercom were the only real options. But if you’ve ever been in the support trenches, you know those tools can feel a bit… clunky and out of sync with how teams work today. That’s created an opening for newer tools, and one that keeps popping up is Pylon.

Pylon’s pitch is that it’s the all-in-one support hub made just for B2B. They promise to bring all your channels together, add a dash of AI, and make everything feel smoother. But does it deliver? Let’s take an honest look at what it’s actually like to use. We’ll dig into its main features, the whole ‘rip-and-replace’ setup, its fuzzy pricing, and see how it compares to a different, more AI-focused way of doing things.

What is Pylon?

So, what exactly is Pylon? Think of it as a single dashboard that tries to pull together your support inbox, some AI helpers, a knowledge base, and customer info. It’s backed by Y Combinator and is aimed squarely at B2B companies that are fed up with hopping between different apps just to talk to their customers.

The main idea is to completely replace your old helpdesk. It connects directly with the places B2B chats are actually happening, like shared Slack channels and Microsoft Teams. The goal is to be the one place for every single customer conversation, from a quick question to a complicated problem. It’s a big promise. Let’s see if it stands up to reality.

A breakdown of Pylon’s core features

Pylon’s platform is built around a few key ideas, each meant to solve a common headache for B2B support teams. Let’s dig into what they’re offering and where the cracks might start to show.

Pylon’s omnichannel support for modern channels

What it is: Pylon’s main feature is a central inbox that gathers conversations from Slack, Microsoft Teams, email, chat, you name it. The point is to give your team one screen to see every customer interaction, wherever it’s coming from.

Why it matters: In B2B, support is rarely a one-off ticket. It’s an ongoing chat in a shared Slack channel or a long thread in Teams. Having one inbox means your agents aren’t constantly alt-tabbing between apps just to keep up.

The catch: Here’s the thing, though. A unified inbox is a great starting point, but it doesn’t magically reduce the number of questions you get. You still have to sort through everything, figure out who should answer what, and then actually respond. The inbox is just a bigger bucket; the real work is still there. Another way to think about it is to power up the helpdesk you already use. A tool like eesel AI hooks into the same channels but works inside the software your team is already familiar with, so you don’t have to throw everything out and start over.

Pylon AI agents and assistants

What it is: Pylon uses AI to handle some of the repetitive stuff. Think automatically sending a ticket to the right person, suggesting a reply based on old conversations, or flagging topics you should probably write a help article about.

Why it matters: Good AI can slash your first response times and take over the boring, repetitive questions that drain your agents’ will to live. This frees them up to focus on the tricky problems where they can really make a difference. It’s pretty much what every scaling support team is looking for.

The trade-off: When the AI is built directly into an all-in-one platform, you’re stuck with their AI, for better or worse. It can feel like a bit of a black box, and you can’t really see how well it works with your actual customer questions until after you’ve already moved everything over. A less risky way to do it is to test the AI first. For instance, eesel AI’s AI Agent lets you run it on thousands of your past tickets in a simulation mode. This shows you exactly how much it would have automated before you let it talk to a single customer. You get real numbers, so you can roll it out confidently, maybe starting with just one or two types of questions.

Pylon’s AI-powered knowledge management

What it is: Pylon gives you tools to write, sort, and even translate your help center articles. Its AI also tries to spot gaps in your knowledge base by looking at the questions customers are asking.

Why it matters: A good knowledge base is everything. It lets customers help themselves and gives your agents a single source of truth so they can answer questions quickly and correctly every time.

The reality of upkeep: Let’s be honest, even with AI nudges, keeping a knowledge base updated is a grind. Articles get old, and new problems pop up that you haven’t documented yet. The real goldmine of information is in the thousands of support conversations you’ve already had. This is where a smart AI layer can be a huge help. Instead of just pointing out what’s missing, eesel AI can actually read your resolved tickets and write draft articles for you. It turns your team’s best answers into permanent help docs, making sure your knowledge base is constantly getting better on its own.

The biggest hurdle with Pylon: platform migration

Switching any major software is a massive headache. When you’re talking about replacing your entire helpdesk, the heart of your support team, the stakes get incredibly high. This isn’t just about adding another tool; it’s about changing how your team does their job, day in and day out.

Moving to Pylon from Zendesk, Intercom, or Freshdesk

If you look at Pylon’s website, they talk a lot about customers who have "migrated off" platforms like Zendesk and Intercom. This "rip and replace" approach is their whole game. They’re not asking you to try a new feature; they’re asking you to commit to moving every single historical ticket, retraining your entire team, and rebuilding all the workflows, macros, and reports you’ve spent years perfecting.

The hidden costs here are no joke. Moving all that data is a nightmare and you risk losing important customer history. Training everyone on a new system means downtime and a productivity slump right when you can’t afford one. And for your customers? They just see a sudden, confusing change in how they get support.

The alternative to Pylon: augmenting instead of replacing

But there’s a much simpler way to get all the perks of AI. Instead of tearing everything down, you can just add a smart AI layer that works right on top of the tools you already have.

This is where a tool like eesel AI comes in. It’s built to plug directly into Zendesk, Freshdesk, Intercom, Gorgias, and a bunch of others. You can be up and running in minutes, not months, because there’s nothing to migrate.

With this approach, you get a few major wins:

• No retraining required. Your team stays in the helpdesk they know. eesel’s AI tools just appear inside it, ready to help.

• You see results, fast. The AI plugs in and starts learning from your past tickets, macros, and help articles right away.

• You’re in the driver’s seat. You get to choose exactly what to automate. Start small with the easy stuff, like "where is my order?" tickets, and expand as you get comfortable, all without messing up your team’s flow.

Pylon pricing vs. transparent alternatives

You can tell a lot about a software company by looking at its pricing page, or lack thereof. Pylon goes the old-school enterprise route: their pricing is a mystery. If you want to know how much it costs, you have to schedule a demo and get on a call with sales.

This just makes everything slow and uncertain. You have no idea if you can even afford it until you’ve already sunk time into a sales pitch. It also makes it nearly impossible to compare it fairly with other options.

Feature	Pylon	eesel AI
Pricing Model	Custom Quote (Requires Sales Call)	Transparent, Public Tiers
Fees	Unknown (Potentially per-seat, per-feature)	Based on AI interactions (No per-resolution fees)
Contracts	Likely Annual Commitment	Flexible Monthly or Annual Plans
Trial	Demo-based	Free trial, fully self-serve setup
Predictable pricing is a really big deal. A lot of AI tools charge you ‘per resolution,’ which sounds good on paper. The problem is, your bill goes through the roof when the AI actually starts working well. You literally get punished for being successful. A more straightforward model, like the one eesel AI uses, is based on AI interactions. Your costs are tied to how much you use it, not how well it works, so there are no nasty surprises on your invoice. Plus, you can often find flexible monthly plans, so you aren’t stuck in a year-long contract right out of the gate.

The verdict: is Pylon the right B2B support tool for you?

So, who should actually consider Pylon? It could make sense for a couple of specific scenarios:

• You’re an early-stage B2B startup without any helpdesk yet. Starting fresh with an all-in-one might be the simplest path.

• Your team is completely fed up with your current helpdesk and you were planning to migrate anyway, no matter what.

But for most established teams who are pretty happy with their helpdesk and just want to add some serious AI muscle, the pain of a full migration is a tough sell. If what you really want is to lower ticket volume, make your agents more efficient, and scale support without hiring an army, ripping out your entire tech stack is a slow, expensive, and risky way to get there.

This video provides a quick analysis of whether the Pylon platform is worth the hype for customer support teams.

Get powerful AI without the Pylon platform migration

Look, Pylon has a nice vision for a unified B2B support world. But its all-or-nothing approach is a huge ask. It demands a full-on platform migration, traps you in their ecosystem, and makes you jump through hoops just to find out the price.

A more flexible and, frankly, modern way to do this is to add a dedicated AI layer like eesel AI to the helpdesk you already use. You get top-tier automation and smart tools for your agents, with a clear and predictable cost, minus all the disruption. You can get started in minutes with AI that plays nice with your existing tools, instead of making you throw them away.

See how it works for yourself, start a free trial of eesel AI.