My AskAI pricing in 2025: A complete breakdown & what to watch for

If you’re running a support team, you’re probably buried in repetitive questions. It’s the same stuff, day in and day out, and it ties up your best people who could be solving genuinely tough problems. This is exactly why so many businesses are looking at AI to handle the simple, frequent queries and give their teams a little breathing room.

My AskAI has popped up as a popular option for plugging an AI agent into helpdesks you already use, like Zendesk or Gorgias. They claim they can automate over 75% of support tickets, which sounds pretty amazing. But before you dive in, you really need to get a handle on how their pricing works.

This guide will give you a straight-up, no-fluff breakdown of My AskAI's pricing for 2025. We'll dig into what you actually get, pull back the curtain on their billing model, and help you figure out if it’s the right call for your team in the long run.

What is My AskAI?

In a nutshell, My AskAI is an AI-powered assistant that lives inside the customer support software you’re already using. It’s built to play nice with the big platforms like Zendesk, Freshdesk, Gorgias, and HubSpot.

The whole idea is that My AskAI learns from your company’s information. You can point it to your help docs, let it crawl your website, or even feed it documents from places like Google Drive or Notion.

Its main job is to cut down on all those basic Tier-1 support tickets by giving customers instant, 24/7 answers. When the AI gets a question it isn't sure about, it smoothly passes the conversation over to a human agent, all within the platform your team is already comfortable with. It's meant to help your team, not replace your tools.

My AskAI's pricing plans

On the surface, My AskAI's pricing looks pretty simple with its cost-per-ticket promise. But there are a few quirks, especially in how they define and bill for a "conversation." Let's walk through the official plans so you know what you’re actually signing up for.

Core pricing plans

First things first, it’s nice that My AskAI offers a 30-day free trial without asking for a credit card. It gives you a good amount of time to see if it works for you. When you're ready to buy, you’ve got two main options.

Feature	Pro Plan	Enterprise Plan
Price	$149/month	From $999/month
Conversations	1,000 per month included	Custom volume
Overage Cost	$0.10 per additional conversation	Discounted volume pricing
Key For	Companies serious about customer service	Large enterprises & agencies
Setup	Self-serve	White glove setup & onboarding
Support	Standard	Dedicated success manager, priority support
Security	Standard encryption	SOC-2 (Type 2) certification
Add-ons	API, Slack & Teams access ($49/mo)	Custom features & integrations included

Understanding the "per conversation" model

Okay, this is the most important part to wrap your head around. Figuring this out is the key to guessing your actual monthly costs and not getting a nasty surprise on your bill.

My AskAI doesn't charge you per ticket or per solved issue. They charge per "conversation," and what that means changes depending on where you're using the tool.

1. For their own website widget: A "conversation" is just a single user asking as many questions as they want within one hour. Easy enough.

2. For helpdesk integrations (Zendesk, etc.): Here’s where it gets a little weird. A "conversation" is calculated as every 2.5 AI responses. This means every single reply the AI sends counts as 0.4 of a conversation.

Let’s make that real. A customer starts a ticket and has a bit of a back-and-forth with the AI. The bot sends five replies. In your head, that’s one ticket. On your bill, that’s two "conversations" (5 replies × 0.4 = 2). If your customers often have complex questions that need a few replies, these costs can climb way faster than you might think. Here's a visual breakdown of how that math works in a real scenario:

This weird fractional model can make it a real pain to predict your monthly spending. For comparison, other platforms like eesel use a simple interaction-based model where one AI reply equals one interaction. It's clean, predictable, and lets you set a budget without doing mental gymnastics for every customer chat.

What features are included?

So, what do you get for your money? The My AskAI Pro plan comes with a decent set of features to get your AI agent running inside your existing setup.

Core features for support automation

• Helpdesk Integrations: The big win here is that My AskAI works directly inside Zendesk, Freshdesk, Gorgias, and HubSpot. Your team doesn't have to learn a new piece of software, and everything happens right where they already spend their day.

• Knowledge Syncing: You can connect and sync as many help center articles and documents as you want. It supports a ton of knowledge sources, from Google Drive and Notion to Confluence, Salesforce, and even Shopify data. This flexibility helps make sure your AI actually has the right information.

• Multilingual Support: The agent can chat with customers in over 95 languages and automatically figures out what language to use. If you have a global customer base, this is a huge help.

• AI Copilot: The plan also comes with a Chrome Extension that helps your human agents write replies faster. It's a nice little bonus that adds value even when a human has to take over from the bot.

Advanced capabilities on the Pro plan

• Live User Data: You can hook up live customer data to make responses more personal. For example, you can let the AI check on an order from your Shopify store to give a customer a real answer to "Where is my order?".

• Advanced Actions & Tasks: The AI can be set up to do things like process a refund or handle a cancellation. This can be really powerful, but it usually takes a bit of technical work to get it running smoothly.

• Automatic Tagging & Analytics: The platform includes a dashboard with insights and can automatically tag conversations by topic, sentiment, and more, which is useful for spotting trends.

While these "Advanced Actions" are helpful, they mostly kick in after a conversation is already underway. If your team needs automation that's a bit more proactive, you might feel a bit limited. For instance, tools like eesel offer a full AI Triage engine that can automatically route, tag, and sometimes even close tickets based on what the customer is asking before an agent even sees them. Better yet, eesel includes a simulation mode, so you can test your automations on past tickets to make sure they work just right before you turn them on for real.

Potential limitations and hidden costs

No tool is perfect, and My AskAI is no exception. While it's a solid choice for straightforward AI support, there are a few things to keep an eye on before you commit, especially if your team is growing.

The unpredictable billing model

I know we’ve already talked about this, but it’s worth saying again: the "0.4 of a conversation" rule is the biggest wild card in My AskAI's pricing. You might think the Pro plan's 1,000 conversations are plenty for your 2,000 monthly tickets. But if those tickets average just three AI replies each, you could actually use up 2,400 "conversations" (2,000 tickets × 3 replies × 0.4). That’s 1,400 conversations over your plan, which would tack an extra $140 onto your bill.

To make things even more stressful, My AskAI's "Flex" pricing for these overages is mandatory on the Pro plan, you can't turn it off. It’s good that your service won't get cut off, but it makes it nearly impossible to stick to a strict budget. One busy month could easily lead to a bill that's much higher than you planned for.

Gated features and security considerations

• Paid Add-ons: Some really useful integrations for internal teamwork will cost you extra. If you need API access or want to connect with Slack and Microsoft Teams, that's another $49 per month.

• Enterprise-Only Security: SOC-2 (Type 2) certification is a major security standard that a lot of businesses need, especially when dealing with customer data. With My AskAI, you can only get this on their Enterprise plan, which is a big price jump. This could be a deal-breaker for any company that takes security seriously but doesn't have an enterprise-sized budget.

This is a pretty big difference compared to other platforms. Modern tools like eesel are built on a SOC2 Type II certified foundation for every single customer, not just the big spenders. Plus, key integrations like Slack are included in their standard Team plan, and MS Teams is available on the next tier up. It means you get security and core features without being pushed into a pricey enterprise contract.

Is My AskAI right for you?

Alright, after all that, how do you decide? Here’s a quick cheat sheet to help you figure out if My AskAI makes sense for your team.

Who it's a good fit for:

• Small to medium-sized businesses where support tickets are pretty simple and often solved in just one or two replies.

• Teams that need a quick, no-code AI agent for basic questions and want to get it running in less than 5 minutes.

• Companies who just want to get something running fast and aren't too worried about a fluctuating monthly bill.

Who should probably look elsewhere:

• Support teams that need predictable, scalable pricing without doing algebra to figure out their monthly bill.

• Businesses that need smarter, proactive automation, like automatically routing tickets or testing workflows before they go live.

• Companies that need SOC-2 compliance and key tools like Slack or MS Teams without having to pay for an enterprise plan.

If your team falls into that second group, a more complete solution like eesel is probably a better long-term move. It gives you the control, clear pricing, and security-first mindset that growing support teams really need.

The final verdict

My AskAI gives you a fast and easy entry point into AI-powered customer support. The integrations are good, and the quick setup is definitely tempting. But the true cost really comes down to how complex your tickets are, all because of that fractional "conversation" pricing.

My best advice? Squeeze every drop out of that 30-day free trial. Hook it up to your helpdesk and keep a close eye on your "conversation" usage in the dashboard. That’s the only way to get a real sense of what your monthly costs will look like before you have to pay a dime.

At the end of the day, the right AI tool does more than just answer questions. It gives you predictable costs, automation you can actually trust, and security that grows with your business, not against it.

Ready to try an AI platform with transparent pricing, powerful automations, and security built-in for everyone? Start your free 7-day trial of eesel AI today.