If you’re running a B2B team, you know live chat isn’t just a “nice-to-have”—it’s often the difference between a closed deal and a lost lead. The problem? Every software vendor claims their chat solution is “enterprise-ready” and “AI-powered.” But when you get down to daily use, things can get clunky, expensive, or just plain overhyped.
This piece is for B2B teams who want to cut through the sales pitches and figure out whether Zendesk Chat or another tool is actually worth their time and money. We’ll look at the real pros, cons, and what you actually need.
Why Live Chat Actually Matters for B2B (and Where It Usually Goes Wrong)
Let’s be honest: B2B buyers don’t want to “start a conversation” just for fun. They want answers—fast—without sitting through a demo or waiting for a sales email. A good live chat tool:
- Gets prospects to the right person, not a chatbot loop
- Hands off chats smoothly to sales or support
- Integrates with your CRM so nothing slips through the cracks
Where most tools fall short:
- Clunky integrations (or none at all)
- Overpromising on AI, underdelivering on actual help
- Pricing that punishes growth (hidden fees, pay-per-seat traps)
The Contenders: Zendesk Chat vs. the Rest
Let’s break down the main players you’ll run into:
- Zendesk Chat (now called Zendesk Messaging in some plans)
- Intercom
- Drift
- LiveChat
- Freshchat
- HubSpot Live Chat
We’ll compare them on what actually matters for B2B teams.
1. Setup and Onboarding: How Painful Is It, Really?
Zendesk Chat:
Setup is straightforward if you’re already using Zendesk for support. If not, be ready for a learning curve—Zendesk’s interface isn’t exactly “plug and play,” and settings are scattered across their product suite.
Intercom:
Slick onboarding, but it’s easy to get lost in their sea of features. You’ll spend time disabling stuff you don’t need.
Drift:
Targets sales-heavy teams. Fast setup, but pushes you toward their “conversational marketing” vision—lots of bot-building and “playbooks” out of the gate.
LiveChat:
Probably the easiest to get started with. Classic chat widget, minimal fuss.
Freshchat & HubSpot:
Both are simple if you’re already on their platforms. Outside their ecosystems, expect a few headaches around integration.
Pro Tip:
If your sales/support folks aren’t techy, LiveChat or HubSpot are the lightest lifts. Zendesk is best for teams already deep in the Zendesk ecosystem.
2. Features That Actually Matter (and Which Are Just Noise)
What You’ll Actually Use
- Routing to the right team/person
- CRM integration (so chats don’t get lost)
- Canned responses and knowledge base links
- File sharing
- Reporting on response times and chat volume
The “Extras” (Usually Overhyped)
- AI bots that “qualify” leads (often just annoy people)
- Pop-ups that stalk visitors on every page
- “Conversational marketing” flows that require a part-time bot manager
How the Tools Stack Up
Zendesk Chat: - Strong routing and agent assignment, especially if you’re using Zendesk Support. - Decent canned responses and knowledge base integration. - CRM integration is okay, but can get messy if you’re not using Zendesk’s own CRM or a supported connector. - Reporting is solid, but takes some digging.
Intercom: - The best bot/routing combos, if you have a complex sales process. - Deep CRM integration—especially with Salesforce. - Tons of features, but you’ll pay for them.
Drift: - Heavy on bots and “qualifying” leads. - Great for teams who want to automate as much as possible, but real conversations sometimes get lost in the shuffle.
LiveChat: - Does basic chat extremely well. - Integrates with almost any CRM, but you’ll be using third-party connectors for fancier stuff.
Freshchat: - Similar to LiveChat—solid basics, some automation, but nothing groundbreaking. - Integrates well if you’re on Freshdesk.
HubSpot: - If you live in HubSpot, this is a no-brainer. If not, expect some friction.
3. Integrations: The Hidden Dealbreaker
You don’t want “yet another silo.” Here’s how integrations play out:
- Zendesk Chat: Best if you’re already using Zendesk Support. Outside that, expect to fiddle with APIs or pay for middleware.
- Intercom: Tons of integrations, but the best ones (like deep Salesforce sync) cost extra.
- Drift: Strong with Salesforce and Marketo, weaker elsewhere.
- LiveChat: Good range via Zapier and native plugins.
- Freshchat: Good inside the Freshworks suite, basic outside it.
- HubSpot: Seamless if your CRM is HubSpot, otherwise a mixed bag.
Watch Out:
Every vendor claims “CRM integration.” Always check if it’s a real sync (two-way, with notes and context) or just dumps chat logs somewhere.
4. Pricing: Where Things Get Sneaky
Let’s cut through the marketing:
- Zendesk Chat: Starts cheap, but real B2B features (routing, reporting, integrations) are locked in higher Zendesk Suite plans. Per-agent pricing can add up.
- Intercom: Notoriously expensive. Costs scale up fast as you add users or want advanced features.
- Drift: Also pricey, especially for sales-heavy teams. AI and advanced routing cost extra.
- LiveChat: Transparent pricing. Reasonable for small teams, but features are à la carte.
- Freshchat: Cheaper, but you get what you pay for—fewer bells and whistles.
- HubSpot: “Free” chat is limited; serious use means buying into their paid CRM tiers.
Pro Tip:
Always request a custom quote if you’re a B2B team with sales/support. Vendors often cut deals, but only if you push.
5. Real-World Pros and Cons
Here’s the stuff you only find out after the trial ends:
Zendesk Chat
What Works: - Reliable for high chat volume - Great if you’re already using Zendesk for everything - Good agent assignment and tracking
What Doesn’t: - Interface can feel dated and clunky - Painful if you want to use it “standalone” - Price creeps up as you add features or agents
Intercom
What Works: - Clean, modern UI - Deep customization and automation - Excellent for SaaS or complex sales funnels
What Doesn’t: - Gets expensive, quickly - So many features it’s easy to get lost
Drift
What Works: - Great if you want to automate first contact and qualify leads - Strong for outbound sales teams
What Doesn’t: - Chatbot-first approach can frustrate real buyers - Learning curve for building “playbooks”
LiveChat
What Works: - Simple, fast, reliable - No-nonsense interface
What Doesn’t: - Lacks advanced sales features - Integrations can require extra tools
Freshchat & HubSpot
What Works: - Seamless if you’re already on their platforms - No extra logins, shared contacts
What Doesn’t: - Not as flexible outside their own suites - “Free” is rarely enough for real B2B teams
6. What Not to Sweat
- AI Hype: Most “AI chatbots” are glorified auto-responders. Unless you have lots of repetitive questions, skip the hype.
- Endless Customization: More settings usually means more headaches. Start simple.
- Every Integration Under the Sun: Focus on your CRM and calendar. Everything else is probably noise.
How to Pick the Right Solution (Without Losing Your Mind)
- List your must-haves. Routing? CRM sync? Mobile app?
- Test drive two tools, max. Don’t fall for a “30-day free trial” on five platforms—you’ll never finish them all.
- Set up a real test. Have sales or support use the tool for a week with real leads.
- Watch for hidden costs. Price out your actual team size and feature needs.
- Go with the tool that’s easiest for your team to use every day. If it’s a pain, nobody will adopt it.
Final Word
Don’t get sucked into the sales pitch. Most teams do just fine with a solid, simple chat tool that connects to the CRM and lets sales or support pick up fast. Zendesk Chat is a safe bet if you’re already on Zendesk, but don’t be afraid to try LiveChat or HubSpot if you want simple, or Intercom if you need all the bells and whistles (and have the budget).
Pick what works, launch it, and tweak as you go. The best live chat is the one your team actually uses.