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OP here. If you have any questions about building this kind of thing, feel free to comment or drop me an email at tim [at] gocardless [dot] com.
Hey Tim, big phone geek here.

I'm assuming this is a quasi-call center environment. Have you thought about how you're going to implement manager eavesdrop and other things of that nature? What you've done is cool, I'm curious about where you're planning to go from here :).

Hi Josh - I'm the same. Building solutions to these kinds of problems is really interesting.

We've not implemented that yet, but I've spoken to another company doing similar things with around 100 agents and they've managed to implement this using Twilio's conferencing facility. It's easy to drop in and out of a conference silently, which is perfect for this.

Our support is certainly not at scale, and lots more features will become appropriate as we grow, from letting people schedule callbacks to manager eavesdropping to more sophisticated management of waiting calls.

Have you built anything like this?

Well,

I work at 2600hz, so we're building stuff like this but for big operators and Fortune100 companies. I'm just curious about what tools you have at your disposal when it comes to building complex applications. I'm a big fan of Twilio because they've really lowered the barrier to entry in the market to basically 0.

So, have I built anything like this: yes, but it's a little different.

I think Twilio's conferencing is the way to go but I'm not familiar enough with their API to know how mute and deaf control states work. Those are pretty essential to a good eavesdropper experience.

Im loving the blog posts from your dev team. Keep them coming!
How has the call quality been?
We've generally found it to be decent, although (naturally) variable. We use Twilio alongside a UK SIP provider called Voipfone (http://voipfone.co.uk) which is how we actually get our calls through to PSTN.

Twilio Client (https://www.twilio.com/client) seems to provide better quality, but we really like the convenience of hardware phones and built-in PBX functionality.

Interesting. I've always had much better quality using Twilio to bridge to PSTN than through Twilio Client.

I keep coming back to Twilio Client because the idea of a softphone (and a web based one at that) is so alluring compared to having to deploy more hardware.

If I recall there was also a cost advantage to using Twilio Client (you only have to pay for one leg of the call instead of both legs).

But every time we've tried to deploy it there have been quality and usability issues which have forced us to fallback to PSTN. Never the less, I'll keep trying it every couple of months... :)

This is cool stuff -- also shows how far things have come in the past decade.

I'm running my company's phone system on a cloud-hosted Asterisk system -- it's basically the same thing that we've been using for years, and works quite well, though we're still tied to physical desk phones.

Curious if anyone has good resources for working with an Asterisk core for an app like this. I recall seeing a Rails framework for Asterisk out there somewhere, but no clue if it's any good. Would love to hear thoughts...

Indeed - Twilio is awesome purely because it allows you to integrate with the phone networks, which are basically a legacy system, naturally within your applications.

I've not really played with Asterisk. How is it to configure, and what has your experience been like? We outsource the PBX side of our system to a SIP provider called Voipfone (http://voipfone.co.uk) but it would be appealing if we could do this in-house and have even more flexibility.

Asterisk is very cool and relatively easy to get started with. It's successor, FreeSwitch [1], is also a beautiful piece of software!

[1] http://www.freeswitch.org/

FreeSwitch isn't really a "successor" to Asterisk -- Asterisk is still very much in active development (as is FreeSwitch - I think). More like a competing (in a good way) project. See:

http://www.freeswitch.org/node/117

Tangentially related (IronRuby on Microsoft's DLR for dialplan processing), SIPSorcery is a relatively unknown combination project/service for developers looking for a high-level language interface for orchestrating SIP solutions:

http://sipsorcery.codeplex.com/