If you’ve spent any time shopping around for SaaS software online, chances are pretty good you’ve been invited to a webinar or two. And if you’ve spent any time actually attending those webinars, I’ll bet you’ve learned the same thing I have…

Webinars are really hit or miss.

Still, if you want to connect with a large number of prospects or customers online, there’s really no better way to do it than with a webinar. That’s why earlier this year we experimented with webinars to try to convert more free trial users into paid customers.

Because we saw some success – webinar attendees convert at twice the rate of those who don’t attend – we want to share with you our strategy from start to finish. Using this as a guide should save you some time versus starting from scratch.

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Why we chose webinars over other tactics

We’re constantly working on improving our free trial. As a SaaS company it’s central to our marketing strategy. If we can’t demonstrate the value of Hubstaff during the trial, trial users won’t convert into paying customers.

We’ve made a lot of changes to the free trial over time, but we still get a lot of questions from users about how to do things we think are straightforward. Among other things, this tells us we need to re-think our UX and deliver information better.

We’re currently taking steps to address UX issues and have already re-worked our trial email sequence in an attempt to improve product knowledge.

Email for free trial conversions is imperfect

Our trial email sequence now includes all the information somebody needs to get up and running with Hubstaff.

But email remains an uphill battle for a few reasons:

  • Not everybody reads the emails
  • Sometimes people want all of the information at once
  • Sometimes they just want to watch somebody else do it

Webinars are an opportunity to address each of these challenges. Webinars are also a great way to provide personal experiences at scale.

The webinar platforms we tested

We spent a few days researching and trying out different webinar software. There are a ton of options out there, but honestly, most webinar software sucks.

We had to find the software that sucked the least.

Platform Bottom Line Price


Stable in terms of uptime but requires users to download software before attending webinars $89/month for 100 participants or less


No lag because it’s self-hosted, but we experienced downtime (right before our first webinar) $45/month for 100 participants or less


A solid platform but the webinar registration page takes forever to load (bad for conversions) $89/month for 150 participants or less
WebinarJam We chose this one but there’s a 10-second delay between the time we say something and when attendees hear it $497/year for unlimited participants


gotowebinar-logoWhen we set out to find the right webinar software, one of our goals was to make the process as easy as possible for users. GoToWebinar is a stable platform with lots of bells and whistles, but it requires users to download the software in order to join the webinar.

The software might be worth it for enterprise-level companies drawing thousands of attendees at a time, but for a smaller company like Hubstaff it just didn’t make sense. We needed to remove any barrier to entry that we could.


webinarninja-logoIt seemed like everyone was talking about how great WebinarNinja was, including webinar heavyweights Pat Flynn, John Lee Dumas, and Chris Brogan. Older webinar platforms like GoToWebinar had their own problems, so I was excited to try WebinarNinja.

But wow was I disappointed when I did. The biggest selling point of WebinarNinja is that, unlike most other webinar software that rely on Google Hangouts, the platform is built on WebRTC — so there’s no annoying audio lag for users. The problem is, because WebinarNinja is self-hosted, it can go down.

And it did – 20 minutes before my first webinar. So at the very last minute I had to email attendees to cancel the webinar. Fortunately I was able to share a previously recorded webinar with them, but it just wasn’t professional.


cc-light-transCrowdcast is one I’d like to look at again. The interface is intuitive and it has some great tools for audience engagement. But while the webinars themselves seem to run really well, the registration page is problematic.

I don’t know how they’ve set it up, but it takes several seconds to load, which could potentially crush our conversion rate on signups. People expect pages to load instantly, and when they don’t, many just hit the back button. While this may seem like a small critique, this is especially problematic if you’re driving traffic to the registration page with paid ads.

Minimizing any obstacle to the process was a huge priority for us, so we couldn’t afford the risk. A lot of our users are on the fence already, and if they’re waiting for the registration page to load, it might just be enough for them to leave the page and forget all about it.

WebinarJam (Winner)

webinar jamWebinarJam is the standard webinar software used by most people in the Internet marketing space. It’s built on Google Hangouts so there’s an issue with audio lag (explained below), but it’s reliable — and users don’t need to download any special software to use it.

There are still some issues though. Because it’s built on Google Hangouts there’s a serious issue with audio lag. There’s a 10-second delay between when you say something and when attendees hear it. This makes it really difficult to ask questions. You’ll ask a question, see nothing in the chat, assume no one cares, and move on. Next thing you know, responses start flooding in.

You’re also at the mercy of Google. For instance, Google made an unannounced change to who was able to use Hangouts on Air, which required changing a setting in our YouTube account and then getting manual approval from them. Fortunately this didn’t interfere with any of our webinars, but that kind of dependency is a little worrisome.

For more options, check out Growth Marketing Pro’s list of the top webinar software.

How we conduct our webinars

A lot of SaaS companies use webinars to drag people through an exhausting tour of every nook and cranny of the software.

Big mistake. 

Especially for a tool like Hubstaff packed with so many different features, you need to be selective about what you focus on in a webinar. Just like the free trial, the goal of our webinar is to show users how they can achieve their desired outcome as quickly as possible.

For most of our users that means bringing accountability to their remote team and streamlining management. So we made an early decision to focus on these things in the webinar. That meant giving webinar attendees a high-level overview of these core features:

  • Onboarding a team
  • Tracking time
  • Viewing reports

While what we cover is important, how we cover it is critical as well. I spent a lot of time attending different webinars, taking notes, and reading up on successful product demos. (Close.io has a really great blog post about this.) 

Rules to Follow

  • Keep it short. Hubstaff webinars are just 30 minutes long: a 15-minute demo followed by a 15-minute Q&A.
  • Ask questions. Keep your audience engaged with a mix of participatory and rhetorical questions. We take advantage of interactive polls as well. (Most platforms have this feature.)
  • Cut the BS. If you can’t answer a question, don’t. “That’s a great question — I’ll look into it and follow up with you” is a hell of a lot better than stumbling to come up with something on the fly.
  • End with a clear CTA. Make it easy for your audience to take action by telling them exactly what they should do when the webinar ends. (I ask folks to sign up for the trial if they haven’t already – and to reach out to me directly with any other questions.)

How we promote our webinars

You can set up your webinar flawlessly and follow the above rules to a T, but all that time and effort is wasted if you’re speaking to an empty room.

For our webinars, we promote them to everyone during the first week of their trial. This gives folks a chance to attend the webinar and actually act on what they’ve learned and try it out.

We do this with an email and an in-app message.

Here’s the email we send using Drip:


And here’s the in-app message we send using Intercom:


Because we keep the webinar short and focused, it also provides a valuable introduction to Hubstaff for people who have not yet explored our platform. So we started promoting the webinar to our newsletter list as well (mainly blog subscribers).

This tripled our registrants overnight.

Of course there’s a lot more we can do, and we’re currently working on expanding our promotional strategy. One experiment in the pipeline entails promoting the webinar with retargeting ads (both to site visitors and an uploaded list of trial user emails).

How our webinars have performed

If we’re doing it right, free trial users who attend a webinar should be more likely to convert into paid customers than those who don’t attend. And so far, the data shows we’re on track.

As I mentioned at the beginning of this post, webinar attendees convert at twice the rate of those who don’t attend.

For us, the webinar does more than just increase free trial conversions though. It gives our users another opportunity to get in touch with us.

Sure we get some replies from people telling us we’re sending them too many emails, but for the most part, I don’t think those are going to be good customers anyhow. And those few cases are drastically outweighed by the larger number of people who benefit from them.

Where we can improve

I’ll be the first to admit we don’t have this nailed down yet. Conversion rates are higher for webinar attendees, but I know we can do better. To do that, we’ve prioritized three areas for improving our webinar.


When we were promoting the webinar only to first week trial users, tracking improvement was relatively straightforward: We wanted to see that people who attended a webinar were more likely to become paying customers after the trial.

There could be some bias to this because people who register for a webinar already may be more likely to become paying customers. But it’s hard to control for that, and I was happy with the data.

Now that we’re also promoting the webinar to people who may not be customers (via our email newsletter), it muddies the water a bit. Specifically, it makes things more difficult to track through Woopra, our analytics platform.

We’re working on trying to figure this out, but if you have any suggestions, please let me know in the comments.


After hosting The Agency Advantage podcast for more than a year, I’m more comfortable behind a microphone than I was. But I want to keep improving so we can make the webinar as fluid and engaging as possible.


We need to get more people into the webinar by incorporating it more into the trial process.

Our plans moving forward

This first crude experiment has shown us there’s a lot of promise here. Trial conversion rates are up for those attending the webinar, we’re giving people another option for learning the software, and we have more opportunities to engage with our customers.

At this point, our primary goal is to get the webinar in front of as many trial users as possible.

In addition to this, we also want to adapt the content to focus on making free trial users feel confident in their ability to use the software. The Q&A portion of the webinars is a great source for this. I’m constantly trying to tailor the content and delivery to hit on common pain points and questions voiced by our attendees.

Advanced webinars

We’re also actively working on expanding our webinar offering beyond “Hubstaff 101.” Because the current webinar is focused on demonstrating overall value, we intentionally avoid some of the software’s more advanced features.

There’s a lot of power under the hood of Hubstaff, but most users arrive at the free trial looking for something specific. If that’s all they’re using Hubstaff for, they’re leaving money on the table. This is why we’re working to develop another webinar that shows them how to use the software to run their business more efficiently.

Broadening scope

Content marketing rules the roost at Hubstaff. Our success is largely driven by content that speaks directly to the pain points of our core audience — agencies, remote team managers, and freelancers.

Most of our blog content, in fact, isn’t focused on Hubstaff software at all, but on helping our target customer run their business more efficiently. (You’re reading one of those posts right now.) The same is true for our Agency Advantage podcast.

The webinar format fits perfectly with this approach. Eventually we’d like to partner with experts who can help our customers improve their businesses in ways Hubstaff can’t directly help with.

What we’ve learned

We’ve only been at it a few months but webinars have been very rewarding for us – and not just because they’ve increased our conversion rate. Webinars are a natural fit with the Hubstaff marketing philosophy that’s based on two things:

  1. Producing content that solves problems for our customers
  2. Interacting with – and learning from – our customers as often as possible

Webinars aren’t for every SaaS biz, but if you’re looking to increase your trial conversion rate, I’d encourage you to consider them. If not webinars, then find a way to consistently reach out to trial users, identify their sticking points, and proactively solve them.

Success isn’t just talking with your customers, but finding ways to communicate value.

Webinars are a great way to do just that.