How HelloSign Delights Customers With Its Signature Support

Reading time: 9 minutes

Written by

Katrina Canizares is a Senior Support Agent at HelloSign, an app that makes signing documents electronically effortless. 

Based in San Francisco, HelloSign is extremely committed to obliterating friction from paperwork, one e-signature at a time.

Katrina Canizares, Senior Support Agent, HelloSign
We managed to catch up with Katrina and chat with her about life at HelloSign and customer support.

How many products do you support, Katrina?

Two! HelloFax and HelloSign.

What channels do you offer support in?

We primarily offer support via email, though we do have a support phone number, as well, for live support.

How many queries do you get every day, on an average?

Around 200, give or take a few.

And what tools do you use?

Email, a ticket tracking system, phones and HipChat to communicate internally.

The HelloSign office

How did your career in customer support come about to be, Katrina?

I feel like I’ve worked in some sort of customer support role for as long as I can remember! I started off in retail and spent a lot of time in retail banking in different roles. I really enjoyed getting to know my customers but always felt limited by the rigid, bureaucratic structure in the banking world. I wanted to find a position that would allow me to still interface with customers, but also make me feel like I was making an impact in what little ways I could. That’s how I found HelloSign!

And the rest, as they say, is history. What does a typical day look like for Katrina Canizares, Senior Support Agent at HelloSign?

A typical day starts off with me setting up myself; I like having a few quiet minutes to myself to prep. Usually, a couple of our offsite part-timers have already been on for a few hours when I get in, so after I’m all set, we do a quick pow wow to see if there are any issues that we should be aware of.

Then, it’s on to our support queues. I look for emergency tickets that need my attention right away. This allows me to go through all our new tickets and sort them into the right categories which makes sure we’re all super efficient. After that, it’s all about resolving pending tickets, troubleshooting new issues and working with our Devs and the Sales team to make sure that we’re taking good care of our customers.

Phew! That’s a busy schedule. How do you motivate yourself (and the team) day in and day out? What drives you to be a better support agent every day?

I like looking at the bigger picture and acquainting myself with the direction of the company. It reminds me that what I do, every day, matters.

This is also how we motivate ourselves as a team. Motivation is unique to each person but when a team, as a whole, is excited and motivated to be the best they can be every day, chances are they’re going to rock!

We also make it a point to socialise outside of work and get to know each other as people since we spend most of our time with each other. Plus, we joke a lot.

Katrina's desk, HelloSign HQ
Katrina’s office, HelloSign HQ, SF

How do you manage taking time off from support?

Careful scheduling is key. We want our support team members get some time to themselves to take a break and recharge, but we need to make sure that our customers are always taken care of.

There is also opportunity to take breaks from support while we are at work – whether it’s learning something new outside of our department, or helping out another team.

It keeps each agent engaged not only in their role, but with the whole company.

Let’s talk numbers. What, in your opinion, is the support metric that should matter the most?

The more the number of satisfied customers that reach a resolution with their issue and walk away happy thanks to our efforts, the better. At the end of the day, it’s the quality of our support over quantity. Without our customers, we wouldn’t be here so we want to make sure that we resolve each issue to the best of our abilities.

We are feedback junkies and believe that feedback from both our internal and external customers is what drives us to success and helps us measure happiness.

We currently use various forms to measure customer happiness and track feedback. We have all of the fancy tools, like retention and renewal measurements, customer satisfaction surveys, and various other feedback surveys. We continuously monitor and respond to feedback received via social media (and other avenues). And we use that feedback to help improve our service and tool.

But most importantly, our internal motto “Does this make our customers feel awesome?”, drives all of us to approach our every day from our customers’ viewpoint.

Tell us about your most memorable customer interaction.

This happened offline, outside of the normal ticketing queues. I was on the Muni train on the way home, carrying a HelloSign tote. One other passenger kept glancing over for a while before he asked me where I got the tote. I told him I worked for HelloSign and  as it turns out, he was one of our customers! He was really excited and told me, in great detail, how our tool really helps him in his day-to-day business operations.

HelloSign HQ, SF

We’re going to throw some situations at you. Tell us how you deal with them at HelloSign.

a) A customer writes to you with a feature request that’s in the works but it’s complicated and you don’t have an ETA. How do you deal with these requests? What if it’s a feature you have no intention of building?

Well, the one thing that we never promise is an actual date or timeframe that a feature will be available. This isn’t because we don’t want to commit – not at all, we actually wish we could! But it’s because it’s really difficult to guarantee a release of a feature.

So many things can change in the time the feature is being built and this is the first thing we tell the user with a feature request, so we don’t mislead them.

Then, we ask them to vote for the feature request on our forum so that we can automatically notify them when this is being worked on. If the feature is already scheduled on our roadmap, we’ll also add them to our product team’s notification list.

When we’re in the design phase, we contact them to get more feedback so we can be sure that the feature is being built to cater to our users’ needs.

As for features we’re never going to build, I’d like to say we never say never! Features that we’re not building right now may end up being a priority in a few months.

If the request is something that is outside of our product’s scope or intended purpose and it won’t be built because of that, then we’ll let them know that that’s the reason.

b) One of your support reps makes a tiny mistake (for example, an outdated workaround) that greatly annoys a customer. The rep’s trying to smooth things over but the customer only seems to be getting more and more frustrated. How do you usually handle this at HelloSign? Do you let the rep make amends or do you step in and take over?

Mistakes happen – we’re human! Apologizing to the customer definitely goes without question and we will provide the most up to date info as soon as possible. If we can provide a courtesy concession, we’ll do that as well. And it doesn’t just end with that – if this happens, then it’s on us as a team and not just the individual.

We would review the reason why this outdated piece of information was given out, make sure we’re communicating new changes in an effective manner, and learn from that misstep to avoid this in the future.

You learn from the past and grow from it.

c) A customer requests a feature that’s not on the plan he’s subscribed to. He’s willing to pay extra but doesn’t want to upgrade to the next plan. Do you categorically deny these requests or make exemptions every now and then?

We always want to make sure we’re giving our customers what they need to do business but there are definitely limits to providing this. If it’s a feature that we can add on to their current package and if it’s within reason, a quick chat with our sales manager will usually allow us to add something on. More robust features are only available systematically when we activate plans that they are included with, so those are a little more difficult since we can’t just flip a switch.

That being said, this is also great feedback and we take these points back to our product team because this could help us structure future pricing plans better.

d) A wild refund request appears. How do you handle these requests? Do you just issue the refund or do you rope in a sales rep to try to woo the customer back one last time?

As fairly as possible. We assess each refund request to make sure that we address any concerns the user might have. If anyone is unhappy with the service, we also get feedback that will help us improve future versions of the product. We rely heavily on user experience to make the best product possible.

If a customer cancels because they had a less than stellar experience, that information is gold to us.

Katrina and colleagues, HelloSign HQ

We understand that HelloSign must field a lot of customers who are concerned about the safety of their signatures. How do you explain to them that you’re secure? Mind jotting down your reply?

Oh, we get this all the time. And to be fair, it’s a very valid concern. Electronic signatures have been around for quite some time now, but it’s only been gaining a lot of interest and actual use in the past few years. We take it as our responsibility to educate our customers about the legality and security behind electronic signatures because we want them to not only be comfortable using the service, but to also be able to use it as best they can.

Here is an example of an email we send out:

“Security is what we’re all about!  Our documents are behind a firewall and authenticated against the sender’s session every time a request for that document is made. The entire site is https. All communications use SSL encryption and all data is stored in a SAS-70 certified data center.

We also have the option of removing the PDF attachments from all confirmation emails, and allowing users to access completed documents only within HelloSign. You can do that on the “Settings” page.

We also have the option of removing your signatures anytime you send a new document if you don’t feel comfortable storing them. Simply click the “x” next to the signature you want to delete the next time you create a doc and add a signature.

Also, if you’re concerned about the documents, you can delete the document inside of the interface; it then gets deleted permanently from our system.”

Tell us about the biggest surprise of your support career at HelloSign.

We had a customer knock on the door once and ask if this was, indeed, HelloSign. When we told her it was, she excitedly told us that she was visiting San Francisco on a few days on business, and had a meeting with another company in the same building we were in. She just wanted to come meet us and let us know she was a big fan – and she even asked for a photo with the team! That was awesome.

Give us some dope on your hiring policy. What do you look for in your support reps?

Empathy, first and foremost.

For most of our customers, their interaction with our support team is the first (and sometimes only!) human encounter with the company.

It’s easy to forget that there are humans behind a SaaS tool that you use day in and day out.

So we want our customers to know that we care and that they are the most important thing in our business. They’re the reason why we built these products in the first place, and they’re still the reason why we continue to do our best to improve it.

Empathy is equally important internally because we spend a lot of time with each other on a daily basis, and empathy builds a nurturing and supportive work environment.

Whose customer service do you admire the most?

Union Square Hospitality Group! That’s the parent company of Shake Shack and they also have some great restaurants under their umbrella. I have never had a less than stellar experience in any of their restaurants, and it’s always consistent whether it’s sitting in one of their more formal restaurants, or grabbing a burger at the Shack.

They take hospitality to heart and it doesn’t feel like it’s just a job for them – it’s true passion.

Name a rep that you’re a big fan, someone you’d like to see featured in this series.

Erica Pang from Stripe is always great to work with!

One last question, Katrina. What would you do in the event of a zombie apocalypse?

Stock up on Popeye’s Chicken and as much red wine as possible, have a dance party with my favorite music and enjoy what time I have left before the zombies come. Unless they enjoy Popeye’s…then they can eat that instead of me, and we can all have a zombie dance party!

We started the Secret Sauce series to find out more about what makes the customer service of some great companies click. We get in touch with one awesome support representative and we pick their brains. We find out what a typical day is like for these support rockstars, their personal work-philosophy, support process and what inspires them to go above and beyond the call of duty to make their customers happy. Know a customer support rep you’d like to see featured here? Drop us a line in the comments or shoot an email to with your suggestions.

Subscribe for blog updates