The Building of Checkbox Support
The problem with support
The first thing to cover about tech support is that the bar is low. The customer knows this better than anyone. They’re the ones who are screaming into the void. An unread email, an outsourced call center, a suggestion box that doubles as a trash can. AI is only the newest way that companies are saying, “Can we solve your problem with no effort? No? Then we can’t help you… Unless you’re paying us a lot.”
And that seems to be the key reason right there: Money. A good support team is expensive. Companies run the numbers and conclude that the sales they lose by having poor support are less than the cost of having good support. Then, industry wide, customers come to expect poor support, and this cycle of denigration continues.
It’s not all doom and gloom, however. Support then becomes a differentiator. It’s something that a plucky young company can excel at, carving themselves a niche in the market. I have and will continue to argue that the value of Support is in its intangibles. The small, positive interactions that you have with customers compound. They lead to retention. They lead to referrals. They put your product in the best light.
Over the last two years, I have had the unique opportunity of shaping how Checkbox approaches support. It hasn’t always been smooth sailing, but there has been some excellent learning along the way. I’ve gotten to tackle what I see as inefficiencies and poor practices, and create a support program that puts its heart in the right place.
I’d like to trace my journey through working in support in order to share my ethos for why Checkbox approaches support the way that we do.
Learning to connect with customers
In my first job working in support at a tech company, we had many non-technical customers. The survey product we sold was often their first experience with a SAAS product. I fielded countless refund requests - they paid last year and didn’t expect it to renew. I would compare SAAS to Netflix or a gym membership and try to put it into relatable terms, but what stuck with me was gap between customer expectation and business practice.
It seems that everyone I talk to knows how a SAAS business works. But I’m in the industry. Myself and my friends went to college, work on laptops, and live on a coast. The idea that software subscriptions support a continually evolving software seems obvious. But it shouldn’t. It wasn’t long ago that I heard of “SAAS” for the first time:
I was in an interview for my first tech job and they mentioned that they were a SAAS company. I asked them to explain the acronym… I was not hired.
6 years later, a key to shaping a quality support program is remembering what it was like to be an outsider. My best metaphor was telling someone that I’m the host of a digital restaurant. I don’t cook the food. I don’t take the order. But I get the patron to where they need to go to enjoy their meal. I set the tone. I make them feel welcome. I make it all seamless.
Customer support is sometimes the only human interaction that a customer has with a company. You have to make that interaction a good one.
Checkbox tends to have a more technical customer. The knowledge gaps that we’re closing are more advanced, but the principle is the same. Don’t lose sight of what it’s like to not know how a product or service works.
My journey into support
Before Checkbox, I worked at a 1200 person company, starting in Customer Support and moving up to Customer Success after a year or two. When I was hired at Checkbox, they rushed me in the door – the founder of the company was leaving at the end of the year, and they wanted me to start posthaste to learn as much from her as I could before she left. She had built an impressive product and support approach, rooted in a decade of knowledge. I had the job of distilling as much of that information as I could to fill in the gap of her absence.
I was brought in for a dual role, working both customer success and support. A fellow hire would be wholly dedicated on support and manage the AIPAC time zone. Due to unforeseeable events, she left the company suddenly, and I was left with the whole plate. Those early days were fraught. I was still learning the behind-the-scenes systems and product while taking over the support queue. If you had a long delayed response from me at that time, you have my apologies. But I do believe that from those flames, we forged something enduring.
The advantages of being small
At my previous company, we were a 50 person support team, and a key metric was responding to every email within one hour, 24/7. But I have to say, a lot of the emails that the support team sent were terrible. You had the newest, youngest, and least paid employees at the company being tasked with sending 10 emails an hour. If a customer had a technical issue, it took 2-4 business days to be escalated to the tech team. And the tech team were not engineers, they couldn’t advise on more serious questions, leading to further delays. An email thread that went for several days might be responded to by 5 or more different reps, passing the buck and starting from square one in comprehending an issue. The support team was specifically asked not to bug other teams, and feature requests didn’t disseminate.
At Checkbox, our median response time to a support ticket is under 3 hours, and we operate Monday through Friday from 3am to 5pm ET. So we’re a little slower to respond. But the first person reading your email is someone who can solve your problem. Or if they can’t they have direct contact with the CEO and the Engineering team. And the engineer who review your email is the VP of Engineering, and he can assign it to the engineer on his team with the most relevant experience to solve your issue.
And because we are a smaller company, you represent a greater portion of our total business. We want to build Checkbox for you. We want your feedback and feature requests. Our mandate is to our customers.
Why do companies use deflection?
A key support metric at my previous company was deflection. A deflected customer is one who wanted to receive a type of support and received a “more scalable” type of support instead. So this would be someone who wants a phone call getting their issue solved with an email. Or someone who wants to email with a representative instead getting a chatbot or an article in the help center. At its best, this is efficient for both the customer and the business. More commonly, this is a source of deep frustration.
One of my goals at Checkbox was to see if we could fully eliminate deflection. Previously, support at Checkbox was available only to two designated email addresses and only for current paying customers. We opened up support. Now, anyone can email support@checkbox.com. We want to encourage conversations with customers and facetime with real people. Our representatives have full freedom to choose the best type of support for any customer regardless of how much they’re paying. We’ll hop on a Zoom call and screenshare. We’ll link in a help center article if it has the clearest presentation of information. We’ll utilize AI to streamline responses and get you accurate information faster. We’ll coordinate with sales, billing, or engineering on your behalf. The bottom line is that being a feedback company means believing in people’s voices and emphasizing interaction.
Checkbox support - Now and Going forward
To go back to our restaurant metaphor: At Checkbox, your host helped build the menu. They’ve got some experience as a sommelier. If you have a question about the food, the head chef will come out and talk to you. If we don’t serve what you want to eat, we’ll work on adding it to the menu. While we have the signature dishes and approaches that we’re known for, the restaurant wants to cater specifically to you.
When our support team receives a feature request, it is share with the team via a quarterly voice of the customer meeting. Leadership, engineering, and support then meet to built our quarterly roadmap for both the company as a whole and for engineering resources specifically. Up to this point, our engineering focus has been on reactive and behind the scenes efforts: infrastructure, security, bug fixing. As our team has expanded and we’ve crossed these hurdles, we now plan to accelerate our feature releases and UI improvements.
Customer Success is an ongoing journey, stay tuned for more from our team as we continue on our path.
So now the question turns to you. What do you want from a support team? What features do you want in a feedback platform?
If you have any thoughts and want to connect, or if we’re missing the mark in any way, let me know directly at bwilliams@checkbox.com
And as always, we welcome your tickets via your support portal or at support@checkbox.com
