Punching Above Your Weight: An Interview with Courtney LeBlanc at Willful


Ibby Syed

Q: Can you give us a brief overview of your role at Willful and the company's mission?

Courtney: I've been working at Willful for about three years now. I was their first dedicated hire focused on customer support. Prior to my arrival, the founders were managing a Gmail inbox and a company phone number, with occasional help from a virtual assistant. My role was to establish a more formal, structured approach to customer support.

Willful's mission is to make estate planning more accessible and affordable for Canadians. Our platform allows users to create key documents like powers of attorney and wills online, without the need for a lawyer. While it's not the right fit for everyone, it provides a much more approachable and cost-effective alternative to the traditional path of hiring an attorney, which can cost thousands of dollars.

Q: Given the sensitive nature of estate planning, how do you approach customer interactions with empathy while still maintaining efficiency?

Courtney: Empathy is absolutely core to our support philosophy at Willful. We recognize that people come to our platform for a wide range of reasons - some positive, like getting married or having a child, and others more difficult, like receiving a terminal medical diagnosis.

When it comes to putting empathy into practice, it starts with hiring. I prioritize candidates with strong soft skills, even if they don't have direct experience in a support role. It's much easier to teach someone the technical aspects of the job than it is to train them to be empathetic. One of my best hires came from a background in fast food and cannabis dispensaries - environments where you interact with a diverse customer base and need to think on your feet. He had never written a business email before, but his ability to problem-solve and connect with people made him an incredible asset to the team.

Beyond hiring, we have robust brand and tone documentation that guides how we communicate with customers, from macros in our Zendesk instance to our support center content. The goal is to establish a friendly, approachable mentor persona. We empower our agents with the flexibility to go above and beyond for customers whenever possible.

Q: How do you leverage data to inform your support strategy and identify areas for improvement?

Courtney: Data plays a huge role in shaping our support operations. We rely heavily on tags in Zendesk to capture the key themes and issues driving customer inquiries. We recently completed a major business intelligence project to integrate data from our order system with our support tickets, allowing us to analyze trends at a much more granular level.

Some of the fascinating insights that emerged from this analysis include:

  • Customers aged 60+ account for about half of our total support volume.
  • This 60+ age group tends to favor email as a support channel and our team has been working on some hypotheses around what drives this and will be experimenting with our support channels to work on validating our hypotheses.
  • On the other end, our youngest customers (18-29) heavily prefer chat support.

While the core questions we receive are fairly consistent across age groups, older customers tend to need more "tutorial" type support in navigating the platform and we recognize that making the platform easier to use for any demographic will improve the experience for all users.

Armed with these insights, we're now making recommendations to our product, marketing and engineering teams about how we can proactively address common customer pain points and queries. If we can implement some of these suggestions, we anticipate being able to meaningfully reduce our ticket volume and alleviate the burden on our support team and improve the user experience.

Q: What's next on the horizon for Willful's customer experience?

Courtney: There's no shortage of exciting projects I'd love to tackle - the challenge is prioritizing them with our limited resources.

In the short term, a major focus is reworking our chatbot experience, informed by another round of data analysis. Our key demographic of older millennials with young families prefer chat support, but we also know that chatbots can be immensely frustrating when poorly implemented. Our goal is to create a truly seamless experience that efficiently answers common queries while quickly connecting users with a human agent when needed.

Looking out a bit further, we're eager to explore how we can better serve customers who prefer phone support, like our 60+ age group. Prior analysis has shown that customers who engage with us by phone are 30% more likely to choose Willful to make their estate plan, so there's a clear opportunity. As we head into planning for the next fiscal year, we'll be assessing different options based on our team's forecasted growth.

In parallel, we're gearing up for phase two of our big data project, aiming to slice the data in new ways and uncover additional actionable insights. It's an iterative process of identifying gaps and limitations, refining our approach, and peeling back additional layers to better understand the customer experience.

In Conclusion

Our conversation with Courtney showcased how a small but agile support team can punch above its weight by combining empathy, data-driven insights, and cross-functional collaboration. A few key themes emerged:

  • Empathy has to be the foundation of support, especially for a product that deals with emotionally weighty topics. This starts with hiring for soft skills and is reinforced through brand guidelines and agent empowerment.

  • Granular data analysis is essential for identifying the key drivers of customer inquiries and proactively addressing them through product improvements, enhanced self-serve resources, and tailored support channels.

  • A tight-knit, collaborative relationship between support and other key functions like product and engineering allows for rapid iteration and meaningful enhancements to the customer experience.

As a company deeply invested in the power of customer experience, it was inspiring to see how Willful has thoughtfully designed its support operation to deliver a high-quality experience with limited resources. Their approach underscores the importance of leading with empathy, leveraging data to work smarter, and breaking down silos to put the customer at the center of every decision.

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