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Leadership Profile: Sara Hillier on hospitality and problem-solving

How ClearEstate’s Director of Estate Solutions & Partnerships Supports Families Through Adversity

Posted on November 5, 2021
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From customer service to the estate space, Sara Hillier has spent a lifetime helping people find solutions to problems. Not only is she good at it but she loves the work, making her a natural fit at ClearEstate, a platform built on empathy and driven by compassion.

As Director of Estate Solutions and Partnerships, Hillier’s role is to explain what the team can do for executors to help make the estate settlement process less cumbersome. Just don’t call it “sales”!

“From a client-facing perspective, we tend to not use the word sales,” she explained. “My role is basically getting in front of people to talk about what we can do to help them with their particular circumstances. There's so much to do, and so much we can do to help.”

Best Practices in Hospitality

Of course, growing up, few decide that they want to work in estate planning and settlement. Rather, in Hillier’s case, it was a journey that began in the hospitality industry where her skills first took shape.

“It's rough, and the hours were hard,” recalled Hillier. “I took the Event and Meeting Management Program at George Brown College but didn't get the job satisfaction I wanted out of hospitality. So I started looking elsewhere to see what would spark my interest.”

That’s when she happened to do a placement at a trust company through the temp agency she was with at the time. Hillier fell in love with the detail-oriented nature of the work, which required a delicate combination of project management and one-on-one client management.

“I started out as an administrator, then I was promoted to trust officer. I would help families when the trust company was acting as executor, overseeing those files and guiding them through the process. I was further promoted to estate and trust advisor, where I was involved in the estate planning side of things, working with clients who were in the process of preparing their wills and providing guidance when needed. I developed an extensive knowledge base and expertise in the practical and logistical aspects of estate planning and estate settlement.”

And like hospitality, Hillier was drawn to the human factors at play and how compassion can go a long way in getting through such sensitive tasks.

“I like family dynamics, and facilitating understanding,” she continued. “This is a very satisfying part of the job for me, helping families get through adversity while continuing to have positive relationships with one another.”

This on-the-job experience was then bolstered by technical training and education to further her qualifications. In 2015, Sara acquired her Member Trust Institute designation from the Canadian Securities Institute, followed by her Trust and Estate Practitioner designation from the International Society of Trust and Estate Practitioners in 2016. Certified and newly inspired, Hillier set out on the next phase of her professional life.

A Commitment to Care

Though grateful for the experience, trust companies typically tend to deal with high net worth clients, which represents a very small percentage of the population. Hillier wanted to do more for more people because everyone needs help with these processes. That was around the time she saw ClearEstate pop up in her network.

“I was just curious, and did some investigating to find out what they were all about. I could see the website developing and I thought to myself, I need to talk to these people. So I reached out, and really connected with their vision and mission. It’s something that’s preoccupied me for years, the need to get less antiquated insofar as how we deal with estates.”

The more she learned, the more she fell in love. Hillier recognized an urgent need for options that were more accessible and user-friendly.

“We have the right technology and the right team to do this, and it's so incredible to see two things come together so well,” said Hillier. “The roadblocks of estate settlement are considerable, and ClearEstate’s mission is to eliminate the needless bureaucracy and red tape that cost time and money. It’s everything I care about and then some.”

Leading with Empathy

In offering a service that carries such emotional weight, there is an underlying duty to do things a little differently.

“It's not even a question,” she stated. “You always lead with empathy. Some of these people are going through the worst times of their lives and are usually feeling quite overwhelmed by everything. And now they're being forced to confront and understand things they've never encountered before. These decisions can impact them in ways they don’t fully understand.”

This is especially true for executors, many of whom are going through the steps for the first time and may not fully appreciate the scope of their responsibilities, and even liabilities. With clear information presented in an empathetic, low-pressure context, Hillier believes it’s possible to find a path that is true to the client’s values.

“I'm a real person when I talk to people; I'm not pretending to be something different. And I think that that resonates with people. It's really just about being real and being helpful. If something is bothering or frustrating you, you can tell me — because we’re all people, right? It has to be genuine, and that's a big part of who I am. I want to help people and ClearEstate is an amazing way to harness my superpowers, so to speak.”

Sara Hillier is ClearEstate’s Director of Estate Solutions & Partnerships. She can be reached at