Jillian Harris of Keepingly: 5 Steps We Must Take To Truly Create An Inclusive, Representative…

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Jillian Harris of Keepingly: 5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society

Look outside of ourselves — Going back to the dangers of the single story, a human being, any human being, views the world through the lens of their own experience. We see the world the way we are. Let’s admit that and look beyond our own lives, and our own existence. Much of what is being created in the product world, is being created for disposable incomes because investors need to see a source of revenue to prove an ROI. There’s nothing wrong with that, but there are also real problems being solved with technology.

As part of our series about ‘5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society’ I had the pleasure to interview Jillian Harris.

Jillian Harris is Chief Product Officer of Keepingly.co, the trusted platform for homeowners to manage, maintain, pay, and keep records of all their home services and expenses.

She is also a multi-faceted, experienced designer and creative director with over 25 years of design experience. Her portfolio spans, the Caribbean, the US, London, and South Africa, and she has worked on over 100 global and national brands across 15 major industries including education, healthcare, alcohol, lifestyle, fashion, and finance where her work helped create a 653% increase in traffic and a 357% increase in conversions over the previous period.

Thank you so much for doing this with us! Before we dig in, our readers would like to ‘get to know you’. Can you tell us a bit about how you grew up?

I grew up in the twin island Republic of Trinidad and Tobago. Because of its history and location Trinidad is very diverse. That diversity has always been celebrated and we pride ourselves on being a melting pot of cultures. It’s only now when I fast forward many years and I’m living in another country, and I have teammates in India and they are surprised that I even know anything about their festivals, that I understand how special it is to be from a place that celebrated Eid and Diwali and Christmas and it was just what we did. Our national motto is “Together we aspire, together we achieve.” In 1962, when we gained our independence from Britain, Dr. Eric Williams gave the country these three watch words “Discipline, Tolerance and Production” as words to live by. There is a line in our national anthem that says “Every creed and race finds an equal place.” In writing these words I’m both surprised and moved at how much pride I still have in them even though I haven’t lived there in almost 20 years. They are ingrained in me. They are a part of my DNA. I’m weirdly very nostalgic about Trinidad. Don’t get me wrong, people are the same everywhere you go on the planet, so of course we have more than our fair share of challenges as well.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

There are a couple of books that I try to reread each year — I’ve been reading them even before I got into the startup world. The Greatest Salesman in the world by Og Mandino is an oldie but a goodie. It comes as a two-volume set and it recounts the life lessons a young camel boy learns as he becomes said salesman. It sits at the crossroads of Christian teaching and esoteric knowledge and my copy is riddled with highlights and notes. Its very relatable and quotable. At it’s core it underscores the importance of mentorship which is critical in the startup / founder journey.

The second is S*** you Ego says by James McCrae. On a good day the founders Journey is not for the faint of heart. When you are a founder of color, the incline is much steeper. This book really helped me distinguish between my Ego and my intuition and with that came a resolution or understanding of my own value. As a woman, woman of color, woman in tech, woman in a creative space, it’s really important to be clear on what you bring to the table. In advertising we called it the USP ( Unique selling proposition) of the product. That “thing that you bring to the table” will get attacked and every effort will be made to chip away at it and surprise surprise, those attacks are not always external.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

One of the things that I loved about the Greatest Salesman is that it was full of life lessons and quotes. But the quotes that are an integral part of my DNA come obviously from my heritage. This one by Novelist Merle Hodge is from her book Crick Crack Monkey. It reads “Who ask don’t get. Who don’t ask don’t want. Who don’t want don’t get, who don’t get don’t care.” It’s easy to dismiss the value of this quote because of its colloquialism, but loosely translated it means if you want something and it matters to you, you need to ask for it. This quote is the epitome of startup life and the funding journey. You have to ask. If you don’t ask, you will not get a single thing.

The second quote supporting me on this journey is “An oak tree will never have to tell you it’s an oak tree.” It’s something my father said to me as a teenager, and it’s akin to Dr. Maya Angelou’s “When someone shows you who they are, believe them the first time.” People never tell you who they really are. They show you. I didn’t understand what my father was trying to say to me until one day when I was having a debate with a classmate and he said to me “Jillian why don’t you trust me, I’m a Christian.” To which I replied. “You shouldn’t have to tell me that.”

To this day, people telling me who they are or even worse telling me to trust them, is a red flag for me. To be clear it doesn’t make them a bad person, it just makes me pay closer attention.

How do you define “Leadership”? Can you explain what you mean or give an example?

There are a lot of books on leadership. HBS online has an entire course on the subject. In it they break down the difference between leadership and management. That work and the writing of Simon Sinek (Leaders eat Last) has helped to define who I am and hope to be as a leader. The title of that book really resonates with me because I’ve experienced firsthand how easy it is to be taken advantage of by management. Leadership should not be predatory. Leaders are people focused, visionary and inspire trust. Leaders are empathetic and invest in the talent of their team. Early in my career I worked with a junior designer, my time with her taught me the importance of validation. She always asked a lot of questions at the beginning of a new project. More questions than anyone else, it drove me a little bonkers to be honest, but I quickly realized that once we went through the questions, I could leave her alone to work and she would nail the project. One day she was being micromanaged by an account person. This exchange is happening behind me, I can’t see it but I can hear it. The account person calls out to me and says have you seen this. I had no clue what they were looking at, but without even looking up I said “Leave her alone she knows what she’s doing.” The beam of light that came off of that designer in that moment taught me a valuable lesson about validation. That moment wasn’t planned — it just happened but it was an incredible teaching moment for me. Validating the work of my team is important to me because of that day. For me being people focused also means, being willing to step in and support when you see them struggling. The struggle isn’t theirs its ours. The credit isn’t mine, it’s theirs.

Ok, thank you for all that. Now let’s move to the main focus of our interview. In the summer of 2020, the United States faced a very important self-reckoning about race, diversity, equality and inclusion. This is of course a huge topic. But briefly, can you share your view on what made the events of 2020 different from racial reckonings in the past?

In chatting with elders in my community, the hardest part of 2020 for them was the disappointment they felt in the realization that we are still here, stuck at this intersection. That said I saw firsthand the importance of allies. I believe there are more now than ever before and I am extremely grateful for them.

Can you tell our readers a bit about your experience working with initiatives to promote Diversity and Inclusion? Can you share a story with us?

Diversity and Inclusion work can sometimes be performative. I’ve been in roles that used me for optics only, I had a title but no real authority. And in 2020 we saw a lot of that performance from companies. The work is important because as UX teaches us we ALL have biases. I’ll say that again we ALL have biases. In the absence of D&I work / initiatives you’re flying solo. So when you’re brought into a client meeting not to speak or present but to “prove that we have a diverse staff” or you have to lead people who have never had to trust or respect someone that looks like you and so they don’t perform at the level that they would for someone else. There is no one there to support. Who counsels you when you have to walk into HR and say “ Hi, it’s come to my attention that I’m managing staff who make more than I do. Do you think that’s fair?” All of these are real stories form my life at a time when there wasn’t a label for the work that needed to be done. These are all scenarios that require support from upper management and HR, and in the absence of a framework that challenges people to confront their own bias and move from tolerance to a place of understanding, you are on your own.

This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

Chimamanda Ngozi Adichie outlined this best in her TED talk the danger of the single story. When we see a problem through a single lens we miss critical understanding. This becomes critically important when you are striving to build a product and you’re betting the farm on mass adoption for your ROI.

Ok. Here is the main question of our discussion. You are an influential business leader. Can you please share your “5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society”? Kindly share a story or example for each.

If Diversity and Inclusion were a flaw in a product, it would be solved already. I firmly believe that. We would interview users to find out what their pain points were and validate our own assumptions about what we think those pain points are. We would balance business needs with user needs. We would test our solution and iterate features till we found something that worked. Because the bottom line depended on it.

How do we translate that to the real world?

For me the five steps to truly create an inclusive, representative and equitable society come squarely out of the basic tenets of experience design.

Look outside of ourselves

Going back to the dangers of the single story, a human being, any human being, views the world through the lens of their own experience. We see the world the way we are. Let’s admit that and look beyond our own lives, and our own existence. Much of what is being created in the product world, is being created for disposable incomes because investors need to see a source of revenue to prove an ROI. There’s nothing wrong with that, but there are also real problems being solved with technology.

Solve real problems.

If your product relies solely on customers having disposable income, straight out the gate, the product is probably not catering to the majority of the population and therefore probably not inclusive.

Dare to engage

Engagement is very different from looking outside yourself. I’m paraphrasing here but there is a famous story in design about designers coming into a rural village. They noticed the women had to walk a significant distance to get to the river to wash laundry, dishes, fetch water for cooking etc. The designers say ah ha! These women need a well. So they set about the business of build the community a well. The very next morning the designers wake up to find their well completely destroyed. That walk to the river, that time at the river, was very important social bonding time for the women in this community. Had the designers engaged the community they were designing for they would have known that and could have used those resources to alleviate real pain points for the community vs perceived ones.

These three points are speaking to designers but the same can be said to investors. Yes there is a lot being done in the impact investing world, but those funds are the first to dry up in an economic downturn.

Design solutions for your own problems, you can’t possibly be the only one going through that experience.

The last two points look in a different direction from the first three, but they come out of Keepingly’s approach to its product. Keepingly was created by Daniel Smith out of his frustration with his own home maintenance journey. It is a platform that helps homeowners maintaining and manage their home. I bought into the idea immediately, because of my own experience as a female homeowner. So we design and create and ideate from a place of shared experience with the people we want as customers. We intimately share their pain, we don’t just perceive them to be researched pain points. And even with that shared experience we still have to look outside of ourselves and engage and refine the problem so that at its core the problem we are solving is a universal one. In our research we discovered that homeowners of color get disproportionately low appraisals on their homes as compared to their white counterparts. That’s an issue that requires some visibility and education around it. And that’s my last point for building a Truly Inclusive, Representative, and Equitable Society — educate your consumer along the way. At Keepingly we’re not just trying to build a platform or a product or a data set. We are trying to change the thinking of this particular consumer and we do that through education. “Home is where the heart is” is lovely and warm and fuzzy. But really your home is your greatest asset and through its podcast Keepwize, Keepingly will look to educate homeowners about the asset management side of home ownership.

We are going through a rough period now. What makes you optimistic about the future of the US? Can you please explain?

The youth. This newest generation is bold, unapologetic and unafraid to challenge the status quo. They were not raised to be seen and not heard. They are all about using their voices and their platforms.

Is there a person in the world, or in the US, with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. 🙂

Chimmanada, Bozoma are either of you reading this? These women are both bold, successful and unapologetic. I’m more soft spoken, I could use a lesson or two. 🙂

How can our readers follow you online?


This was very meaningful, thank you so much. We wish you only continued success on your great work!

Jillian Harris of Keepingly: 5 Steps We Must Take To Truly Create An Inclusive, Representative… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.