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Kim K. Melillo: “It’s a time to look internally”

It’s a time for coming together to weather the storm. While Sure Oak has always had a phenomenal community that is bound by a shared vision, this moment has given us the opportunity to further entrench those bonds. I realized early on in the pandemic that my first priority as a leader was to ensure […]

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It’s a time for coming together to weather the storm. While Sure Oak has always had a phenomenal community that is bound by a shared vision, this moment has given us the opportunity to further entrench those bonds. I realized early on in the pandemic that my first priority as a leader was to ensure that my team felt safe and taken care of. They are the company. There is nothing without them. I feel exactly this way about my family. Never has it been more true than now that we are all in this together.


The Covid-19 pandemic has affected nearly every aspect of our lives today. Many of us now have new challenges that come with working from home, homeschooling, and sheltering in place.

As a part of our series about how busy women leaders are addressing these new needs, I had the pleasure of interviewing Kim K. Melillo.

Kim served as VP of Marketing and National Marketing Director for companies in the Fintech and leisure industries, as well as successfully ran and sold her own agency. She currently serves as the CEO of Sure Oak, a thriving agency in New York. Now, as a C-level professional and passionate woman leader, she is in a position to tackle the very real challenges faced by a world looking for solutions to a whole new set of obstacles. A wife, mother, avid gardener, and volunteer for various causes close to her heart (Food for The Hungry, Hope Kids, and Phoenix Rescue Mission, to name a few), she is a huge advocate for integrating career success into a life that is packed with meaning.


Thank you so much for doing this with us! Before we dig in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

The path from gymnast to CEO may not seem like an obvious one — but straight lines never make for interesting stories, nor are they food for real growth.

I have been an entrepreneur for as long as I can remember. From running a profitable sucker-making business in Grade 7 that turned over a whopping 200 dollars a week to roping my friends into teenage business schemes with festive names like The Sunshine Club, being an entrepreneur is utterly intertwined with my identity.

To be born with an entrepreneurial spirit is both a blessing and a curse. While it offers you a lifetime of adventure, it is also known to unleash absolute fury if you ignore it for even a moment. As the magnificent poet Mary Oliver said, “The most regretful people on earth are those who felt the call to creative work, who felt their own creative power restive and uprising, and gave to it neither power nor time.” I see entrepreneurship as a creative pursuit — one that I would only abandon at my own peril. Entrepreneurship for me is not simply about making money. It is about finding solutions to the world’s problems. It’s about creating things that were never there before and fulfilling the needs that are expressed when the world cries out.

You’re probably wondering at this point what any of this has to do with gymnastics. Fair question. Well, I was a competitive gymnast from the age of 5. That means, from the age of 5, I learned how to work hard, to never give up, and to understand that there are benefits to putting the hours in. I also learned the falsity that relaxation and pause are not necessities — something I’ve spent years unlearning.

When at the age of 12, I injured myself and was no longer able to compete on a professional level, I poured myself into productive activities. All my favorite books were about how to be a successful businessperson, even then. I held down a plethora of jobs simultaneously during my middle school years. From nannying to working in both a movie theater and t-shirt shop simultaneously before I was of legal age, I simply never stopped. This drive led to the opportunity to be editor of my high school newspaper and having a column in the city newspaper — and finally to the life-altering opportunity of interning, while still in high school, at an advertising agency.

I accepted a full-ride scholarship to a college an hour away from my hometown in Idaho, but I couldn’t shake the lure of the big city and all the opportunity that awaited there. So instead of taking the easy, well laid-out path, I persuaded my parents to let me hit the road to Los Angeles — with 300 dollars in my pocket, a bag full of dreams, and Janet Jackson’s “Control” blaring through the stereo. I made my own way through college, working in various capacities to both gain work experience and pay my bills. A non-linear academic path ended with a degree in Business Management and Marketing — and a freelance position doing the newsletter for the largest golf course management company in the world. With 350 golf courses, American Golf was thriving in a burgeoning (and completely male-dominated) industry. The journey with American Golf was one that shaped much of my career — but while it was fulfilling in many ways, that entrepreneurial spirit of mine would not rest. So I did what every overworked person should (never) do, and started working on developing my next company as a side-hustle out of my house, late nights and weekends, with a tiny baby daughter attached to my hip.

My agency InOne Advertising quickly turned into my main hustle and I was able to leave my job to focus on it. After year-over-year growth, I sold it in 2004 for the reason that many women end up dead-ending professional projects that they still care about: work-life balance and the fact that too often, it can be a complete fallacy. The thing was, I was pregnant with my second child and, not only did I want to focus on my role as a mother in a more intentional way and not repeat my last mistake of bypassing any maternity leave at all, but the doctor had also put me on bed rest for five months. My company simply was not going to last through having an inactive leader for that long. I spent my newfound “extra” time focusing on passion projects — of course, starting other side-hustles, first a B&B in the bucolic North Fork of Long Island, NY and, later, an organic gardening business.

This, I was to learn, was only the beginning of a descent towards the darkest time in my personal and professional life. After having given up my business to focus more on family life, I found myself in the midst of a divorce that did its best to try to destroy me both financially and emotionally. As a now-single mom, I simply couldn’t spend adequate time and capital getting a new business off the ground. I had to reinvent and get back to a more regular “job.”

After some time commuting to Los Angeles to work with American Golf again, collaborating on developing a philanthropic marketplace called The Network of Giving, and finding my forever husband, I somewhat serendipitously connected with Sure Oak. As I spend every day communicating with a remote team of stellar team members and engaging with clients whose dreams I care about as if they were my own, it now seems hard to see the story turning out any other way.

Can you share the most interesting story that happened to you since you started at your company?

Perhaps one of the most interesting Sure Oak-related stories did not occur after starting with the company, but rather on my journey to it.

I’m a firm believer in visualization. When we make a decision about what we want in life — if we think about it and turn our focus to it, and if we’re willing to put in the work to make it happen — the universe concedes. There is enormous power in intention.

And that is why I began building myself a home office “she-shed” so that I could start working from home. I wasn’t quite sure what I was going to be doing in said shed. I just knew that it would be a hive of productivity in the not-too-distant future.

So there I was, at the precipice of a new beginning, visualizing what I wanted my work life to look like. I made the firm decision that I didn’t want to travel in the way that I had been for so many years. I wanted a job that provided me the flexibility to work from my home in Arizona, while at the same time offered me the degree of professional stimulation that I always crave.

While brainstorming new businesses to start, I (for a reason that is now hard to fathom) took a quick look on Indeed — and there it was. Tom Casano, the founder of the agency Sure Oak, wanted assistance running and building an agency. I was compelled to reach out.

Tom was a young entrepreneur and with big dreams and big aspirations, who wanted help building something special and then replacing himself. We quickly found ourselves in an ideal symbiotic relationship. Here was the opportunity I had wanted — and the shed wasn’t even done yet.

Of course, the metaphors abound. This was my Sure Oak, the thing that I was looking to grow. I learned again as I had before that the end is not the end but rather the beginning of something else.

As Lynn Andrews says, “The seeds of wisdom and enlightenment are planted within the wounds of grief. What is lost can only come back to us again in higher ways.”

No matter where you’ve been or what you’ve been through, no matter what you’ve given up or what you’ve lost, there is always a way to rebuild. There is always a path to bring your hopes and aspirations to the fore. Connecting to Sure Oak was the physical manifestation of this and it continues to yield fruit again and again.

Are you working on any exciting new projects now? How do you think that will help people?

Amidst our usual daily adventures, we’ve decided to work on an exhilarating team-building project. While we’ve cultivated a healthy culture at Sure Oak that prioritizes the individuals that make it up, the introspection we have done over this time has allowed us to go even deeper. We want benevolence to be part of the scaffolding of our company. As a result, we are holding a virtual retreat for all our team members where they will have the opportunity to select a cause that they are personally passionate about and spend the day giving back — and all on the company’s dime.

Ultimately, an organization is made of individuals, each with their own talents, passions, dreams — and callings — that when given attention can make even the most restless souls more fulfilled, more complete. My mission as a leader is to ensure that each one of the members of my team feels valued and respected, and to recognize their talents both as professionals and as individuals that I truly care about as people. I want to play a part in not only building a great company, but in helping and inspiring our team to suck every ounce out of every opportunity in life — every day is a gift! — and to offer something of themselves, something of value to the world. By giving them this opportunity, they in turn can give to others. I want us all to live in a world where giving increases exponentially, and this is my way of aiding that cause.

We’re also looking to connect to non-profits on catchafire.org that we can offer our services to pro bono. It’s the time for giving back, for not hoarding our expertise and experience. Entrepreneurship is nothing if it doesn’t exist within a culture of giving. At this time, and always, we have to help each other.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

The list is long and seems to be ever-growing but one person that truly helped me get to where I am today is a marvelous entrepreneur by the name of Garry Pearson. Garry was not only an exceptional business mentor to me when I was starting out, but also a father figure, providing me counsel when my own father had passed away and I needed business advice.

Garry was good friends with one of the major leaders of American Golf where I worked at the time. They were part of the same country club and he asked me to let Garry quote on some large printing projects. Now, I’ve always found it difficult to promote myself. As is the case with many women in business, the line between self-promotion and bragging always felt too thin — so when Gary told this important leader that he was super impressed with me, he gave me the boost that we as women so often don’t give ourselves.

Garry taught me the importance of doing this for others in turn. When you are excited by the work of your team members (or your clients), say so. You never know how a brief remark might do anything from boosting someone’s esteem to launching their career.

The Covid-19 pandemic has affected nearly every aspect of our lives today. Can you articulate to our readers what are the biggest family related challenges you are facing as a woman business leader during this pandemic?

There are currently two concurrent family-related challenges that I am experiencing, and I imagine many women business leaders are finding themselves in the center of these as well. The first is negotiating the emotional needs of my family, and the second is navigating what feels like the most complex time management conundrum a person could ever be faced with.

I have two teenagers. I often imagine that, if we as adults are finding a socially-distant world hard, it’s difficult to even fathom what they might be experiencing. As if being a teenager wasn’t hard enough, they have been placed right in the center of a Venn diagram where an uncertain future, isolation, and sheer boredom meet. I am a leader in my home as much as I am in our company. I have to be a motivating force to them. I have to show them that there is hope. I have to lead by example in a way that lets them understand the beauty of resilience, all the while negotiating my own anxiety around an uncertain future for all of us.

As I am sure is the case with many families at the moment, striking a new balance has been hard. While this period has called on me to dig in even deeper, work even harder, and spend even more time searching for solutions for our business, the rest of my family is faced with more extra time on their hands than they have ever been used to. The vacuum that has been left behind by the cancellation of the routines of school and extra-curricular activities screams loudly through our house. This is coupled with the fact that my partner who works in sales has more time on his hands than usual — no business lunches, no going on the road, no hopping from one city to another. We have been left with a house full of people with a whole lot less to do — with me being the complete exception to the rule, of course.

Learning the steps to this dance is difficult, and often just as we think we have it down, it feels as if they change the song.

Can you share what you’ve done to address those challenges?

I highly recommend Costco’s pre-made dinners. Seriously. I’ve dialed back on many of the homemaking tasks that were part of my daily routine — including feeling the weight of perceived expectations for me to be perfect. You know what? It turns out that everyone has been just fine.

Instead, I’ve used the time I do have to spare to have the big conversations with my family about the times we are in and to collectively navigate our shared grief.

Perhaps my biggest piece of advice, both at home and in the workplace, is that strong communication is everything. We need to recognize this moment we are in. Going forward in a way that pretends business as usual will leave all of us all attempting to suppress the gravity of this. It is simply an unhealthy approach. To find any comfort in this discomfort, we must be able to say, “Whoah. Isn’t this difficult?” We have to know that we are struggling through this together, not because of any faults of our own but because This. Is. Hard.

Some days I feel as if I’m getting none of it right. My kids are a confusing mixture of distraught and bored, I don’t feel as if I’m doing enough for them or for my husband, and my work life feels overwhelming. I am learning however to not take this on myself. This is not because of anything I have done wrong or because I am not enough. It is simply the negotiation of the challenge we have been faced with.

This is an opportunity to create threads of resilience, both in ourselves and in our families. We are called to tackle the task head-on in a way that is brave, open, and honest.

Can you share the biggest work related challenges you are facing as a woman in business during this pandemic?

I don’t need to tell you that we are submerged in a culture of fear — and understandably so. So many businesses are looking to see where they can cut expenses to ensure their longevity in an environment that is decimating dreams left, right and center. For many, the cash flow simply isn’t there. Many of our clients have felt a dramatic negative impact due to Covid. Sadly, we’ve watched our travel clients’ businesses come to a screeching halt, taking their scopes of work with them, while others have had to make tough decisions about where they can conserve cash — and it has hit us right in the gut.

is a long game and, in a world where people are wondering about immediate futures, investing in a strategy that will bear fruit at a later date seems all-too-much of a gamble for some companies, especially if they are more cash-crunched or short-term focused.

While we experienced some fairly significant pain in the first few months of the pandemic, we have persevered and are finding our way back to growth. We have always been solutions-based. Now that the problems have changed, we’re looking for new ways to respond to them. What I know and what we’ve found is that in the midst of every crisis, there is ALWAYS opportunity.

Can you share what you’ve done to address those challenges?

I do what women always do when it comes to everything from scraped knees to broken hearts to fragile financials: I respond to the problem at hand.

And it hasn’t been all bad news for our company. As more and more people move online to fulfill their daily needs, companies are seeing the importance of focusing on organic search. In an increasingly digital world, they simply have to be found or they don’t stand a chance. In this way, we are starting to see the potential growth viability of this moment. We’ve had to maneuver a few things however to accurately respond to this need.

One of the things we’ve looked at is shorter range contracts or early-out clauses that respond to the current appetite. Many companies are not in a position to think long term.

We’ve also taken this time to take a hard look at every aspect of our internal processes, to find areas of weakness that create opportunities for improvement. On the back side of this pandemic, we want to come out stronger.

We’ve also fully embraced our GIVE FIRST philosophy. We’ve offered a lot of complimentary work to those in need where we offer high-level insights with no strings attached. I fully believe in the Law of Reciprocity. So far, I’ve never lost anything by giving what I have to offer.

To assuage fears within our team, we have focused on further improving the strength of our internal community. We’ve decided to institute a program where we pay our employees for a day of service for a non-profit they care about. Essentially, it’s about coming together to do good for people.

When we step outside of ourselves and focus on others, it’s amazing how our purpose gathers steam. I’ve always found this to be a way out of tight spots: the answer lies in what you can do for others.

In this time, as in any, I believe we’re given our talents to make a difference in the world. We’re called to share, not hoard. We’re here for a reason, to leave this world better than we found it.

If we focus on how we can help other people in times of strife, we find meaning within ourselves and within our communities.

Can you share your advice about how to best work from home, while balancing the needs of homeschooling or the needs of a family?

I had a lucky head start in this regard. Because our company was already 100% remote pre-pandemic, I was already practiced in the complicated balance of working from home.

It’s important for me to have my own space to work from. I understand this is not possible for everyone but I do recommend setting aside even a corner of your home and dedicating it to work — and then communicating with your family that when you’re in that particular space, you need to be left alone to work. (Of course, this is not always possible with younger kids, but we do what we can.)

Homeschooling on the other hand? Well, that was new to me. While getting through the curricula doesn’t seem to offer too much of a challenge in our household, the after-school empty hours do. We’re still negotiating this. What I do know is that stimulation for kids of all ages is necessary beyond the bounds of simply understanding the day’s schoolwork. I’ve tried to cultivate some excitement around activities that can be done from home, gardening being my personal favorite. Also, I have found it imperative that we are all encouraged to engage in some sort of physical activity (in a safe way). It does wonders to ameliorate the compounded stress of a full house of people.

Can you share your strategies about how to stay sane and serene while sheltering in place, or simply staying inside, for long periods with your family?

Meditation. Breathing. Praying. Factoring in quiet time.

For me, this means getting up at 4.30 am. (Don’t worry, it can mean something totally different for you.) I cuddle on the couch with my dogs. I drink my coffee, listen to the silence, meditate, pray.

We’re all more powerful than we know. Most of us only scratch the surface of what we’re capable of. We need those moments for ourselves or we don’t stand a chance against the noise that the world throws at us.

Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. From your perspective can you help our readers to see the “Light at the End of the Tunnel”? Can you share your “5 Reasons To Be Hopeful During this Corona Crisis”? If you can, please share a story or example for each.

  1. It’s a time to look internally. Sure Oak has found this period incredibly useful in terms of allowing us the time to take a deep dive into our internal needs. It’s been a period of major introspection. When things were clipping along at their normal pace, we never seemed to have a moment to spend on truly evaluating our own marketing strategy, analyze our structures and workflows and see where there was room for internal growth. This period of introspection has not been exclusive to my work life. At home, we have also navigated what it means to be together as a family and how one cultivates the resilience to cope when the rug gets pulled out from underneath you.
  2. It’s a time to reinvent ourselves. And what better outcome for a process of introspection than productively reinventing ourselves? From how much time we spend in malls to understanding the inner-workings of our businesses, this moment is fraught with potential epiphanies. We don’t have to continue repeating behaviors simply because that’s the way we’ve always done things.
  3. It’s a time for coming together to weather the storm. While Sure Oak has always had a phenomenal community that is bound by a shared vision, this moment has given us the opportunity to further entrench those bonds. I realized early on in the pandemic that my first priority as a leader was to ensure that my team felt safe and taken care of. They are the company. There is nothing without them. I feel exactly this way about my family. Never has it been more true than now that we are all in this together.
  4. It’s a time for creativity. While I have my eyes fully open to the weight of grief around me, I also see this as a period where creativity and innovation will thrive. We need new approaches to our ways of doing business, as well as to formulating something that resembles a work-life balance. I am continually inspired by the entrepreneurial pivots many companies are making, from taking their businesses online to entirely revamping their products and services.
  5. It’s a time to do good together. As we continue to explore ways of helping nonprofits and companies that are struggling, as we take the time to encourage the passion for giving in our team, as we kindly navigate the difficulties our clients and our team members are facing right now, I have come to a new understanding of the importance of doing good together.

From your experience, what are a few ideas that one can use to effectively offer support to their family and loved ones who are feeling anxious? Can you explain?

My philosophy in both my home and professional life has always been one of transparency. In terms of our company, this means having honest conversations with both our team members and our clients. With my family, it means the same thing. I strive to cultivate an environment where open communication thrives. There is enough fear in our lives. We are inundated with disarming rhetoric from every media source. I want our family and our company to be a retreat from that inundation.

Anxieties should be spoken about before they fester. I have found time and again that when we name our fears, their power dissipates.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Be bold and mighty forces will come to your aid.” (Basil King)

Never let fear get in the way. You have to just go for it. You may have a mountain ahead of you but the only way to conquer it is to put one foot in front of the other. We can find a million excuses as to why we can’t do things. They will always be there waiting to pull us back — but often we just need to jump. The worst thing that can happen is we fail. Is that so bad?

I realized way before the pandemic that some of the worst things can happen — the things that you most feared can come true — and you can get through them.

For most successful people, it’s never a straight line to the top.

We just need to learn to not be afraid. Fear is nothing but limiting, and overcoming it is a practice like any other. Life is too short to be afraid, to let our fears limit what we’re able to do. Carpe diem. Every day is a gift.

How can our readers follow you online?

You can find me on Linkedin and Twitter.

Thank you so much for sharing these important insights. We wish you continued success and good health!


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