Women Of The C-Suite: Janet Dillione Of Connect America On The Five Things You Need To Succeed As A Senior Executive

Charlie Katz
Nov 24 · 10 min read

If your instincts say ‘no,’ then move on. The people will not change, and you can’t change the culture from the bottom.

a part of our interview series called “Women Of The C-Suite” , we had the pleasure of interviewing Janet Dillione.

Janet Dillione is Connect America’s CEO, with experience building innovative strategies and strong teams that transform businesses for sustained growth and profitability. Throughout her career, she has been focused on leading important developments in healthcare technology by solving long-standing issues in the delivery of care. Prior to joining Connect America, Janet worked in the healthcare information services industry as CEO of Bernoulli Enterprise, Inc., GM of Nuance Healthcare, and CEO of Siemens Healthcare IT. With leading roles in both large-scale global businesses as well as start-up scenarios, Janet is a dynamic leader who knows how to effectively instill a customer- and market-centric culture within an organization to drive the business forward.

​​Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

healthcare journey began when I was a pre-med student. My father was ill, so I took a year off after graduation and worked at a hospital that was going through a conversion to an automated revenue cycle system. I was assigned to the project and became fascinated by what technology could do to improve healthcare and never looked back.

Can you share the most interesting story that happened to you since you began leading your company?

We serve the senior and vulnerable patient market, so we take our responsibility to our customers very seriously. A few months into my new role, I received a letter of complaint from a customer addressed to me personally, which was the beginning of what became a bit of a pen-pal relationship.

I did what most CEOs would do, and I acknowledged receipt with a personal email to the customer and handed it off to the operational owner, who quickly handled the matter. I closed the loop with the customer and felt that we had promptly taken care of the issue.

A day or two later, I received an email from the customer, who thanked me for the assistance but made me aware we were not quite at the finish line. Once again, I worked with the operations leader, whose team again moved quickly and resolved the issue. The customer was an intelligent and gracious woman. She communicated her concerns from a very personal place, and her graciousness and vulnerability stuck with me.

This exchange happened quite early in my tenure and reinforced my opinion that our work is always about the customer; they depend on us to always deliver our very best.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Early in my career, I was asked to complete an analysis of a remittance advice from a large payer. Now, at that time, I had absolutely no idea what a remittance advice was and had never had a business course. But I knew how to do an analysis of variance, so I took a science-based approach to it.

When I presented my version of the reconciliation, which was entirely incorrect, I wasn’t lectured for my mistake or excoriated. In fact, my CFO decided to use it as a true learning experience, and I got a master class in healthcare reimbursement. That experience always stuck with me, not for the mistake I made, but for the lesson I learned about using those moments to teach.

People will follow the leader that treats them with respect and engenders trust. It’s a basic concept we’re taught as children, but treating others as you’d like to be treated can pay dividends in the professional world.

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?

When I was coming through the management ranks within Siemens Medical Solutions, a very important leadership role opened. It was in the revenue and profit center of the business, and no woman had ever held the role.

The hiring senior vice president, Dave Perri, was brilliant; I interviewed for the role and was offered the position. It was clearly the pivot point of my career. I would be handling millions in revenue, hundreds of employees, and millions of data center transactions per year.

The position was a perfect challenge, but the important part of the story is that the senior vice president gave the role to me, a woman who was nine months pregnant. I was named to the role, walked over to the department I’d be overseeing, met the executive assistant, and then went on maternity leave the following week. All became possible because of Dave.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high-stakes meeting, talk, or decision? Can you share a story or some examples?

I find the best way to manage stress is to be prepared. Several years ago, I worked for a leader who was a phenomenal presenter. He always owned the room, whether it was ten people or 1,000 people. Prior to a time when I was about to present to a room of 100 people and a live video feed, he shared his secret: he practiced in front of a mirror.

That stuck with me, and I adopted a mindset that practice counts. Over time, my marketing teams became familiarized with leaving me to myself prior to key addresses. I need to ‘get in the zone,’ so to speak. If possible, I will use a mirror. If not, I will walk through the pitch in my office, in the hotel room, anywhere I can find time for private, quiet prep.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality, and inclusion. 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?

It is somewhat obvious but bears mentioning that talent and intelligence have no gender or race. Business is inherently competitive, and to win we need to field the best team. It’s a meritocracy, and ultimately, I have a higher probability of assembling the best team if I spread my net far and wide.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

The most critical first step is to ensure that opportunities are truly available to all. Most of us got our start because someone let us get a foot in the door. As leaders, we need to keep the door open as wide as possible so people who are interested can take their shot.

We are building relationships with local schools and chambers of commerce to develop pathways and programs that will make sure Connect America looks more like the communities within which we do business. Additionally, COVID-19 showed us how to open up geographically, so remote roles must be offered, too.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words, can you explain what an executive does that is different from the responsibilities of the other leaders?

The larger your role, the less time you spend thinking about tactics to execute on a project or task. You spend more time thinking about how we can best get it done and who you need on the team to execute it successfully.

As people climb the career ladder, they can be intimidated by not being the smartest person in the room anymore. But if you want to make that leap to the C-suite, you can’t limit yourself to thinking you’re always the smartest person. As a matter of fact, you need to be compulsive about ensuring you are surrounded by the best and the brightest.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

I have come across many styles of CEOs in my time, so it’s difficult to say what the tried-and-true myths are. Overall, I have found that CEOs with sustained success are not solo artists; they understand how to both build and lead a team.

Successful CEOs are people who love a good challenge as well as the joy of winning as a team. While some organizations may have what I consider a high ‘toxic quotient,’ most sustainable companies are run by well-balanced, perpetually curious leaders.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

One of the biggest challenges for women executives is the reality that there simply is not much room for error. If you get a seat at the table, your seating is a bit more tenuous, especially if you are the first or only woman there.

Early in my career, I had a performance appraisal from a manager who commented that while I produced quality work, I was at times ‘aggressive’ in my behavior. I countered that a man likely would have been described as ‘confident’ or ‘bold.’ I don’t consider myself an activist, but I stood my ground and refused to sign the review until we could come to an agreement on the text.

What is the most striking difference between your actual job and how your thought the job would be?

I love the pace of change in my job and trying to mix all these ingredients into making a phenomenal company. Since I joined Connect America, we have executed two transformative acquisitions of Philips Aging and Caregiving Business and 100Plus, which has moved us into a rapid pace of digital transformation. Now, the company I lead is vastly different than the company I joined.

I enjoy executing a pivot and helping a company steer in a new direction. I’m enjoying my role at Connect America but even more than I expected coming in.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I don’t think everyone is cut out for every role in the world. For instance, I’m not cut out to be a downhill skier. Trust is huge for leaders, and I don’t think there’s any time for braggadocio when you’re part of a team trying to accomplish something great.

Frequently, with people I mentor, I mention that most successful leaders are also committed, lifelong learners. They establish trust through actions and behaviors. They stand up and take the incoming bullets. They are comfortable not being the functional expert in every aspect of a business, and they actively listen.

They should embrace healthy market competition and want the team to win. They recognize that authority is an aspect of their role, not their divine right, and they should exercise authority both sparingly and with grace.

What advice would you give to other women leaders to help their team to thrive?

Some people focus too much on the vertical rather than the horizontal relationships and leadership. Ensure you are the type of leader your peers, not just your superiors, would select as their next boss.

How have you used your success to make the world a better place?

That strikes me as a grand statement, but I have spent my career in healthcare, and I often tell my teams that we are morally compelled to do our best for the customers we serve.

I could have done IT work in any other vertical, but fixing problems in healthcare has always stood out to me. I would like to believe that in my very small slice of the world, I am leaving it better than I found it.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. The first job does not have to be perfect: A career does not follow a linear path. Those who do well bounce well, and they adapt and find ways to go over, under, or around obstacles.
  2. There will be people you cannot work with. That’s fine and is to be expected.
  3. If your instincts say ‘no,’ then move on. The people will not change, and you can’t change the culture from the bottom.
  4. There are more smart people than there are great leaders. Still, it’s important to recognize that not all smart people are great leaders.
  5. When you see great behavior, model it. Steal inspirations shamelessly.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Beyond healthcare, it’s climate change. There is not a more existential or menacing threat to our way of life than the effects of climate change. We have seen it with these recent hurricanes, wildfires, and ice storms; natural disasters are an element of danger that we don’t have adequate protection from.

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

Over my career the quote which most often comes to mind is, “Two roads diverged in the woods, and I took the one less traveled by and that has made all the difference.” You will recognize it from the Robert Frost poem, which I first read as a young student. It simply makes a perfect statement about an approach to the life I embrace.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Billie Jean King. Many leaders grew up playing team sports, and she exemplifies what leaders should do. She worked hard. She excelled as an individual, but that was not what she wanted her legacy to be. She found a way to raise all boats for women and is still committed to that mission.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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