Jackie Morales: Pivoting at the height of your career

Jackie Morales was at the height of her career in the Insurance industry when she decided to leave her safe, predictable corporate role to enter the startup world. We talk about the advantage of pivoting later in your career, why her career story makes her proud, and the advice she has for other women navigating career shifts. Plus–how her childhood growing up on a farm influenced the way she sees gender.

Q&A

Your whole career you worked in established insurance companies. Then, a few years ago, you left to join a startup. More recently, you joined a different stealth mode startup. Tell me about your pivot from the corporate to startup world.

You're right, my whole career I was in financial services and insurance with traditional, major carriers. I was working as Chief Operating Officer at a more than 150-year-old company when I got a call from a recruiter. You know, sometimes you take the call and sometimes you don't. Sometimes you take the call just so that you can help others because it is all about networking and helping others along the way. So when the recruiter initially called me, I said, Thank you, but no, thank you. He waited about a week and called me back and he said, “give me five minutes.” 

He started to tell me the story about this company–how it was different, how it wanted to do things to change the industry. What happened in my mind was I started to reflect on every happy hour I'd ever been at. You go to these events and see other carriers or clients and you all sit around at a happy hour with your glasses of wine and you say, if I could change the industry–I would do this. And then you list your laundry list of the things you would change . I started thinking about all those times I'd said if I could do it differently, I would. And here was an opportunity for me to put my money where my mouth was.

I was in my 50s by then and I said, If I don't choose to make a change, if I don't choose to step forward and do something to help this industry that I love so much. When am I ever going to have that opportunity again? And if not me, who? So I started listening and before I knew it, I was talking to the CEO of the company. He convinced me to dive off that big diving board and it turned out it was not really that far a leap for me.

A lot of women I interview realize the leap is not as big as they feared. When you were on the edge of the diving board, what were you feeling? What were you contemplating? 

Here is what you're so afraid of. You become used to certain norms. What is it going to be like salary wise? What is it going to be like benefit wise? If you work for a traditional company, you have a history there. You know that it's going to be stable. When you hear the word startup, you think, what happens if it doesn't work? What happens if something doesn't go right?

For me, I had to get to the moment of saying, it's okay. Even if I make a bad decision, even if this doesn't work out, I'm still going to be okay. I knew I had my career history and experience. There was always going to be that traditional industry to go back to if something went wrong. At that point I said, even if this doesn't work out, I'm going to be okay. And that's what helped me make the decision.

I will also say, I was fortunate that I didn't have mobility restrictions. I didn't have small children. I didn't have a lot of dependencies that a lot of women and men have, who can't take those risks. 

It sounds like timing was important. Having a track record of success in your career to fall back on. Did you contemplate any pivots earlier in your career? 

I've always been willing to make career moves, logistically from one city to another within the industry. That was something many people weren’t willing or able to do. I was always willing to say, if there's an opportunity for something new, exciting, something that I can learn from or advance in my career, I can move to a different city and I can work for a different company. I proved to myself that I could do that. 

Making such a big pivot from traditional companies to startups was about knowing myself well enough. Did I trust myself enough? Did I feel confident enough to leap into something that is truly unknown? You need to have a lot of confidence in yourself. And that's something that you gain over years of experience, and also by making some mistakes and realizing it’s not the end of the world. I've made mistakes in my career in traditional companies and you realize–this is going to sound crazy–you don’t die! You can always recover. You can always start over. You can always do something different.

I've made some great career moves and I’ve also made some that weren't so great. And I learned from both. I learned from the good and I learned from the bad. 

Your first big pivot was moving into the startup world. What was it like to change again, and leave your first startup for a different one?

I'm not afraid of startups anymore. It doesn't frighten me at all. So I'm now with a startup that's in an earlier stage. 

I pivoted to something that was closer to my heart. I’m working for a company in the insurance space that is focused on agents. I found that a lot of insurtechs hold the belief that agents and advice are not important–they think people will just go to the internet and buy. But insurance is a purchase that you make once or twice in your lifetime. People need help. So the agents really matter. There is always a need for agents to help people, to allay their fears, to protect their retirement, to protect the people that they love. I thought if I can help in that space–then I should.

I had been at the startup I was at for three years, which is about forever in the startup world. I decided it was time to make a different move. I kept my mind open–I was willing to go back into the traditional insurance space, I was willing to look at a startup, I was willing to look for an industry role. When I came across this startup, I said, wow, it's going to leverage exactly what I know. There was an equilateral triangle where all sides had the right measure. It was going to leverage my years of experience in the insurance business, what I had learned in the startup insurtech space, and it was going to be focused on an area that I think is extremely important, which is agents and advice. 

I also knew I would have the opportunity to learn and grow. That is super important to me. I don't want to go into a job that I can't learn or be challenged or grow from. I knew it really was going to challenge me to be not only a leader, but also a doer. 

When it comes to career, keeping an open mind is underrated in my opinion. Careers are becoming more fluid, like a river. Being open to flowing in a new direction is critical. Do you agree? How did that play out in your journey? 

I would say fixed paths are a trap. If you put in your mind you're going to do this, and this, and this, and this–you're always going to be disappointed in yourself. Also I’ve learned titles and all that come with them can be awesome, but it’s more about proving yourself to somebody else rather than proving to yourself who you are. 

Many of the pivots that I've made have been things that have really enabled me to grow and learn. And if you had talked to me 15 years ago and you had asked me if I thought I'd be at a startup in my late 50s? I would have said you’re crazy. I would have thought it would be too scary and too challenging. But it's funny. Steve Jobs had a quote about how you can only connect the dots looking backwards. And I think that's absolutely true. I look back on my career and I realize I'm where I'm supposed to be. But I never would have predicted this is where I would end up.

When you were in the traditional phase of your career, how did you measure success? How has the way you measure success changed at this point in your career? 

Earlier in my career, in the traditional space, success was about title and money and how many people you managed. There were some very tangible measurements in my head when it came to success. 

In the last 10 to 15 years, even when I was still at a couple of my last traditional roles, I learned that the work became less about the job and more about the people. I had that awakening during the financial crisis in 2008. I was managing a variable annuity shop in the New York metro area. When the financial crisis hit, that was one of the areas hit hardest. It was a watershed moment for me. I had to manage an office with customers terrified they were going to lose all their savings. I had employees who were struggling with impacts on their jobs and families. They were trying to manage themselves through a financial crisis that hit them closely. My work became all about, How do I help these people through the most difficult time of their lives? 

I laid off over 100 people within three years. It was a terribly difficult time. But trying to maintain people's dignity, trying to help them through the difficult adjustment became my work. That’s when mentoring became really important for me. I took a strong focus on mentoring both men and women, but especially women in the industry. I wanted to give them an opportunity to find their personal strengths and to define their own success–not to be measured by a job, but by what they felt was important. Women thought they had to be able to do it all. They had to be able to have a family, a career, to do all of that. It was difficult for them to understand they could make choices. And a choice to focus on family versus career or something else they wanted to achieve didn't mean they were failing. It meant they were making the best choice for them. 

The mission behind my writing is to show women that they can create their own narrative. It’s easy to cling to the narratives we see in culture–the hard-hitting businesswoman, or how to “have it all.” But if it’s not working for you and you’re not meeting the success metrics you have for your own life–what’s the point?

I had an amazing woman say this to me very early in my career. She said: “I coached a person who had been spending their time climbing the corporate ladder. 20 or 30 years into their career–they realized their ladder was leaning against the wrong wall.”

That's why I encourage people to be true to themselves. Whatever that success or happiness is for them–that is theirs and no one can judge that.

What a powerful image. On the topic of gender, you mentor a lot of women. How did being a woman impact your career trajectory, if at all?

It’s interesting. I grew up on a farm and I was one of six children. When you're on a farm, you work hard and you don't really know whether you're a boy or girl. You're just out in the fields, doing the work. There were no gender roles. We were all just hard workers expected to do a lot. So when I went into my life and my career, I didn't really think about gender–until it slapped me in the face. 

I worked really hard in my career. I thought, you know, I can work as hard as anybody else. But gender came in and hit me when I was negotiating for a new role at a company I had been at. I negotiated with my boss for relocation and I also negotiated adamantly for an increase in salary, because I knew it was going to be a really difficult job and there was a lot of risk. We worked out the details and I decided to make the move.

My boss’ boss called me into his office and told me that I had negotiated really aggressively as a woman. I kind of laughed at the time and made a good statement on my feet–I said “well I didn’t think I was negotiating as a woman, I thought I was negotiating as the most qualified candidate to take the role.” He backed down, but I thought to myself, when did I become “aggressive” because I was a woman? And how many times had that happened before in my career that I was completely oblivious to? 

I was always identified as the hardest worker. I've always been the person who would put in the most hours. I was always the person who would sacrifice for the company. And then suddenly, I became “the aggressive woman in the room.” 

Do you think being blind to gender helped in your career?

I think it was mostly a plus for me. Because I didn't see gender and I always believed that I could be a hard worker, I thought that gender wouldn’t limit me. My new boss told me recently, “You don’t brag about yourself when we’re on client calls. You have an impressive resume. You should leverage that when we’re having these conversations.” When I said I don’t like to do that, he said, “Men brag about their resumes. Women just assume you’re going to see them on LinkedIn or look at the resume. You have something to be proud of. You should talk about it more.” 

You know what, he’s right.

What's been the best part about your pivot from traditional corporate to startup?

I’m proud of myself for jumping. I'm proud of myself for never thinking it's too late to try something new. The greatest part of the change is to know that I could do it, and in doing it, maybe I blazed the trail for other people as well. 

What's been the hardest part of the pivot?

It's been very humbling. I have had to question and be challenged on the norms that I’ve accepted for years and possibly even decades. Some people get to this point in their career and they think, I'm an expert. You can’t tell me I’m wrong. It was really, really hard in the beginning to have people question the things I had spent decades perfecting or learning. You have to be willing to be humble. You have to be willing to question yourself. You have to be willing to be wrong. When you're young in your career, you think you're so smart. And then you realize over the years–you're really not that smart! It's all about being willing to be questioned, willing to learn, and possibly even be wrong. And in some ways I shortchanged myself because I'd never been in a space in my career before to do that. 

What advice do you have for women who are thinking about making a pivot in their career trajectory?

I always think about the Sarah Barreilles song, “Brave.” I encourage women to be brave. Don't be afraid. You have to be brave. You have to believe that you know what's best for you. Now, that is very difficult for people if they haven't figured out what they want. So if you're just stumbling around trying to find a career, it's a little harder to tell people to be brave. But even then, be brave and try different things, especially if you're early in your career. 

I think the generations that have come through this pandemic have been so influenced. During this pandemic, people have been willing to make some life shattering changes. The pandemic will be the thing that this decade is remembered for. It's allowing people to be a little bit braver now than they might have been 10 or 15 years ago. When you come out of something like the financial crisis, you’re terrified not to have a job. But today there’s so many jobs out there it’s bizarre. 

I also tell people to find people you trust. Allow them to help you along the way. But make your own decisions. Don't let other people make decisions for you. 

And at the end of the day, be brave.

Jackie, thank you for sharing your career pivot story! You can connect with Jackie on LinkedIn and watch for the exciting announcement when her company emerges from stealth mode in early 2022!