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Caryn Kent Dean

Caryn Kent Dean

Introduce yourself to our audience. Tell us who you are and what you are currently focused on.

I'm Caryn Kent Dean, CEO, Founder & Managing Member of Once Upon an RFP.

I live outside of Chicago with my husband, 3 kids and Scout the rescue dog. I've been an entrepreneur for 3 years because, after 10 years raising my kids full-time, I re-entered the corporate world and couldn't find the right combination of balance, challenge and creativity.

I founded Once Upon an RFP in 2018 as a boutique proposal consultancy specializing in Request for Proposal (RFP) based proposals. I've realized that this is just one piece of the Government contracting puzzle and that there is a lot of inequity in the services available to supporting government contractors that aren't large corporations. I'm working on building sustainable solutions for small businesses that work with government.

Tell us about your favorite Ellevate Network memory or success story. Why are you a member?

I joined Ellevate based upon a recommendation. A business connection, accountability partner and now good friend told me about it when I was feeling unsupported by another program.

I've been a member for a few months but just started participating in a Squad. We've met 3 times and the energy of the group, the way we show up for one another, is absolutely amazing. I'm so glad I took the leap.

How would you define your professional mission?

My mission is to identify and create opportunities for businesses and individuals where they didn't exist in the world of RFPs, whether government or large corporate.

What qualities does it take for someone to be successful in your line of work?

There are a number of different roles in this work, but at the Proposal Manager, Writer and Capture Manager levels, you need to observe and listen, read, evaluate and analyze, collaborate and lead others, manage and mitigate risk, and work well under the pressure of deadlines.

What is one of your most memorable career accomplishments?

Founding my own business and discovering how fun it is to connect with others. I've always been shy and I thought that I'd be happiest in a corporate job, However, I've learned that corporate roles were too defined and limiting for me and entrepreneurship has helped me open up in so many ways.

What are some career challenges on your radar?

Scaling my business is currently my biggest challenge.

What project have you worked on that you’re most proud of? Why?

Entry-level proposal roles require 1 year of experience. However, you can't get the experience if you can't get the job.

We're developing a program called "RFP Bootcamp" to get people the knowledge, skills and experience they need to get the job.

We’d love to hear more about your career path. What led you to where you are today?

No one grows up to be a Proposal Writer -- at least not yet. After I graduated from college, I worked part-time in a library while helping my parents move. When that was wrapping up, I applied for a research position in a law firm. I’d worked in libraries and was comfortable with the idea of that work.

While there, I applied for a local Master of Library and Information Science program. I worked full-time and studied full-time, paying my way and completing my degree in just two years.

While working on my Masters, I met the founder of a software company in the library marketplace. They needed a Proposal Writer with library expertise, and I got the job. I had no idea what I was getting into.

That was more than 20 years ago now. That company taught me many hard-won lessons. I met so many amazing people. It set me on a path that I never imagined for myself.

I learned that I was good at writing business proposals. I was also good at process improvement and implementing programs.

And I met the love of my life there. We married in 2002, spent a few years working and going on amazing adventures, and brought three beautiful children into the world. I had the great honor of being their full-time caregiver for ten years.

Being a parent is hard. We had our first child in 2005, the second in 2007 and the third in 2009. Three children, four and under, are a handful! Once our youngest came along, our family felt complete.

The kids grew up. One by one started school and activities. In 2014, our youngest was ready for Kindergarten. We’d just moved to a dream home. It made sense for me to return to work. I looked at job ads and wondered what I would do.

A former colleague, who I’d helped develop in her career in business proposals, reached out to me one day. She asked if I knew anyone who might be looking for a Proposal Writer position. I responded that I might be.

She was surprised, but I applied. The interview process went well. She supported me throughout. I think the recruiter was very skeptical about my technology skills. After all, it had been ten years! How could he possibly think I’d know how to use modern office technology. It was pretty amusing.

Their interview process took several months. The week before they made a job offer, a recruiter from another company reached out to me. I had three phone screens and one in-person interview with the team within a week. They sent me a job offer right away.

In the end, I had two job offers and chose the opportunity that felt best. I was elated and chose to work with my former colleague. I joined the company at a lower level than my last professional position. I felt it was exactly right for balancing work and family.

I was a quick learner and had a positive impact on the team quickly. I had to get used to instant messaging and Skype meetings. After a while, I realized that the position and company were not the right fit for me.

Looking back, there were a few catalysts. My career ambition and passion for learning kicked back into gear. I didn’t feel like I fit with the team or organization. And I was beginning to struggle with balance.

Not two years into that position, I saw that the other company that had offered me a position was looking for Proposal Managers. I refreshed my resume and sent it off to the recruiter I had worked with previously.

The process went quickly again. I interviewed them as carefully as they interviewed me. The following month I was in the new role. It seemed like the perfect fit!

There was a very steep learning curve, but I was up for the challenge. Everything was going my way. I learned their complex processes and policies quickly. And I was able to work from home three days a week once fully trained.

I was polite. Worked hard. Stepped up for special projects. Got to know the team. And felt I was making a difference.

But I was drowning. I was influential in my work and assigned a heavy workload. I tried to push back but frequently wasn’t successful.

I was stressed and frequently wearing too many hats at once. I remember one summer day when I was working from home. The nanny texted me a question and was having trouble with the kids fighting, my husband walked into the office to ask a question, and my boss was trying to call – all in the space of a couple of minutes!

At one point, I ended up very sick and in immediate care on intravenous antibiotics. I had a deadline, though, so I pushed through once home and got the work done.

A senior colleague left the team shortly after that, and suddenly I was being assigned the highest-profile deals that required executive approvals. The pressure was even more intense.

Just a year into the position, I realized that the team approach to proposals that I had been led to expect based on my careful questioning during interviews just wasn’t there. I was giving up vacations and holiday time due to work assignments.

I was also the only woman on that team based in that office with young children at home. And my boss would frequently tell me, “You are not a housewife.”

It was just before Christmas that I hit my limit. My dad would be going into surgery in January. He had experienced severe complications after previous surgeries, and I was worried. I felt I needed to be in the hospital with him and might even need to take a week or two off.

My boss told me I would not be allowed to take time off because “You are not a housewife.”

I was offended, angry and done. Over the holidays, I told my husband I would need to leave corporate. He was amazing and supportive. I was terrified and hopeful all at once.

I muddled through the next six months, and my last day as an employee was June 1, 2018.

And during that time, I came to the realization that I am unemployable. I founded my business on August 24, 2018.

What is the most rewarding part of your job?

Helping others. Whether taking care of those frustrating RFPs or creating training that leads to a new job, I really love to help others.

What legacy do you hope to leave through your work?

That work can be fun and make a difference.

What is it about your job that makes you feel it’s the right fit for you?

I'm not boxed in by a job description. I have the freedom to explore my creativity and deliver client projects.

Who are your role models?

My parents - who worked hard and were entrepreneurs at various points in their careers.

My husband, who has supported me 100% - including in leaving a stable job with a good salary.

What is your morning ritual?

I'm still working my way into a good morning ritual and the right balance of caring for others and myself. However, I'm usually at my desk between 8 and 9 am.

What is your favorite social media site? Why?

I love LinkedIn. I'm really passionate about my work and love to learn about what others do and connect.

What would you say your personal superpower is?

Empathy and strategy are my superpowers.

What does success look like to you?

Creating opportunities for as many others as possible, while also earning a great income.

Is work-life balance a problem for you? What is one no-fail tactic you use to create balance?

Yes, especially since I work with deadlines. Leveraging team members - whether employees or contractors - has had a positive impact balance for me.

What advice would you offer future leading ladies wishing to break into your industry?

Please connect with me so we can grow together.

What is the best career advice you ever received?

My dad always says, "If it is to be it is up to me."

I've realized that it means we get to be the CEO of our careers because no one else is responsible for our professional fulfillment and financial stability.

What is one piece of advice you’d offer working moms?

Network and meet other working moms. Being a mom and being an entrepreneur can both be lonely jobs. Meet others who know what it's like to do both so that you can support one another.


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