Disruptors. They are the few and the fierce. In our series, Leading between the Lines, I have the opportunity, and the pleasure, of meeting with some of South Florida’s most dynamic female business leaders, ones who are disrupting their industry, approaching things in a new way, solving new problems, and effectively pushing the status quo into a new frontier. I want to learn about their journey, what it really takes, what they’re actually up against, and how it feels each step along the way. Meet Casita Simpson, Owner & CEO of Simpson & Associates, a firm dedicated to streamlining operations from hopeful prospect to satisfied client, including CRM, sales process, client onboarding process, fulfillment, and more.

Casita holds several degrees, including a bachelor's degree in English from FIU, but her roots have long been in corporate law, including a tenure in Crystal Cruises' legal department, where she spearheaded digital transitions for Virgin Voyages and Crystal Cruises, developing their legal database. 

Today, as an entrepreneur, Casita has dedicated the last four years to helping firm founders and boutique firm owners navigate legal operations complexities to optimize and scale their firms. Her passion for helping others extends beyond business. Casita champions a number of local charities within our community, and is particularly dedicated to combating food insecurity within South Florida.

Read my full interview with Casita to learn about her leap from corporate into entrepreneurship, the importance of trusting in your skills and strengths, and the importance of holding onto YOU in order to achieve success.

‍Nicole: Tell us a little bit about you and the services you provide through Simpson & Associates. What is the problem you’re solving for your clients?

Casita: I have worked in big law for nearly two decades, and I have experienced firsthand how efficiently a corporation can run when processes are streamlined, tools are leveraged, and team is optimized. Small and emerging midsize businesses struggle to achieve this due to limited time and resources. For many firm founders and boutique firm owners, common challenges include struggling to get organized, struggling to manage a team effectively due to established but not enforced processes, and wasting too much time on manual processes and repeatable administrative tasks instead of leveraging automation and focusing on revenue generating tasks.

I have nearly two decades of industry experience, and as a paralegal, I have worked closely with attorneys to resolve these issues in-house. In my firm, we provide a “done for you” service that helps firms achieve the efficiency and optimization necessary to scale their business.

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Nicole: What is the biggest mistake clients make when engaging in this type of service? What is the biggest misconception about optimizing systems and processes? 

Casita: The absolute biggest mistake I see is business owners who purchase a CRM based on the suggestion of a colleague who doesn't understand the specific challenges of the business at hand. Many neglect the critical step of shopping around for the right CRM and demoing the software to ensure it has what they need. Or worse, they delegate the task of finding a CRM to someone within their firm who doesn't quite understand the nuances of the challenges and problems the software should be resolving.

A big misconception is thinking a CRM may not be necessary or effective for the practice. Others think setting up a new CRM is a hassle, or worry that a CRM cannot safeguard or protect their data, or understand the nature of billable hours.  

I wish more people knew how powerful tools like this can be for your business- they can become your best employees! A game changer! And implementing it can be so easy when you hire Simpson & Associates. From recommending the right software solutions for your needs and budget, to getting firms up and running quickly, we are pros at seamless implementation so owners and their teams can focus on the business, instead of a complex project.

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Nicole: What motivated you to start this business? What led to the entrepreneurship decision? What was going through your mind on that day?

‍Casita: Four years ago, I took a leap of faith and decided to bet on myself. I remember the day perfectly. COVID-19 was very prevalent and I had just been furloughed. I interviewed for a paralegal position, and at the end of the interview, I asked if the position was hybrid, and the response was no. That was a struggle for me because I was terrified of getting COVID-19. I was offered the position, but after weighing the pros and cons, I turned it down.  I realized I had built an excellent reputation for my operations and optimization skills and had the confidence that I could build my career with those skills, on my terms.  I turned down the job and immediately opened Simpson & Associates.

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‍Nicole: What has been your proudest achievement in your career so far? Why?

Casita: I would have to say that successfully building and growing my business has been my proudest achievement because, despite the setbacks, I have been able to navigate this path and build a business asset doing what I love. I am truly blessed.

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Nicole: Let’s talk about some of those setbacks. What have been some of your challenges along the way? What have you learned from them? What have you most improved on and how? 

Casita: Team building has been one of the biggest challenges for me. In the beginning, I hired people that didn’t fit the company culture or vision I have for the business. I spent too long trying to make it work instead of terminating those people at the first sign of the misalignment. I hired a staffing company to support me through this process. I’ve learned to hire slow and fire fast, and prioritize experience over personality. I’ve also learned that no one will love my business the way I do- and that’s ok.

Sales has also presented a learning curve for me. In my corporate life, sales was not much of a focus for my roles, but as a business owner, it’s a vital function.  In the beginning, I relied too much on one client as a main source of revenue, making my business dangerously dependent. I would find myself letting others dictate my value, and would discount my fees or avoid negotiation to try to close a prospect.

I’ve learned that networking is crucial and constant, regardless of my current client volume. I have joined networking groups based on my goal of connecting with other professionals who can make quality introductions or referrals for my work, and vice versa. I commit to a minimum number of sales calls each week, and I hold myself to it. When a client is happy with the work we’ve done, I make a habit of asking them for a referral. I’ve found that quality referrals will value the work I do and the prices I charge.

Overall, entrepreneurship has really challenged me to prioritize time management so I don’t get burnt out. I take small moments for self-care throughout the day, I modify my calendar to ensure I have a schedule that prioritizes my family, and I hire support to help with the workload so I’m not depleting myself physically, mentally, and emotionally. It’s been an evolving process for me, but I am trying to adapt and make sure I am operating sustainably. 

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Nicole: These are such common challenges for new entrepreneurs and you’ve made some major strides in overcoming them- pretty quickly too! What has surprised you most as you’ve navigated these challenges in particular?

‍Casita: My resilience. I’ve wanted to quit so many times. I had no clue about the struggles I would experience through entrepreneurship. I had no idea how these challenges would rock my self-confidence. But overcoming these challenges has been incredibly empowering. It’s proven to me what I’m capable of, and made me less intimidated when new challenges present themselves. It’s like I’ve built an invisible armor that empowers me to keep going. 

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Nicole: What influences and inspires you?

‍Casita: This may sound cheesy, but I am inspired by my clients and the degree to which my contributions impact not only the law firm but, more importantly, the firm’s clients.  People hire me for two reasons: they are either completely overwhelmed by all the fires they are putting out daily due to a lack of efficient systems and processes, or they want to grow and need someone to implement the necessary infrastructure to make that possible. Regardless of why they come to me, they place a tremendous amount of trust in us to help them achieve their goal. I strive to exceed expectations every time- that’s my standard. I am inspired by the twinkle in my client’s eyes when they realize they can finally focus their time on important work and goals or spend more time with their families. In many ways, the work I do completely changes lifestyles for firm owners and that is incredibly rewarding for me. One day, I hope to become a global brand that can help attorneys across the world so I can give that twinkle to more people.

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Nicole: What advice would you give other professionals who are thinking about stepping away from corporate to embark on a similar entrepreneurial journey?

Casita: Find your niche, your zone of genius, the thing that comes the most natural to you, the thing you love doing the most- and share it with the world! The world needs it. It needs you. And on those bleakest of days, hold on to you. Nurture you! That’s what will keep you going.