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Meet Lindsey Head: Trailblazing CFO and Entrepreneur

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I recently spoke with Lindsey Head, the founder of Head Consulting, a fractional CFO and business consulting firm. Lyndsey is a sought-after public speaker and award-winning CFO. Amongst other accolades, she has been a CFO of the Year Award Winner, Connected Women of Influence Award Winner, and nominated for the CWLA Women to Watch. Highlights of our conversation are below.

Tell us a little about your life before the start of your professional life. Where did you grow up, and what was your first job?

I grew up in Truckee, CA with hard-working parents—an incredible special education teacher mother and a director of public works father. Their dedication to providing the best for my sister and me instilled gratitude and a sense of accountability within me. I was heavily involved in sports, participating in activities like soccer, basketball, wakeboarding, and more. These experiences taught me the value of teamwork, dedication, and a strong work ethic. My first jobs included being a summer camp counselor, babysitter, and lifeguard at a private country club community.

While in college, I initially pursued a computer programming career but discovered that my passion for understanding the bigger picture, coupled with my engineering and creative mindset, led me to business and technology. This realization ignited my passion for finance, and after completing my degree in Operations Management & Information Systems at Santa Clara University, I embarked on a life-changing solo backpacking trip around Europe, Morocco, and the Greek Islands, visiting 13 countries in total.

Why did you choose finance as a career?

Finance became my career path through the guidance of my mentor, Gina Kloes, an attorney and entrepreneur. As I embarked on my professional journey, I discovered my natural talent for managing financial operations and understanding the interconnectedness of various business components. Colleagues referred to me as the "business architect" due to my inclination for designing systems, implementing automation, and developing financial models to streamline operations. This realization fueled my commitment to finance, driving me to continuously optimize business performance.

What do you like most about being a CFO?

As a CFO, I find great satisfaction in taking a broad perspective when managing a business. It's a crucial executive role where I execute the CEO's vision, ensure seamless implementation of growth plans, and manage key financial metrics to enhance company value. I enjoy designing operational and financial infrastructure, often assisting CEOs in turning their visions into reality. Being that key person for companies and contributing to their success brings me immense fulfillment.

You are currently self-employed as a consulting CFO. What type of clients do you work with, and roles do you fill?

As a fractional CFO at Head Consulting, Inc., I work independently with a diverse range of clients, including CEOs, executive teams, and business founders. My role is to strategically guide them in decision-making, driving productivity, financial clarity, and bottom-line results. I thrive on the variety and challenges that come with each business I work with. I act as their biggest cheerleader, providing them with a roadmap to achieve their business goals. Whether it's rapid growth or future sales, I ensure their internal financial and operational functions are optimized. This involves overseeing financial and operational activities, guiding accounting teams, and producing accurate and timely financial reports for executive management. Additionally, I offer high-level analysis and consulting to increase efficiency, reduce costs, implement systems, and enhance customer responsiveness.

What do you see as the biggest challenge in your role as CFO?

A major challenge as a fractional CFO is resisting the temptation to assume a full-time position with clients. While I envision accomplishing much more, my role as a consultant necessitates suggesting new systems, infrastructure, and the hiring of key team members to effectively support critical tasks and align with the business's needs.

How has the role of the CFO changed during your career? Do you have any predictions on where it is headed?

The CFO role has undergone significant changes throughout my career, with an increasing emphasis on innovation and technology leadership. Understanding all divisions within a company has become essential for modern CFOs, as each division impacts finance in some way. Looking ahead, I predict that future CFOs will need to be even more tech-savvy and innovative in guiding a company's finances and operations.

What are the most important yet not obvious metrics to track, financial or otherwise?

When it comes to tracking important but less obvious metrics, in my work with service-based organizations, I prioritize evaluating staff utilization as a percentage of revenue. This is a critical item on the profit and loss statement (P&L) and requires consistent monitoring and management. I often challenge the HR team to explore alternative approaches to staffing, asking if we can work more efficiently rather than immediately hiring. Understanding the lifetime value of clients and the cost of acquiring new clients is also vital for driving company growth. Additionally, I focus on monitoring staff utilization, profitability, EBITDA, and overall trends. Implementing models with triggers to notify early on any deviations is crucial for taking preemptive measures and ensuring positive outcomes.

Share something about yourself that might surprise people.

I am a wife and mother to four boys under the age of six. In addition to my role as a CFO, I run a hair product company called Curls Poppin' and a doll company called Curls Poppin' Dolls.

I am glad you mentioned having four sons. I admire the way you and your husband balance your professional responsibilities with your role as parents. I would love to discuss your experiences and insights as a parent to four boys. Your ability to navigate the demands of both work and family life is truly inspiring.

Ever since having our first son, I knew I needed to step into my new role as both a mother and executive as I truly believed that I could continue to be both. I have a very optimistic perspective on life and I'm lucky that my husband is as equally motivated and optimistic as me (or more).

When we met, we knew we wanted a large family, and we began the journey as a unified couple planning for the long-term future. We knew there would be challenges and we knew it would take grit to make it through one of the busiest times of our lives. In growing our family, it may appear that it was simple, but we also experienced the heartbreak of having several miscarriages. We grew closer and stronger through it and found our own way to navigate the journey.

Early on, we started a parenting group called Boss Parents, with the intent to have fun while connecting working/entrepreneurial parents with each other to help navigate the journey of parenthood while growing businesses and babies.

As two full-time working executives, our life with a growing family is challenging and we know we need to be impeccable with our time and our schedules to balance it all.

We learned to share a family email address for the important items relating to our kids' care, school, etc. This also resulted in sharing a family calendar. I know this sounds small, but there are many friends we talk to who are amazed that such a small thing would make such a big difference. In doing this, it created equal accountability for us and allowed us to parent together as true partners. Of course, we have our days when things fall apart (as things do), but we must support each other in getting back on track. We are creating our journey one day at a time, prioritizing our children while equally maintaining our careers so we can provide the life we want for them.

Communication is also highly important. We are always talking about what’s next and how best to manage whatever might come our way. We have also committed to being together to have dinner and put our boys to sleep every night (unless one of us is traveling), so they know we are present and always there for them. We try to have a no phone policy when we are all together as well, so the kids never feel like they come second to our phones, work, emails, etc.

Ultimately, when it comes to having it all, we both must show up 100% as often as possible in every area of our lives to create a balance.

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