Celebrating Women’s History Month at Insight

The month of March is dedicated to celebrating, commemorating, and paying tribute to women’s essential role in American History. In observance of Women’s History Month, we spoke to some of our outstanding female colleagues about their experiences at Insight, their career advice, and valuable mentorship moments they’ve experienced.

What do you do at Insight?

Nikki Parker: I am the Executive Vice President of Marketing Strategy and Communications at Insight Partners. I’m responsible for articulating and amplifying the firm’s leadership position in the industry and the value it brings to our portfolio of software and technology companies.

Hilary Headlee: I am an Advisory Leader on Insight’s Growth Team. Part of my role is to lead an amazing team of Onsite Advisors across multiple Centers of Excellence — Sales, Customer Success, Channels, Marketing, Product and Technology, Pricing — where we support our portfolio companies on the $10M to $100M+ journey. The other part of my role is to do the actual advising for our portfolio companies, with a focus on sales, rev ops, and enablement. 

 TLDR: I work with super smart people who help other super smart people build and grow their companies efficiently and effectively.

Jessica Green: I am a Business Partner on our Human Capital Team. At the highest level, I ensure that we strategically think about and support Insight’s employees to the best of our ability every day. More specifically, I serve as a trusted partner to our Growth Platform and Engineering teams by driving initiatives across our employee life cycle, including performance reviews, promotion cycles, compensation reviews, and day-to-day, people-related projects.

Additionally, I support our teams with matters related to employee relations, learning and development, and onboarding and offboarding. Outside of my day-to-day job responsibilities, I co-head Insight’s Black ERG, Black@Insight.

Minna Fingerhood: I am a member of the investment team, so my time is split between sourcing, engaging with prospective companies, and supporting our existing founders and management teams. I focus largely on supply chain, logistics, and industrial software. I also work on our 20/20 Vision Capital Fund (a fund-of-funds vehicle backing emerging managers from under-represented backgrounds).

What is one thing you wish you had known when you began your career?

Nikki Parker: I’d tell my younger self — and any professional — that it’s less about the “right” job and more about the right mindset. It’s about embracing every opportunity to add value, relentless pursuit of knowledge, and nurturing the skills that make you indispensable — no matter the industry or the role.

When I started my career, with a degree in political economics in hand, the path ahead was anything but clear. Early on, I was intrigued by technology but felt sidelined without a technical background. The industry seemed impenetrable. Yet, I found my niche in a role as ambiguous as “innovation,” which, at the time, was still taking shape in the business world. There, among engineers and product developers, my talents in storytelling, business strategy, and stakeholder management found a home. These skills became central to driving projects forward.

This path wasn’t laid out for me; I carved it by leaning into my strengths and always seeking ways to enhance the endeavors I was involved in. Looking back, this strategy honed my business instincts and helped me build a career more fulfilling than I could have envisioned.

I want to impart this message to the next generation of women leaders: Your unique value is your superpower. Cultivate it, and the roles will follow.

Nikki Parker recently hosted our annual “Real Talk from the Top” webinar for our software community this year. Read insights from the conversation and watch the recording.

Hilary Headlee: My career began almost 25 years ago in the Midwest, so the easy answer is “almost everything,” but I wish I had more deeply understood the importance of people in my career. 

I started in the workforce before LinkedIn was invented, and phrases like “Your network is your net worth” were used; before aligning your values to a leadership team was discussed; and before common-place advice like “Work hard, keep your head down, don’t make any waves, and maybe you can get promoted” became outdated. 

I misunderstood that people will not remember you for your work, but how you worked with them. I underestimated how important finding people who thought differently from me was to have, to ensure I wasn’t thinking or building in a vacuum. And I undervalued the impact I can have on other people.  

I didn’t know that customers I supported would help me when I needed a critical work reference, that vendors I worked with would ask me to speak at their conference and change the course of my career, or that I’d get to work with former colleagues again and again over the years.  

I simply didn’t know in 2000 that all of the people you meet along the way actually are your career; they are the ones helping you, guiding you, and cheering you on to be the best you that you can be.

Jessica Green: Before joining the workforce, I approached potential jobs and career paths by exploring different roles and considering how my skills and abilities applied to the outlined responsibilities of the job. As I have advanced in my career, I have uncovered what I believe to be a more effective approach that is more likely to lead to success and happiness.

Think about what you enjoy doing and what gives you energy; don’t be afraid to admit what you are good at (and, more importantly, what you may not be good at), and try to find a job that is a good fit for you versus finding a job where you are the best fit. You are more likely to excel when you are doing something that you enjoy and are passionate about!

Another big learning came from the way my life was structured before entering the workforce versus after. Many of our paths for the first two decades of our lives were linear, well-defined, and prescriptive. Our careers are unlikely to follow the same trajectory. Lean into the messiness and learning that can come from the beginning of your career — there is no “right” way to go about your career, as long as it works for you.

Minna Fingerhood: Before joining the workforce, I underestimated the power and importance of emotional intelligence. In school, we were never really graded on how well we collaborated with our peers or how dependable we were in a group project.

In an industry like venture capital and private equity, partnering with a company means spending many years of your life with those colleagues — liking the people you work with and earning their trust is immensely important. I feel grateful to be in an industry where our value as partners isn’t just about the hard skills but also considers and appreciates the dimensions of our character.

Talk about a significant mentorship moment or influence in your life

Nikki Parker: At Insight, mentorship is inherent to such a fast-paced and dynamic environment. I have the privilege of working alongside many of our most seasoned managing directors; each interaction, even the briefest one, is a chance to learn. They might not realize it, but their insights are like informal mentoring sessions for me. Every piece of advice or strategic thinking they share adds to my skill set. I’m always asking questions or considering where I can add value for them. I’m thankful for the time they invest in responding, which contributes significantly to my professional development.

In turn, I aim to offer similar access to anyone who asks. Mentorship, I’ve learned, isn’t always about structured programs or formal relationships. It’s about being open to giving and receiving knowledge, being humble enough to acknowledge that everyone you meet has something to teach you, and being generous enough to share your time and insights with others.

Hilary Headlee: I have had a million mentorship moments in my life, as I feel they happen when someone listens deeply, cares about you, and asks great questions that make you think differently and gain perspective. Mentorship is sometimes about giving advice from experience, but certainly not the only way. And I love that someone’s age, life stage, role, or experience doesn’t matter for them to be a mentor. Mentors are everywhere for us when we view it that way, and I love that so many of the people I have worked with over the years — across departments, levels, companies, and the globe — have played a role in helping me improve.

The most significant mentorship moment for me, though, was 20 years ago. I was complaining to my mom that my male colleagues at work were making more money than me for the same job. She listened to me, asked thoughtful questions, and could see I was stuck. She then said very matter of factly: “You need to ask for it, Hilary. If they say no, then you know.” That advice is so simple, but it did what needed to happen — it got me unstuck (and the raise for equal pay). I’ve used this again and again over the years — for myself to ask for change — and for others to hopefully be as helpful as my mom was to me.

Jessica Green: As a woman of color in a predominately white industry, several people have forged the path that I have been able to follow. I would not be where I am today without the sacrifice, mentorship, and sponsorship of those who came before me.

I have always been a big believer in intentionally acknowledging the distinct role of a mentor versus a sponsor. A mentor is someone you can go to for advice and guidance — someone who can use their past learnings and experiences to help guide you to make decisions in your own life. A sponsor, on the other hand, is someone who has the leverage and authority to influence others on your behalf. I have been fortunate throughout my career to encounter mentors and sponsors who have truly helped shape me into the professional that I am today.

I want to call out one incredible woman who has influenced the trajectory of my career at multiple inflection points. Edith Cooper has been an incredible sponsor for me since before I began my career. She has always seen my potential, encouraged me to reach for the “impossible” (or at least, what I thought was the impossible), used her voice and influence to amplify mine, and has continued to lift me up throughout my career. I am forever grateful to Edith for her belief in me, and I hope to “pay it forward” and impact someone’s career in the same way that Edith has influenced mine.

Minna Fingerhood: I have been fortunate enough to have several different mentors throughout my career, all coming from different corners of my life. A common quality among them, however, is the ability to express the various and different sides of their identity while remaining authentic to themselves.

As a woman in the corporate world, there is often pressure to fit into a particular mold, which probably and most closely resembles the archetype of a “girl boss.” In truth, there are infinite versions of a successful woman, and the best versions showcase the depth of our personalities. It’s possible to be respected and outspoken while also being empathetic and kind; it’s possible to love enterprise SaaS and LBOs while loving Rihanna.