Women across the tech industry are leading change, shaping solutions, and redefining what’s possible. At Precisely, we’re proud to celebrate and support the women driving this transformation through our Precisely Women in Technology (PWIT) program. Each month, we spotlight a different member of PWIT, offering a glimpse into her journey, challenges, and impact. Continue reading to learn more about Lorraine Whetstone, VP, Revenue, and her experience in tech over the last 22 years.
Why did you choose to pursue a career in technology?
My career began in public accounting, where I had the opportunity to work across a variety of industries. Among them, technology quickly stood out as my favorite because its only constant is change, and it offers endless opportunities to grow beyond the boundaries of accounting. In technology, there’s never a standstill; it demands a mindset of continuous learning and adaptation. That challenge has kept me engaged and, even after 22 years, I’m just as excited as when I first started!
Who has been your greatest professional mentor? What’s one thing you have learned from them?
I’ve been fortunate to have several mentors throughout my career. I learned to “get comfortable being uncomfortable” from watching Jessica Soisson, CAO UKG, navigate her career, and from the many opportunities she presented me to stretch beyond what I thought I could accomplish. She always believed we could rise to the occasions presented.
Discomfort isn’t something to avoid—it’s a signal that growth is happening. Professionally, I apply this by stepping into roles or projects that stretch my skills, even when I feel uncertain. This insight was especially meaningful in my role as VP, Head of Commercials, where I helped refine and implement the post-go-private ELT strategy for a renewals-focused commercial operating model. Leading that transformation required training cross-functional leaders on customer negotiation strategies that balanced ARR growth with margin discipline, all while navigating shifting priorities and limited precedent. It demanded resilience and grit, but it was also exhilarating. Embracing discomfort has allowed me to lead with confidence, adapt quickly, and empower others to do the same.
What’s the biggest risk you took in your career? What was the reward?
The biggest risk I took in my career was stepping into a global leadership role where I also accepted a stretch assignment to spearhead the largest companywide transformation project: implementing the ASC 606 accounting standard, alongside a major systems overhaul. This transition came just as the company was in the early stages of shifting to a SaaS model, adding layers of complexity and uncertainty. It was a leap that made me feel both incredibly energized and deeply challenged—what I often describe as imposter syndrome and exhilaration in equal measure. But the reward was immense: I gained global perspective, built resilience, and proved to myself and others that I could lead through ambiguity and deliver impact at scale.
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As a woman, what challenges have you faced in the technology industry? How have you overcome them?
One of the most persistent challenges I’ve faced is navigating limited access to informal networks; those behind-the-scenes spaces where key decisions are often shaped and opportunities quietly surface. Early in my career, I noticed how these circles could influence visibility and advancement, yet they were rarely inclusive. Rather than let that discourage me, I focused on building my own network through mentorship, cross-functional collaboration, and by showing up consistently with curiosity and clarity.
What’s the best advice you’ve ever been given? How do you apply it to your personal and professional life?
“We won’t have a perfect set of information for most important decisions. Inaction and delaying for more or better data and analysis can cost more than piloting, failing fast, and course correcting.”
I apply this mindset by embracing decisive action with thoughtful risk. In my professional life, it means moving forward with well-informed but imperfect data, especially when leading initiatives or navigating ambiguity. I prioritize momentum over paralysis, knowing that iterative learning often yields better outcomes than waiting for certainty. Personally, it’s a reminder to trust my intuition, take calculated risks, and be open to adjusting course. Progress thrives in motion, not in hesitation.
What’s one piece of advice you’d offer to younger women entering the industry?
Here’s one piece of advice I’d offer to younger women entering the industry: It’s okay to be vulnerable.
- Embrace Vulnerability as a Strength: It’s okay to not have all the answers. Admitting mistakes and being open about what you’re learning builds trust and shows emotional intelligence. Vulnerability isn’t weakness—it’s a gateway to authentic leadership.
- Create Safe Spaces for Collaboration: Foster environments where teammates feel heard, respected, and safe to share ideas or concerns. Psychological safety is the foundation of high-performing teams.
- Own Your Growth Journey: Every misstep is a lesson. Share what you’ve learned because it not only helps others but reinforces your own growth mindset.
- Seek Out Mentors and Allies: Find people who uplift and challenge you. Don’t be afraid to ask questions or request feedback. Tech is a team sport.
- Lead with Empathy and Confidence: Whether you’re coding, managing, or strategizing, lead with empathy. It’s a superpower that drives innovation and inclusion.
As a successful woman in technology, what’s one thing you do to pay it forward and advocate for other women in the field?
As a leader, I believe in investing in the next generation of women in tech through everyday actions that foster growth and confidence. I regularly mentor early-career women by offering guidance during projects, sharing career insights, and helping them navigate challenges. I make space for their voices in meetings, ensuring their ideas are heard and credited. I also share resources that have helped me grow and take time to explain complex topics in approachable ways. Whether it’s advocating for their visibility, modeling healthy work-life balance, or simply being a sounding board, I strive to create an environment where they feel supported, empowered, and seen.
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