In an era defined by rapid technological upheaval and a widening global skills gap, the communications industry faces a critical dilemma: how to harness the power of AI and automation without sacrificing the human connection that is its very foundation. Many leaders see technology as a force of displacement, but Jeanette Winters, the Chief Human Resources Officer at 8×8, Inc., sees it as a tool for liberation and growth. Her unique approach confronts this industry-wide challenge head-on by operating on a powerful, human-centric principle: training & knowledge eliminates fear.
While others focus on managing change, she focuses on building the conditions that allow people to adapt and lead through it – championing lifelong learning as career insurance, using automation to free time for higher-value work, and reinforcing a culture grounded in collaboration, accountability, and customer centricity. Her credibility is validated not only by recent organizational awards for 8×8 but also by a career-long dedication to inclusive excellence, exemplified by honors such as the Intel Diversity Champion Award. This is the story of a leader who is redefining the future of work by ensuring that, as the industry transforms, its people are not left behind but are empowered to lead the charge.
The Foundational Truth of Success is a Collective Journey
From the start of her career, Jeanette embraced a guiding principle that when the team succeeds, everyone succeeds, which shaped her leadership philosophy and drew her to work that elevates performance through training, coaching, or conflict resolution, making the process of helping individuals, teams, and entire organizations become more productive both fascinating and deeply rewarding.
The core of her motivation was a desire to help others be and do better. Yet, in a deeply human twist, she discovered a secret: supporting others was equally enriching for her. She learned from them, shared in their accomplishments, and vicariously experienced their joy. This reciprocal exchange cemented her conviction that we all deserve the opportunity to do great things. These early experiences were not just tasks; they were the turning points that forged a leader dedicated to collective success and the belief that true leadership is about enabling others.
A Mission Aligned Where Heart Meets Innovation
Jeanette’s journey to 8×8 began with a practical, people-first purpose guiding the HR function through a leadership transition and then evolved into a deeper realization of a strong alignment between the company’s mission and her own vision for work.
- The Human Foundation: From her very first day, she was struck by the authentic culture, where people genuinely care for one another, readily offer help, and truly have each other’s backs, establishing a foundational spirit that builds an organization designed to serve colleagues effectively.
This intrinsic culture of support aligned with her values, and the synergy deepened as 8×8’s core mission in the CPaaS space emerged. The focus on making customers heroes through communication resonated with her core belief in the power of human connection.
- The Strategic Synergy: For Jeanette, technology, especially automation and AI, is the ultimate enabler of connection, designed to make vital interactions faster and easier, and she takes pride in seeing tangible results as customer service improves through 8×8’s platform.
She highlights that 8×8 is evolving culturally and strategically, driven by three key pillars:
- Embrace the need for speed.
- Solve problems permanently.
- Become change agents.
The collective excitement around using technology to empower people is, for her, awe-inspiring, and it serves as the perfect engine for her personal vision for workplace transformation.
The Antidote to Fear and How Learning Fuels the Future
Working through the fast-evolving tech environment has taught Jeanette a crucial lesson: training eliminates fear, since the unknown is always far scarier than the known, a reality especially evident in the widespread conversations around AI.
While headlines warn that “AI will eliminate jobs,” Jeanette views a broader perspective: history shows that each new wave of technology may phase out certain roles but also creates new and different opportunities, all unfolding alongside a significant demographic shift.
- A Dual Challenge: She points to the ~11,000 Baby Boomers reaching retirement age daily, leading to over 4.1 million potential retirements per year and a profound skills/talent shortage. In this context, AI can be one of the answers to transforming the workforce and finding new ways of serving.
The leader’s role, therefore, is to directly address fears by championing technology’s benefits. Her philosophy is simple yet powerful:
- Lifelong Learning as Insurance: The belief that if you learn something new every day, you are more competitive. She frames knowledge as career “insurance”, making driving lifelong learning a critical objective.
At 8×8, investing in AI training has delivered tangible wins for individuals, teams, and the entire company, as making continuous learning central to the strategy transforms anxiety about the future into agency, empowering people to shape their own next chapter.
A Human-First Strategy for a Global Team
Within the dynamic world of communications, Jeanette Winters focuses her leadership on solving universal challenges amplified by 8×8’s global scale. She has identified three primary issues requiring collective attention: Cross-functional collaboration, customer centricity, and Personal accountability.
While these are common goals, their execution becomes uniquely critical for a company serving 55,000+ customers with teams in 22 countries.
Her approach differentiates itself through a rigorous, integrated discipline:
- Deep Strategic Alignment: At 8×8, they have meticulously aligned corporate strategy, annual and quarterly objectives, with team and individual deliverables. This is embedded in team meetings, 1:1s, and initiative sessions, where they constantly ask how their work demonstrates these three characteristics.
- Investing in Leadership & Mindset: The strategy involves building the best-functioning senior leadership team, training managers and leaders to serve, and reinforcing that none of us succeed without all of us in the mix.
Most distinctly, her team’s internal operating model redefines the people function:
- Automation to Enable Humanity: The People & Workplaces team has crafted a strategy centered on automating their mantra, “Automate everything,” to free up human energy for the issues that people are best suited to address.
This has proven amazingly productive, transforming the people function into architects of a collaborative, accountable, and customer-focused culture.
Intelligent People Operations with Data, Discipline, and AI
At 8×8, Jeanette Winters and her team have developed frameworks and internal practices that surpass conventional HR, establishing a new benchmark for strategic people operations through a disciplined, three-part methodology.
First, they’ve made a strong, intentional commitment to data acquisition and data utilization, viewing industry benchmarks as a helpful starting point, not a finish line. By learning from what others have already done well, they can strategically incrementalize progress in ways that are tightly aligned with what 8×8 truly needs. For the team, data opens the door to real insights, and this data-led philosophy is grounded in action: each year, they concentrate on just 2–3 areas for improvement to keep momentum strong, guided by a simple but firm belief: don’t ask if you haven’t acted since the last time you surveyed.
The most transformative force is their AI strategy, which she describes as a true game changer and a major differentiator. Built as a dual strategy, it focuses first on self-discovery through learning, with AI training made broadly available across the organization and strong participation from Team8s globally, supported by open access to AI tools as part of everyday work. At the same time, they advance business-specific innovation designed to directly support customers’ needs. Together, this blend of democratized access and strategic application reshapes workplace strategy, turning potential disruption into a unified engine for growth and service.
The Conversational Catalyst: Learning and Leading in Public
True thought leadership, for Jeanette, happens in conversation, where she actively fuels industry progress by turning 8×8’s experiences into shared knowledge and participating in dozens of professional discussions across podcasts, conference proceedings, and industry organizations.
Her objective is never self-promotion, but collective advancement: to share our learning and move the performance dial forward. “There is so much to be learned right now,” she states, driven by a belief that dialogue must have purpose. She is routinely amazed at what she learns from colleagues worldwide, valuing this exchange above all.
A commitment to a two-way street, where she shares experiences, learns from others, and brings new perspectives into the dialogue, drives her full engagement. This approach likely explains why several of her podcast appearances this year ranked in the top five with listeners, as she is motivated by a goal to build understanding, not just broadcast it.
Impact Measured in Team Success and Enduring Values
While she emphatically states that she doesn’t work for individual accolades, the recognitions garnered by Jeanette Winters and her team at 8×8 powerfully reflect her impact as a leader, where she views awards as affirmations of collective effort and cultural progress.
- Recent Organizational Honors:
- 8×8 named in Top 100 Most Loved Workplaces under her leadership
- Won Brandon Hall Award for manager training
- i4CP Innovative Practices Award finalist, highlighting people operations excellence
However, two personal awards reveal the core values that drive her authority beyond the workplace:
- The 2002 Intel Diversity Champion Award, earned when tech was just beginning to prioritize creating welcoming cultures for all.
- The 2022 Texas Governor’s Award for Volunteering, for coaching women recently released from long-term incarceration.
For Jeanette, these honors are not just trophies but meaningful reflections of a lifelong commitment, as she notes that both awards recognized work that continues to represent a critical part of her identity, underscoring that true authority in people leadership is rooted in inclusion, second chances, and service that extends well beyond the office.
Creating an Ecosystem and Not a Wall – 8×8’s Partnership Philosophy
When discussing strategic relationships, Jeanette points to the role people and operating models play in enabling 8×8’s broader ecosystem strategy. From a People and Workplaces perspective, her focus is on ensuring teams are structured, equipped, and aligned to collaborate effectively across the App Marketplace and the company’s third-party ecosystem, including TPES (Third-Party Ecosystem Strategy). The goal is not to dictate vendors, but to support a model that gives customers flexibility, choice, and confidence – while ensuring internal teams can integrate, support, and scale those relationships effectively.
Together, these initiatives reflect a partner-centric approach that prioritizes customer choice and operational readiness. A key differentiator, she emphasizes, is that the company does not force customers to align with specific vendors; instead, the strategy is to provide an array of tested, validated, and world-class functionality that aligns closely with their needs, placing customer choice, flexibility, and growth firmly at the center of the approach.
How Feedback Shapes a Customer-Centric Culture
Gathering employee and customer feedback is approached as a deliberate, multi-channel practice designed to drive action, with Jeanette Winters and her team embedding it into everyday operations. Their award-winning customer service team uses Qualtrics to regularly capture and measure customer insights, while the People & Workplaces team relies on the same platform to assess employee engagement twice each year, ensuring feedback consistently informs meaningful change.
Beyond these metrics, they prioritize direct dialogue through annual Customer Appreciation Board (CAB) sessions with engaged clients. A pivotal moment came this past summer during these sessions when customers articulated a powerful, defining insight. They stated clearly: “We buy because of the service heart and technical capability of your team.” This feedback was more than praise; it became a strategic compass that, once internalized, brought clear direction to the organization and now informs priorities and reinforces decisions across the organization, ensuring every initiative reinforces both the empathetic service mindset and the technical capabilities customers value, allowing strategic priorities to fall seamlessly into place.
An Open Letter to Emerging Leaders
To the future-shapers and culture-builders,
As you step into your power, remember that leadership is as much about what you choose to carry with you as what you consciously let go. My hope for you, inspired by lyrics from Frozen and Wicked playing in my own home, is that you embrace the simple power of letting it go.
Carry these forward:
- Challenging the status quo with respect and intention. Progress dies when we protect “how it’s always been.” It thrives by asking better questions, welcoming healthy debate, and being brave enough to change.
- Saying “no” or “not now” to preserve focus. This isn’t doing less; it’s concentrating on what matters most. True prioritization gives your team clarity and purpose.
- Staying deeply aligned with your culture and talent expectations. Speed and collaboration are born from a shared understanding of values, behaviours, and performance.
Have the courage to leave these behind:
- Failing to innovate because it’s the easiest route. Complacency is the enemy. Change is a constant.
- Only partially solving problems. Reject the temporary fix. Pursue the total solution.
- Ignoring the need for speed. The world moves at warp speed. Embody urgency in all you do.
Finally, hold onto this truth from Defying Gravity: “Together, we’re unlimited.” Your greatest strength will always be the team beside you. If we work in tandem, there’s no fight we cannot win.
Lead with empathy, act with integrity, and never stop pioneering with innovation.
Yours in solidarity,
Jeanette Winters
Chief Human Resources Officer, 8×8, Inc.
Key Takeaways:
- Go slow to go fast; stakeholder alignment is your true accelerator.
- Training eliminates fear; lifelong learning is career insurance.
- Automate everything to free your time for the human work that matters.
- Culture is built on three pillars: cross-functional collaboration, customer centricity, and personal accountability.
- It is not all about you; leadership is a service, not a title.
- Build ecosystems, not walls; empower customers with choice through strategic partnerships.
