Some people stumble into leadership; Jenn Sebastian builds it—brick by brick, system by system. “Success isn’t just about outcomes—it’s about how we achieve them, the culture we create, and the impact we make,” she believes and practices.
Jenn is the President & Chief Operations Officer at Women Rocking Business (WRB), where she partners with Sage Lavine – the company’s CEO, best-selling author of Women Rocking Business, and keynote speaker – to serve at the forefront of the women’s entrepreneurship movement, helping women build sustainable businesses in a way that’s aligned with feminine values.
Jenn has been a big part of the engine behind the company’s growth—scaling it to seven-figure revenue, growing a thriving and capable team, and implementing structures and processes designed for efficiency and productivity—for almost 11 years now.
Her inspiring leadership journey began at a young age. Jenn was mastering discipline in martial arts and NJROTC, excelling in competitive environments. It shaped her resilience and problem-solving mindset and proved her belief that, “No matter what happens, there’s still a lot of opportunity out there.
Her grandfather’s advice stuck with her early on: “If someone at work ever asks if you want to learn something new, always say yes.” Jenn once envisioned a career in the military and law. As a young adult, a temp job at a small startup—Latitude Communications—set her on an unexpected path. What started as customer service quickly became a hands-on education in troubleshooting and systems management, leading her to Cisco Systems after an acquisition. Soon, Jenn mastered complex operations and managed major corporate accounts.
Motherhood shifted her priorities, inspiring her to redefine success. She focused on college, earning a Bachelor of Business Management and a Master of Business Administration in Project Management. When a corporate layoff abruptly ended her decade-long tenure at Cisco, she pivoted into entrepreneurship and in 2014 she joined Women Rocking Business, which was a small startup at the time. Today, she channels her expertise into shaping strategy and operations in her partnership with Sage. She proved a “challenge accepted” mindset can change unexpected turns into a powerful career. She articulates, “Your business will only grow as far as your leadership allows.“
Innovating with Impact: Game-Changing Milestones
Jenn’s passion for excellence is aligned with Sage’s vision for delivering value through business. It has earned her a spot among the “Top 10 Empowering Women Leaders to Follow in 2025.”
But accolades aside, it’s the milestones she’s achieved at WRB that showcase her impact. WorldChanger.ai—WRB’s custom-built AI platform, designed by Sage to give clients a transformative and time-saving tool—is one of those milestones. It helps entrepreneurs refine their personal stories, define their ideal clients, craft marketing assets, and develop their signature talks—all with clarity and authenticity. Jenn saw the potential for innovation and spearheaded its development. Seeing clients flourish with WorldChanger.ai has been one of her most rewarding moments.
In the inescapable times of AI, Jenn and Sage helped pioneer the first AI program designed specifically with women’s values in mind with the intention of supporting women to do more good in the world. At its core are values including sustainability, impact, and community.
What started with just three members has grown into a powerhouse team of nearly 30. She’s crafted hiring, onboarding, and training systems that attract A-players. “A strong business is built on strong systems, but a strong team is built on trust.” No drama, no gossip—just a culture of integrity, direct communication, and collaboration. This strong foundation has helped WRB navigate market shifts, scale sustainably, and remain resilient despite challenges like the COVID-19 pandemic. She consistently praises her team for their remarkable trust, cohesion, and professionalism. “Creating this environment, especially with a fully remote team,” She remarks, “is something I’m deeply proud of, and I believe it has played a huge role in our long-term success.”
Leading with Strategy: Balancing Vision, Teamwork, and Execution
As President & COO of WRB, Jenn knows that the strength of an organization depends on the people. Her team is equipped with resources to do their best work, empowered with leadership training and resources, and fully in sync with the company’s mission. Her leadership philosophy aligns with Simon Sinek’s observation: “A boss has the title, but a leader has the people.”
Jenn believes business survives on human connection. In her words, “At the core of my leadership, I believe in humility—I will roll up my sleeves and get in the trenches with my team when needed.” She holds weekly one-on-one meetings with her direct reports to stay ahead of challenges, solve problems, and keep a pulse on daily operations. Structured reporting, a daily ritual, provides a panoramic view of team dynamics – progress, priorities, and even the subtle nuances of morale. This balance of monitoring and authority allows her team to take charge while keeping her eye on the big picture.
Much of her leadership approach is built on trust—especially in her partnership with CEO Sage. Their investment in coaching and mentorship programs ensures they continue refining their management skills, always keeping the company’s best interests at heart.
Jenn believes clarity is the key to streamlined operations. She brings metrics and data to company decision-making. Meetings are meticulously documented, and brainstorming is scrupulously differentiated from concrete commitments—an approach she credits to her Executive Business Coach.
Jenn creates and treats blocks on calendar like non-negotiable business commitments, silencing notifications and tuning into a “Deep Focus” playlist on Spotify. She knows the right work environment is key to productivity. But high performance comes with a risk: burnout.
Over the years, Jenn has learned that just because she can do something doesn’t mean she should. She applies a two-step process: First, she finds an immediate solution to keep things moving. Second, she builds a system or process that ensures the task can be delegated in the long run.
Finding Success Beyond the Bottom Line: Jenn’s Perspective
Earlier in her career, success was about setting ambitious goals and pushing limits. Now, with her three children grown, she values freedom—the ability to take weekend trips with her husband, connect with loved ones, and immerse herself in nature. She loves reading about Business and self-development, and even building custom GPTs to simplify both work and home life.
Now, she measures achievement by the strength of the team, not just financial milestones. She believes a thriving workplace is built on trust—where people feel safe to voice challenges, own mistakes, and collaborate without fear. Jenn sees leadership as steering a company ship—navigating challenges, setting the course, and ensuring every part of the team moves in sync toward success. She prioritizes market research, metrics analysis, strategic partnerships, and big-picture planning. She feels that, without those, long-term growth is at risk.
Instead of “work-life balance,” Jenn embraces the concept of “counterbalance.” She encountered this principle in the book “The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary Results” by Gary Keller and Jay Papasa. As the book points out, “Purpose, meaning, significance—these are what make a successful life,” she applies it.
Jenn’s Crash Course in Reinvention—And How It Paid Off
Jenn knows that being in charge transcends a title or just having all the answers. It pertains to trusting yourself to figure them out. It is the most significant evolution in her leadership journey and a key factor in leading WRB.
WRB had built its success on high-impact, in-person events. But during the pandemic, with just three days’ notice, California went into lockdown. An 800-person event was about to kick off. The easy choice? Cancel. The bold choice? Reinvent. Jenn and her team pivoted overnight, moving the event onto a private Facebook group and streaming sessions live via Zoom. Attendees tuned in from their hotels and Airbnb while the team improvised from home.
Leaning into adaptability, Jenn sought out mastermind groups where WRB was the smallest company in the room—because progress, she believes, comes from being challenged. That experience reshaped her leadership.
A Day in the Life as Women Rocking Business’ COO and President
Jenn starts her day with intention. After a slow and mindful morning – dressing, enjoying tea or coffee, and savoring a healthy breakfast – she logs in to find her team already hard at work. Slack is her command center, buzzing with updates from the East Coast team. Jenn sets a packed and strategic meeting schedule, averaging 22-25 hours per week, often starting as early as 7 or 8 AM Pacific Time. However, she carves out Fridays as a meeting-free zone and dedicates them to reflecting on the week, reviewing KPIs, and making plans for the future. Off working hours are for hitting the gym, followed by a relaxing dinner with family or friends.
Designing a Life, Not Just a Business: The WRB Philosophy
WRB champions the idea that a business should create freedom, flexibility, and purpose in one’s life. Jenn recalls that when she first started as a consultant, being present for her children was a top priority. The thought of spending hours in Bay Area traffic, missing out on precious moments, was never an option. This vision of balance and purpose-led work became deeply aligned with WRB’s mission, shaping how the organization continues to uplift future generations of women leaders.
WRB provides a community where women can see what’s possible and grow purpose-based businesses. The organization also teaches its clients how to integrate philanthropy into their business models, encouraging them to support causes they’re passionate about, such as protecting endangered wildlife to funding Kiva loans for aspiring entrepreneurs or aiding survivors of domestic violence.
The organization is set for the upcoming years. Jenn and Sage ensure every move aligns with WRB’s mission, market changes, and audience needs. WRB’s Executive team amplifies communication, fostering open dialogue and collective problem-solving. The organization operates like a machine and every team member and vendor plays a vital role. Insights, concerns, and ideas shape the company’s path forward. At its core, WRB’s resilience is a team-driven collaboration, aligned by a shared belief that women can change the world through business.
Advice for Aspiring Women Leaders
Jenn says, “Be your own best friend. If you wouldn’t say it to someone you love, don’t say it to yourself.” She emphasizes self-compassion and support as crucial tools to overcome self-doubt so success can be achieved. Recognizing the power of accountability, she stresses the importance of having a mentor or a trusted confidante.
Jenn highlights that leadership is more than skill acquisition. It involves a holistic approach encompassing effective communication, authentic presence, and continuous personal growth. Drawing from her own eight-year journey of personal development and leadership coaching, she says this transformative process has not only honed her leadership abilities but also enriched her personal life, making her a more fulfilled individual in all her roles.
Jenn urges aspiring leaders to prioritize self-investment. She advocates for creative solutions, such as initiating mastermind groups with like-minded women to foster collective growth and support. Ultimately, she believes that true success lies not solely in achieving goals but in the profound personal evolution that accompanies the journey.
Guiding, Not Doing: Jenn’s Evolving Leadership at Women Rocking Business
Jenn’s journey at WRB aligns with the quote, “There is no force more powerful than a woman determined to rise,”. She started as a behind-the-scenes manager, but as the company scaled, so did her responsibilities—elevating her from Online Business Manager to COO and ultimately to President. Through experience, mentorship, and working alongside high-level business leaders, Jenn learned to own her leadership and trust her decisions fully.
“I would describe my leadership style as collaborative, supportive, direct, vision-driven, and empowering,” explains Jenn. Initially, her instinct was to be the fixer. However, she soon realized that constantly providing solutions prevents people from developing their own critical thinking and decision-making muscles. She advocates that true leadership is teaching people how to make decisions, not just making them yourself.
She recalls how Sage modeled this approach for her during WRB’s growth, often affirming, “I trust your leadership on this.” Jenn explains that this simple statement instilled confidence in her. She began modeling it, implementing tools like a decision-making matrix that empowers team members to analyze potential solutions before coming to her. This process promotes independent problem-solving. And when mistakes inevitably happen (because they will), Jenn reframes them as learning opportunities. She openly shares her own thought processes, risk assessments, and analytical strategies. As WRB has grown, Jenn’s focus has shifted from less on doing to more on guiding, mentoring, and aligning her team with the company’s overarching vision.
Jenn cultivates a synergistic leadership dynamic with CEO Sage. Recognizing the unique perspectives each brings, they engage in productive and goal-focused conversations, probing deeply with questions like ‘What do you know that I don’t?‘ This dialogue results in total alignment in strategic and problem-solving decisions.
The Future is Female, Flexible, and Powered by Purpose
According to Jenn the rapidly transforming business landscape is shaped by a powerful force: women entrepreneurs. The rise of online and home-based businesses has opened incredible opportunities. Technology is essential, and AI has great promise for efficiency and success. Jenn deems that it’s easy to get caught up in the “bright shiny object syndrome.” WRB differs by understanding strategy is key. By leveraging proven strategies, community-based growth, and timely marketing training, WRB empowers clients to grow transformative businesses that make a big impact.
