From Teacher to Tech Leader: Jennifer Dulski on Resilience, Leadership, and Building Connected Teams
Jennifer Dulski’s story is not one of straight lines or predictable steps. She began her career in a classroom, teaching high school students and running a nonprofit designed to help first-generation college students succeed. From there, she moved into the tech industry at the dawn of the internet, rose to executive roles at Yahoo, Google, and Facebook, and later became president and COO of Change.org. Today, she is the Founder and CEO of Rising Team, a platform that helps managers lead more effectively and build deeply connected teams. She also teaches leadership at the Stanford Graduate School of Business and is the author of the Wall Street Journal bestselling book Purposeful.
In her conversation on the Badass Women in Business podcast, Jennifer reflected on her unconventional journey, her philosophy of leadership, and the resilience required to keep going through both failure and success. This blog draws from that conversation and her other published insights to create a detailed picture of a leader who is reshaping how we think about teams, connection, and purpose at work.
Early Rules for Leadership: Earn Trust, Do Not Ask Permission
Early in her career, Jennifer created two rules for herself. The first was to be great at her job. The second was not to ask permission. When she needed to leave the office for her daughters’ school events, she would simply inform her colleagues: “I am going to the Valentine’s Day party, I will be back at three.” She never asked if it was okay, but she also never left anyone wondering whether her work would be done.
These rules, she explains, are rooted in trust. If you consistently deliver, you earn trust. Once you have that trust, you can use it to create the kind of life and career balance you want. The lesson is simple but profound: prove yourself with excellence, and then claim the autonomy to live by your values.
From the Classroom to Yahoo: A Nontraditional Path into Tech
Jennifer did not begin her career in technology. She studied psychology and education, then taught high school biology, psychology, and health. At the same time, she ran a nonprofit that helped students from under-resourced backgrounds become the first in their families to attend college.
What drew her into tech was the desire to scale her impact. The internet was just emerging, and a board member introduced her to Yahoo when it was still a small startup. Jennifer realized that technology could amplify her mission of empowering others on a much larger scale. She completed her MBA, interned at Yahoo in 1998, and joined the company full-time.
She stayed for ten years, growing alongside the company as it expanded from a few hundred employees to thousands. She moved from brand manager to group vice president, running one of Yahoo’s six major business units. This experience set the stage for her next steps in Silicon Valley.
Lessons from Big Tech and Bold Exits
Over the years, Jennifer has held senior roles at Google and Facebook, where she shaped global online communities. She also served as president and COO of Change.org, helping scale the platform from 10 million to nearly 200 million users.
Yet what stands out in her career is not just the companies she worked for, but the moments she chose to leave. She left prestigious roles not for comfort or stability, but for impact and growth.
When she stepped down from Google to join Change.org, some saw it as a risky move, leaving a tech giant for a B Corp focused on social good. When she chose to take a demotion at Yahoo to pursue a general management role, colleagues thought it unwise. But for Jennifer, these choices were investments in long-term learning and the chance to shape meaningful change.
She describes her career as a series of deliberate shifts between large organizations and small startups. Each taught her something different. Big companies offered resources and reach; smaller teams offered speed, scrappiness, and the chance to shape culture directly. By moving back and forth, she collected lessons that informed her own leadership style and, eventually, inspired her to start Rising Team.
Resilience: Living in the Space Between Joy and Fear
For Jennifer, entrepreneurship is not glamorous. It is a cycle of getting knocked down and standing back up, again and again. She describes it as living at the intersection of joy and fear.
At one point, she founded a startup that failed repeatedly. The product idea changed multiple times. The company name changed three times. But she kept going. That resilience, she argues, is the most essential entrepreneurial skill.
She compares it to climbing a mountain. Some days are sunny picnics with clear views of the summit. Other days are stormy, with valleys that feel impossible to cross. What keeps her moving forward is perspective: all storms pass. She leans on optimism, gratitude, and reframing challenges as temporary setbacks.
In Rising Team workshops, she now teaches resilience strategies that include mood shifters (breathing and physical activity), reframers (gratitude and perspective), and activators (taking small steps forward). For her, resilience is both mindset and practice.
Rising Team: A Platform for Connected Leadership
Rising Team grew out of Jennifer’s personal experience leading large, distributed teams. She faced three persistent challenges:
Learning leadership skills from coaches but struggling to scale them across her team.
Receiving employee engagement survey data without actionable tools to respond.
Creating team activities to build connection, but failing to remember the insights over time.
Rising Team solves these problems through guided workshops and an AI coach named “RD.” Managers can run sessions that foster trust, clarity, and connection, while the AI remembers details and helps leaders personalize their support.
The platform is used by companies ranging from Google, Cisco, and Airbnb to nonprofits, schools, and government agencies. What unites these organizations is the universal need for teams to feel valued, understood, and connected. As Jennifer puts it, “It is not rocket science. We just make it easier for managers to do the things that make them great.”
The Three Cs of Leadership: Clarify, Coach, Connect
Jennifer distills great leadership into three Cs:
Clarify: Leaders must articulate a clear vision and define what winning looks like. People need to know the mountain they are climbing and how their role contributes.
Coach: Leaders should understand each person’s unique strengths, preferences, and potential. Like a sports coach, they help people grow into their talents.
Connect: Leaders must create a sense of team. Without connection, especially in distributed work, individuals drift apart. Even small investments, three to four hours per quarter of intentional team-building, can dramatically improve performance.
This framework draws on her experience as a coxswain on the rowing team, where she learned to motivate, align, and connect people who were working toward a common goal.
Purposeful: Starting Movements That Matter
Jennifer’s book, Purposeful, reflects her belief that everyone has the capacity to start movements, whether through campaigns, businesses, or community projects. The book outlines three more Cs: courage, community, and commitment.
Courage: Taking the first step, even when uncertain.
Community: Building a team of people who share and amplify your vision.
Commitment: Staying the course, even when critics or setbacks appear.
She compares courage to being the first person to stand up in a standing ovation. Most of the time, others will follow, but even if they do not, the act itself is a meaningful expression of leadership.
At Change.org, she witnessed countless examples of small movements that grew into global change. One of the most powerful was Amanda Nguyen’s campaign to extend the preservation of rape kits, which led to unanimous passage of the Sexual Assault Survivors’ Bill of Rights in Congress and later inspired similar laws across the United States.
For Jennifer, movements start with small, brave steps and grow through community and persistence.
Balancing Leadership and Parenthood: Guilt Does Not Help
Jennifer raised two daughters while leading at some of the world’s most demanding companies. She is candid about the guilt she felt, especially when her children imitated her by “pretending to be in meetings” while playing.
Her mantra became GDH: Guilt Does Not Help. Instead of letting guilt consume her, she focused on being present when she could and integrating family into her work life. She created a “work-life mash-up” rather than chasing balance. She brought her children on international work trips, set up her office near their dance classes, and modeled for her teams that blending family and work was acceptable.
Her advice to women is also clear: stop pre-apologizing. Too many women begin ideas with disclaimers like “this might not be a good idea, but…” She urges leaders to state ideas with confidence and apologize only when truly necessary.
Building Communities at Work and Beyond
Jennifer believes that building communities is much like hosting a party. You must welcome people, introduce them to others, nurture early connections, and resolve conflicts quickly. The two questions everyone asks when joining a community are: “Are they like me?” and “Will they like me?” Leaders who help people answer yes to both create strong foundations.
This philosophy applies not only to online platforms like Facebook and Change.org but also to teams within companies. Traditions, rituals, and shared language build belonging. At Rising Team, internal culture is intentionally shaped with practices that create a sense of community.
The Future of Work and AI
Jennifer is clear-eyed about the role of AI in the workplace. She sees it as a tool that can reduce friction, provide memory, and help managers with scripts or roleplays, but insists that human connection must remain at the center.
She warns against letting AI replace human conversations, such as performance reviews, but sees value in using AI to prepare, practice, and remember. The key, she says, is to balance clarity and compassion, with technology serving as an aid rather than a replacement.
What Leaders Need Most Today
Asked what leaders most often lack, Jennifer points to connection. Many focus exclusively on hitting goals and driving performance, but neglect the relational glue that makes teams effective.
Her advice is simple: invest a few hours each quarter in intentional team connection. It does not require elaborate off-sites or endless meetings, just consistent, thoughtful moments where people feel seen, valued, and supported.
Legacy and Advice for the Next Generation
Jennifer’s purpose has always been to empower others to be their best selves. She believes the greatest regrets come not from failure, but from never trying. As she told the podcast hosts, “We have far more regret for the things we do not try than for the things we try and fail to do.”
Her advice to her own daughters, and to the next generation of leaders, is not to follow a specific career path, but to find their “ikigai,” the sweet spot where passion, skill, and need intersect. For her, Rising Team represents that intersection: the work she loves, the work she is skilled at, and the work the world needs.
Why Jennifer Dulski’s Leadership Lessons Matter Now
Jennifer Dulski’s career illustrates that leadership is not about titles or companies, but about impact, resilience, and connection. From classrooms to boardrooms, from startups to tech giants, she has carried a consistent purpose: helping others grow.
Her frameworks, the Three Cs of clarify, coach, connect, and the movement-building Cs of courage, community, and commitment, offer practical guidance for leaders at every level. Her candid reflections on resilience, failure, and parenting remind us that leadership is both human and imperfect.
In a world where hybrid work and AI are reshaping how teams function, Jennifer’s message is clear: build trust, invest in connection, and never stop climbing the mountain, no matter the weather.
