An Interview With Vanessa Ogle
Create flexible work policies: Offering flexible work arrangements, such as remote work options, flexible hours, and parental leave policies can help women better balance their professional and personal responsibilities. The goal is to help women feel that they’re capable of pursuing leadership without sacrificing their career advancements or compromising their family commitments.
Despite strides towards equality, women remain underrepresented in leadership and management roles across various sectors. In this series, we would like to discuss the barriers to female advancement in these areas and explore actionable strategies for change. We are talking with accomplished women leaders, executives, and pioneers who have navigated these challenges successfully, to hear their experiences, tactics, and advice to inspire and guide the next generation of women toward achieving their full potential in leadership and management roles. As part of this series, we had the pleasure of interviewing Lee Rubin.
Lee Rubin, CEO and Founder of Confetti, is a visionary leader with over a decade of experience in B2B sales. In 2014, while tasked with planning an event for her team, Lee conceived the idea of creating a tool that helps companies plan their events faster and better. This groundbreaking concept not only sparked the creation of Confetti but also ignited her journey as a pioneer in the corporate events space. Following the 2020 pandemic, Lee successfully pivoted Confetti from in-person to virtual team building, showcasing her deep expertise in excelling and adapting to changing landscapes. Her passion lies in leveraging her experience to help companies scale and enhance their company culture.
Confetti is loved by 8,000+ companies, including Google, Facebook, and Spotify. Lee has recently been featured in interviews with Authority Magazine and has been awarded #124 in the Inc. 5000 and also Inc. 200 Top Female Founders. She spearheads a company where every member of the team shares her unwavering passion for providing the best customer experience.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
Confetti was born out of my own experience as an office fun planner, juggling event planning alongside a packed to-do list. Like many others, I volunteered to organize events for my team, only to realize the immense workload involved. Determined to find a better way to create enjoyable office experiences with less effort, I embarked on a mission to build a solution when I couldn’t find one that met my needs.
From a young age, I aspired to be an entrepreneur, recognizing the plethora of problems waiting to be solved in the world. Recognizing the need for a streamlined solution for corporate events, I envisioned a single platform where teams could easily discover and book activities, fostering genuine connections.
Leaving ZocDoc behind, I brought this vision to life. Initially, I crafted a simple website on Wix.com featuring a range of team-building activities, primarily tailored to in-person experiences pre-COVID. From portable laser tag to puppy parties, our offerings aim to enhance workplace camaraderie. However, as I delved deeper into this venture, I realized a fundamental truth now embedded in our ethos: not all vendors deliver exceptional experiences. We understood that subpar activities detracted from the opportunity to foster genuine connections among teams — a responsibility we took seriously. Thus, we prioritized curating experiences that truly resonated, ensuring each interaction facilitated meaningful connections and lasting memories.
Can you share the most interesting story that happened to you since you began your career?
The pandemic is something that happened to all of us, but it was probably by far my most interesting career story. Confetti originally helped companies plan events in the office, face-to-face. Everything from donut walls and happy hours to puppy parties in the office. When COVID hit and people couldn’t gather together, I initially felt like the spirit of what we do was being threatened, but it turned out to be a pivotal moment for us to reimagine and redefine how we create meaningful connections and experiences in a virtual world.
Can you share a pivotal moment in your career that significantly influenced your path to leadership?
As I mentioned earlier, my desire to be an entrepreneur started from a very early age, largely thanks to the influence of my father. I always naturally gravitated towards building little businesses since the age of six — but he always encouraged me to dream and think about solutions to everyday problems. He always took my ideas seriously.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
Once I graduated from college, the person and moment that was pivotal to starting this journey was with a friend and colleague, Jonathan Messika. He was the CEO of an up-and-coming tech start-up and I shared with him my dreams and ideas. He told me to ‘go for it’ and he helped with all my hundreds of questions in those early formative years of building this solo.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky for its insightful guidance on navigating the challenging stages of any ambitious project (something we all have been through at one point in our lives). Belsky emphasizes that success is not just about the exciting beginning or the triumphant end, but about managing the messy, often frustrating middle phase. I love how the book inspires its reader to embrace the messiness — a lesson I’m always trying to remind myself of during the day-to-day craziness of building a business.
Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
A sentence I regularly go back to is, “You can discover more about a person in an hour of play than in a year of conversation.” — Plato.
To me, this sentence really encapsulates the essence of Confetti.
How have you used your success to make the world a better place?
I first want to give a shout-out to the many other jobs and industries that I think very obviously do this: teachers, doctors, environmentalists, etc. With regards to Confetti, the way I view it is that our experiences spark happiness — and with so much darkness around us, it feels good to be a part of a company that makes people feel good.
I often say that life is too short to hate your job and the people you work with. Our experiences are designed to provoke a memorable moment — a joyful moment.
Our hope is that if you find yourself disliking your boss, and then the next day you’re laughing with them over a game of trivia, maybe our experiences will positively influence your work relationship with them.
And if we can all become better colleagues to one another, research shows that the success of the company will follow.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this report, only about 31.7% of top executive positions across industries are held by women. This reflects great historical progress, but it also shows that more work still has to be done to empower women. In your opinion and experience what is currently holding back women from leadership and management?
The underrepresentation of women in top executive positions is multifaceted with various contributing factors ranging from gender bias and discrimination, work-life balance challenges, and implicit and explicit biases in hiring and promotions. Many organizations lack comprehensive training programs to address unconscious biases among employees, including hiring managers and senior leaders. Addressing these issues requires a concerted effort from the organization, its leaders, and society as a whole. This includes implementing policies and practices that promote diversity and inclusion, fostering mentorship, and challenging stereotypes at all levels of society.
This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become leaders and managers?
- I truly believe and see within my work, that when you invest in more diverse perspectives and decision making you’ll have more enriching and innovative solutions.
- Research indicates that companies with great gender diversity at the executive level tend to outperform their less diverse counterparts.
- Women in leadership positions serve as advocates for gender equality and diversity within the organization.
Can you please share “5 Things We Need To Increase Women’s Engagement in Leadership and Management?”
1 . Promote mentorship and sponsorship programs: I feel very lucky to the hundreds (maybe even thousands?) of people who have helped me along the journey. I know from experience that when I reach out to ask for help, there are many people out there who want to help — and a tip that I have for other women who are looking to increase their leadership and management experience is to not wait until that mentor gets paired with you, but to go out and find these people yourself.
2 . Address implicit bias and stereotypes: We only very recently finally got to standardizing our payroll, which finally paves the path towards transparent salary structures. This wasn’t easy to achieve, but came to life through employees vocalizing this desire. By promoting a culture of fairness, organizations can mitigate biases in hiring, promotion, and decision-making.
3 . Create flexible work policies: Offering flexible work arrangements, such as remote work options, flexible hours, and parental leave policies can help women better balance their professional and personal responsibilities. The goal is to help women feel that they’re capable of pursuing leadership without sacrificing their career advancements or compromising their family commitments.
4 . Establish clear pathways to leadership: Create transparent pathways to leadership positions by implementing clear criteria, advancement opportunities, and planning processes. If you’re hiring for a new role, first consider potentially promoting internal candidates before looking outside. Usually, it’s amazing to see what people can do if they’re just given the chance. You can always align their expectations by setting clear performance metrics for success.
5 . Foster a culture of accountability and recognition: Having a culture where each leader is held accountable for their goals and recognized/rewarded equally based on those achievements. By acknowledging and valuing the contribution of all people in leadership roles, but also women in leadership, we can inspire other women to pursue similar paths and create a more supportive environment for their advancement.
In your opinion, what systemic changes are needed to facilitate more equitable access for women to leadership roles?
It starts with reviewing and ideally eliminating any types of gender biases in recruitment and promotions. Organizations must implement fair and transparent processes that are held across the organization. Then you should ensure equal pay for equal work. Conducting regular pay audits and adjusting salary structures to eliminate any disparities. From a larger context, advocating for legislative and policy reforms that support gender equity in the workplace, such as anti-discrimination laws, paid family leave policies, and measures to promote diversity.
What strategies have you found most effective in mentoring and supporting other women to pursue leadership positions?
The most important one is to lead by example. If you demonstrate a strong leadership quality and behavior in your own work and life interactions that is where inspiration is bred. It’s really an honor to serve as a role model — and I don’t take the responsibility lightly. Through this responsibility, I have the opportunity to bring out the confidence, resilience, and authenticity in those other women — through my leadership approach.
How would you advise a woman leader about how to navigate the challenges of being a woman in a leadership role within a male-dominated industry?
The journey starts with your self-confidence. You must first believe in yourself and your capabilities because otherwise, no one will do it for you. Don’t hesitate to assert your ideas and opinions in a professional way. Confidence has a beautiful way of commanding respect and establishing credibility. It’s also important to surround yourself with allies and supporters either within your organization or industry who want to see you grow. It takes work to cultivate those relationships, but eventually, they champion your advancement — which will then become a reality!
How do you balance the demand for authoritative leadership with the stereotypical expectations of female behavior in professional settings?
I think it’s important to first embrace your authentic leadership style. Authenticity breeds confidence mentioned above — and confidence breeds trust and credibility, regardless of gender stereotypes. You should never lose focus, however, on leading with integrity, transparency, and empathy.
I think women can practice assertive communication to convey their ideas while also still being respectful of other viewpoints (just like any other person in the workplace should).
Focus on results and data — and let those speak for themselves. By consistently delivering high-quality work and achieving measurable outcomes, you can earn respect and credibility as a leader, irrespective of traditional expectations.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
I envision a movement centered around empathy, aiming to foster a deeper understanding and appreciation for the experiences, perspectives, and emotions of others. The goal is to cultivate greater compassion, connection, and kindness in our communities and society at large.
Empathy, the ability to empathize and respond with care, has the power to bridge divides, heal wounds, and build stronger, more inclusive communities. In a world often marked by division and misunderstanding, fostering empathy is crucial.
Through this movement, I advocate for empathy to be taught and practiced in various settings, starting from a young age and continuing throughout life. I encourage individuals to actively engage with people from diverse backgrounds, challenging biases, and approaching interactions with openness and compassion.
While there are many pressing issues in the world, I believe improving relationships in workplaces can have a significant positive impact on our day-to-day because such a significant portion of our waking hours is dedicated to work. By enhancing the connection between colleagues and their work, perhaps we can also contribute to the greater good and the consciousness of our planet.
How can our readers further follow your work online?
Feel free to connect with me on LinkedIn! You can also subscribe to my bi-weekly LinkedIn newsletter, “Culture Corner,” where I share insights on workplace trends, leadership skills, corporate culture, and employee engagement.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children.
Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.
Lee Rubin of Confetti On How We Can Increase Women’s Engagement in Leadership and Management was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.