Embracing Self-Awareness and Leadership: Insights from My Conversation with Jenn Southan
In the customer support and tech space, it’s easy to get caught up in the fast-paced environment, moving from one challenge to the next. But taking a step back to reflect, reframe, and grow can lead to some of the most pivotal moments in your career. That’s exactly what I learned from my conversation with Jenn Southan, Senior Director of Customer Support at Olo. Jenn’s journey is a testament to the power of self-awareness, authentic leadership, and building a career that aligns with your values.
Jenn’s story is one that resonates with many of us who’ve found ourselves in transition, whether it’s pivoting in our careers, embracing leadership roles, or taking time to reflect on what we truly want.
1. Stepping Back Before Stepping Up
Jenn shared a powerful story of how stepping back from her career for several years to focus on her family allowed her to gain clarity and perspective. When she returned to the workforce, she initially sought an individual contributor (IC) role, deliberately avoiding the leadership track she had once been on. This break gave her a fresh perspective, helping her rediscover her passion for support and ultimately leading her back to a leadership position at Olo.
"I just wanted to come to work, do a good job, and close my laptop at the end of the day. I didn’t want the responsibility of leadership at first."
— Jenn Southan
What Jenn didn’t expect was how taking a step back would eventually lead her to a stronger, more intentional leadership role. By giving herself the space to grow, Jenn reignited her passion and confidence, which ultimately made her a better leader.
2. Building Teams with Intentional Leadership
One of the things that stood out to me during our conversation was Jenn’s approach to leadership. Rather than focusing solely on technical skills, she emphasized the importance of hiring for character and empathy. Jenn looks for people who want to grow and contribute to a collaborative environment, knowing that technical skills can always be taught later.
"We hire people who are conscientious and eager to improve. It’s more about their mindset than their technical skills."
— Jenn Southan
This philosophy is one I deeply resonate with. Leadership is about building trust and creating an environment where people feel valued and supported. Jenn’s ability to foster a space where her team can flourish and move up within the company—while avoiding unnecessary competition—is a testament to the power of intentional leadership.
3. Taking Ownership and Overcoming Imposter Syndrome
Like many of us, Jenn has struggled with imposter syndrome, even after years of experience in the tech industry. But she’s found ways to overcome it by focusing on the facts and results of her work. Jenn shared how she revisits the glowing recommendations she received on LinkedIn as a reminder of her impact and accomplishments.
"If I’m ever feeling down, I go back and read the recommendations my colleagues left me on LinkedIn. It reminds me that I’ve got this."
— Jenn Southan
Taking ownership of our achievements and recognizing our value is crucial to overcoming self-doubt. Jenn’s strategy of acknowledging her wins, no matter how big or small, is a great reminder to all of us: we have to be our own advocates.
4. The Importance of Feedback and Transparency
Jenn has fostered a culture of transparency on her team, emphasizing the importance of giving and receiving feedback in real time. She believes in immediate feedback, not just for corrective purposes but to help her team grow. This approach not only builds trust but also ensures that mistakes are seen as learning opportunities, not something to fear.
"Mistakes are going to happen. What’s important is taking ownership, learning from it, and moving forward."
— Jenn Southan
This open approach to feedback is something I’ve always strived to embody in my own leadership. Jenn’s commitment to providing constructive, timely feedback helps her team members feel secure in their roles and confident in their ability to improve.
5. Leading Without Ego
One of the most refreshing aspects of Jenn’s leadership style is her emphasis on leading without ego. She doesn’t view leadership as a power play but as an opportunity to serve and support her team. This means being open to feedback, empowering her team members to grow into new roles, and never taking things personally.
"There’s no place for ego in leadership. It’s about creating an environment where everyone feels safe to contribute."
— Jenn Southan
In a world where competition often takes center stage, Jenn’s approach is a breath of fresh air. She shows that when leaders focus on the well-being of their teams, everyone wins.
Key Takeaways:
Self-Awareness Leads to Growth – Sometimes stepping back from leadership or career goals gives you the clarity and drive to succeed when you return.
Hire for Mindset, Not Just Skills – Fostering a team of conscientious and growth-minded individuals creates a stronger, more adaptable team.
Overcome Imposter Syndrome by Owning Your Achievements – Revisit the wins and positive feedback to remind yourself of your value and capabilities.
Immediate Feedback Builds Trust – Give feedback in the moment to create a culture of learning and growth, not fear of failure.
Lead Without Ego – True leadership is about empowering others, not boosting your own ego.
Conclusion: My conversation with Jenn Southan left me inspired by the way she’s navigated her career with self-awareness, intention, and grace. Whether you’re in a leadership role or looking to grow in your career, Jenn’s story reminds us of the importance of embracing change, empowering others, and staying true to our values.
If you’re someone who’s struggled with imposter syndrome, navigating career transitions, or finding your leadership style, Jenn’s approach offers invaluable lessons on how to step into your power and lead with empathy. It’s about building the right foundation, hiring for growth, and giving yourself permission to evolve.
