Interview Kickstart has been shaping careers for nearly a decade, with some of our team members growing alongside us from day one. IKatalyst celebrates these pivotal journeys of growth and a relentless pursuit of excellence. In this edition, we shine the spotlight on Stephanie Rosson, our esteemed Associate Director of Operations, whose contribution and dedication to IK are truly remarkable. Below is her inspiring story:
Mapping the Journey of an Early Leader: Stephanie’s 7-Year Stint at Interview Kickstart
Stephanie hopped on board when our team was still in its early days, turning what began as a side gig into a full-blown career. She joined us as an intern in 2017 & within a span of 7 years, she has grown to become the Associate Director of Delivery Operations.
We asked her the following questions & here’s what she had to say about her growth journey with us.
How did you join Interview Kickstart?
I come from a non-traditional background; I was actually studying to be a chiropractor in the US. I finished my academic coursework early and was looking for a part-time job to supplement my income. That's when I discovered a part-time position at Interview Kickstart through Indeed. I applied and had the opportunity to meet Soham, who ultimately hired me. At that time, IK was still a small startup with only a handful of instructors in Santa Clara.
What were your responsibilities during your initial months?
My responsibilities back then were quite different from what they are now. I assisted instructors, uploaded videos, cleaned whiteboards, managed meals for students, and coordinated with restaurants and delivery services like DoorDash. My role was heavily focused on operational tasks and hands-on activities, all conducted offline. At that time, we typically had about 20 to 30 students in each class, with only one cohort running, so everything was done in person.
How did your role and responsibilities evolve over time?
After graduating, I launched my own business while continuing to work at IK.
But as IK grew, so did my responsibilities. By the end of my second or third year, we were seeing approximately 100 students per month. We moved to a larger space, increased the number of cohorts, and brought on more instructors. Eventually, we transitioned to a hybrid model and later went fully remote during COVID, which significantly transformed my role as I began managing remote teams and operations.
I officially joined IK full-time in 2019, I chose IK because I loved what I was doing, and the company provided me with ample growth opportunities and mentorship. I had a lot of autonomy to make decisions that I believed were right, and nothing could compete with my experience of working with the IK team.
How did moving to a remote model impact your team?
Transitioning to remote work was a big shift. Initially, it was challenging as we lost the in-person connection with both students and instructors. However over time, we adapted, which opened up opportunities to hire instructors from across the US and even Canada. Eventually, we expanded into India, presenting its own set of challenges and learning experiences. We had to swiftly adjust to remote operations, which involved streamlining processes and managing teams across different time zones.
During this period, we also launched multiple new courses, significantly expanding our offerings, which increased our workload and demanded rapid innovation. Acclimating to a different culture was another challenge as we integrated our India operations. What truly surprised me was the growth and retention within my team. Since I joined, we’ve successfully retained most of our members, despite losing a few along the way.
A significant highlight for me has been witnessing the career growth within our team. For instance, a delivery intern who began her journey with us a few years ago advanced steadily from an associate to senior associate, and is now the sole data analyst for the operations vertical, managing all data analytics and dashboards. Similarly, another intern has grown into the role of an assistant manager, showcasing the strong potential for growth and development within our team.
Can you share some pivotal moments in your journey?
Yes, I've definitely experienced pivotal moments. One of the biggest was when we transitioned the management from Soham to my current manager, Sreejit. It goes without saying that any change in management can be challenging, particularly when you've invested significant time adjusting to a specific leadership style.
One thing Soham did right was stepping back and giving me the space I needed to adjust. This transition period became a pivotal moment for me, as Sreejit offered a level of autonomy that is essential for growth as a manager. He trusted me to make decisions and consistently sought my input, which enabled me to evolve from an individual contributor into a confident manager.
Another significant milestone was the pandemic, as it was for most. While it was a challenging period, our team adapted to working with fewer resources while still supporting the same number of students. During this time, I also took on HR and payroll responsibilities for the U.S., broadening my scope beyond operations. This experience was a pivotal learning opportunity that significantly expanded my skill set.
Over the years, especially as the team expanded, I frequently took on new projects and launches, which I found immensely rewarding. From initiating our Clubhouse project with the marketing team to coordinating conferences, I’ve always embraced new challenges. Even when it came to HR and payroll—I initially took them on to learn how to build and manage them from the ground up. My approach has been to establish systems and processes, ensuring they run smoothly, and then happily passing them on once they’re stable.
Whether it was with Sreejit, Soham, or Ryan, whenever I expressed an interest in taking on something new, I was always encouraged to do so which significantly expanded my learning horizons at IK.
As a leader, how do you manage your teams and ensure the same mentorship you received?
In my team, I dedicate a lot of time to understanding my team members. Each quarter, I make it a priority to ask if there are any new initiatives they’d like to pursue. I hold regular meetings with the entire team to align on work objectives. For those who are not my direct reports, I ensure we connect at least once a month. For my direct reports, I conduct weekly one-on-ones to discuss projects, progress, and any challenges that they may be facing.
In a remote environment, it’s crucial to be intentional about maintaining connections; otherwise, it can become purely transactional. If team members sense that no one is genuinely invested in their development, their motivation to engage diminishes. However, when they feel that someone genuinely cares about their growth and well-being, they are more likely to reciprocate with their time and effort.
I believe it’s essential to share mutual interests with your team members—it demonstrates that you care about them as individuals, not just as employees. Building strong relationships involves asking about things that go beyond work.
One aspect I truly appreciate about Interview Kickstart is that from the very beginning, leaders like Ryan and Soham have consistently shown that they care about me as a person, not just my work. That personal connection made a significant difference in the way I related to work. When I was starting my career, Soham took the time to invest in my development.—he made it a priority for us to connect at least once a week to stay aligned. That level of personal investment has profoundly impacted me.
What advice would you give to someone joining Interview Kickstart?
Take ownership of your work and fully immerse yourself in every opportunity that comes your way. Working at a startup presents countless chances for learning and growth; the more you embrace, the more you’ll develop your skills and advance your career.
What stands out for those who begin in entry-level positions at IK is the consistent growth they experience. With their dedication, effort, and alignment with our culture, they learn quickly and progress rapidly. I consider this a significant perk of being part of this organization. Always be on the lookout for new projects that pique your interest, and communicate with your team about where you want to pitch in and add value.
