Her Story
About Lindsey
Lindsey Chervitz is a Showroom Lead at Proper Cloth Proper Cloth in Chicago, where she plays a key role in overseeing showroom operations and guiding a team of Client Advisors. In her current leadership role, she supports day-to-day performance by mentoring staff on product knowledge, sizing expertise, and client service standards, while also stepping in as acting showroom manager when needed to resolve escalations, coordinate scheduling, and ensure smooth operational flow. She also contributed directly to the successful launch of the Chicago showroom, including hiring and onboarding team members to establish a strong market presence.
Her career reflects a dynamic progression from technology and operations into client-facing retail leadership. Prior to joining Proper Cloth, she held roles spanning onboarding, systems operations, sales management, and CRM strategy across several fast-paced companies, where she developed strengths in process optimization, training, and cross-functional collaboration. She earned a Bachelor of Science in Informatics from Indiana University Bloomington Indiana University, building a strong foundation in systems thinking, communication, and analytical problem-solving that continues to inform her work.
At Proper Cloth, Lindsey has advanced from an individual contributor in New York to a leadership position in Chicago, reflecting both adaptability and consistent performance in high-growth environments. Her work focuses on custom made-to-measure menswear and building long-term client relationships, with an emphasis on helping customers feel confident and well-supported throughout their experience. Across her career, she has combined operational discipline with a people-centered approach, emphasizing mentorship, empathy, and continuous improvement in both team development and client service.
Her Interview
Ten minutes with Lindsey
01What do you attribute your success to?
I've been incredibly fortunate to have mentors who have shaped my approach to work and life. My current manager Sebastian leads with such grace and empathy, with this direct ability to make you feel seen and heard. He wants your successes for you, but also recognizes they reflect on him as well, so he sees you as somebody he wants to be successful and will do anything he can to help you achieve whatever you're looking to achieve, whether in business or in your personal life. My own mother has been an amazing mentor throughout my life. She's worked her entire life in sales, and it's always been wonderful to see the way she builds relationships. Sales isn't just about selling a product, it's about selling yourself and building relationships. Being able to see her do that throughout my life really inspired me. I was never in sales until this position, and I think I found this natural groove by reflecting on all the advice she had given me throughout my life, both inside and outside of work, that led me to success in my career.
02What advice would you give to young women entering your industry?
It's really important to be yourself. Of course, there's a certain business acumen that you should have, but also allow yourself to shine through as far as who you are and what it is that you want to accomplish. Be direct, but be respectful. Be open to new ideas, be open to growth, and be open to starting somewhere low with your eyes set wide on something that has the opportunity to grow and even go into leadership if that's something you'd like to do. Really ensure that you don't lose yourself in the process. Finding jobs can be disheartening in a lot of ways, to feel like you're not seen, or you're passed over, or you feel like you're trying to convince somebody of something that you know, which is that you're full of this power and this ability and this grace to want to be part of an organization that's bigger. The biggest thing is to really be yourself. Know what you know, and be okay with knowing what you don't, and be open to learning that, because ultimately, in the long scheme of things, it's about growing and about learning. It's okay to make mistakes, and it's okay to learn from them. That should be really valued and seen as a way of growth and integrity in the workplace.
03What values are most important to you in your work and personal life?
Navigating change with grace has been one of my biggest accomplishments. I've worked across different environments, from several tech startups to this fashion-forward, tech-adjacent company, and finding success in each while finding my own voice and something that makes me happy has been huge. What matters most to me is making an impact and changing people's lives. Having the opportunity to make that kind of impact is something I feel very honored and grateful to myself for, allowing myself to be successful in those ways and to find opportunities that value what I bring on a day-to-day basis in my work. I'm passionate about health and wellness, particularly women's wellness and healthcare access. I'm also deeply interested in strategic and forward thinking, bridging gaps in communication and understanding between different parts of organizations. Growing up, my family helped shape my approach to forward thinking, strategic thinking, and logical thinking when it comes to bigger problems in business. Ultimately, I believe in being authentic, being open to growth and learning, and not losing yourself in the process of building your career.
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