Transitioning from Entrepreneurship to a C-Suite Role

Samantha Shih, following an extensive 14-year journey with her custom clothing company, 9Tailors, made a significant career leap by joining a startup as a chief brand officer. This transition necessitated the sale of her established business to embrace a new professional chapter.

In 2008, Samantha Shih embarked on her entrepreneurial journey by founding 9Tailors, a custom suiting and shirting company, in Boston. Despite initial challenges, including a lack of retail and fashion experience, she leveraged her business strategy knowledge from her previous consultancy role at Deloitte. Her venture quickly adapted to the online market, focusing on young professional males, and achieved profitability by its second year. However, the COVID-19 pandemic necessitated a strategic pivot to mask production due to the high-touch nature of her business.

Unexpectedly, Shih’s journey took a new direction when her brother introduced her to LookSky, a direct-to-consumer fashion brand from Asia. This connection sparked several consultations that led to job discussions. Although 9Tailors experienced booming post-pandemic demand, the opportunity with LookSky promised not only a C-suite position but also a considerable salary increase and personal time realignment.

The decision to join LookSky was facilitated by their offer to allow Shih to design her ideal job role. Despite her initial suggestion for a creative director position, she was offered the chief brand officer role, a move she found significantly appealing. Additionally, the role’s flexibility would enable her to spend more time with her family, a priority since the birth of her first child in 2017.

During a six-month transition phase, Shih balanced her responsibilities between 9Tailors and LookSky. Although LookSky required her to sell her business, she ensured the continuity of 9Tailors by selling it to her Chief Marketing Officer, someone familiar with the company’s operations and clientele.

Working remotely for LookSky, Shih encountered challenges but also enjoyed increased flexibility. Despite the initial adjustment period, she valued the ability to manage her schedule efficiently, allowing for personal pursuits and family commitments. Engaging with her son’s activities and maintaining personal growth through literature and podcasts became feasible components of her routine.

Last summer, Shih faced an unexpected personal challenge with a breast cancer diagnosis. Despite this, she found unwavering support from her LookSky team, which reinforced her decision to join a nurturing and encouraging workplace. This support not only enabled her to navigate her health journey but also fostered her professional growth in a dynamic environment. While she cherishes her time with 9Tailors, Shih remains content with her current role, although the idea of future entrepreneurial ventures remains open.

Samantha Shih’s pivot from running her own company to joining a startup’s executive team illustrates a dynamic career trajectory marked by adaptation and growth. Her story underscores the importance of seizing opportunities that align with both professional aspirations and personal life balance.

Source: Businessinsider

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