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AI is upending entry-level jobs. Three teens tell us how they’re responding

Experts in tech and economics largely agree that AI is poised to disrupt many jobs and may eliminate some altogether. And entry-level roles are likely to be at the forefront of that shift. While employment remains fairly high among all groups, it’s recently taken a dip for 20- to 24-year-olds.

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Jason Chow

Investment Banking & Financial Services Expertise

Jason brings more than 25 years of experience across investment banking, corporate financial planning and analysis (FP&A), and corporate business development at leading companies such as Citi, JP Morgan, Google, and Yelp. Throughout his career, he has personally hired over 75 undergraduates and MBA students as well as managed and mentored dozens of early-career professionals—helping them build confidence, develop practical skills, and advance within investment banking and financial services industries.

As a specialty advisor, Jason’s passion is guiding students and mentoring young professionals to achieve their career aspirations. In particular, he understands how great finance organizations operate and how they evaluate, develop, and promote early-career talent. Having worked on the front lines—reviewing resumes and conducting behavioral, technical, and case interviews at elite colleges and MBA programs—Jason understands not only the common questions but also the unspoken criteria used to judge candidates in a highly competitive process. With the proper coaching and practice, Jason believes all candidates can improve meaningfully. 

Currently advising early-stage start-ups and early career professionals. Jason previously served as the VP of Corporate Business Development at Auctane, where he led global strategic partnerships that drove over $1B in annual transactions. Before Auctane, Jason spent ~15 years as a senior leader in FP&A and strategic partnerships at Google, Yahoo, and Yelp. He began his career in investment banking at Citi and JPMorgan, where he gained foundational experience in financial analysis, corporate transactions, and executive communication. Jason graduated cum laude from Williams College with a BA in Economics.

Sherry Lin

Asset Management & Investment Management Expertise

Sherry is a seasoned investment leader who has over 25 years of global asset management experience, and broad multi-asset class knowledge of alternative assets and public securities. She has built and led four investment offices from the ground up, managed large multibillion-dollar portfolios, anchored and seeded numerous fund strategies, and served in advisory board roles at large, best-in-breed, institutional investment managers, as well as at small emerging funds. Passionate about mentoring young professionals. Sherry has hired, developed, and promoted dozens of asset and investment managers around the world. Her superpower is coaching junior team members critical problem solving, analytical thinking, and communication skills, so they can flourish in their role.

Sherry is currently a Senior Advisor to Argentum Peak, a dual-family investment office which she built and led as Chief Investment Officer from 2021 to 2023 for the co-founders of Silver Point Capital, a $25B diversified credit platform based in Greenwich, Connecticut. Previously, Sherry co-headed Global Private Investments and served as Global Venture and Asia Head at Willett Advisors from 2021 – 2023, managing assets for Bloomberg Philanthropies, Michael Bloomberg’s family office. Sherry was a Managing Director and Partner at Mousse Partners, where she managed assets for the owners of Chanel from 2005 – 2018. At Mousse, Sherry led the Global Illiquid Portfolio in New York and later built and headed two Asia offices in Hong Kong and Beijing as the Head of Asia. Sherry also previously held capital allocator, investment banking and equity research roles, respectively, at the James Irvine Foundation, Thomas Weisel Partners, and Goldman Sachs. Sherry is an Aspen Institute China Fellow and a member of the YPO Presidio Gold chapter in San Francisco. She holds a JD/MBA from Northwestern and a BA from Columbia.

David Leibowitz

Biotech & Pharmaceutical Expertise

David Leibowitz brings 25 years of experience in the biopharmaceutical and biotech industries. He has extensive experience in product strategy, commercialization, and cross-functional leadership across a wide range of therapeutic areas. He is currently Senior Director, Portfolio Strategy at Roche/Genentech, where he leads strategic portfolio management and lifecycle planning for immunology and ophthalmology assets across all development stages. David has hired, developed, and promoted dozens of strategy, marketing, planning and product managers for many different therapeutic areas and functional domains. His superpower is coaching junior team members on understanding pipeline development, regulatory challenges, market research, cross-functional and stakeholder management so they can succeed in their role.

David has also previously led Patient Marketing for the US launch of Evrysdi, a spinal muscular atrophy drug at Genentech. He has also held leadership positions in pipeline marketing, managed care strategy, and business development. He holds an MBA from UCLA Anderson and a BA from UC Berkeley in Biology.

Rachel Blankstein, Co-Founder

Rachel Blankstein has over 14 years of experience coaching clients and has personally guided several hundreds of clients to obtain their goals. Rachel’s passion is to help her clients not only succeed in their internship and job searches but also to help in their professional and interpersonal growth. Previously, Rachel was Co-Founder and Co-CEO of a college consulting firm, Spark Admissions, which she founded, scaled, and successfully exited to a private equity company. In this role, she personally coached hundreds of clients, while hiring, training and mentoring dozens of coaches.

Her superpower is understanding what each client needs at the right time, providing the insights and support to help them shine. Her coaching style is supportive, yet rigorous, and is always tailored to the needs, goals and personality of her clients. She has a 100% success rate with getting her clients to achieve their goals.

As Co-founder of NextGen Advising, Rachel helps students and young professionals discover their career objectives and helps them with every stage of the internship and job search process. She understands how to uncover her clients’ interests and learn how to excel at each step of the job search process through determining where to apply, how to improve their hard skills, developing strong resumes, teaching effective networking skills and how to master each type of interview. She also has her finger on the pulse of what hiring managers are seeking in a tremendously wide range of industries from financial services to entertainment and biotech to non-profits and much more. Rachel motivates clients through concise, strategic guidance along with detail-oriented support at each step of the process.

Previously, Rachel was Co-Founder and Co-CEO of a college consulting firm, Spark Admissions, which she founded, scaled, and successfully exited to a private equity company. In this role, she personally coached hundreds of clients, while hiring, training and mentoring dozens of coaches. During her tenure, the company maintained a 5-star Google review with the majority of clients coming from word of mouth. Additionally, she led the marketing, finance, technology and operations functions. Most of all, she took pride in helping her clients reach their goals through creating strategic roadmaps to reach their goals and by coaching them to discover their interests, develop communication and leadership skills and reach their milestones each step of the way.

Ms. Blankstein has also previously held several roles in hi-tech product management, marketing consulting and management consulting.

Ms. Blankstein earned a B.A. in Economics from University of Miami, receiving a full merit scholarship, graduating in three years and was awarded the Mortar Board Award for the student who most represented Leadership, Scholarship and Service. In addition, she earned an MBA in Finance, Entrepreneurship and Marketing at the University of Chicago Booth School of Business.

Scott Bonds

Software Engineering & Start-up Expertise

Scott Bonds brings 20 years of experience leading product management, engineering, and AI-driven consumer services across fast-growing startups and Fortune 500 companies. He has scaled teams of over 100 people, guided companies through major technology transformations, and built some of the internet’s most engaging web, mobile, and social products. Scott has hired, coached, and mentored hundreds of early-career professionals—helping them grow into stronger builders, collaborators, and product thinkers. His passion is demystifying complex product and engineering concepts so candidates can confidently showcase strategic thinking, technical depth, and leadership during interviews. Known for his ability to turn ambiguity into clear frameworks, Scott helps clients sharpen their storytelling, elevate their judgment, and communicate like seasoned product leaders.

Throughout his career, Scott has held senior leadership roles at Indeed, Mixbook, Smule, Electronic Arts, and multiple consumer-tech startups. At Indeed, he led a 100+ person organization focused on international expansion, pioneering an AI-powered system that personalized job distribution across thousands of talent micro-markets. As VP of Engineering at Mixbook, he doubled revenue and turned the business profitable while driving one of the fastest culture transformations observed by The Table Group—improving team health, collaboration, and customer experience. At Smule, he helped build multiple #1 mobile apps, including Magic Piano, featured at Apple’s iPad launch. Earlier at Electronic Arts, he scaled Pogo.com into one of the world’s top casual gaming platforms, created EA’s first microtransaction system, and shipped dozens of AI-powered games. Scott holds a BSE in Electrical Engineering and Computer Science from UC Berkeley, where he was a Regents’ Scholar.

Caroline Sheu, Co-Founder

Caroline has 25+ years of general management, senior marketing, and board director experience at public, private, and non-profit companies such as Google, Disney and Adobe, where she has hired and mentored hundreds of young professionals. Caroline’s passion is mentoring young people to help them identify their own passions and translate them into a meaningful and fulfilling career.

As the Co-Founder of NextGen Advising, Caroline understands how to connect interest areas and skill sets to potential positions and career fields. Having managed hundreds of young professionals, she is an expert at helping clients set career goals and build detailed career plans. Caroline’s super power is coaching clients on how to tell compelling stories that make them stand out during the job search and promotion planning process. She provides both strategic and tactical support, tailored to her client’s specific needs, so they can acquire lifelong professional skills such as personal brand storytelling, networking, interviewing, and much more.

Prior to NextGen Advising, Caroline built and led world-class, go-to-market organizations for multi-billion dollar businesses across consumer internet, retail, high-tech, gaming, and entertainment. As a general manager and senior marketing executive at iconic brands like Google, Disney, Electronic Arts, Sony, Gap, and Adobe, Caroline built and led multiple teams of over 100 employees – personally recruiting, mentoring, and advising young professionals on their career development and personal growth. She understands first-hand the complex hiring and promotional practices across a broad range of industries, companies (large and small; public, private, and non-profit), and job functions (finance, legal, marketing, product management, analytics, strategy, business development, HR and more).

Caroline herself struggled to find her true passion early in her career. With a J.D./M.B.A. from the University of Chicago, Caroline tried corporate law, investment banking, business development, and product management, before finding happiness in the field of marketing! Her love for creative storytelling combined with her strong proficiency in data and technology made her an invaluable asset for companies needing to adapt to the latest consumer and technology trends – from web and mobile to social media and AI.

In addition to NextGen Advising, Caroline is currently on the board of PROG Holdings (NYSE: PRG), a fintech holding company that provides competitive payment options to consumers, and previously sat on the board of Lulu’s Fashion Holdings (NASDAQ: LVLU), a well-known online fashion brand. She is on the Advisory Board of Evoto.AI, a popular AI-powered, photo editing solution that revolutionizes photography, as well as a Board Member of USTA (United States Tennis Association) Northern California, the governing body for the sport of tennis. Caroline holds B.A. degrees in Political Science and East Asian Studies from UCLA, an M.A. in Asian Studies from UC Berkeley, and a joint J.D./M.B.A. from The University of Chicago.