Caleb O. | Leland

Caleb O.

5.0

(3)

Studied at Harvard Business School

Worked at DoorDash

Available tomorrow at 11:30 AM UTC

Please message me separately about coaching on the weekends!

Protected by the Leland Experience Guarantee

Available tomorrow at 11:30 AM UTC

Please message me separately about coaching on the weekends!

Questions? Start chatting with this coach before you get started.

Interested in coaching?

Select a category below to view Caleb’s offerings.

About Caleb

Born and raised in Washington, DC, I have always enjoyed living and working surrounded by a global set of perspectives. I attended Brown University where I studied International Relations & French and spent several summers working in film & television, discovering a passion for storytelling in a digital environment. I worked in strategy consulting for 2 years, helping media organizations adapt to new ways audiences are consuming information, and then spent 3 years launching new business lines at DoorDash in a General Management function, deep-diving into user stories to create new products and solve unmet needs. I am now pursuing my MBA at HBS with the hope to continue exploring the intersection of media, technology, and storytelling.

Why do I coach?

Understanding different perspectives, whether through learning a new language or spending time in a different cultural environment, has always been important to the way I live. I coach because I get just as much as I give when working with clients to take their lived experiences and craft a compelling narrative. I believe everyone has something interesting to share: the hard part is figuring out how to communicate it. At Brown, I served as a peer writing coach (Writing Fellow) to 4-8 students per semester in academic and creative writing across humanities, social sciences, and STEM disciplines. I also served as a peer writing mentor to first-year students without strong writing backgrounds, providing feedback and guidance on academic writing during the first semester. I know how important it is to feel confident in presenting oneself, and I am committed to helping my clients put their best selves on display for admissions committees.

Work Experience

Strategy Manager

DoorDash

May 2022 - June 2025

Hiring Manager

P&L ownership with a focus on scaling the New Verticals business. Most recently working on consumer affordability, pricing, and new product development. Participated in hiring for 5+ roles ranging from Associate level (0-2 YOE) to Senior Manager level (8+ YOE).

Senior Business Analyst

Activate Consulting

August 2020 - April 2022

Hiring Manager

Tech, media, and entertainment management consulting firm. Focused on growth strategy and commercial due diligences (buy & sell side). Project work included digital publishing/news, streaming video, gaming, e-commerce, sports betting, online marketplaces, ad-tech, art/auctions, and film/TV production. Participated in on-campus and off-cycle recruiting efforts, interviewing 20+ candidates for summer and full-time consultant positions.

Marketing Intern

A24

August 2019 - May 2020

Interned with the Marketing & PR teams to publicize and conduct audience research for A24 theatrical releases, organizing test screenings during the 2019-2020 school year.