Estevan Santiago
HBS and Stanford Grad | First-Gen College Student | Startups / Ex-Bain
Studied at Harvard Business School
Works at Column
Available today at 2:00 PM UTC
Questions? Start chatting with this coach before you get started.
Estevan's Offerings
Custom hourly · $75/hr
Get help with Application Strategy, Essays, and .
Estevan also coaches for MBA and Career Coaching. View all.
Estevan’s College Qualifications
As a first-generation college student, I've had to learn a lot of things the hard way. That experience is exactly what brought me to coaching — I want to be the coach I wish I had when I was applying to schools. I graduated with a B.A. in Human Biology from Stanford and my MBA from Harvard Business School. I've spent most of my career at high-growth health tech companies in business operations, with some time as a consultant at Bain & Company. I specialize in helping people craft and communicate their unique stories. I also know that sharing something that personal with someone new can feel intimidating — that's been true for me too. So I'm intentional about creating a space where you feel comfortable being open and honest, because at the end of the day, digging deep and telling a clear story of who you are and what you bring to the table is the most important part of this whole process. If any of this resonates with you, I'd be excited to help you on your journey to getting into your dream school!
Estevan can help with:
Application Strategy
Essays
Financial Aid & Scholarships
General Exploration
Interviews
Resume
Estevan also coaches for MBA and Career Coaching. View all.
About Estevan
As a first-generation college student, I've had to learn a lot of things the hard way. That experience is exactly what brought me to coaching — I want to be the coach I wish I had when I was applying to schools. I graduated with a B.A. in Human Biology from Stanford and my MBA from Harvard Business School. I've spent most of my career at high-growth health tech companies in business operations, with some time as a consultant at Bain & Company. I specialize in helping people craft and communicate their unique stories. I also know that sharing something that personal with someone new can feel intimidating — that's been true for me too. So I'm intentional about creating a space where you feel comfortable being open and honest, because at the end of the day, digging deep and telling a clear story of who you are and what you bring to the table is the most important part of this whole process. If any of this resonates with you, I'd be excited to help you on your journey to getting into your dream school!
Work Experience
Business Operations
Column
November 2025 - Present
Senior Operations Manager
Headway
March 2025 - November 2025
Hiring Manager
Built and scaled Headway's Payment Operations and Claim Systems teams. Expanded teams from 4 --> 7. These highly cross-functional and analytical teams focused on optimizing Headway's claims submission infrastructure, ensuring payment success for transactions made across Headway's platform, and maintaining accurate financial records. People Management, Business Strategy and +1 skill
Operations Manager
Headway
September 2023 - March 2025
Hiring Manager
Built and managed Headway's Claims Foundations team, a product operations function responsible for developing and maintaining the operational rulesets that power Headway's revenue-cycle management platform. Hired and managed 4 direct reports. In this role, I frequently coordinated cross-functional initiatives with engineering, product, and analytics teams to drive systematic improvements that reduced claims loss and enhanced platform efficiency.
Consultant
Bain & Company
July 2022 - September 2023
Admissions Committee
Primarily specialized in technology and healthcare engagements, including conducting an outside-in diligence to develop a new product-strategy and leading an end-to-end post-merger integration. Recognized as a top 10% performer within cohort.
Summer Associate
Bain & Company
June 2021 - August 2021
Partnered with a large SaaS company to design and implement a comprehensive go-to-market strategy that addressed declining sales performance
Operations Manager
Collective Health
January 2020 - August 2020
Hiring Manager
Managed a team of 13 and oversaw operations related to various high-risk / high-volume processes (including medical Stop Loss, health funds, claims data/reporting, and claims systems health). People Management, Data Analysis and +1 skill
Team Lead & Senior Associate
Collective Health
November 2018 - December 2019
Hiring Manager
Managed a team of 11 and oversaw operations for various claims products and services (including health funds and new product development).
Team Lead
Collective Health
October 2017 - October 2018
Interviewer
Managed a team of 6 and oversaw medical plan operations for 15K members
Estevan was also given offers to work at
Boston Consulting Group
Education
Harvard Business School
Master of Business Administration - MBA
2020 - 2022
Grade: Second Year Honors Activities and societies: VP of Admissions for the Latino Student Organization; CFO of the Brew Club; First-Year Technology and Operations Management (TOM) Course Tutor
Stanford University
Bachelor of Arts (B.A.), Human Biology
2011 - 2015
Activities and societies: Class of '15 Cabinet; Resident Assistant (Larkin House | Xanadu); Volunteer @ Arbor Free Clinic; Impact Abroad Trip Leader; Student Staff @ Diversity and First-Gen Office; Stanford Men's Club Volleyball