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Chester Nielsen

Executive Chief of Staff and Strategic Operations Leader across SaaS, government, and national security

DatasiteMIT Sloan School of ManagementWayland, MA20 Years ExperienceExecutive LevelWorks On-Site

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About

Entrepreneurial consultant who relocated to Boston to build a practice from scratch through intensive networking and pro-bono work, leading to being listed as a trusted provider in Leader Bank's CEO toolbox and generating qualified leads. Uses structured strategic frameworks (OODA, Porter's Five Forces, SWOT) to evaluate risk, resource lift, and enterprise/customer impact, with a strong ownership-and-accountability orientation.

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Key Strengths

  • Built a consulting practice through grassroots networking and informational meetings
  • Converted relationship-building into qualified lead flow via inclusion in Leader Bank CEO toolbox
  • Structured decision-making using OODA loop with enterprise-wide impact and risk lens
  • Disciplined prioritization of initiatives based on time-to-implement, cost, and tradeoffs
  • Strong ownership mindset; prefers accountability where final responsibility rests with them

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Experience

Chief of Staff to the COODatasite · Mar 2025 – Jul 2025
PresidentBespoke Solutions · Jan 2016 – Jan 2025
Investment Bank’s Executive in ResidenceTrue North Advisory Group · Jan 2023 – Jan 2024
Chief of BaseCentral Intelligence Agency · Jan 2014 – Jan 2016
Operations OfficerCentral Intelligence Agency · Jan 2009 – Jan 2016
Management ConsultantScience Applications International Corporation (SAIC) · Jan 2006 – Jan 2009
Senior Legislative AssistantUS House of Representatives · Jan 2005 – Jan 2006

Education

MIT Sloan School of Managementmaster, Executive MBA (2027)
University of Kentuckydoctorate, Law
University of Wisconsin–Madisonbachelor, Political Science

Awards

  • CIA Exceptional Performance Award (three awards) - Central Intelligence Agency
  • Commissioned U.S. Diplomat - U.S. Senate
  • CIA Exceptional Performance Award (3x) - Central Intelligence Agency

Languages

English

Certifications

Certified Scrum Master (SSGI)Six Sigma Agile Leader (SSGI)McChrystal Group Academy: Certified Chief of Staff ExecutiveCertified Information Privacy Professional/United States (CIPP/US) - IAPPCentral Intelligence Agency: Field Tradecraft Course I-IIIUnited States Parachute Association: Class A Skydiving LicenseMassachusetts Bar Association/Board of Bar Overseers: Member/ActiveU.S. Senate: Commissioned U.S. DiplomatMassachusetts Bar (Member/Active)CIA Field Tradecraft Course I-III ("The Farm")

Memberships

  • Massachusetts Bar Association
  • Board of Bar Overseers
  • International Association of Privacy Professionals (IAPP)
  • United States Parachute Association

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Typically responds within 24 hours

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Chester NielsenExecutive Chief of Staff and Strategic Operations Leader across SaaS, government, and national security