After graduating from West Point, Chelsea served as an Army Engineer officer in Alaska for five years, spending one year doing construction management in Iraq. She continued her military time working in logistics and then managing a human resources team. After leaving the military, Chelsea spent a year volunteering in the Philippines, running a professional training center and life-coaching deaf young adults and inmates before attending Wharton. She spent her Wharton summer as a management consultant with McKinsey & Company (summer associate).
Chelsea also coached a high school cross-country ski team in Anchorage.