Executive & Personal Assistant

Executive & Personal Assistant
Job Family: Administrative Assistant
City/State: Colorado Springs, CO USA
Type and Schedule: Full-Time, Salary / Exempt, Hybrid, with required Colorado Springs in-person availability.
Annualized Salary Range: $95,000.00 - $120,000.00 commensurate with experience.
About Us:
Caliola is an award-winning woman-owned small business that is improving and protecting our Nation's way of life through secure collaboration and resilient communications. Our engineers, subject matter experts, and veterans are developing and delivering trusted solutions for mission-critical communications. We seek teammates who share our core values:
I3 for C3 - Insight, Innovation, and Integrity for Command, Control, and Communications
These values guide how we work every day. At Caliola, you will find technically challenging, mission-focused work within a flexible and collaborative culture that is uncommon in the defense industry. We offer flexible PTO, subsidized health insurance, 401(k) matching, professional development, and a competitive compensation structure designed to support long-term growth.
Position Description:
Looking for more than a traditional assistant role? Become a trusted partner to two entrepreneurial executives, with the autonomy to solve problems, influence how things get done, and make a meaningful impact across their businesses and personal lives.
Caliola is seeking an Executive & Personal Assistant to work directly with our CEO and Chief Scientist. This unique position combines executive support, family-office operations, financial administration and special project management across a portfolio of businesses and personal interests.
We are looking for a resourceful, detail-oriented professional who takes pride in getting things done right. You combine systems thinking, sound judgment, discretion, technical aptitude, and curiosity. You'll have the opportunity to deliver results across both Caliola and family-office operations, while gaining firsthand experience in how entrepreneurial leaders manage businesses, evaluate opportunities, and make decisions.
Essential Responsibilities:
Special Project Execution

• Own assigned Caliola, family-office, and personal projects with clear outcomes, timelines, budgets, and decision authority.
• Coordinate resources, solve problems, and deliver results with timely updates and minimal oversight, adapting to changing priorities and business needs.

Administrative Systems, Technology & AI

• Use AI and technology to improve workflows, automate appropriate tasks, and reduce the CEO's administrative workload.
• Maintain accurate, accessible files, records, expenses, contacts, and preference guides, while building documented, repeatable processes and reliable tracking systems.

Financial & Business Entity Administration

• Manage day-to-day financial administration, including tracking transactions, managing accounts, coordinating payments, and supporting tax preparation across all business entities and family accounts.
• Coordinate with property managers, tax professionals, and financial advisors. Track documents, discrepancies, deadlines, and outstanding items, and follow up until resolved.

CEO & Chief Scientist Personal Support

• Own personal scheduling, errands, purchases, travel and expenses, and vendor coordination from request through completion, anticipating needs, learning preferences, and handling sensitive details with discretion.
• Oversee home operations, including maintenance, repairs, vendor management, and special projects, ensuring the home is well maintained whether the family is present or traveling internationally.
• Provide occasional backup family support, including transportation and childcare when primary arrangements are unavailable, with flexibility to step in during emergencies.

Executive Time & Priority Management

• Provide flexible administrative and operational support to Caliola leadership, including assigned projects, process improvements, and evolving business needs.
• Manage calendars and meeting preparation for the CEO and executive team.
• Protect time for priorities, resolve scheduling conflicts, and surface tradeoffs before they become problems.

What We Require:

• Bachelor's degree.
• Minimum of five years of professional experience in executive support, personal assistance, business administration, project coordination, or a combination of these areas.
• Demonstrated ability to independently manage competing priorities, deadlines and workflows through completion, with strong problem-solving and systems-thinking skills.
• Intermediate or advanced AI proficiency with demonstrated experience implementing practical AI solutions.
• Strong organizational, administrative and project coordination skills, including Microsoft Office proficiency, attention to detail and ability to learn new systems;
• Ability to collaborate effectively and communicate clearly and professionally with executives, employees, family members, vendors, and professional advisors; handle confidential information appropriately; and work in person in Colorado Springs.
• Availability during traditional business hours, with flexibility to respond to emergencies. Must be willing to adjust working hours occasionally to accommodate international time zones and changing priorities. Regular evening and weekend work is generally not expected.
• Reliable transportation and the ability to safely transport three children when needed.
• Ability to obtain and maintain a U.S. Government Secret security clearance.

What We Value:

• Systems thinking and process improvement: Identifies recurring problems, builds documented and repeatable processes, and uses technology to create systems that others can operate and maintain.
• Ownership through completion: Takes responsibility for outcomes, follows up persistently, resolves outstanding details, verifies results, and closes the loop.
• Strong technology and AI skills: Confidently learns and troubleshoots tools, uses AI effectively, evaluates its output, and improves workflows. Works confidently with Apple devices, multiple accounts, and separate company and personal technology environments.
• Financial competence: Practical experience with bookkeeping, financial software, reconciliations, expense reporting, spreadsheets, and financial administration, including investigating discrepancies and organizing information across multiple entities.
• Personal and family service orientation: Enjoys supporting a family and interacting with children. Comfortable handling practical errands, household needs, and occasional backup childcare and transportation.

Minimum Physical Requirements:

• Must possess strong written and verbal English communication skills, with the ability to communicate clearly and professionally with employees, leaders, vendors, and other stakeholders.
• Must be able to navigate a standard office environment, including prolonged periods at a desk and frequent use of computers, screens, phones, and digital communication tools.
• Ability to maintain sustained focus, organization, and attention to detail while managing records, coordinating deadlines, preparing documents, and working across multiple systems and business priorities.
• Must be able to periodically move throughout the office to support meetings, events, visitors, and day-to-day operations. Requires the occasional ability to lift, move, and set up office supplies, packages, and equipment weighing up to 20 pounds.

Please contact Human Resources ([email protected]) with questions about ADA accommodations.
More About Us:
Our performance has driven rapid growth and national recognition, being named twice to the Deloitte Technology Fast 500™ and inclusion on the 2026 Inc. 5000 list of America's fastest-growing private companies. We have also been recognized as a Colorado Company to Watch, a ColoradoBiz Top Company in Aerospace & Defense, and the #2 Gazette's Best Workplace (medium size) in 2025.
Headquartered in Colorado Springs, CO, we operate in a leading aerospace and defense hub with proximity to major military installations. Set against the Rocky Mountains, the region offers year-round outdoor recreation and a high quality of life for professionals and families considering relocation.
As a part of our selection process, we ask all applicants to complete a short, 10-12-minute survey from Culture Index. This is a survey, not a test; no passing or failing. The purpose of this survey is to identify your unique strengths as they relate to our open positions. Please copy and paste the following link into a separate browser window to complete: https://go.cultureindex.com/s/5i6Gpe3wge
Expression of Interest: By applying to this job, you are expressing interest in this position and could be considered for other career opportunities at Caliola Engineering. Should a match be identified between your skillset and Caliola's requirements for this or a future opening, you may be contacted.
The posted salary range represents our good faith estimate for this role based on current organizational needs and the qualifications reasonably expected for the position. Final compensation will be determined based on factors such as experience, skills, education, clearance status, and business needs.
This position will remain open until filled, at least three business days, and applications will be reviewed on a continuous basis.
At Caliola, we believe that true innovation can only occur when teammates bring their authentic selves to collaborate in a supportive, encouraging environment. We are an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or veteran status, age, or any other federally protected class.
Caliola participates in E-Verify, an internet-based system used to confirm the employment eligibility of all new hires. Upon hire, all employees are required to complete Form I-9 to verify their identity and employment eligibility to work in the United States.
All candidates will be required to pass a basic background screening.
#BI-Hybrid