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:

Caliola Engineering is seeking an Executive & Personal Assistant to serve as a trusted partner to our CEO and Chief Scientist, helping bring structure, organization, and execution to their busy professional and personal lives. This unique role is ideal for someone who enjoys solving problems, managing complex details, and taking ownership of responsibilities from start to finish. By keeping priorities organized, commitments on track, and important details from falling through the cracks, you will help two visionary leaders focus their time and energy where they can make the greatest impact.

We are looking for a resourceful, detail-oriented professional who takes pride in getting things done right. You thrive when given responsibility, enjoy creating order out of complexity, and are comfortable independently managing a wide variety of tasks, relationships, and projects. You combine sound judgment and discretion with strong technical aptitude, curiosity, and a willingness to find smarter ways of working. Whether coordinating executive priorities, managing financial and administrative details, or handling personal and family logistics, you will have the opportunity to build trusted systems, solve meaningful problems, and make a tangible difference every day.

Essential Responsibilities:

CEO & Chief Scientist Personal Support

• Own personal scheduling, errands, purchases, travel and expenses, and vendor coordination from request through completion.
• Anticipate needs, learn preferences, and handle sensitive details with discretion to give the CEO time and peace of mind.
• Provide dependable family support, including backup childcare and transportation, and oversee home checks, maintenance, repairs, and vendors while the family is home or traveling.

Financial & Business Entity Administration

• Own coordination and completion of monthly accounting, expense reporting, financial reviews, and tax preparation support 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 each item is completed or explicitly reprioritized.

Special Project Execution

• Own assigned personal and business projects with clear outcomes, timelines, budgets, and decision authority.
• Coordinate resources, solve problems, and deliver completed results with timely updates and minimal oversight.

Executive Time & Priority Management

• 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.

Administrative Systems, Technology & AI

• Maintain accurate, accessible files, records, expenses, contacts, and preference guides.
• Build repeatable processes and a trusted tracking system so recurring responsibilities and requests are handled reliably. Use technology and AI to improve workflows, automate appropriate tasks, and reduce the CEO's administrative workload.

What We Require:

• Bachelor's degree in Business Administration or a related field.
• Minimum of five years of full-time, professional experience in executive support, personal assistance, business administration, project coordination, or a combination of these areas.
• Demonstrated ability to independently manage recurring responsibilities, deadlines, schedules, and administrative workflows while balancing competing priorities and following work through completion.
• Strong administrative, organizational, and project coordination skills, including proficiency with Microsoft Office applications; accurate recordkeeping; careful proofreading and document formatting; and the ability to learn new systems quickly.
• Ability to collaborate effectively and communicate clearly and professionally, verbally and in writing, with executives, employees, family members, vendors, and professional advisors; handle confidential information appropriately; and work in person in Colorado Springs as needed.
• Availability during traditional business hours, with flexibility to respond to emergencies. 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:

• 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. Brings curiosity and a willingness to experiment.
• Mac and iPhone proficiency: Works confidently with Apple devices, multiple accounts, and separate company and personal technology environments.
• Financial competence: Practical experience with bookkeeping, Quickbooks, 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 (HR@Caliola.com) 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.