How to Showcase Multiple Roles in One Job Without Hiding Your Best Experience

A friend of mine—a former Lieutenant Colonel with 20 years in the Department of Defense—recently reached out for help with a resume makeover. With a long career full of progression, he wanted to highlight his most recent experience in a way that would resonate with hiring managers in the tech industry. But his original resume had a few problems:

1. It Looked Like Job-Hopping - Listing each role separately made it seem like he was constantly switching positions, which could make a recruiter eye confused.

2. Older Roles Took Up Space - Early roles, while impressive, were less relevant to his new career path but were still catching the eye and distracting from his recent, high-level experience. With a one page resume, those early roles took significant space.

When structuring a resume, I like to think from the hiring manager’s perspective. They want to quickly know three things:

1. Can you do the job? – Is there clear, relevant experience that shows capability?

2. Are you a winner? – Does your resume show results, personal success, drive, and a strong work ethic?

3. Is the story straightforward? – Does your resume layout provide a clear, honest view of your experience?

With these goals in mind, here are several ways I considered structuring his resume and why each might—or might not—work.

Three Strategies to Showcase Multiple Roles Without Losing Focus

1. Use the Most Recent Title with Key Projects Underneath

The simplest approach can often be the most effective. Listing only his latest, most senior title with subsections highlighting key projects from across his career keeps things concise and directs attention to his highest role.

Example (details were obfuscated for privacy):

Lieutenant Colonel, Department of Defense, 2000 – 2024

AI and Machine Learning Initiatives

1. Directed a $450M hardware project that advanced aviation capabilities through collaboration with top tech firms, increasing operational efficiency by 30%.

2. Led R&D for advanced navigational models, managing a team of 100+ engineers to implement computer vision solutions that enhanced real-time decision-making for aviation.

Strategic Partnerships and International Alliances

1. Built alliances with defense agencies across allied nations, overseeing multi-national technology projects to expand aviation and communication capabilities.

2. Managed the expansion of secure information-sharing programs with international partners, enhancing joint operational effectiveness and technology transfer.

Technology Modernization and Infrastructure Development

1. Led the migration to cloud-based infrastructure across defense systems, reducing operating costs by 25% and strengthening system resilience.

2. Spearheaded the development of secure communication protocols for aviation operations, coordinating a team of engineers to ensure robust, encrypted communications and real-time data integrity.

Why Yes:

• Highlights Seniority – Shows the highest title for the entire employment, positioning him as a senior leader.

• Focuses on Impact – Key projects capture attention and prove capability.

• Removes unnecessary information – Hiring Manager is unlikely to care about what your title was during a specific project.

  
  

Why Not:

• May be considered misleading - Would someone who just got promoted to CEO list 20 years of projects under the CEO title?

• Projects may not make sense - If you are VP of Engineering, and you used to be Director of Sales, would you list managing salespeople under VP of Engineering?

• No career progression - promotion is success. People may not know how many promotions there are between engineering and VP, hiding your success.

2. Group by Expertise Area

Since his roles covered multiple areas, another option was to group his experience by expertise—like “Leadership in Technology” or “Strategic Partnerships.” This approach shows his versatility across different functions without listing every role separately.

Example:

Lieutenant Colonel, Department of Defense, 2000 – 2024

Leadership in Aviation Technology

• Directed multi-million-dollar AI and hardware projects, enhancing aviation capabilities and managing teams across defense sectors to drive innovation in autonomous systems.

Strategic Partnerships and International Collaboration

• Established alliances with defense agencies in allied countries, leading joint technology initiatives to expand secure aviation operations.

Operations and Team Management

• Oversaw a team of 100+ engineers, implementing agile methodologies to boost project efficiency by 30% and accelerate deployment of secure communication protocols.

Why Yes:

• Broad Skills Highlighted – Grouping by skill showcases his range, which is valuable for executive roles. He can ensure subsections fit the executive skillset.

• Best when projects do not align well – If you are moving from the military to tech, usually projects won't map nicely but the skill set will.

  
  

Why Not:

• Confusion - without the context of the project, it's hard to know what you did.

3. Write More About Your Recent Experience.

Since his career is extensive, using a two-page format allowed him to dedicate the first page to his recent, relevant roles. Earlier positions could be summarized on the second page, ensuring they don’t take attention away from recent experience.

Page 1

Lieutenant Colonel, Department of Defense, 2020 – 2024

• Led a $450M hardware and AI initiative to enhance aviation capabilities, collaborating with global tech partners and boosting operational efficiency by 30%.

• Managed cross-functional teams, scaling from 50 to 120 engineers to drive advancements in navigational and secure communication technologies.

Director of Strategic Partnerships, Department of Defense, 2016 – 2020

• Oversaw international collaborations, leading joint aviation and secure communication programs with allied agencies to expand secure information-sharing capabilities.

Page 2

Various engineering and leadership roles, 2003 – 2016

• Spearheaded R&D for secure communication systems, ensuring robust, encrypted protocols across defense operations.

• Progressed through increasingly senior roles, building a strong foundation in advanced technology and team leadership.

Why Yes:

• Emphasizes Recent Work – Keeps his most relevant, senior roles on page one where they’ll get the most attention.

• Complete Work History – Page two provides a full timeline without cluttering page one.

• Honest and Transparent – Allows him to showcase his entire journey without losing focus on recent roles.

Why Not:

• Verbosity – by specifying multiple roles, you have to write something in each section, which can lead to unnecessary verbosity and emphasize less important information.

Takeaway: Structure for Clarity, Fit and Impact

When you’ve held multiple roles within one job, structure your resume with the hiring manager’s perspective in mind. Highlight your top achievements, focus on recent experience, and avoid letting early roles take the spotlight. By experimenting with these combinations, you can create a clear, compelling resume that tells your career story without clutter.

PS: Need more resume tips? Register to my email list at applicationowl.com