Middle skilled or new collar jobs, veterans, and the skilled workforce sit at the heart of this Dream Job Cafe conversation as host Larry Port talks with Emily Bose, managing director at Transition Overwatch. Emily works with companies and veterans through structured employment programs, retention support, and wraparound support that connect strong go getter people with employers who want to hire more veterans.

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She shares how recruiting can be really meaningful work, from placing a mechanic who totally changed the course of his life to helping veterans navigate military transition, tricky workplace communication, and promotions into the next level. Emily breaks down middle skilled and new collar jobs that do not always require a college degree, often pay well, and offer room to grow, especially in healthcare, manufacturing, aviation, and the skilled trades. She also highlights shift based work, flexibility, and how these jobs can help people build actual careers and even start their own businesses.

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👤 Guest Bio

Emily Bose is a managing director at Transition Overwatch, a startup that works with companies and veterans through structured employment programs and a retention program for the first one to two years of employment. She has been with the same company and the same CEO for about seven or eight years, starting in recruiting for manufacturing, where she placed around 90 people, including plant managers and roles from top to bottom in the organization.

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Emily talks every day with veterans about what they are trying to do next in their careers, their motivations, goals, and how programs can support that. She also hosts a podcast live on LinkedIn called the Emily Bow Show, talking about workforce things for the skilled trades and the next generation of skilled technicians.

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📌 What We Cover

• How Transition Overwatch serves two real customers, companies and veterans, through structured employment programs, wraparound support, clear growth paths, and optimized benefits, with program lengths of one to two years and average retention pushing three years.
• Emily’s path from radiology and working as a student tech to recruiting in manufacturing, placing about 90 people, touring plants, and getting excited about this skilled workforce and middle skilled or new collar jobs.
• Why recruiting can be really meaningful work, including the story of a mechanic found on LinkedIn who was stuck in a dead end job and moved into a higher level of responsibility, traveling and representing his company.
• Skills for recruiting and sales, like quickly building rapport, getting people to open up about what they are really looking for, asking clarifying questions, taking lots and lots of notes, doing follow up, communication, and thinking creatively about search terms, titles, and adjacent industries.
• A grounded explanation of applicant tracking systems as a glorified CRM and filtering system, how answers in applications can be disqualifying, and why recruiters want to help people get hired rather than act as an evil A T S gatekeeper.
• A clear picture of middle skilled or new collar jobs that do not necessarily need a college degree, may come with on the job training or technical and trade schools, help people earn while they learn, and lead to growth in areas like radiology, healthcare, manufacturing, and other skilled arenas.
• The reality of shift based work, overtime and shift differentials, weekend and night work, and how schedules can support flexibility for young moms, students, and people who do not enjoy sitting at a desk all day.
• Why these jobs are not dead end jobs, with pathways into more advanced modalities, management, instruction, operations, quality, supply chain, safety, cybersecurity, and other roles that support plants, factories, and data centers.
• The difficulty of military transition, including many moving parts, unclear fits in the civilian marketplace, different communication styles, and how structured support for one or two years helps veterans handle vague emails, tricky conversations, and promotions into the next level.
• High demand across aviation, air traffic control, automotive, heavy equipment, construction, transportation, and data centers for trades like boiler makers, HVAC, plumbers, welders, and technicians, especially as experienced workers retire.
• How many industries are intentionally trying to bring in more non traditional talent, creating more inclusivity, belonging, and welcoming cultures for women, people of color, veterans, and other groups in the skilled workforce.
• The strong connection between skilled trades and entrepreneurship, including Emily’s note that 28 percent of people who go into the skilled trades start their own businesses compared to around 8 percent of the general workforce, and how entrepreneurship can help people control their own destiny.

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🔗 Resources Mentioned

• Transition Overwatch
• Wall Street Journal article: “They are hot. Upwardly mobile jobs. Here’s why they are so hard to fill.”
• Emily Bose on LinkedIn
• The Emily Bow Show, live on LinkedIn, talking about workforce things for the skilled trades and workforce development across aviation, automotive, heavy equipment, construction, and more.