From time to time, my network reaches out for guidance on job searches. Often, these requests come from individuals who have spent months diligently searching for a new opportunity without success. It is not surprising that most of these individuals belong to my generation: the Baby Boomers.
A Call for Help
This week, I received one of those calls from Jack, whom I have known for over twenty years. Jack is among the last of the Baby Boom generation and could easily be mistaken for a Gen Xer. He has enjoyed a solid career and gained valuable experience, including serving as Chief Marketing Officer at several restaurant companies. However, his tenure at his recent jobs has been relatively brief. Jack has been searching for a new position for 6 months. Frankly, I am surprised he had not reached out sooner.
Seeking Guidance
Jack shared with me his struggle to understand why finding a full-time job has been so difficult. Someone had advised him to speak with a coach to improve his interview skills, but the $ 500-per-hour fee made him hesitant to pursue that option. Jack called me for a second opinion, and I asked him to provide full background of his situation.
Jack’s Situation
Jack is six months into his job search and has participated in approximately fifteen interviews. He is seeking a senior-level sales and marketing position and is open to various industry segments. His approach has been traditional, focusing on emerging companies that are inherently volatile. As empty nesters, he and his wife have flexibility regarding job location, though his preference is to stay at their current residence. Jack’s main concern is that he is not connecting with millennial hiring managers. He believes improving his interview presentation will help address this issue.
Marketplace Situation
Without a doubt, the current market is challenging for senior-level professionals, particularly for Baby Boomers. Ageism presents a real obstacle. Most hiring managers are millennials who harbor concerns about Baby Boomers’ energy and drive, technology proficiency, and ability to relate to younger staff and customers. Fortune 500 companies are generally uninterested in Baby Boomers unless they are prominently recognized in their field. These companies prefer younger professionals with the potential to grow with their brand, even though the average tenure currently stands at two to three years. Changing companies to elevate one’s career level has become the favored strategy. For Boomers, the most viable opportunities exist with smaller, emerging companies, though these roles carry greater risk and offer lower compensation.
MY RECOMMENDATION
Many senior executives have successfully navigated today’s challenging job market by adopting a flexible approach, such as offering a 1099 consulting contract. This arrangement allows the hiring manager to evaluate a candidate’s skills and fit without the risks associated with committing to a long-term hire. From the hiring manager’s perspective, the biggest concern isn’t just poor performance; it’s the financial and legal consequences of making a bad hire, including potential litigation and severance costs. By proposing a 1099 contract, candidates demonstrate an understanding of these risks and position themselves as low-risk, high-value options.
The advantages of a 1099 contract are clear. It gives both parties the opportunity to test the working relationship, assess performance, and ensure alignment before making a full-time commitment. This “try before you buy” model minimizes legal and financial exposure for the employer, while also allowing the candidate to showcase their abilities and gain valuable experience. If the arrangement proves successful, it often leads to a full-time offer. For example, an executive I know accepted a 1099 consulting contract with a mid-sized tech company. After delivering strong results and building trust, he was offered a permanent leadership role within three months.
However, there are potential drawbacks to consider. The candidate may forego employee benefits and job security during the consulting period and must ensure the contract complies with IRS guidelines. Still, proactively addressing the hiring manager’s risk assessment demonstrates professionalism and adaptability—qualities highly valued in today’s marketplace. By presenting themselves as a solution to the employer’s concerns, senior job seekers can stand out as reliable, low-risk hires, increasing their chances of securing the right opportunity.I believe this strategy is so important that I created ITB Partners, a platform designed to support candidates pursuing this path.
In summary, Baby Boomers seeking full-time employment must modify their job search strategy to consider the hiring manager’s risk assessment. Offering a consulting contract is a viable option for validating one’s viability without committing to full-time employment. Understand, the candidate and the hiring manager must fully understand the Federal Guidelines to be considered an independent contractor.
I appreciate your interest in ITB Partners. For further information about ITB Partners and its Value-Added Strategy, please visit our website at www.itbpartners.com, or contact Jim Weber.
Jim Weber – Managing Partner, ITB Partners
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Jim.Weber@itbpartners.com