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The co-founder of Tier1 Coaching and Development, Inc, a small training and development firm, had to hire an entirely new staff after 10 years in business. Drew Nault was one of the first three on that new team, and he was hired into a newly created position that merged two different sets of operational responsibilities. Over time, Nault realized he was frequently asked to justify what he was working on and how it added value. This case provides an opportunity to critically examine an employee's struggles with job expectations and performance objectives in a newly created position within a small firm. What steps can be taken to address the job and career concerns? What exit strategy might be needed? Students also examine the employee's perceived psychological contract with his employer.