For the work-related expense deduction, you can't deduct expenses needed to qualify for a new position. The fact that you were hired contingent on providing your own training and were not previously a pilot means you can't deduct the cost as a work-related expense.
If you paid tuition to an institution of higher education that is accredited by the US Dept of Education, then you can apply the tuition toward the Lifetime Learning Credit, assuming you meet the other eligibility requirements for it. https://www.irs.gov/credits-deductions/individuals/llc
