Are there known techniques to transform features X classified as C to features Y classified as C'
This problem can be addressed from an Economics perspective, even with existing data and without complicated algorithms.  There is some existing research in the Labor Economics field about transferability of skills between occupations.  For example, this &quot;The estimation methods of occupational skills transferability&quot; paper: https://link.springer.com/article/10.1007/s12651-016-0216-y
There is one method it discusses, referencing another 2016 paper by Ormiston, that could be helpful to you.  It involves calculating &quot;the ratio of shared, standardized knowledge, skill and ability categories across occupations&quot;.
Here are some relevant excerpts:

It &quot;employs a “skills” approach by explicitly estimating the proportion of knowledge, skills and abilities (KSAs) utilized in occupation i that can also be applied in occupation j.&quot;
&quot;To estimate this proportion, it used data from O*NET – the U.S. Department of Labor’s occupational database – to examine the commonality of occupations across 120 standardized knowledge, skill and ability dimensions.&quot;
&quot;O*NET examines each occupation and measures each component on the level (0–7 scale) of proficiency needed to function within the profession and the importance (1–5 scale) of each component to the occupation; multiplying these values together generates a comprehensive score, $S_{im}$ , for each component m of occupation i.&quot;

There is a formula given that

&quot;estimates the skills transferability across 500 occupations based on the three-digit occupational codes and then aggregates these transferability estimates into 22 occupations in the two-digit level by taking the arithmetic mean within each two-digit category for the comparison with Shaw’s skills transferability. As a result, this study derives the 22 × 22 occupational skills transferability matrix based on two-digit U.S. census code, representing the estimated proportion of occupational human capital transferability.&quot;

There is an example given:

The data indicate that HR managers can apply only 16.01 of their 19.68 points utilized in their current profession into a new role as an industrial engineer. However, given differences in occupational skill portfolios, HR managers could apply all of their required knowledge in engineering and technology (1.03 points) and sales and marketing (5.99) in a new position as an industrial engineer. Summing the amount of shared points between occupations i and j (23.03) and dividing by the total points employed in occupation i (26.70) results in an estimated transferability rate of 86.30 % (t ij  = 0.863).

You could use this data and methods to then figure out the areas where someone's skills are lacking and make recommendations from those findings.