As someone who has worn the shoes of a hiring manager, my take for Imran’s career predicament are as follows:
Big Picture: The Singapore labour market is generally very unkind to PMEs. Most MNCs will start managing out employees in their late 40s and early 50s if they get stuck at mid managerial and cannot reach Senior Executive Level.
Another thing is many HR people have this idea that they need to hire someone with enough runway ahead, i.e. if they are hiring for a middle managerial or professional position, they want someone they think can move up to senior managerial level in 5 – 10 years. For a late 40s guy, they will only consider if you demonstrate you have potential to move up to top level positions in a few years.
Obviously the writer lands in a cold spot from a big picture point of view in terms of his age and his patchy experience.
Small Picture: For people who don’t wish to pursue the corporate ladder in people and functional management Marketing roles (i.e. don’t wish to become CMO, Director / VP of Marketing), the smart ones usually start to build up their personal branding earlier.
This means people must know you as a person more than the company you work for, i.e. when someone talks about the marketing activities of the VC, people must remember the author, Imran Johri, not the VC company.
From what Imran has shared, I have a feeling his so called “Head of Marketing” in a VC is a one or two man show in a small company, i.e. he wasn’t heading a well-established MNC’s marketing function with operations and headcount across multiple countries.
On the other hand, he didn’t seem to be aware of the need to build up his personal brand during his 5 year stint in the VC either. This much is obvious because if he had done so successfully, people would be looking for him either to freelance, contractual project if not make a permanent offer. The fact he was applying for jobs conventionally and attending interviews from company to company suggests he did not do so.
In summary, Imran’s current state is a combination of the nature of our labour market and also due to the lack of personal planning in his own career.