How you, as a young entrepreneur, should go about making a senior hire


As you’re going about building your company as a young entrepreneur, you’re going to reach a point where you need some experienced folks. It’s inevitable. Experience can mean different things to different people, but just for simplicity's sake, I mean someone who is relatively much older than you and is going to do something which you or your team don’t have much of an idea about/experience in.

What can you do in such a situation? And how do you go about it? Here is something that my co-founders and I have learnt through our experience with Belong and prior to that ExotelPracto and Grey Orange.


Like it or not, we’re living in a candidate driven market. This is 100x more true if you’re a young start up. In this era, we need to move beyond a job description and have a candidate description or a persona.

A persona talks not just about functional skills, but also about other factors like what should this person be like: traits and suchlike. While you can put out a JD on the site, internally, you definitely need to have a persona that you can turn to when evaluating candidates (more so, when it's a senior hire).

Infact, in reality we’re not looking for a CFO or VP Engineering or VP Ops. We’re looking for someone like Amit, or Irfan or Jessica (or whoever it is that we’re bench marking against).

Approaching them

Sourcing is the top of the funnel. The success of this determines the success of the rest of the funnel. Some of the ways to approach a senior person:

  • Ask to meet them for advice on how you should think about this role or maybe the function itself. If they’re good (and excited by your vision), you can then suggest to them, why not speak to us? If it doesn’t work out, it saves you the awkward situation.
  • Go via a mutual trusted connect. More often than not, it’s not that hard to find a common friend/acquaintance
  • In the monthly mail that you send to your advisors/well wishers (I hope you do!), do regularly ask for recommendations. Do ask for the same thing to other founders who are at a further along stage in their company’s journey.
  • Ask other ecosystem players who might get to see a lot of folks. For example for a CFO, makes sense to ask folks working at Big 4 since they interact with a lot of CFOs.
  • Plain old search. Ramp up those boolean strings.

Get an interview panel ready

If you current team isn’t adequately qualified, have a panel ready via friends from other places who are capable/relevant. In our case, if we’re looking for senior engineering talent, we’ll probably involve some of our grey haired friends from Exotel, Successfactors, Yahoo or Microsoft. Or you can look at something like an aircto, not sure if they have super senior folks to interview, but you get the idea.

Go apeshit on reference checks

You might disagree on the number. For example some people think that 6–7 ref checks, which is really the minimum we’d do for a senior hire, most likely more, is a tad insane. But the idea is most likely if you’re hiring someone super senior (like a CFO, or a Head of Operations or VP Engineering), it’s probably a role that’s super critical and you don’t have much of an idea about what would make for a great candidate (beyond the culture rounds). Reference checks help give comfort in this case to check for functional skills, people management skills etc.

Here’s a nice list of questions to ask during reference checks here.

Just be careful that with reference checks, it’s important that you balance it out. Most likely, there will be some dirt emerging and you have to try to remain unbiased and look at it as something which you can work with (say bad temper) vis a vis something which is non negotiable (say ethics)

Get your core team to meet this person and get their buy-in

Every leader (& more so for senior folks) has to ultimately command respect, not demand it. Your core team (who are also young) have to be able to respect or feel they can learn from this person.

The young folks in your team, if they’re smart and ambitious like you, will want to be taken seriously by this potential candidate. Often, your team members will know something about the business better than anyone else. Anyone new joining the company should have the ability to respect that.

Always have atleast 2 folks you’re talking to. Ideally more (atleast 3–4 serious candidates)

You need benchmarks for comparison. Otherwise, it becomes too ambiguous. Also puts you, the entrepreneur in the drivers seat and helps create urgency in the mind of the candidates as well as lets them know that you’re serious.

Have patience and start early

It’s going to take time. Deal with it.

Start early. I can’t stress this enough. More often than not, when you start having that first tingling feeling that you need an experienced hire, you might tell yourself “maybe we’re too early”. You’re not. Since it will take time to find the right person, better start early.

We did this with our CFO, our Chief of Staff and many other roles and in hindsight these were all excellent decisions.

Would love to hear your views on how it’s worked out for you as a young entrepreneur trying to hire someone very senior for your team. Hit me up on to share your experiences, would love to hear.

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