How to Become an Executive Headhunter

Editor at Better Headhunting

20+ years in executive search across software, games, and technology leadership

Two main routes into executive search

So, you want to become an executive headhunter? How do you become part of the industry? Most people enter the headhunting industry through one of two routes;

They join in an entry level role and spend most, if not all of their career in the headhunting industry. We might affectionately call these individuals “lifers”.
They join later in their career from a different industry.

The advantages of starting early

There are advantages and disadvantages to both approaches. Those who become an executive headhunter early in their career get the benefit of deep experience in the industry. By working their way up through the industry – usually with research roles providing a helpful entry point – career executive headhunters will usually have considerable experience to leverage by the time they reach the more senior level roles in the industry.

The downsides of starting early

There’s a lot of learning on the job in executive search as there is in any industry – knowing how to pitch different companies and roles, learning how to assess candidates across different functions, how to manage candidates and clients through processes and so forth. Challenging searches provide great learning experience, especially for relatively new headhunters.

The advantages of joining from industry

The downside of being a “lifer” when it comes to a career as an executive headhunter is that your experience, by definition, is fairly narrow. By always (or mostly) having worked in the industry throughout your career, it’s harder to have conversations with candidates and clients where you really understand and empathize with them compared to a headhunter who has worked in industry in a similar role. Furthermore, executive headhunters with industry experience may well have a useful personal network of potential clients and candidates they can leverage in the role.

The downsides of joining from industry

So executive headhunters from industry are likely to have impressive sector and functional knowledge in their area, as well as a useful network of contacts compared to “lifers”. There are, however, a few potential downsides in joining headhunting firms from industry. The first is that you won’t be sure that the industry is for you in the long-term. Make no mistake about it, headhunting can be a grind at times, and can create a lot of pressure and stress. You might be desperately looking for candidates in a tough market with a demanding client getting increasingly impatient for results. Executive headhunter roles are less about cocktail parties and more about thoroughly mapping markets for customers using tools like Linkedin. It’s much less glamorous in reality than many people from the outside might imagine.

The other major disadvantage to coming from industry is that it takes time to become familiar with how headhunting works – whether that’s research, candidate approach, interviewing candidates or winning projects. There is a learning curve for everyone new to the industry. The older and more senior you are when you start in the industry, the higher the expectations are when you join. Being a graduate researcher is one thing, being a Partner-level hire straight from industry with business development targets is another. Expectations can be high and difficult to meet due to inexperience. Furthermore, will “lifer” colleagues always appreciate a highly-paid new arrival with zero headhunting experience?

What the job is actually like

Executive search can look glamorous from the outside, but much of the work is quite process-heavy. The job often involves market mapping, identifying candidates, approaching them, interviewing them, writing candidate reports, managing client expectations and keeping difficult processes moving forward. Success in the industry usually depends not just on being personable, but on being organised, resilient and comfortable with repetition.

What makes a good executive headhunter?

Strong executive headhunters tend to combine several skills. They need curiosity to understand markets and roles, judgment to assess candidates, resilience to handle rejection and setbacks, and communication skills to build trust with both clients and candidates. Commercial instinct also matters, particularly in more senior roles where winning work and managing client relationships are a major part of the job.

Which route is better?

It’s not better or worse to come into executive headhunting early or late in your career – both have their pros and cons. Both routes into executive headhunting have clear advantages and disadvantages, and much depends on the individual. Starting early in the industry gives you the benefit of deep process experience over time. Joining later from industry can give you stronger sector credibility, more relevant functional insight, and a potentially valuable network of clients and candidates.

In practice, the better route is usually the one that best matches your strengths and motivations. If you enjoy the craft of search itself and want to build long-term expertise in the industry, starting early can be a strong path. If you already have meaningful experience in a particular sector or function and want to bring that knowledge into a client-facing search role, joining later can also work very well.

So it is not really a question of one route being better than the other in the abstract. The more useful question is what kind of headhunter you want to become, and which path gives you the best chance of getting there.