When Is the Right Time In Your Career To Take a Step Down In Title?

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After 7.5 years of being the VP of Sales for Next Caller – a Y-Combinator backed technology company based in New York City focused on enterprise contact center fraud and authentication – I decided to take a leap of faith on a Director-level opportunity with budding Artificial Intelligence superpower Cresta.ai. Why is that?

It might seem taboo in your career to take a proverbial “step back” in your title – it feels like you might be going backwards. After all, we are taught to fight to climb the corporate ladder and earn promotion after promotion, earning more and more money along the way. But sometimes it can indeed be a very good thing for you in your career. It just depends on the circumstances. What are the things you should look out for when making that assessment? I outline a few suggestions below.

  1. Growth Opportunity

A title is exactly what it is: a title. It does not define who you are and how good you are. Being a VP in one place could be the equivalent of being a C-Level officer in another place. There are different skillsets required to perform different tasks depending on their size and growth-stage.

The point here is that what you really need to focus on in your career is constant betterment. Quite simply, if you are not getting better, you are wasting your time. If you are a leader in an organization, for example, and you have never done the work functions that your subordinates perform on a day-to-day basis, you are going to struggle in getting through to them. For one thing, they will likely respect you more if they understand that you were once like them. For another, you often learn by doing. So sometimes you need to get your hands dirty in order to be a better leader.

In my case, it is as simple as being surrounded by top-notch sales talent. It is one thing to be the guy in your organization who is responsible for bringing in all revenue. With that comes great power and great responsibility. But if you want to be pushed, you need to be surrounded with friendly competition and other like-minded individuals who you can bounce ideas off of. All this to say, if you perceive that taking a step back will actually allow you to hone your skills in a way that allows you to be better at your craft – and a better leader in the future – then you should strongly consider that option.

2. Unique Opportunity

Sometimes in life you come across an opportunity that is too good to be true, and you know it when you see it. It might be a company whose vision you adore for personal reasons. Or maybe it is a technology you strongly believe in based on what you know about the market. Or maybe they have an amazing set of founders or investors. Maybe it is all of the above!

When you believe in something strongly enough that you just want to be a part of it, you need to put your ego aside and follow your passions. You only live once, as they say, and there is nothing more powerful for the human mind than acceptance. And when you are part of a team with shared values towards a common mission, that is the pinnacle of acceptance.

Not to get too existential, but we do not know why we are here and what our purpose is. All I know is that I want my life to be as happy as it can be. If you have to choose between sacrificing your happiness for an artificial measure of worth, you should opt not to make that trade.

3. Role & Responsibility

Sometimes titles are not necessarily a reflection of ability and more so a placeholder for specific roles and responsibilities. In the sales world, there is staunch differentiation between sales leaders who manage individuals, and individual contributors who go out and close new business. Occasionally, you come across hybrid roles, or what I affectionately refer to as the “player/coach.” However, those roles are few and far between, often found in early stage companies, and the model is swiftly abandoned once said company reaches enough critical mass to begin scaling its operation.

In the sales world specifically, it is common for top individual contributors to out-earn their boss year-over-year. The sales leader usually assumes a higher equity position with lower year-over-year upside. The idea behind this is that the leaders in the organization will be made whole if they can successfully lead the company to success down the road.

What this means is that sometimes there might be legitimate financial motivations or other motivations related to roles and responsibilities that behoove you to take a proverbial step down in title. If you do not enjoy the functions of leadership as you get higher in an organization or if you are in a stage of your career where you require a certain type of upside or stability, these are all factors that would weigh into your decision-making.

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