You've made it! Or at least that's the common perception. When you head home for the winter holidays, your relatives might finally understand you have a fancy title, but here's the reality: at our stage, titles don't tell the whole story.

So why does society place such value on leadership titles? It comes down to perceived power and compensation. But these aren't great reasons to take on a leadership role.

Leadership at an early-stage startup requires wearing many different hats. Some days you're the recruiter, some days the strategic thinker, some days you're building the thing itself, and some days the decision-maker for your entire function. If you can become great at all these things, then the score will take care of itself.

It's not a promotion, it's expanded responsibility

At Straddle, there is no such thing as a "promotion" that separates you from the work. Whether you have a team or not, you're taking on leadership responsibility while staying close to the output. This is intentional and reflects our stage.

At Straddle, compensation isn't just tied to whether you have direct reports. Leadership value comes from ownership of outcomes, not just management of people.

What does it mean to be a leader at Straddle?

Technically speaking, your role is to drive output in your domain—whether by doing the work yourself, through a small team, or some combination of both—and by establishing the processes and standards that will scale as we grow.

However, that's such a dry way of looking at it. Leadership is about ownership. You own a domain. You set the quality bar (through your own output or your team's). You make decisions that affect the trajectory of your function. You're building the foundation that will scale with the company.

Leadership is not for everyone. If you don't enjoy both craft/execution and thinking systematically about how work should be done, then it's probably not for you. And that's completely fine.

So why become a leader? We think there are two core reasons:

1. Finding joy in building the foundation for scale. You get to define how your function operates at Straddle. Every process you create, every decision framework you establish, every standard you set—these will outlast you and shape how your domain grows.

2. Finding joy in ownership and leverage. Whether you're achieving outcomes through your own work or through a team, you're responsible for an entire domain. This means making hard calls, representing your function in company decisions, and sometimes saying no to protect what matters.

As a leader, you have a responsibility to think beyond immediate output. You're building for the future while delivering in the present.

The paradox of leadership at our stage

The paradox is that the attitude that got you here isn't the attitude that will make you successful in this role. What made you successful as an IC? Probably some combination of hard work, domain expertise, and shipping quickly.

But as a leader, you can't just focus on your own output anymore. When you encounter problems, it's tempting to put your head down and solve them yourself. At Straddle, we call this "heroing." Sometimes it's necessary at our stage, but you need to ask yourself: "Am I building something repeatable, or just fighting fires?"

If you have a team, you have to balance your own output with developing others. If you don't have a team yet, you have to balance execution with building the systems that will support future team members. Either way, it's no longer just about you.

How leadership is different from management

The terms "leadership" and "management" are often used interchangeably, but they are actually two distinct things. In short, management is tactical and leadership is strategic.

Management requires dealing with the day-to-day realities of hiring and developing people, such as one-on-ones, performance reviews, coaching, etc. Leadership means looking forward, owning a domain, setting standards, making decisions, connecting dots, and representing your function in company discussions.

At Straddle, your role likely involves both—just in different ratios depending on whether you have direct reports. If you have a team, you're doing both management and leadership. If you don't have a team yet, you're primarily doing leadership work while preparing for eventual management.

Both functions are critical, but they require different skills.

Why you'll likely evolve (or get leveled)

Straddle is a startup that will scale with unnaturally high growth. As the company expands, it requires different types of talent. It's common for the company's growth rate to outstrip yours. When that happens, you might get "leveled": a senior leader with more experience is recruited above you, or you might choose to focus on a different aspect of leadership that plays to your strengths.

This shouldn't be bruising to the ego. Practically no one is capable of consistently scaling themselves at startup speeds. Rather than taking it personally, you should realize this isn't a zero-sum game. Adding experienced leaders will only give you more opportunities to grow and focus on what you do best.

There is only one way to delay or avoid being leveled, and that is through self-growth. It requires deep introspection, which means being honest with yourself about your strengths and weaknesses, seeking feedback, and being committed to improving.

Don't panic

This all might sound like a lot to take on, and it is! Being a leader at an early-stage startup means context-switching constantly and often doing multiple jobs. However, remember that every great leader started somewhere similar. With practice and the right attitude, you will figure it out. And Straddle will be alongside you, supporting you every step of the way.This handbook

Let's highlight the skills necessary to be a great leader before digging into each one in more detail throughout the rest of the handbook.