What is a Senior Autonomous Leader and why they should be your first senior hire

February 19, 2024

August 25, 2022

Before you raise money, you’ll be doing everything. As Mark Suster says, “doer of all tasks” is an early-stage founder’s most accurate title. You need to be hands-on during the early days. If you hire a Series A team too early, you’ll burn through money with subpar results. But, if you keep your early-stage team and don’t ever add to it, at some point you’ll break. 

Once you’ve raised money, you need to start delegating. What has gotten you from point A to B won’t be what gets you from B to C. If you have a team largely made up of high-slope people and have just raised your first money, you probably need to hire a Senior Autonomous Leader.

A Senior Autonomous Leader is someone you can delegate important projects to AND know they will do an amazing job.

TL;DR: Hiring and delegating to Senior Autonomous leaders can unlock your growth

  • Senior autonomous leaders are senior hires who deliver high-quality work, have good judgment, and work well with you 
  • You trust that you can delegate important work to senior autonomous leaders, and they free you up to work on the stuff only you can do
  • If you control everything while you try to scale, things will break down
  • Hire senior executives based on their competencies, cultural fit, and potential to grow with you
  • Write down what you’re great at, bad at, and what you like and don’t like doing to help you decide what you need to hire a senior leader to do 
  • Hire executives who are as good or better than you at what you’ll be delegating to them
  • Hire with the next 12 months in mind

If you hold onto control over everything, things will break down 

Founders, especially first-time and underestimated founders, often hold onto control of every decision in their startup for too long. Raising funds might be an early signal that you’re on the right track but it also changes the game, and you need to level up to succeed in the new game you’re playing. Founders are the most valuable resources to a startup, and leveling up means you need to hire people who can get things done and provide you leverage so you can spend more time on the things only you can do.

You need to hire a senior autonomous leader whom you trust to deliver high-quality work, have good judgment, and work well with you. Senior autonomous leaders give you the leverage that you need.

If you cling to control over everything in your startup for too long, things will start to break down. As top solo VC Elad Gil says, “Things will initially seem to just truck along as usual, and then suddenly everything at the company will break at once. Most, but not all, of this breakage is avoidable, but most first-time founders screw it up.”

If you remain the “doer of all things” as you try to scale, you’ll start to notice these common signs that things are about to collapse:

  1. Most of what you do is reactive. You feel like you’re always a step behind 
  2. You don’t have time to finish the important things 
  3. You feel like you don’t have time to think
  4. Things start moving slowly because you’re the bottleneck on all important decisions
  5. You’re stressed and showing signs of burnout

Suddenly, things will start breaking all at the same time. Your team will be overwhelmed and unhappy with you, your customers will be frustrated with your product, and you’ll be frustrated with your own performance.

At this point, founders realize they need to hire someone who can help get important things done. They slam on the breaks, flip all their attention to hiring, and message me saying “we urgently need someone to start ASAP.” Usually, they’re right. 

In most cases, extreme urgency to hire leads founders to hire the first person they think might be able to do the job, and skip important recruiting steps like knowing what you really need to hire, planning where to find top talent, interviewing well, working with the candidate, and referencing candidates. Sometimes you’ll get lucky and the person you hire will be great in the role. However, more often, you’ll hire someone who turns out mediocre, or worse, you’ll have to fire them and rehire for the role. 

Messing up important hires can be a death spiral. The good thing is that if you are proactive about bringing on key senior hires, you can avoid this worst-case scenario.

Delegating to Senior Autonomous Leaders helps you grow faster and avoid breaking down

Founders often don’t delegate because:

  • They feel like nothing will get done if they don’t do it
  • They don’t think their team is good enough to delegate to
  • Controlling everything has worked so far, why fix what’s not broken?
  • Their startup is their entire identity, and they are worried about someone else making important decisions

VCs invested in you because they think you can build a business that scales 10-100x. An important part of being able to scale is hiring and retaining top-tier talent that gives you leverage. You need to transform from just a doer to being a doer and a leader. Detach your company’s growth from your personal capacity.

Delegating important tasks and projects to someone else doesn’t mean that you won’t be involved in anything, it means that you don't have to be involved in everything. Hiring a senior person allows you to do less and finish more. As Mark Suster says:

Do less. And do the things that you ARE doing better and with higher quality. Have a shorter to-do list with more things that are in the “done” category.” 

The qualities to test in Senior Autonomous Leaders: Competencies, Culture, and Potential

When top executive search funds recruit for executive roles, they evaluate candidates using three main criteria: 

  • Competencies: The skills the candidate needs to do the job well today 
  • Culture: How well the candidate matches your mission and fits into your team 
  • Potential: The candidate’s ability to grow and handle more responsibility in the future

Regardless of the specific role, all Senior Autonomous Leaders share key qualities across the “competencies, culture, potential” framework. Common traits include:

Competencies: senior autonomous leaders are:

  • Experts in the area they are leading. 
  • They should be at least as good as you are at the function or part of the company that they will lead
  • Autonomous leaders who take ownership over a part of the business. 
  • They keep you in the loop with the important stuff but don’t need hand-holding. They are good people leaders. They can build, manage, and ideally develop a team in their function
  • Results focused. 
  • The right scale for where your company is today. 
  • Don’t hire someone who has only worked at companies 10x your size or 1/10 your size. 
  • Strong communicators. 
  • They effectively work with you, their team, and other leaders in the company.
  • Thought partners for you. 
  • You can have strategic conversations with them about the mission and direction of the company

Culture: senior autonomous leaders:

  • Are company-first. They are aligned on the mission of the company and are more focused on the company goals than their individual goals. 
  • Develop the B players on their team and empower their A players to take on more ownership

The shared qualities in Competencies and Culture are table stakes that senior autonomous leaders need to have to be successful. The best senior hires also have high potential:

Potential: the best senior autonomous leaders:

  • Have the qualities of high-slope people. They are curious, have a bias for action, are self-motivated, and finish what they start.
  • Grow with the company. You hire them for the leverage they can give you day 1, but they show they can take on more as the company grows. 

Senior autonomous leaders are competent, which allows you to trust that they’ll produce high-quality work. They are cultural fits and cultural adds, which allows you to work well together and trust in their judgment. They have the potential to grow with you, so they can be a thought partner for you over time.

How to know which senior hire to make 

You raised your first money and you want to avoid things breaking down. You want to hire one senior person but are unsure what role to hire for. 

Every founder is different and every business is different. When I work with a founder, or co-founders, making their first big hire, I ask 4 questions:

  1. What are your best talents? 
  2. What are you weak at?
  3. What parts of the job (be as specific as possible) give you energy? (or, what do you like doing?)
  4. What parts of the job (be as specific as possible) drain your energy? (or, what do you not like doing?)

Answer these questions and put them into a 4-quadrant graph that looks like this: 

This simple activity makes it clear what you should be, and just as importantly, what you shouldn’t be, spending your time doing: 

Quadrant 1, things you’re great at and that give you energy: This is your sweet spot. Keep doing all of these, and try to spend as much time here as possible

Quadrant 2, things that you’re not good at and that give you energy: This is the easiest place to waste time. Offload the tasks in this box to someone on your team, or hire a senior leader who can do them.

Quadrant 3, things that you’re not good at and drain your energy: You should spend zero time on these tasks. Hire someone who can do this.

Quadrant 4, things that you’re great at and drain your energy: You’re never going to be 100% optimized in quadrant 1. You need to keep doing these things at an early stage. Maybe down the line, you can find someone who is just as good or better than you at these things who you can hire or offload to. 

The first Senior Autonomous Leader you should hire should be doing the bulk of their work in tasks that fall into your quadrant 2 and 3. Here are a couple examples of how to use your quadrant to decide on who to hire:

  • (Quadrant 2) You love managing Product but you’re average at it. You excel in telling the company vision to the team, but you’re a lousy product lead. Hiring a senior person to lead Product will help you focus on the stuff you’re best at, while also allowing someone great to lead, and unlock potential, in product.
  • (Quadrant 3) You hate all things admin and finance. You’ve had to manage all of it up until now, but you usually put it off until the last minute. Hire someone, usually a finance lead or controller type, who can make sure the ship runs smoothly and to whom you can offload the stuff you don’t like and aren’t good at. 
  • (Quadrant 4) You don’t like fundraising at all, but you’re good at it and the only person who can do it at this stage. You can have some people on the team help you during the fundraising process, but, at least for now, you need to own it. 

Try to spend as much time on the things that only you can do. As former Chairman and CEO of Adtalem Global Education Lisa Wardell says, “If you’re doing something that others on your team could do just as well, you’re just wasting your time.”

Don’t confuse this advice for going crazy and hiring an entire C-suite once you’ve raised a seed round. You need to prioritize what is most important. Start by picking one key senior hire you can make that will have the biggest impact on your company today. 

Recruiting for your first senior hire 

You know you need to hire someone senior, but you’ve never done it before, and you don’t have a head of people yet. Your company is small and relatively unknown to top talent. 

Just as building market awareness for a new product is hard, building awareness of your early-stage startup to top talent is hard. Our recommended steps to reach the best candidates and have a chance at hiring them are:

  1. Answer these 14 questions before you start recruiting for the role.
  2. Build a Work With Us page to show, rather than tell, what it’s like to work at your company. The best talent can work anywhere they want, so you need to stack the decks in your favor to have a chance at getting them to join your mission. 
  3. Build a quick recruitment roadmap to figure out what candidates you want to talk to.
  4. Use your network, your investors, and your existing team to help source candidates so you have multiple data points and candidate options to choose from.

Hire for the next 12 months to avoid hiring mismatched candidates 

When hiring executives, think only about hiring for the next 12 months. I like using Brad Feld’s general rule when looking for the best candidates:

“If you are a CEO who is interviewing for a new member of your leadership team, ask the person you are interviewing if they have ever been in the same role as a company that grew from size -50% to +200% of yours.” - Brad Feld

So if you have a team of 30 people, look for people who have been at a company that grew from 15-60 people. If you have a team of 50, look for someone who has been at a company that grew from 25-100 people. 

Use this as a guideline, not a hard and fast rule. In Latin America, fewer people have helped scale a startup once or twice before than in the US. And remember, not all scaling is created equal. You’d much rather hire someone who has led smaller but more sustained growth than someone who believes you need to 3x your team to 3x your top line. Team size can often be unrelated and sometimes even inversely related to company success. 

Common mistake: don’t hire a Series B person for your Seed startup

Say you have a couple hundred thousand dollars in annual revenue today and you just raised a seed round. You and your investors think you can eventually grow to $10M in annual revenue. 

You know you need someone to lead sales. A friend of yours knows the head of sales at a company in your industry doing $10M in revenue. Your friend tells you this head of sales is looking for a new role and “you need to hire them!” While hiring this person can work, most of the time it doesn’t.

Don’t skip steps.

It’s great that you have lofty expectations. But getting from a couple hundred thousand USD in annual revenue to $10M is not getting from a→b. It’s more like getting from a→z. 

The head of sales at the big company might be a great hire for when you get to z. But first, you need to hire someone who can take you from a→b, and hopefully b→c. Don’t skip steps and overhire. 

Companies often overhire, resulting in what I call organ rejection: the company rejects the leader because the leader has no idea how to manage a smaller team with fewer resources. The head of sales from a bigger company is probably used to having a team of 40+ people, and unless they have grown a company from the earliest stages before, they probably don’t have the skill set to do what you need. 

To avoid making organ rejection hires, I recommend hiring for the next 12 months. Hire someone that you know can get you where you want to be in 12 months. Answer these 14 questions and you’ll know what that is. Don’t hire for future potential problems, hire for today’s real problems.  

Hiring more senior autonomous leaders as you scale

While the focus of this article is on how to decide and make your first senior hire, I often get questions from Series A companies about bringing in more senior talent versus promoting from within. Every case is different.

While you want to promote your high-growth people, a common problem that startups make is over-promoting your best do-it-all team members into leadership roles that they are not ready for. This is the Peter Principle, promoting your best employees until they’re in a role that they are bad at, leaving you with a company full of people who are incompetent in their roles. 

As former Google and Stripe executive Claire Hughes Johnson says in her book Scaling People, it is your job as a leader to “retain high performers you might be tempted to promote into management when you recognize they could be much more effective in non-manager roles”

Give your best high-slope people more opportunities, but keep in mind that different skill sets are necessary for different roles. The analyst you hired 4 years ago, who excelled and was promoted several times, might now lead a team of 10. However, the skills needed to manage a team of 10 won’t overlap much with the skills that first got them promoted. You need to judge if they will be able to do well in the new role before you promote them to it. When the person is able to keep growing and excel in their new role, it’s a huge win for your entire team and culture.

In all companies, hiring vs promoting internally is a balance. Your team will continue to grow and expand. Some of your longest-tenured people will continue to get promoted and grow with your company. You’ll also have to hire several senior executives who are experts in a specific domain and can take you to the next level. You’ll even have to periodically review if you are in the best role to push the company forward. Each of these decisions are difficult and nuanced, but incredibly important. At Magma, we help portfolio companies through this process, but by using tips in our People guides, you can stay on top of your team, and make better people decisions. 

Build your early-stage team the right way with select senior hires

Building a great early-stage team is all about having a high output/team member multiple. The two types of team members to hire, identify, and retain in early-stage startups are:

  • High-slope people who seize opportunities within your startup and grow fast, and
  • Senior autonomous leaders who you can delegate important work to who you know will do an amazing job

The bulk of your early-stage team should be high-slope people who are young, smart, and can help you grow. But once you raise your first money, you need to start thinking about hiring a Senior Autonomous Leader who you can delegate to with confidence that they’ll do a great job. Hiring these two types of team members helps you execute, recruit, uplevel the rest of your team, and fundraise

Understand that your team is constantly evolving, just as your company is. One of the most important jobs you have as a founder is building and retaining a great team. Use frameworks like the A, B, C player framework, Danny Meyer’s 4 Types of Employees, and Keith Rabois’ Barrels and Ammunition to keep the pulse of your company. 

Always try to hire the most high-impact people you can. Build a strong recruiting and interviewing process so you don’t make avoidable mistakes, and remember that hiring the right people at the right time can make all the difference for your startup.