Guide to Executive Hiring for Your Startup

Smiling businesswoman shaking hands with businessman.

Startup founders and co-founders are tasked with assembling a winning team to help them build and grow their startups. One of the most important early milestones in achieving this is hiring your first executives.

Hiring executives for your startup can be a frightening process. What roles should you hire? When should you begin recruiting? Should you outsource these roles or this process? How do you build a great startup team? In this guide, we’ve got you covered.

What Is Executive Hiring?

Executive hiring simply refers to identifying and recruiting executives to join your startup’s leadership team.

In a startup's earliest days, founders and co-founders usually take on the majority of management and leadership roles in the company. However, once a startup begins to grow, founders and co-founders have less and less bandwidth to take on all of the responsibilities of the organization. That’s when they need to consider adding executives to their startup leadership team.

Executive Roles

So, what executive roles will you need to fill? That all depends on the industry that your startup is in, your business model, and the stage of the startup.

There are a number of roles that you will find in most startups. These include:

That’s not to say that all startups need every role. For instance, non-tech startups probably don’t need a Chief Technology Officer. Nonetheless, in most startups you will find the need to fill most of these functions.

There is no magic formula for determining the makeup of your startup’s leadership team. In the early days, founders and co-founders take on most of these roles. However, as growth allows and the startup’s needs demand, founders and co-founders will need to begin considering hiring executives to help lead and grow their startups. 

CEO

The chief executive officer, or CEO, is the leader of a startup. Often the visionary of a company, the CEO is primarily responsible for overseeing the overall operations of the business. As the highest-ranking executive within a company, the CEO is the leader of the startup team and the top decision-maker.

CEOs are responsible for the organization’s direction and strategy and for implementing the company’s short and long-term plans. CEOs of startups are often deeply involved in all aspects of the organization, from designing and building the product to acquiring users and making sales.

In many cases, a founder or co-founder of the startup is tapped to serve as CEO. This usually makes sense, as they have likely been serving in the role of top decision-maker since founding the startup. However, founders are often the inventors, and the person who invented a product or service is not always the best person to manage a company over the long term — nor do they always want to.

Skills to Look For:

  1. Vision: A CEO needs to have lots of ideas. They need to see and understand the big picture and be able to convey that vision to others. CEOs are also passionate about their ideas, and it’s this passion that helps them sell their vision to others.
  2. Expert Decision-Making: A CEO needs to be comfortable with calling the shots. To do so, they need to understand the startup inside and out and maintain a close eye on trends in the industry, the market, and the competition to guide the company successfully.
  3. Execution: A CEO needs to be able to get things done. Not only do they have to make decisions, but they must also be able to carry out those decisions in enacting the startup’s strategic plan. CEOs should be natural leaders who can rally the team around a common goal and push the startup toward that goal.

COO

A chief operating officer, or COO, is the executive who oversees the entire startup’s operations including the day-to-day management of the company. The COO acts as an extension of the CEO to take things off their plate. The COO reports to the CEO and is a part of the C-suite or executive team. 

The COO is responsible for supervising the startup’s operations. Although the specific roles and duties of a COO may vary greatly depending on the type of startup, COOs are tasked with turning the strategic vision and plans of the startup into action.

Often, a founder or co-founder of the startup will serve as COO. When a startup has co-founders, this is likely the role one of them has been filling since joining the startup. This is often the first executive hire when a startup doesn’t have co-founders.

Skills to Look For:

  1. Strategic Thinking: A COO needs to be an expert at strategic thinking. It is up to the COO to turn the startup’s vision into strategy and strategy into profitable operations. A great COO should have the experience and ability to think strategically and make data-driven decisions. 
  2. Problem-Solving: A COO needs to be an expert problem-solver, ready to develop solutions for events and circumstances that are both predictable and unpredictable in nature. A great COO understands the company inside and out, is adept at coming up with and evaluating alternatives, and can proceed with the best possible solution. 

CFO

A chief financial officer, or CFO, is the executive who is in charge of a company’s finances and financial activities. The CFO reports to the CEO and is also a part of the C-suite or executive team. 

The CFO is responsible for establishing and standardizing systems for processing business transactions, bookkeeping and accounting, and financial reporting. CFOs track cash flow, set up systems for compliance and control, and work to automate these processes.

In addition to overseeing accounting and reporting, a CFO is also instrumental in guiding firm strategy. The CFO usually works closely with the COO and other members of the executive team, providing financial planning and analysis, guidance on funding, and strategic input and recommendations in developing firm strategy.

Skills to Look For:

  1. Financial Aptitude: A CFO needs robust accounting and financial knowledge along with the business acumen to assist with the financial and strategic planning within a startup.
  2. Strategic Thinking: A CFO should be able to think critically and have a problem-solving mentality. Good CFOs can look through the numbers and contribute to developing the vision and long-term financial plan for the startup.

CMO

A chief marketing officer, or CMO, is the executive who is responsible for the startup’s marketing (and sometimes sales) efforts. They are the voice of your startup's brand. Like other startup executives, the CMO also reports to the CEO and is a part of the C-suite or executive team. 

CMOs are responsible for driving revenue and growth through marketing and sales. CMOs develop brand strategy and positioning, plan marketing campaigns, and manage advertising budgets. The CMO will also often lead efforts into customer feedback, research, and product development.

On top of advancing the startup's marketing efforts, the CMO also works closely with the CSO and sales team to propel lead generation, customer acquisition, and customer engagement and retention.

Skills to Look For:

  1. Marketing and Communication Expertise: A CMO needs a deep understanding of marketing and communication. They need to be able to set a direction for the startup’s brand and tell the startup’s story in a way that customers respond.
  2. Customer-Centric Thinking: A CMO should also be able to put themselves in the shoes (or minds) of the startup’s customers. This includes the ability and know-how to conduct and analyze customer research in order to guide the startup’s branding, messaging, and product development.

CSO

A chief sales officer, or CSO, is the executive that is the head of a company’s sales-related activities- charged with the mission of selling your startup's product or service. They are the hustler of a startup. The CSO reports to the CEO and is a member of the C-suite or executive team. 

The CSO is responsible for establishing and leading the company’s sales division. In startups that are just entering the market or ramping up sales, the CSO may need to recruit and build the sales team. Once built, the CSO often directly manages the VP of Sales and other sales managers and oversees the sales team.

CSOs are also responsible for overseeing the planning and implementation of the company’s customer acquisition and sales strategies, developing effective sales tactics, forecasting sales and revenue, and driving revenue growth to meet sales and revenue goals. 

A CSO collaborates closely with other executives, including the CMO, to propel lead generation, customer acquisition, and customer engagement and retention and the CFO to forecast sales and revenue. 

Skills to Look For:

  1. Sales Expertise: A CSO needs to have a deep understanding of sales and sales leadership. Ideally, they have experience selling within your company’s industry, sector, product type, or sales channels. They also need to understand your company’s customers and develop efficient sales strategies to sell to them.
  2. Customer-Focused Strategies: Like a CMO, a CSO should also be able to engage in customer-centric thinking. They will need to be able to put themselves in the shoes of the startup’s customers. This includes the ability and know-how to conduct and analyze customer research in order to shape the company's sales strategies.

CTO

A chief technology officer, or CTO, is the executive who spearheads the startup’s technology and innovation efforts. They are the company’s innovator. Again, the CTO reports to the CEO and is a part of the C-suite or executive team.

The CTO is a leading voice in the technological direction and vision of the company. CTOs help build the development or engineering team, define the technology stack, and are responsible for all aspects of the technology development process. 

The CTO often collaborates closely with the CMO, CSO, and CPO on a startup’s customer-focused development efforts, such as conducting customer research, soliciting feedback, organizing focus groups, and administering user studies.

Skills to Look For:

  1. Technologically Savvy: A CTO needs to be technologically savvy. CTOs are responsible for building the technology team, choosing the technology stack, and all aspects of the tech development process. They must understand the technology better than anyone else in the company.
  2. Big Picture Thinking: A CTO should also be a big picture thinker. Startup CTOs are responsible for setting the long-term technological vision for the company and need to be able to visualize the end result. Big picture thinkers also usually have great creative vision, helping CTOs foresee where the industry, market, and technology is headed.

CPO

The chief product officer (CPO), often known as the head of product, is the executive who heads up a startup’s product development and production. They are the company’s builder or creator. A chief product officer is to a company’s product what a chief technology officer is to its technology. The CPO reports to the CEO and is a part of the C-suite or executive team. 

The CPO is responsible for all things product development. This includes product vision, product design, product development, product innovation, and project management. In many startups, the CPO is also often tasked with overseeing production, which may include procurement, manufacturing, and distribution. 

The CPO often collaborates closely with the CMO, CSO, and CTO on customer and user research to inform product development as well as with the CTO in determining innovation and product vision and strategy.

Skills to Look For:

  1. Product Vision: A CPO needs to be a visionary. They need to be able to see the big picture and envision not only the final product, but also the way to get there. CPOs need to be able to determine the "why" of a product and plan out the next steps in its development. They must then coalesce the entire organization around their product vision.
  2. Customer-Centric Thinking: A CPO also needs to be able to put themselves in the shoes (or minds) of the startup’s customers. The CPO needs to have the ability and know-how to conduct customer and user research and analyze the data in order to inform product development.

When Should Your Startup Hire Executives?

So how do you decide when you should hire your startup’s first executives? Startups should avoid hiring executives until it is clear that they need one.

In the earliest, cash-strapped days of a startup, founders and co-founders tend to take on the majority of the responsibilities within the company. Startups typically need to keep their costs and burn rate low until they have developed their product or service and raise seed funding.

However, a time will come when you and your co-founders can’t handle all of the responsibilities of the organization. In some cases, your roles have grown where you don’t have the capacity to get everything done that needs to be completed. In others, you are at a point where you need the help of a seasoned veteran to move your startup forward. It is at these times that you should begin considering bringing on an executive.

Hiring vs. Outsourcing

One question you may face is whether you should hire an executive or outsource these roles. From tapping into your advisors and mentors to hiring contractors or freelancers, there are a number of options for outsourcing the expertise you may be looking for. 

If you need expertise but are not ready to add a full-time executive role, you may be able to tap your advisors, mentors, retired executives, or others in your network to serve as an executive on a temporary or part-time basis.

You also may be able to outsource many functions to contractors, freelancers, or other professionals. While you shouldn’t outsource any of the core functions of your startup (i.e., those that are essential to your core business), you should consider outsourcing functions that you are not great at but that still need accomplishing.

Recommended: Find freelance talent with Fiverr.

Here are a few roles to consider outsourcing:

Accounting Services

Administrative Work

Communications and PR

Financial Advising

Human Resources

Legal Services

Marketing Services

Payroll Services

Web Development and Programming

While most of these are not executive-level functions, knowing what you can and cannot (and should and should not) outsource is helpful in planning and building your startup team.

How to Build a Great Startup Management Team

When it comes to the success of your startup, having a great startup team is one of the most important success factors and should not be overlooked. 

A startup is nothing without a great team. While founders bring their vision, it is up to the startup team to execute.

Here are the nine steps to building a great startup leadership team:

  1. Identify Roles and Positions
  2. Assess the Skills You Already Have
  3. Determine the Founders’ Roles
  4. Find Out What You’re Missing
  5. Know What Makes a Successful Startup Team
  6. Write Effective Job Descriptions
  7. Identify Top Talent
  8. Select Top Talent
  9. Go Through With the Hiring Process

1. Identify Roles and Positions

The first thing you need to do before starting to hire executives is to identify the roles you will need to fill. As covered above, the seven most common roles within startups are:

  • CEO
  • COO
  • CFO
  • CMO
  • CSO
  • CTO
  • CPO

However, depending on the type of startup you are launching, other roles that you may need could include:

  • Chief Business Development Officer (CBDO)
  • Chief Creative Officer (CCO)
  • Chief Compliance Officer (CCO)
  • Chief Communication Officer (CCO)
  • Chief Diversity Officer (CDO)
  • Chief Human Resources Officer (CHRO)
  • Chief Information Officer (CIO)
  • Chief Legal Officer (CLO)
  • Chief Revenue Officer (CRO)
  • Chief Risk Officer (CRO)

Of course, most startups don't need all of these positions. It highly depends on the industry that your startup is in, your business model, and the stage of the startup. For example, many small, early-stage startups won’t have the need or budget for a chief human resources officer or a chief legal officer. However, startups that focus on staffing or law may need these roles early on.

Begin by identifying the roles that will be crucial. This usually includes a CEO, a COO, a CFO, and a CMO or CSO. It will also likely include either a CPO, a CTO, or a hybrid of these roles.

That’s right — just as founders often wear many hats at the beginning of launching a startup, many of the first executives in a startup have hybrid roles. It’s not uncommon to see a “chief marketing and sales officer” or a “chief product and technology officer” until the company grows large enough to justify both roles.

Thus, when planning your startup and hiring executives, it may be helpful to plan what roles you will need to fill at different stages of the startup’s growth.

2. Assess the Skills You Already Have

Next, you will need to do an honest internal assessment of the skills you and your co-founders have. 

Consider your own and each other's skill set, as well as your respective strengths and weaknesses, to ensure that everyone understands where they can contribute. Ask yourself:

  • What are you best at? 
  • Where can you help the company most?
  • What are you not good at?
  • What do you not like to do?

By understanding your strengths and weaknesses, and what you like to do and don’t like to do, you can maximize the contribution of each member of the startup team and gain insights on the best roles for your founders and cofounders and where you need to add talent and expertise.

3. Determine the Founders’ Roles

Once you assess yourself and your own unique set of strengths and weaknesses, it’s time to determine the roles of the founders and co-founders. Who will lead? Who will be in charge of the product? Who is going to be responsible for marketing? Who will lead sales?

In many cases, founders and co-founders take on the roles of CEO and COO, leading the startup they founded. However, some founders lack the right set of skills to guide the startup through its various stages. Technical co-founders may prefer to settle into the role of CTO or CPO, and business- or marketing-minded co-founders may prefer the roles of CFO or CMO or CSO.

As founders and co-founders, you will likely continue wearing many hats as you build and grow your startup team. However, it is important to know where you will help the startup best and what roles the founders and cofounders will eventually occupy.

4. Identify and Prioritize Roles You Need to Fill

Once you have determined the founders and co-founders’ roles within the company, you will need to identify the roles eventually needed to complete your startup team. And then you will have to prioritize them.

Pre-seed and seed-stage startups are usually on a pretty tight budget. It is unlikely you will be able to fill out your startup leadership team all at once. You will need to consider the following questions:

  • What roles will be most crucial to my startup’s success?
  • Where do I need the most help right away?

Some startups begin filling these needs with hybrid roles until the company grows large enough to justify multiple positions. For instance, many startups recruit “chief marketing and sales” officers or “chief product and technology” officers until the startup grows to a point where it is too much to handle both roles.

When prioritizing the roles you need to fill, you may need to get creative. In many cases, startups fill out their startup team with a mix of executive hires, outsourcing and freelancers, and non-executive roles. Consider others in your organization who could handle these duties or advisors you could tap to fulfill these roles temporarily or part-time (if that’s all you need). 

You can also outsource some of the non-core functions of your startup. This can allow you to focus your priorities and resources on building your product or service, marketing, or the other core functions of your business.

5. Know What Makes a Successful Startup Team

The startup team is pivotal in the success or failure of a startup. In fact, evidence suggests that up to 60% of startups fail due to problems within the startup team. So, before moving along any further in the hiring process, it is crucial to know what makes a successful startup team.

Obviously, your startup team members need to have the knowledge and skills to carry out their respective roles. Although many startup founders learn on the fly, you will want and expect that your executives have the knowledge and know-how to carry out their roles.

In addition to knowledge and experience in their role, successful startup team members also tend to have prior experience in the same industry or sector, preferably with other startups. Knowledge and experience in the industry, sector, product, and other startups can prepare executives for many situations and problems that your startup may face.

However, several soft skills are strongly related to successful startup executives in addition to these hard skills. In particular, research has found that passion and a shared strategic vision are nearly required to achieve success.

So, when you’re assessing what you are looking for in a candidate, from writing job descriptions to interviews and selecting, consider the core skills required to complete the task and previous startup experience and the soft skills it takes to lead a startup.

6. Write Effective Job Descriptions

The importance of writing an effective job description is often overlooked. Writing a job description requires you to think through:

  • The aspects of what the job will entail
  • How it relates to the other functions of the startups
  • How it will alleviate time and responsibilities for those who are performing these functions now
  • What new capabilities adding this role will add to the company

Importantly, just as you judge your candidate’s resumes, candidates will judge your job description. If your job description is unclear, you are less likely to attract qualified candidates. If your description is too broad, it shows that you may not know what you are looking for. 

When writing job descriptions, you also need to remember that if you are trying to hire seasoned executives, they will have their own expectations. If you are looking to hire an executive with years of experience and the proven expertise to help you lead your startup, they are unlikely to be willing to work “grind culture” work hours or perform the routine tasks that lower-level workers might typically complete. If hiring a CFO, you likely won’t find an experienced executive that would be happy to be asked to handle the bookkeeping. 

So before beginning to identify top talent, figure out exactly what you are looking for. Try asking your advisors, mentors, or an executive recruiter for help if you are unsure.

7. Identify Top Talent

Hiring anyone can be a challenge, but hiring executives is much more than just posting a help wanted ad. Talented executives can be hard to find, and most of the time, they’re not exactly looking for a job. In many cases, you will have to sell them to take the risk on your startup.

There are two primary ways that startups find potential executive talent:

  1. Through their networks of board members, advisors, mentors, and other founders and executives in their field
  2. Hiring a professional headhunter, recruiter, or executive search firm.

Many startups tap into their networks to identify potential executives to join their leadership team. Investors, board members, advisors, mentors, and other founders and executives in your network can help identify possible candidates.

Other startups hire headhunters, recruiters, or search firms to identify executive candidates. Recruiters can help clarify what you need, draft job descriptions, identify top executive candidates, and even teach you how to interview them. But, most importantly, they are connected to a vast network of talent.

8. Select Top Talent

Once you have identified potential candidates, the selection process usually begins with an interview. An interview is an opportunity to assess a candidate’s knowledge and experience, personality, and fit with the startup, as well as to sell your startup vision to the candidate. 

Prior to interviewing candidates, you should spend some time crafting a structured interview. Unstructured interviews are very poor predictors of performance on the job, and an unfocused interview tells candidates you don’t know what you’re looking for.

If you have never hired an executive before and have limited experience in that executive role, it is unlikely that you would know what you are looking for in a candidate. Before committing resources to search for and interview candidates, ask for help. Again, tap back into your advisors, mentors, or someone you know who works in that role. You can also talk to an executive recruiter, who can tell you what to look for, how to assess qualified candidates, and how to conduct a good interview.

Remember, you are recruiting seasoned executives and trying to sell them your startup vision as well. An interview is a chance to show your vision and passion and convince your top candidates why they should take the chance on your startup too.

9. Go Through With the Hiring Process

After interviewing candidates, you will want to fact-check candidates' backgrounds and verify their credentials and expertise. Even if you are recruiting through your own network, you will want to do your own due diligence on executive candidates. Making the wrong hire can be a costly mistake.

Once you’ve selected who you would like to hire, you will need to agree on additional details of the role and relationship and negotiate compensation. Keep in contact with executives throughout this process, and keep in contact through onboarding after an executive is hired.