5 Qualities to Look for When Hiring Your First Sales Leader
By Richard Frankel
February 26, 2023

As a tech startup entrepreneur, hiring your first sales leader is an exciting step. You can look forward to scaling with a great sales leader who will pave the way for future growth. But it’s important to get your first sales hire right – the wrong sales hire can hinder your company’s growth and drain your resources.

In this article, we will cover what you must look for in your first sales hire. 

1. Goldilocks Experience

One of the biggest challenges in hiring your first sales leader is finding someone who is just right. The ideal candidate should have a proven track record of success, but not so much experience that they’re overqualified for the role.

The Dangers of Experience

Many senior sales leaders are not a good fit for startups. Startups have limited resources and more flexible roles, while senior sales leaders are often used to a structured, hierarchical corporate environment with teams of people to whom they can delegate. 

A senior sales leader used to this hands-off approach may struggle to adapt to the do-it-yourself requirements of a startup. In a startup environment, your first sales hire must be willing and able to do every step of the sales process themselves. They need to be able to get their hands dirty and lead by example, building your startup’s sales pipeline from scratch. 

When it comes time to hire future salespeople, your first sales hire must be able to train them independently. They need to be able to demonstrate to their team how to sell, how to build a pipeline, and how to close deals. Senior salespeople may be skilled at running existing sales teams, but they may not know how to scalably build the sales pipeline of a startup from scratch.

The Risks of Inexperience

However, it almost goes without saying that a sales leader who is too inexperienced will not be a good fit for your startup, as they won’t have the experience necessary to succeed. 

Look for a candidate with at least a few years of experience in sales leadership positions. A candidate with a few years of experience has likely had experience building processes and teams and understands the entire sales cycle. 

The ideal candidate has had successes and failures, which means they know what works and doesn’t. They have the skills and expertise necessary to build a sales team, but they’re ready to do the bulk of the sales work themselves in the first few months after you hire them.

To find the perfect candidate, look for someone with a few years of experience who is still hungry for growth. They should be experienced enough to bring value to your team, but not so experienced that they need to be more set in their ways.

Enthusiasm for Entrepreneurship

Startups are not for everyone. While you are hiring your first sales leader, you must look out for candidates excited about working at a startup. Your first sales hire must be ready to work long hours when necessary, build innovative sales pipelines from scratch, and tackle new surprising challenges as they arise – all of which your sales hire is guaranteed to need to do at some point.

Someone with experience in a startup environment or who has started their own company might be particularly well-suited to the role, as they will already have experience with the challenges and rewards of entrepreneurship. 

2. Key Sales Skills

There are several areas to assess when hiring your first sales leader:

A Charismatic Personality

So much of a sales leader’s success rides on their personality. It is the personality of a salesperson that is crucial in motivating a team and building customer relationships. Charismatic, approachable, and outgoing people who can connect with team members and customers on a personal level is ideal.

Startup sales environments often call on salespeople to be powerful solo hunters. Still, your first sales hire must also be a deft hand at cross-functional collaboration, as they will certainly need to work with members of other departments to close sales and build your first pipeline. 

Last but not least is assessing your candidates for cultural fit. Not only should your candidate be prepared to work in a startup and it’s attendant dynamic atmosphere, but they should also gel with your particular company culture. Your first sales hire will work closely with your c-suite and product team, so finding someone whose personality fits the rest of the organization is essential. 

Experience Working with Startups Your Size

Not all startups are made equal. Startups with a head count of 150 are much different than startups with a headcount of 5. As you look for the perfect hire for your first sales role, keep an eye out for candidates with enthusiasm or experience for working at startups of your particular size and business model. 

Consider your individual organizational needs. Look for candidates with proven experience hiring teams and building sales pipelines in similar organizations. Ask about specific examples of winning clients at previous companies to understand their capabilities.

History In Your Industry

Equally as important as startup expertise is industry expertise. Your sales leader should have experience in your industry or a similar one. They should be able to learn and understand your product or service quickly. 

If you’re in a complex or technical industry, look for someone with experience selling similar products or services. In any case, make sure to ask candidates what their process is for getting up-to-speed on the products and services they sell. You want a candidate who is familiar with their own learning styles and won’t need their hand held while they get up to speed. 

A Proven Track Record

And, of course, search for a candidate with a proven track record of closing sales and managing the sales process at a high level.

Look for someone with a history of success in sales leadership roles. During interviews, the ideal candidate will be able to point to specific achievements and metrics demonstrating their ability to lead a team and drive sales. They should be able to describe activities in their career that show they know how to turn a marketing plan into market engagement, find leads, engage with prospects, and follow a structured process for efficiently converting opportunities into clients. This is the hard work of sales that turns their repeatable activity into repeat customers.

3. Willingness & Flexibility

In the early stages of your startup, your first sales leader will likely have to wear many hats and work long hours. Look for someone willing to do whatever it takes to help your business succeed. When evaluating candidates, ask for examples from their careers when they took on new challenges and helped in areas beyond their job description. Some ways in which the ideal candidate will be willing and flexible include:

Willingness to Work Hard

In the early stages of your startup, your first sales leader will likely have to wear many hats and work long hours. Look for someone willing to do whatever it takes to help your business succeed. As you evaluate candidates, ask for examples from their careers of times they went above and beyond for their work, branching out in areas like their level of effort, building diverse skills, and occasionally working beyond their job description.

Flexibility and Adaptability

A successful sales leader in a startup environment is someone flexible and adaptable, as startup leadership teams need to pivot quickly and make changes on the fly. Look for a sales leader that can adapt to new processes, products, and services. They should be can-do, willing to take on any challenge, and have a strong sense of ownership over sales success. 

Growth Mindset and Openness to Feedback

Startups succeed or fail based on their ability to respond to environmental information and continuously improve. Therefore, all team members at a startup, not just your sales team, benefit tremendously from the ability to accept feedback and maintain a growth mindset about themselves and their performance. 

Because of this, your sales leader should be open to feedback and willing to learn from their mistakes. Your ideal candidate should be ready to take on new challenges and grow with your startup. Ask candidates questions about how they have responded to feedback in prior roles and how they proactively manage their own skills development and growth.

4. Excellent References

Of course, it doesn’t matter what a candidate says or does if you cannot get accurate references from previous business associates. Checking references while hiring your first sales leader is a critical step in the hiring process that can help you avoid making a costly mistake. Here are some guidelines that can help you get the most out of your reference checks:

Ask for a Complete Picture

When checking references, ask for input from the candidate’s previous managers or colleagues. Make sure you get as complete a picture as you can. In addition to their previous performance, ask about their work style, communication skills, and ability to motivate and lead a team. Your goal is not only to understand how well they perform but to understand how they work with others and how they approach their role as a sales leader as well.

Seek Diverse References

Don’t only seek references from direct managers. Ask for references from people who have worked with the candidate in different kinds of roles. For example, speak with someone who worked with the candidate at a startup and someone who worked with them at a larger company. This can help you form a complete picture of the candidate’s experience and skills.

Back-Channel References

It’s also a good idea to seek references from people who the candidate has not provided. These are known as “back-channel references.” They can be precious because they can give a more candid and unbiased perspective on the candidate’s career.

While seeking back-channel references can provide valuable insight into a candidate’s character, conducting this practice ethically is important.Here are some guidelines for conducting back-channel references ethically:

  • Respect candidate privacy: Back-channel references can be an excellent way to gain additional insight into a candidate’s work history, but ensuring that the information you gather is relevant to the job at hand is essential. Avoid asking questions that may be perceived as an invasion of privacy or irrelevant to the job.
  • Use your network carefully: Back-channel references should be conducted carefully to protect your network. Only contact individuals who you trust, who have experience working with the candidate, and who can provide valuable insight into their work history.
  • Treat all candidates equally: All candidates should be treated equally in the hiring process, including conducting ethical back-channel references. Ensure you’re not selectively contacting certain candidates or using back-channel references to discriminate against any candidate.

Ask Open-Ended Questions

When speaking with references, ask open-ended questions. Don’t ask whether the candidate was a good employee; ask for examples of their performance. Ask about how they approached challenging situations, collaborated with other team members, and contributed to the company’s success. You are more likely to uncover useful information when you allow references to direct the conversation instead of directing the conversation yourself.

5. A Process-Oriented Sales Approach

A process-oriented sales approach uses data, analytics, and structured processes to identify new opportunities, drive growth, and scale the business. It involves setting up clear steps to move prospects through the sales funnel and regularly measuring and optimizing these steps for maximum efficiency. 

In contrast, a relationship-oriented sales approach emphasizes building strong connections with prospects and customers to drive sales. It relies on networking, referrals, and personal relationships to win business. 

While both approaches have their merits, a process-oriented approach is more effective for startups and companies looking to grow quickly. It is scalable and provides a more reliable way to achieve long-term success. As you begin hiring your first sales leader, look for a candidate with a strong process-oriented approach instead of a relationship-oriented one.

Avoid Overreliance on Relationships

Relationships from past work are perhaps the least important weapon in a candidate’s arsenal. While candidates may want to talk about their great connections that will give them a head start in the market, this can be a red flag if they rely excessively on those relationships. While establishing connections can undoubtedly help jumpstart the sales process, relying too heavily on those relationships will not enable a sales leader to scale the business over the long term.

Emphasize Process, Data, and Hard Work

Look for a sales leader who can combine an emphasis on process, data, and hard work to engage markets and develop new business relationships. The best sales leaders know how to build and execute a sales process that can scale as the company grows. They use data and analytics to identify new opportunities and build processes and structures to drive growth. 

Ask the Right Questions

When interviewing candidates for your sales leadership role, ask questions about their approach to sales. Ask for specific examples from past roles with questions like:

  1. How have they built new relationships in the past?
  2. How have they leveraged data and analytics to identify new opportunities?
  3. How have they built processes and structures to drive growth?
  4. How have they ensured their sales team worked efficiently and effectively?
  5. Tell me about a time you overcame objections to close a deal?

By asking these types of questions, you can get a better sense of how the candidate thinks about sales and whether their approach aligns with the needs of your business.


Hiring your first sales leader is critical for your tech startup’s success. Look for a candidate with a few years of sales leadership experience, as well as excellent references and critical sales skills. Evaluating their personality, industry expertise, and willingness to work hard is essential to find the perfect fit for your startup’s culture. While relationships can help jumpstart the sales process, don’t overemphasize them. Focus instead on a process-oriented sales approach that includes data, analytics, and scalability. You can ensure their approach aligns with your business’s needs by asking the right questions. 

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