Building High – Performance Teams
Sales Management 02.07.2023

Building High – Performance Teams

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On this episode of Sunny Side Up, host Eric McIntyre is joined by Dave Woolwine, Vice President of Sales for Americas at HackerOne. Dave has extensive experience in sales with mini high-growth companies and provides insights on the importance of building a high-performance team. Dave shares his journey from AE to leadership positions in the SaaS space and how companies should define their ideal employee profile (IEP) when hiring for high-growth positions. They discuss the difficulty and complexity of the hiring process for salespeople, as resumes often lack the information needed to determine if a candidate is suitable for the position. Additionally, Dave shares tips on creating an environment where employees can continually better themselves through training and leadership – even in a remote work environment.

About the Guest

Dave Woolwine has been a part of the sales motion of many high-growth companies such as Verint, Sprinklr, and Fuze.  For the last two years, he has been the Vice President of Sales for the Americas at HackerOne. 

HackerOne was started by ethical hackers and security leaders are driven by a passion for making the internet safer. HackerOne partners with the global hacker community to surface the most relevant security issues of our customers before criminals can exploit them.

Connect with Dave Woolwine

Key Takeaways

  • Most companies have not done the same exercise around identifying their ideal employee profile (IEP) as they have for their ideal customer profile (ICP)
  • Recruiting is the hardest and most important part of a sales leader’s position. And when recruiting, look for three things: grit, determination, and drive.
  • Spend time with the team to understand what drives them and how to help them achieve their goals
  • Be tight on value when approaching prospects/opportunities
  • The recruiting process across the tech sector is not bad, but companies are not recruiting in the right way and not looking for the right traits in potential hires.
  • It is easy to get complacent in sales and a mentor can help identify areas for improvement

Products that sell well in good economies are not always addressing a true need, meaning that they may not be as essential or vital to customers as products that solve a real problem.

  • Being tight on the value brought to the customer is important in the current economy because, with the decrease in spending power, customers are more cautious about the value of the product they are buying.


“Highly skilled and motivated people have a strong desire to master their craft”. – Dave Woolwine

“I always say that we can’t make someone successful but we can help them on their journey to become successful”. – Dave Woolwine

Highlights from the Episode 

Could you tell our listeners a little bit about yourself and your background working with hyper-growth organizations?

Dave Woolwine has spent the last 20 years in the SaaS space, primarily working with early to mid-stage companies. He began his career as an AE and has since worked his way up to his current role at HackerOne. Throughout his career, he has held roles at companies ranging from pre-revenue to billion-dollar organizations. He is passionate about working with companies that have initially proven a market fit and are looking to scale their organization from roughly 20 million to over a hundred. He has found that his skill sets are most valuable to these types of companies in terms of the sales team and customer value. Additionally, he enjoys helping reps and sales leaders become better at their craft by avoiding the mistakes he made earlier in his career.

What is the biggest thing you learned during your transition from an individual contributor to a management or leadership position, as you made the journey from AE to leadership today?

Dave learned that the transition from an individual contributor to a management or leadership position is difficult. He also learned that everything becomes more complex as a company scale from 20-30 million to 100 million. Dave also learned that in his role at HackerOne, he was making history every day and facing unknown challenges that required him to constantly adapt and redefine his skillset to find solutions that would impact not just himself but other parts of the organization as well.

A lot of organizations find it challenging to identify and recruit high-performing individuals. Why does this happen? Is the recruiting process broken across the tech sector?

Many organizations find it challenging to identify and recruit high-performing individuals. This happens because many companies have spent a lot of time developing and redefining their ideal customer profile (ICP) but have not done the same exercise around the people they want to hire, which is the ideal employee profile (IEP). In the tech sector, during the recruiting process, many CEOs can talk about where they are in the market, where they want to get to, and also where their product fit is, but they are unsure of what their IEP is and what makes a great salesperson. One of the reasons why most companies do not accelerate as fast as they desire is that they are hiring the wrong profile. Specifically, they might be hiring the wrong profile for high growth, high accountability sales work, which is a different profile than someone who wants to work at a large established software company.

If you had to recruit a high-performing individual, how would you go about it? Is there a framework one could follow?

When recruiting a high-performing individual, it is important to standardize the interview process and not just focus on the candidate’s resume. Traditional interview questions may not reveal important characteristics such as the individual’s ability to adapt to an ever-changing environment, their determination and drive, or their willingness to be coached and become the best in their field. To avoid making mistakes in the hiring process, which can have a significant impact on the organization, a framework should be followed that focuses on three key areas: recruiting, retaining, and revenue. This includes identifying the characteristics that are known to make successful salespeople and creating an environment where new hires can improve within the organization. The hiring process should also be treated as the most important and difficult part of the position. If a mistake is made, it is possible to course correct it within six months, but the impact on the territory and revenue can be significant in the long term.

How are you assessing grit, determination, and drive during the interview process for salespeople who are skilled at answering questions, as it seems difficult to determine based on resumes and interview questions alone?

Assessing grit, determination, and drive during the interview process for salespeople who are skilled at answering questions can be difficult because it is challenging to determine based on resumes and interview questions alone. The interviewer wants to understand who the person is and how they deal with adversity and challenges. They look for examples of tough situations where the candidate rose above most people and did not throw in the towel. The interviewer also wants to align these qualities with the candidate’s ability to hit quota and represent the company in a greenfield territory and create large deals within a short period. It is ultimately a combination of assessing their past performance and their drive and determination, with a preference for hiring those who have grit and drive, and can be taught the industry and how to sell, over someone who has high skill but a low will to put in the work.

Could you throw some light on the 3R’s framework? – Recruit / Retain / Revenue?

According to Dave, the concept of what motivates salespeople is often misunderstood. He argues that salespeople are not solely driven by money and that they have an internal drive to become better in their profession. He believes that if the right person is hired and given the proper training, coaching, and mentoring, they will be able to focus on revenue. Woolwine also suggests that companies often have it backward by focusing solely on revenue and not on hiring the right person and creating an environment that allows them to become better in their career. He also emphasizes the importance of providing salespeople with a clear understanding of their duties and responsibilities and teaching them how to close big, complex deals.

People often don’t realize that the process doesn’t end at recruiting. Retaining great talent is just as crucial. Once you hire the right people, how do you ensure they stay motivated? Also, how do you help them become better in their career?

It is often not realized that the process of recruitment does not end at hiring. Retaining great talent is just as crucial. Once the right people are hired, it is important to ensure they stay motivated. One way to do this is by consistently providing training and education, and by truly understanding what drives them and their career goals. It is important to remember that while a company cannot make someone successful, it can help support and guide them on their journey to success.

An area that you are passionate about is mentorship. If anyone of our listeners is currently looking out for mentorship, what would be your advice to them in terms of identifying the right mentor?

Dave believes that mentorship is an important area that can change one’s career. One mistake that sales representatives often make is only focusing on their commission, jumping from one job to another for small pay increases, or being lured by companies that promise stock options and wealth. Instead, Woolwine advises that sales representatives should focus on identifying the right mentor who can help them improve their skills and advance their careers. He suggests that sales representatives should interview the person they will be reporting to, to understand how they can help them become better at their job. Woolwine himself had a similar experience early in his career, where he felt he was a good salesperson, but had a lot to learn. A mentor helped him to identify the gaps in his skills, and he became driven to improve himself. Woolwine believes that those who want to take the next step in their career, need to find a mentor who they can trust and have open and honest conversations with to become a better sales professional.

How are you and your organization adapting to the current economic downturn?

Dave asserts that there are two ways to describe a product: as a “vitamin” or as an “aspirin.” He explains that during good economic times, there is a lot of extra money flowing, and many products that sell well simply because the money is there, but they do not necessarily address a significant need. On the other hand, he explains that products that are “aspirin”–those that solve a significant need regardless of the state of the economy–will continue to do well even in a downturn. In his organization, HackerOne, they sell an “aspirin” by helping to strengthen companies’ security posture and protect them from catastrophic breaches. As a result, they are continuing to hire even during the current economic downturn and are seeing great success.

Have you, and I guess your teams, adjusted or made any pivots in how you go to market or how you approach opportunities or prospecting accounts with the economy in mind, or have you not noticed anything?

Dave and his team have adjusted their approach to how they go to market and prospect accounts with the economy in mind. They have found that there is extra scrutiny on spending, and finance is heavily involved in negotiations. To address these concerns, the team has slowed down the sales process and is working with champions in their accounts to develop a rock-solid justification for why they should choose HackerOne, the problems it solves, and the money it will save. They have developed a deck that can be shared with executive staff and CEOs to explain the reasoning behind picking HackerOne.

Do you have any tips or suggestions on how to interview well for a position, for listeners who may not have much experience interviewing?

Dave suggests that when interviewing for a position, it is important to come prepared and treat the process as a sales process. This includes researching the company, understanding who you will be speaking with, and having detailed questions about the role and the company’s strengths and weaknesses. Following up with emails after the meeting is also recommended. Dave also emphasizes the importance of showing the interviewer that you are highly motivated and that you are trying to decide if the position is the best move for your career. Additionally, Dave suggests looking for candidates who ask thoughtful questions and are a bit skeptical in their conversations, as they tend to be highly talented and motivated.

Is there a book, blog, newsletter, website, or video that you would recommend to our listeners?

A book:  

A podcast:


John McMahon — Board Member at Snowflake 

Cedric Pech — CRO at MongoDB

Chris Doggett — CRO at Acquia

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