Constructing an Indomitable Sales Team
Sales Management 05.11.2023

Constructing an Indomitable Sales Team

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On this episode of Sunny Side Up, host Rory Costello talks with Benjamin White, VP of Business Development at Ironscales, about his successful career building a sales team in cybersecurity. Ben emphasizes the importance of creating a familial culture, personalization in outbound sales communication, and hiring and training efficient business development representatives (BDRs). He also discusses the challenges of working remotely and provides tips on overcoming isolation through daily standup meetings, continuous learning, and supportive team culture. Ben stresses the significance of asking questions as a leader and embracing continuous learning for personal and professional growth.

About the Guest

Ben White is a VP of Business Development at Ironscales, overseeing the Global inbound and outbound BDR teams. Ben has almost a decade of experience in Cyber Security. He is based out of Charleston and is a father of 2 boys with one on the way

Connect with Benjamin White

Key Takeaways

  • Ben discusses how to construct an indomitable sales team and adapt to changes in business development leadership
  • The role of a BDR has become harder due to increased noise and tools like outreach, making customization more difficult.
  • Business development is where most salespeople start their careers, and Ben finds it rewarding to help people grow into successful salespeople.
  • The landscape of business development has changed, and adapting to those changes is necessary.
  • Personalization should focus on the recipient’s role and interests
  • Finding intrinsically motivated team members is important for success
  • Hire people who have written down their goals and have a specific plan to achieve them.
  • Look for individuals who are passionate and can have higher-level conversations.
  • Asking straightforward questions can help find out whether someone is a good fit for the role.
  • The interview process is a discovery process, and it’s crucial to understand where interviewees are coming from.
  • A manager who gets upset when mistakes are made due to a lack of understanding is counterproductive.
  • Continual learning can be achieved in a variety of ways, including pursuing personal interests.
  • Encouraging personal growth can lead to professional growth.


“It is okay to not know it all. That was the biggest learning experience that I had.” – Ben White

Highlights from the Episode

What is your experience with the changing landscape of business development over time and how have you adapted to it in your leadership role? Can you begin by giving us a brief overview of your professional background in business development?

Benjamin has a professional background in business development that began in 2012 after graduating from college. His first role was as a Business Development Representative (BDR) for the American Medical Association where he gained an understanding of what it takes to be a professional. He continued to work his way up the career ladder, transitioning from an SDR to an AE, and eventually becoming a BDR team manager at Infosec about four and a half years ago.

In his current leadership role at Ironscales, Benjamin has faced the challenge of building a team around a remote work environment, which has been a struggle for many organizations. He understands the difficulty of the transition and uses his experience to relate to his team. He has also experienced the changing landscape of business development over time and has adapted accordingly, continuously building and growing his team. Since starting at Ironscales with only three BDRs, he has increased his team to seven.

What was it that brought you back to business development, after climbing the ladder and reaching the role of an AE in the enterprise?

Ben stated that what brought him back to business development after achieving the position of an AE was his innate desire to train and develop others. He likened his role to that of an older brother who enjoys helping others succeed in their careers. He finds it extremely rewarding to watch his protégés grow and flourish in the sales industry. Although some may find the job repetitive, he continues to work towards training and developing more successful salespeople. He admitted that it can be difficult to let go of talented BDRs who are ready to move up to the role of an AE, but he understands the importance of training and developing new salespeople to take their place. This motivation to train and develop others is what continues to drive him in his role.

Was creating an aura of family and a culture that represents your top priority when you moved back into business development, to achieve a familial feel? Could you walk me through that?

Ben explained that creating a familial culture was indeed his top priority when he moved back into business development. He wanted to ensure that his team did not feel left behind, as he did in his previous role. To achieve this, he built personal relationships with each team member and made sure that he understood what motivated them. He also worked to coach underperforming team members effectively so that they could improve and find the right role for them. He rarely had to let people go because he would have conversations with them about their happiness in their current role and would help them decide to move on if necessary. For those who were passionate about their role, Ben put in the same amount of effort and passion to help them move forward in their careers.

Have you seen any changes in the BDR role over the last decade or so, considering it’s a tough gig?

To Ben, the BDR role has become more challenging over the last decade due to an increase in noise. With the advent of outreach and other tools, it has become easier to send out numerous emails. However, the focus has shifted towards slowing down and personalizing messages for each individual to make them stand out. There are tools available to segment messages for specific roles, but it is important to focus on providing value in each message rather than relying on bump emails or lengthy emails with no clear value proposition. The goal is to build on each touchpoint and provide value to the recipient, making it more likely for them to engage and set up a meeting.

How are you coaching your team to balance personalization with avoiding dense emails that people may not read? Can you walk me through that process?

Ben coaches his team to balance personalization with avoiding dense emails that people may not read by focusing on individualized personalization. He starts by asking his team members what personalization means to them and encourages them to personalize emails according to each recipient’s role and interests. For targeted accounts, his team looks through job postings and understands what the individual’s requirements are for their new role.

After identifying if any of their tools can help with those requirements, they call it out specifically in the email. The goal is to show that they have done their research and are not sending a generic email. They also try to reference things that the recipient has shared on social media or mentioned in conversations. Ben emphasizes that the emails should be focused on the recipient’s interests and not just a list of product features. By doing this, they hope to create emails that will capture the recipient’s attention and encourage them to respond.

How are you getting your team to cut through the buzzwords that exist in the tech space in general, considering that terms like “operational efficiency” can often be unclear and confusing?

To cut through the buzzwords that exist in the tech space, Ben’s team is using storytelling to connect with their audience. They have full control over the messaging that is being sent out and they try to avoid using marketing buzzwords. Instead, they focus on the practical benefits of their services and how they can help organizations improve their operations. By using relatable examples and connecting with their audience’s specific pain points, Ben’s team can convey its value proposition without relying on unclear or confusing buzzwords. They aim to make sure that their emails are not filled with operational efficiency buzzwords, and instead focus on telling a clear and relatable story.

How can you ensure personalization doesn’t become difficult when tying it back to a business’s value proposition and prevent phoning it in on the outbound side?

In ensuring personalization doesn’t become difficult when tying it back to a business’s value proposition and preventing phoning it in on the outbound side, it is important to avoid putting numbers on the team, such as setting quotas for the number of calls or emails. Instead, it is crucial to find the right people who are excited and passionate about their work and are intrinsically motivated to put their best foot forward as the face and entry point to the organization. These individuals are not just dialing to reach a set number but are going above and beyond because they are driven by something else. Finding these top-performing individuals is not easy, but it is important to benchmark their performance across the industry and measure effective behaviors that drive results, such as customization in emails and connect rates in cold calls, rather than just the number of dials or calls made. Ultimately, it is about understanding what can be done to drive efficient behavior and making the most of the team’s time to achieve success.

What indicators do you look for when hiring for a BDR role, to identify a person who will go the extra mile and make more than just the required number of dials for all the right reasons?

When hiring for a BDR role, the ideal candidate should possess certain indicators that signal their potential to go the extra mile and make more than just the required number of dials. Ben looks for competitive individuals, even if they are not necessarily sports-driven. He values the diversity of thought in the candidate’s background and seeks someone who is intrinsically motivated and passionate about something. During the interview process, he asks candidates about their passions and looks for those who can express themselves with enthusiasm and have effective conversations. Additionally, he values candidates who have written down their goals and have a methodical approach to achieving them. These individuals are more likely to complete assigned tasks and achieve their objectives, which is important in a BDR role.

How do you find that out during the interview process? Do you ask if they have any goals written down or is there another way to approach it?

During the interview process, one approach to finding out if the candidate has any written goals is to ask them directly. Asking questions such as where they have their goals written down and how often they read and update them can give insights into their level of preparation and commitment toward achieving their goals. By observing the candidate’s hesitation or thought process, one can also tell if they genuinely have their goals written down or not. It is important to note that having written goals is crucial for the success of a role, and physical actions such as writing things down on paper can aid in remembering and preventing burnout by separating work and personal life. Therefore, it is recommended to ask specific questions related to their goals during the interview process to gauge their level of commitment toward achieving them.

How do you manage to work from home and build a culture on a remote team? Any tips?

When managing a remote team and working from home, one effective way to build team culture is to have a daily standup meeting where everyone can come together before starting work. This is a time to chat and connect, much like in an office setting. It’s also important to encourage continuous learning and growth by having team members share what they learned over the weekend or something they are passionate about. Additionally, providing channels for team members to communicate and share wins and losses can help create a supportive and fun work environment. Encouraging team members to quickly move on from difficult calls and celebrate successes together can help boost morale and build a strong team culture. Overall, building a remote team culture requires intentional effort and consistent communication to foster a sense of connection and belonging among team members.

Have you as a leader made any missteps in the past and learned from them? What are some of those mistakes that you would like to share with the world so that others can avoid them?

When asked if they have made any missteps in the past and learned from them, Ben responds that failures are inevitable, but taking responsibility for them is essential. White explains that the biggest learning experience they had as a leader was realizing that it is okay to not know everything. In the past, they have put a lot of time into projects they didn’t fully understand, which was hard for them. They had to learn to put their ego aside and ask questions when they were not sure about something. Ben advises others to always ask questions and not be afraid to do so, as other people in the room may have the same questions but are too afraid to ask. Ben emphasizes that continual learning is extremely important to them, and they are always trying to learn new things to avoid being left behind by new technologies. 

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



Sam Nelson – Founder at

Jake Bernstein – Director of Business Development at SPINS

Jarrod Mayes – Head of Americas Sales at Infosec 

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