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Mastering Sustainable Sales with Jeff Goldberg – This is one you are not going to want to miss!

Updated: Apr 25

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Three characteristics of all great salespeople: They're the best question askers, the best listeners, and the best storytellers. Do you have those qualities? – Jeff Goldberg

Welcome to an insightful discussion on mastering the art of sales with Jeff Goldberg, a seasoned sales expert with nearly five decades of experience. In this interview, Jeff joins forces with Rache Brand from Superstruct and Joe Milam, offering a deep dive into the strategies and philosophies that drive successful sales. Together, they explore the evolving landscape of sales, the importance of integrity and relationship-building, and how to harness traditional and modern techniques for maximum impact.

This engaging conversation promises valuable takeaways for anyone looking to enhance their sales approach and achieve sustainable growth in today's competitive market. Tune in as we unpack the secrets to successful selling with these industry veterans.

Here’s the kicker: 'no' frees you up. It means not wasting time on a prospect who’s not ready or willing to commit. This allows you to move on and focus on others who might say 'yes.' – Jeff Goldberg

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Interviewers: Rache Brand, Joe Milam

Interviewee: Jeff Goldberg, Sales Problem Solver

Rache Brand: Welcome everyone to our conversation. I'm Rache Brand from Superstruct, and Star Strong Capital. Our focus is on enabling businesses to thrive by navigating market challenges and enhancing their revenue, most of the itme through key sales strategies.

Today, we're excited to have Jeff Goldberg with us, a seasoned sales expert known for his pragmatic approach to solving sales problems.

Joe Milam: Hello everyone, I'm Joe Milam, also from Superstruct. Like Rache, my focus is on strategic growth and financing for companies. Jeff, it’s great to have you here. Could you start by giving us a brief overview of your background in sales?

Jeff Goldberg: Absolutely, Joe and Rache, thank you for having me.

I’ve been in the sales industry for nearly five decades, primarily focusing on sales training and coaching. I help organizations and individuals globally to achieve sustainable and measurable improvements in their sales performances. I emphasize selling with integrity and not being pushy, which I believe is crucial for modern sales strategies.

(Yes! Jeff, you have us captivated)

Rache Brand: That’s impressive, Jeff. With your extensive experience, you’ve surely seen the evolution of sales strategies over the years. Could you share the first sales experience you remember?

Jeff Goldberg: Certainly, Rache. My first real sales job was with Encyclopedia Britannica. Back then, encyclopedias were sold physically, a concept quite alien in today’s digital world. I learned the ropes of professional sales in this role, adhering strictly to the training provided, which quickly propelled me to the top of the sales charts nationally.

Joe Milam: That’s a classic start, Jeff. Given your long tenure in sales, how do you see the role of digital tools and AI in today’s sales processes?

Jeff Goldberg: Great question, Joe. While AI and digital tools are transforming how we approach sales, I firmly believe that the essence of sales still revolves around person-to-person interactions. These tools are aids, not replacements. They enhance efficiency but the core of sales remains in building relationships and understanding customer needs deeply.

Rache Brand: So, leveraging technology without losing the human touch. Jeff, could you delve a bit into how you adapt traditional sales techniques in the modern digital context?

Jeff Goldberg: Absolutely, Rache. The fundamentals of sales haven’t changed—what has changed is the medium and speed of communication. Today, we need to be more direct and transparent due to the information overload customers face. My approach involves integrating traditional sales techniques with modern tools to maintain effective communication and relationship-building, even through digital channels.

Joe Milam: That’s insightful. Speaking of challenges, what are common hurdles you see sales teams facing today, and how do you recommend they overcome them?

Jeff Goldberg: One major hurdle is the reluctance towards prospecting; many salespeople find it daunting. I focus on breaking down these barriers by developing structured and repeatable processes that sales teams can follow confidently. Also, the inability to adapt to customer’s changing needs quickly is another hurdle. Continuous training and staying updated with market trends are crucial in this regard.

Rache Brand: Training seems to be a key theme here. Jeff, could you expand on how you approach sales training differently?

Jeff Goldberg: My training programs are very hands-on. I believe in interactive learning where participants not only learn concepts but also apply them through role-playing and real-time feedback. This ensures that they not only 'know' but 'understand' how to apply the techniques in their specific contexts.

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Joe Milam: Practical application is crucial indeed. Jeff, for businesses looking to scale their sales efforts, what strategies would you recommend?

Jeff Goldberg: For scaling, businesses need to ensure their sales infrastructure is solid. This includes having a clear ideal customer profile, a scalable lead generation process, and a sales team that is continuously trained. Additionally, aligning the sales strategies with overall business goals is critical to ensure cohesive growth.

Rache Brand: To start, could you discuss why technical founders often struggle with the sales aspect of their business?

Jeff Goldberg: Absolutely, the main issue I see with technical founders is that they’re deeply invested in the product development side—obsessed with the technical details, the "speeds and feeds," as we might say. However, they often neglect the sales component because it requires a very different mindset. Engineers think in terms of solving technical problems, whereas sales is about understanding and solving people's problems.

Joe Milam: That's insightful, Jeff. From your experience, how should a founder who is technical begin to tackle the sales process?

Jeff Goldberg: Joe, the first step is recognizing that you might not be the best person to handle sales. The smartest thing a tech founder can do is hire someone who knows sales—someone who can both manage and sell. If you’re starting small, this might mean hiring a "selling manager" who can both do the job and build a team over time. This dual role is vital as it lays the groundwork for scaling up sales efforts without constant oversight from the founder.

Rache Brand: On hiring, what traits do you look for in a potential sales candidate, especially for a tech company?

Jeff Goldberg: I look for two main things: innate traits that can’t be taught, like ambition, integrity, and competitiveness, and the potential for leadership. You need people who are self-starters but also capable of eventually leading a team. They need to be good, not just at selling, but at inspiring others to sell.

Joe Milam: Management skills seem crucial then. Could you elaborate on why sales management is different from other types of management?

Jeff Goldberg: Absolutely, Joe. Sales management is unique because it’s not just about overseeing people; it's about actively driving and measuring their performance based on specific activities. You’re constantly looking at metrics like call numbers, meeting rates, and conversion percentages. It’s more dynamic and immediate in its feedback loop than other types of management.

Rache Brand: Speaking of dynamics in sales, you've touched on how external factors like seasons affect sales activities. Could you explain that a bit more, especially the common misconceptions around the summer vacation period?

Jeff Goldberg: Sure, Rache. There’s a common myth in sales that during the summer, everything slows down because everyone is on vacation. It’s what I call "head trash"—a limiting belief. The truth is, while some people might be on vacation, it's only for a week or two. The summer is long, and business continues. Effective sales strategies don’t get paused. If you’re proactive, there’s no reason for a summer slump. You just need to keep pushing, keep calling, and keep engaging.

Joe Milam: It seems like maintaining momentum regardless of the season is key. So, how do you keep sales teams motivated during perceived down times?

Jeff Goldberg: It’s all about mindset and management. As a manager, you need to help your team adjust their perspectives and refine their strategies continuously. It’s about not letting external factors dictate your success but rather focusing on what you can control: your actions and your attitudes.

Do not be afraid of hiring strong personalities who can compensate for your weaknesses. Sales might not be your passion, but it is crucial for your business's survival. Find someone who is passionate about it and can translate your technical capabilities into market success. And remember, sales is a craft—respect it as much as you do the engineering part of your business.

Rache Brand: Could you elaborate on why, contrary to popular belief, a 'no' can be just as valuable as a 'yes'?

Jeff Goldberg: Absolutely, Rache. Most salespeople dread hearing 'no' because it sounds like failure. But it's not. The fear of 'no' prevents many from even asking the closing questions. But here’s the kicker: 'no' frees you up. It means not wasting time on a prospect who’s not ready or willing to commit. This allows you to move on and focus on others who might say 'yes.' Also, a 'no' can eventually turn into a 'yes' with proper nurturing. So, I don’t just accept 'no'; I welcome it.

Rache Brand: That’s a refreshing take! Shifting gears a bit, I have a scenario involving a technology company struggling with long sales cycles that suddenly shortened them. What strategies would you suggest for them to make this new efficiency repeatable?

Jeff Goldberg: First off, it’s crucial to analyze what changed. If something worked, there's no reason it can't again unless it was purely coincidental. They need to evaluate every step of their revamped process—what did they do differently with new prospects compared to older ones? Understanding these nuances can help standardize the effective strategies. Additionally, they should consider revisiting older prospects with a renewed pitch, emphasizing the changes and improvements made since their last interaction.

Rache Brand: And for sales teams facing longer sales cycles, how can they adapt to ensure they aren't just waiting on prospects that seem perpetually undecided?

Jeff Goldberg: That’s where your mindset comes into play. You must be proactive. Salespeople often hope prospects will consider their proposal seriously on their own time, but that’s rarely the case. Instead, engage them actively. If a prospect seems hesitant, clarify and address their concerns immediately. Also, constantly replenish your pipeline with new prospects to avoid relying too much on a few.

Rache Brand: Before we wrap up, Jeff, could you share a piece of advice for new salespeople entering the field?

Jeff Goldberg: Certainly, Rache. My advice would be to focus on learning continuously. Sales is dynamic; what worked yesterday might not work tomorrow. Be adaptable, listen to your customers, and most importantly, be honest and ethical in your dealings—this builds long-term relationships, which are the foundation of successful sales careers.

Listeners can reach out via my website,, or directly through email for coaching or training inquiries. I also offer on-demand training programs which are great for reinforcing skills over time. Whether it’s one-on-one coaching or group sessions, I’m here to help sales teams excel.

Joe Milam: Thank you, Jeff, for those golden nuggets of wisdom. We hope this session has provided you with valuable insights into refining your sales strategies.

Rache Brand: Absolutely, thanks again, Jeff, for sharing your expertise. To our audience, keep an eye on our future webinars for more insights from industry experts like Jeff. Jeff's Webinar is May 14th. Have a great day, everyone!

Unexpected Insight

One insight from the conversation that we all loved:

Jeff's view on how salespeople are seen and their common attributes. He humorously noted that despite the critical role they play in business, many salespeople, including himself, consider themselves "lazy."

He elaborated by saying salespeople are often looking to maximize their earnings while minimizing their efforts. This candid admission is surprising and refreshing, as it counters the common stereotype of salespeople as always being highly energetic and relentlessly driven. Jeff uses this self-awareness to stress the importance of effective sales management and structured processes that ensure productivity and accountability, turning this insight into a constructive perspective on managing sales teams efficiently.

Key Takeaways from the Conversation with Jeff Goldberg:

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  1. Honesty is Key: Ensure that salespeople understand the importance of honesty in building trust and long-term relationships with clients.

  2. Service Commitment: Salespeople should approach their interactions with a service-first mindset, focusing on how they can help the client rather than on earning commissions.

  3. Effective Questioning: Train salespeople to be great at asking questions. The ability to ask the right questions, listen effectively, and engage with the client’s answers is crucial.

  4. Follow-Up Strategy: Implement a strong follow-up strategy that emphasizes the importance of consistent communication to move the sale forward without being pushy.

  5. Best Next Action Step (BNAS): Never end a meeting or phone call without agreeing on the next step. This practice shortens the sales cycle and maintains engagement.

  6. Understand the Client: Encourage salespeople to have a deep understanding of their Ideal Client Profile (ICP). They should tailor their approaches based on the specific needs and behaviors of each client.

  7. Persistent Politeness: Cultivate a culture of polite persistence. Salespeople should be encouraged to continue engaging with clients thoughtfully and respectfully, even when initial efforts don’t immediately convert.

  8. Regular Training and Refinement: Regularly train and update your sales team on best practices, market changes, and new strategies to keep them sharp and effective.

  9. Client-Centric Customization: Adapt the sales approach based on client feedback and market conditions. Avoid a one-size-fits-all strategy.

  10. Leverage Metrics and Feedback: Use data-driven insights to understand what works and what doesn’t. Regularly review sales processes and outcomes to refine strategies and improve results.

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