20Sales Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers Mark Goldberger, Head of Enterprise Sales @ Ramp

Mark Goldberger, Head of Enterprise Sales at Ramp, shares his journey from the wine industry to leading enterprise sales teams in Silicon Valley, emphasizing the importance of product-customer fit over product-market fit for early sales. He advises against hiring a VP of sales too soon, instead suggesting that founders or junior salespeople should initially establish the sales playbook. Goldberger highlights the significance of building a sales team with the 'four H's'—hunger, hustle, humility, and heart—and stresses the necessity of creativity and adaptability in reps for exponential growth. He also underscores the critical role of traditional outbound sales methods in pipeline generation, despite the shift towards digital interaction. Furthermore, Goldberger discusses the strategic integration of customer success teams early in the sales process and the value of equity in compensation for sales hires. Host Harry Stebbings also touches on the utility of Pocus and SalesLoft in optimizing sales team performance.

• Product customer fit is essential for initial sales, especially for the first seller in enterprise sales.
• Revenue should not be the main focus in the early stages; acquiring logos and credibility is more important.
• A salesperson needs to prioritize opportunities that align with the company's vision and core competencies.
• It's important to qualify opportunities effectively, knowing when to lean in, pivot, or walk away.

"You don't need product market fit in order to sell an enterprise, especially as that first seller. What you need to find is product customer fit."

This quote emphasizes the importance of finding a match between the product and the individual customer's needs, rather than trying to fit the product into the broader market immediately. It suggests a targeted approach to early sales.

"Those first sales don't think about revenue as being important. The revenue or the currency that matters in those first sales are the logos."

Mark Goldberger advises that in the initial phase of sales, the focus should be on building a portfolio of credible logos (well-known companies) that use the product, rather than prioritizing immediate revenue generation.

• Founders are crucial in achieving product market fit by engaging with customers and understanding their pain points.
• The sales playbook should originate from the salesperson, who may or may not be the founder.
• Early hiring should focus on a salesperson who can test the product in the market, not necessarily a VP of Sales with a predefined playbook.

"For product market fit, I think that is driven more by the founder being out in the field, talking to customers, talking to prospects, really understanding their pain points and being able to dive in at that level."

Mark Goldberger points out that founders play a critical role in achieving product market fit by deeply engaging with the market and understanding customer needs.

"But in no circumstances do you really want to bring in a vp of sales before you have a seller, because they're going to come in with the preconceived notions that ultimately might not mesh with your particular business model."

This quote explains that hiring a VP of Sales too early can be counterproductive due to their existing notions and strategies, which may not align with the startup's unique business model and needs.

• Hiring the first salesperson should occur once there is a product ready to be tested in the market.
• Logos and customer feedback are more valuable than revenue in the early stages.
• It is beneficial to hire exceptional sales talent as soon as they are found, rather than waiting to hire multiple people at once.

"I think they should make that first hire as soon as they have a product that they really want to be testing out in the market, I think it's a lot sooner than a million ARR, to be honest."

Mark Goldberger suggests that startups should hire their first salesperson early in the product lifecycle to begin testing and gaining market feedback, rather than waiting to reach a certain revenue threshold.

"When you find someone who can provide that ten x level of growth, they're a rare find. To find two at the exact same time and to be able to recruit them and have them join at the same time is an exceptionally rare opportunity."

This quote highlights the challenge of finding multiple high-performing salespeople simultaneously and suggests that startups should hire exceptional talent whenever they become available, rather than waiting to hire in pairs.

• A deal champion is someone who can influence the decision-making process and bring the seller to the executive buyer.
• Testing whether a stakeholder is a true champion is crucial; this involves asking them to help present to the executive buyer.
• Setting the expectation of meeting with the executive buyer from the beginning is key to avoiding miscommunication.

"There is only one way to know if they really are a champion for you. You have to test them. And the way that you test them is asking them to take you to the executive buyer."

Mark Goldberger explains that the true test of a deal champion is their willingness and ability to connect the seller with the decision-makers, indicating their influence and commitment to the deal.

"You need to set that expectation from the start. Literally, in the first meeting."

This quote stresses the importance of clear communication from the outset about the seller's expectations to engage with high-level decision-makers, ensuring alignment and transparency in the sales process.

• Mark Goldberger emphasizes the importance of establishing a partnership rather than a typical vendor-customer relationship.
• Open dialogue between executive teams is crucial for understanding and addressing the concerns of the CFO and other key stakeholders.
• The partnership approach ensures that the sales process aligns with the client's needs and expectations.

"This is not a typical vendor customer relationship, but it's a partnership."

The quote highlights the philosophy behind Mark Goldberger's sales approach, which is based on building a partnership with the client, ensuring mutual understanding and collaboration.

• The right time to engage the executive buyer is after establishing the business value assessment and agreeing on the value provided.
• Salespeople can leverage their network, board members, and executive team to reach the executive buyer.
• The champion should accompany the salesperson to present findings to the executive buyer.

"Typically, you want to be able to get some kind of a business value assessment where you're agreeing on what the value is that we can provide for an organization."

This quote explains that understanding and agreeing on the value proposition with the client is a prerequisite for engaging the executive buyer.

• Mark Goldberger is strongly against outsourcing the salesperson's job to a champion within the prospect's organization.
• Being present in meetings with CFOs and other executives is critical to handle challenging questions and discussions.
• Relying solely on a champion is risky as they may not have answers to all questions, which could jeopardize the deal.

"There is not a world that I would ever be comfortable living in where I want to outsource my job to a champion."

The quote conveys Mark Goldberger's insistence on the salesperson's direct involvement in critical meetings, rather than relying on a champion to represent their case.

• Sales reps must be skeptical and question everything to anticipate potential issues in a deal cycle.
• Asking tough questions and considering all the ways a deal could fail helps in preparing for objections and challenges.
• Creating a safe environment where sales teams can ask difficult questions without fear is essential for effective sales strategies.

"The way that you see around corners is you ask the hard questions, you run toward the danger, and what scares you? Not away from it."

The quote suggests that facing potential problems head-on and proactively addressing them is key to successful sales strategies.

• Deep discovery is critical in sales qualification to uncover secondary and third-level pain points.
• Sales reps should not rush to sell their solution but rather focus on understanding the full extent of the client's pain.
• The MEDDPICC qualification methodology is recommended for a thorough understanding of deal dynamics.

"You need to go deep. You need to do some significant discovery where you get to secondary, third level pain and really let someone stew in that pain."

This quote emphasizes the importance of in-depth discovery to truly understand a client's needs and pain points before offering a solution.

• Urgency in a sales cycle is driven by the client's pain points.
• If there is not enough pain, sales reps should revisit discovery or find other stakeholders with more significant pain.
• Multi-threading and building multiple champions within an organization can help create urgency.

"If you don't have enough pain, there's not a world where I can get you to have the urgency you need, short of discounting."

The quote explains that urgency in a sales cycle is inherently linked to the magnitude of the client's pain points, and without it, creating urgency is challenging.

• Discounting is common in sales but should be minimized by selling the value of the solution.
• Sales reps should focus on matching their solution to the client's pain points to reduce the need for discounting.
• Asking for customer referrals or permission to use logos should be approached confidently without sounding desperate.

"The more pain that you find and the more your solution matches with the pain that you're solving for, the less you need to discount."

This quote suggests that understanding and addressing the client's pain effectively reduces the need to rely on discounting to close deals.

• Many salespeople lack confidence, especially when they are new to the field and encounter unfamiliar situations.
• Experience and pattern recognition, referred to as "scar tissue," help build confidence and improve sales performance.
• Mentorship is key to helping sales reps recognize blind spots and develop a more well-rounded skill set.

"You have what? One of my mentors, Carlos Delatore, he had a great colorful phrase for it. It's called scar tissue. And scar tissue is also known as pattern recognition."

Mark Goldberger uses the metaphor of "scar tissue" to describe how experience and pattern recognition contribute to a salesperson's confidence and ability to handle various situations.

• Effective mentorship helps sales reps identify and navigate their blind spots.
• Sales leaders should encourage reps to build more pipeline and prepare for different outcomes.
• Great mentorship involves guiding reps to become more well-rounded and capable of handling diverse sales situations.

"The key to mentorship is helping people see their blind spots."

The quote underscores the importance of mentorship in revealing areas for improvement that sales reps might not be aware of on their own.

• The "Four H's" of hiring in sales are hunger, hard work, humility, and honesty.
• Intangible qualities like desire, work ethic, and the ability to learn are crucial for success in sales roles.
• Sales leaders should look for candidates who demonstrate these qualities during the hiring process.

"The four h's is something that I came up with that really is about saying the intangibles matter more than the tangibles."

Mark Goldberger's quote introduces the "Four H's" as a framework for identifying the key intangible traits of successful sales candidates.

• The concept of "hustle" is important for growth and involves working harder than others.
• "Heart" is seen as a special sauce, akin to grit, which is essential for champions.
• Reed Hastings' book "No Rules" is mentioned for its discussion on talent density.
• Grit density, the collective perseverance of a team, is argued to be as important or more than talent density.

You need to use that to fuel your growth. The last h is heart. It should be table stakes, but instead it's more like special sauce. Think of it like grit.

This quote emphasizes the importance of not just working hard (hustle) but also having the resilience and determination (heart) to overcome challenges.

• "Thinking outside the horse" is a metaphor used to describe looking beyond conventional wisdom, especially in sales hiring.
• A faster horse and buggy versus an automobile is used as an analogy for traditional versus innovative product development.
• The metaphor extends to sales teams, where traditional "A players" may not be enough for exponential growth.
• Creativity and adaptability are highlighted as essential qualities for salespeople beyond the conventional criteria.

You need to think outside the horse.

Mark Goldberger uses this phrase to encourage unconventional thinking in hiring practices, especially for sales teams, to achieve greater productivity.

• The best salespeople often do not fit the traditional mold or come from the expected backgrounds.
• Creativity and adaptability are key traits of top salespeople.
• Hiring is focused on potential for growth, not just current capabilities.
• During interviews, deep questions about the candidate's reasoning and decision-making processes are crucial.

The best salespeople, in my experience, rarely fit the mold of what great salespeople should look like.

Mark Goldberger points out that exceptional sales talent often defies expectations and traditional hiring criteria, emphasizing the need for a broader perspective in recruitment.

• Interview challenges should simulate real-life situations, testing candidates' ability to adapt and think on their feet.
• Selling the interviewer's solution back to them is a way to assess research skills and comprehension.
• The ability to handle unexpected changes, such as a shortened meeting time, is a valuable trait.

I want them to sell to me, not what they're selling today, but I want them to sell my solution back to me.

Mark Goldberger explains that this approach in interviews is designed to evaluate a candidate's research and adaptability skills, which are critical in a sales environment.

• Experience in selling enterprise deals is emphasized over experience in a specific market segment.
• The ability to manage multiple complex deals simultaneously is seen as a critical skill for enterprise sales.

Can you play 20 simultaneous games of chess?

This analogy illustrates the complexity and multitasking required in enterprise sales roles, as described by Mark Goldberger.

• Sales leaders should be involved in mentoring and creating low-stakes situations for reps to learn.
• It's important to provide tools for success and allow for controlled failures.
• Sales leaders' performance is tied to their team's success.

You need to create space for them to fail when the stakes are low so they can succeed when the stakes are high.

Mark Goldberger discusses the importance of allowing sales reps to experience failure in a controlled environment to prepare them for high-stakes situations.

• The hiring process should quickly assess candidate quality and potential.
• It should include deep-dive interviews and challenges, as well as meetings with other stakeholders.
• The goal is to understand the candidate's motivations and capabilities comprehensively.

You want to go deeper. You want to spend an hour with them. You want to really go deep.

Mark Goldberger advises spending significant time with candidates to thoroughly understand their abilities and fit for the role.

• Assumptions about a candidate's fit based on their experience can be risky.
• Testing for compatibility with the company's culture and needs is crucial.
• Hiring mistakes can be costly in terms of time and resources.

I've certainly made mistakes.

Mark Goldberger acknowledges past hiring errors and stresses the importance of thorough evaluation to avoid misjudging a candidate's fit.

• Early sales hires should be offered equity, not just cash compensation.
• Equity aligns the salesperson's interests with the company's long-term vision.
• Founders often overlook the importance of equity for sales roles.

I think when it comes especially to early sales hires, there's not enough emphasis placed on equity in sales.

Mark Goldberger highlights the lack of focus on equity compensation for sales roles and suggests that it is an important element to consider.

• Quotas should be realistic and achievable, aligned with company goals.
• Working backward from goals helps identify potential obstacles and paths to success.
• Building a large pipeline is essential for meeting quotas.

You need to, in the early days, figure out what is the goal that the board is setting for you or that you're sharing with the board.

Mark Goldberger advises on the importance of setting realistic sales quotas that are informed by company objectives and strategic planning.

• Traditional outbound sales is crucial for pipeline generation.
• Persistence in outreach is necessary as it often takes multiple contacts to get a response.
• Providing solutions through outreach can lead to significant opportunities.

Traditional outbound is the most important thing, Harry.

Mark Goldberger argues for the continued importance of traditional outbound sales tactics, contrary to the belief that it may be outdated.

• Sales should benefit both the salesperson and the customer.
• The approach to sales is not about pushing unnecessary products but providing something genuinely helpful.
• Successful sales interactions are based on the idea of mutual benefit.

"We're not trying to sell them something that they don't need."

This quote emphasizes the ethical approach to sales where the focus is on meeting customer needs rather than just making a sale.

• Onboarding should be a combination of structured and unstructured learning.
• New sales reps benefit from shadowing experienced reps and receiving one-on-one coaching.
• Early exposure to real situations helps assess a rep's ability to adapt and perform.
• It's important to balance between a challenging start and providing manageable opportunities for new reps.

"I think it needs to be a mix of structured learning and unstructured learning."

This quote highlights the importance of a balanced approach to onboarding, combining different learning methods for optimal results.

• Lack of engagement, such as not asking questions, can be a red flag.
• It's crucial to differentiate between a lack of understanding and a lack of curiosity.
• Quick action may be necessary if a new hire is not a good fit.

"But if someone is not asking a lot of questions, if they're not vocal in that first month or two, to me, that's a red flag that I want to at least dig into."

This quote points out the importance of proactive engagement from new hires and the need to investigate any lack thereof.

• It's important to ask probing questions about a candidate's past sales experiences.
• Understanding the context of a candidate's achievements is crucial, such as the size of the company they sold to and the nature of the deal.
• Deal attribution is a complex factor and should be considered carefully.

"It's why you need to ask those why questions."

This quote stresses the need for in-depth questioning to truly understand a candidate's sales track record and capabilities.

• Deal reviews should be frequent and involve any significant potential deals.
• Understanding the intricacies of each deal is essential to avoid losses and missed opportunities.
• The process should involve thorough stakeholder mapping and risk assessment.

"I think you should do a deal review for any deal that is going to be impactful toward you hitting your goal for that quarter or that year period."

This quote underlines the importance of frequent and strategic deal reviews in the sales process.

• Losing to competition can happen for various reasons, including price sensitivity and stakeholder influence.
• Understanding the customer's priorities and mapping the organization are key to preventing losses.

"There are a variety of reasons you could lose, but you need to map the organization."

This quote highlights the necessity of organizational understanding as a strategy to mitigate the risk of losing deals.

• The transition from sales to customer success should be seamless and begin before the deal is closed.
• The sales process should include discussions about implementation and success metrics.
• Building relationships with the customer success team early on is beneficial for the customer.

"Implementation, onboarding how we're going to make you successful as a customer is part of the sales process."

This quote illustrates the integration of customer success into the sales journey to ensure a smooth transition and ongoing customer satisfaction.

• Customer Success (CS) teams are typically compensated based on product adoption and usage.
• CS involvement in the sales process indirectly contributes to their compensation through successful adoption.

"CS, often in most organizations, are going to be compensated based on adoption, at least in companies that are based on usage."

This quote explains the compensation model for CS teams, which is tied to the successful implementation and use of the product they support.

• Fundamental sales tactics like cold calling and emailing remain unchanged.
• In-person meetings have declined, with digital tools taking precedence.
• The CEO and executive team involvement is crucial for significant deals.
• Founders should avoid hiring salespeople who only fit a specific mold.
• Sales leaders should aim to constantly improve their teams.
• The perception of sales as an art rather than a science needs to change.
• After missing goals, pipeline coverage is key to recovery.
• Companies like Starlink are noted for impressive sales strategies despite being less visible.

"The fundamentals, cold calling, cold emailing, that pipeline, generation qualification champion building, getting to the EB."

This quote points out that despite the changes in the sales landscape, the core principles of sales remain constant.

• Understanding the root causes of missed goals is essential.
• Maintaining morale involves addressing issues and focusing on pipeline coverage.
• Everyone in the organization shares responsibility for pipeline coverage.

"You have to start with understanding why it happened, who's responsible."

This quote emphasizes the need for analysis and accountability in addressing missed sales goals to prevent recurrence and maintain team morale.