20 Sales How To Build Sales Teams with a ProductLedGrowth GTM, What is a Sales Hiring Scorecard and How To Construct Yours & How To Structure the Onboarding Process for all New Sales Hires with Dannie Herzberg, Partner @ Sequoia Capital

Summary Notes


In the latest episode of "20 Sales," host Harry Stebings interviews Danny Herzberg, a partner at Sequoia Capital and former head of enterprise sales at Slack. Herzberg shares her journey from caring for her sick mother to scaling sales organizations at Slack and HubSpot, emphasizing the importance of culture, community, and customer understanding in sales success. She highlights the need for sales leaders to love selling, break glass, and have effusive references, while advising founders on the criticality of hiring revenue ops and sales enablement early. The discussion also touches on fostering strong relationships between sales and product teams, the significance of a founder selling initially, and the transformative power of proactive outbound efforts. Danny's personal story of family-first values and her proactive approach to life, including how she met her husband, adds a unique depth to the conversation.

Summary Notes

Introduction to "20 Sales" Podcast

  • "20 Sales" is a monthly show hosted by Harry Stebings.
  • The show features interviews with ten of the best sales leaders to uncover insights into scaling sales organizations.
  • Transcripts of the discussions are available through the Twentyminutevc.com newsletter.

This is 20 sales with me, Harry Stebings.

Harry Stebings introduces the "20 Sales" podcast.

Where we interview ten of the best sales leaders to reveal their tips, tactics and strategies when it comes to scaling some of the best sales orgs in the world.

The purpose of "20 Sales" is outlined, emphasizing the sharing of expert tips and strategies in sales.

Guest Introduction - Danny Herzberg

  • Danny Herzberg is a partner at Sequoia Capital.
  • He has a history of sales leadership, including four years at Slack as head of enterprise sales.
  • Danny built and scaled sales organizations at Slack and HubSpot.
  • Pat Grady and Carl Eschenbach were thanked for their pre-show input.

I'm thrilled to welcome a friend and phenomenal sales leader, Danny Herzberg.

Harry Stebings introduces the guest, Danny Herzberg, highlighting his accomplishments.

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Danny Herzberg's Tech Journey

  • Danny's parents were refugees from the Soviet Union, which influenced his career path.
  • He moved to Boston to care for his sick mother and joined HubSpot during its early stages.
  • His passion for HubSpot's culture and community led to a job offer despite lacking formal sales training.

Combination, like all good things of personal priorities, a little bit of serendipity, and I would say professional ambition in terms of what got me into tech in the first place.

Danny describes the personal and professional factors that led him to a career in tech.

Key Takeaways from HubSpot Experience

  • HubSpot's culture and community became benchmarks for Danny's career choices.
  • The company had a strong focus on culture, with a culture code document and dedicated resources.
  • The community was actively engaged, with user conferences and a vibrant ecosystem.

HubSpot created the spec for my future career decisions, both as an operator and an investor.

Danny's experience at HubSpot shaped his future career and investment decisions.

Assessing Company Culture and Community

  • Danny evaluates company culture and community by their content creation and user engagement.
  • He uses Notion as an example of strong community engagement.
  • He inquires about operating principles and culture in meetings with founders.

It's a great question. So let's take notion as an example.

Danny explains how he assesses culture and community engagement using Notion as an example.

Takeaways from Slack Experience

  • At Slack, people and cross-functional relationships were paramount.
  • Sales and success departments needed to collaborate closely due to the importance of expansion.
  • Reflecting and conducting retrospectives were valuable exercises.

Nothing matters more than people.

Danny's primary takeaway from Slack is the importance of people in a company's success.

Conclusion and Handover to Danny Herzberg

  • The host expresses excitement for the interview and acknowledges the positive feedback from colleagues.
  • The conversation is set to provide insights into Danny's career and sales expertise.

Capital 3210, you have now arrived at your destination. Dan, Annie, this is such a joy for me to do.

The host concludes the introduction and transitions to the main interview with Danny Herzberg.

Founder as the Initial Head of Sales

  • Founders must initially act as their own head of sales to understand customer needs, objections, and the sales process.
  • Early sales by the founder build empathy for future salespeople and inform product direction.
  • Founders can hire a seasoned head of sales after gaining firsthand sales experience.

"So the founder needs to sell the product before anyone else can. So day one, founder equals head of sales."

This quote emphasizes the importance of the founder's role in sales at the inception of their company, highlighting the need for direct engagement with the market and customers.

Hiring the Next Head of Sales

  • After the founder, the next head of sales could be a "player coach" who sells and hires the next account executives.
  • The next sales leader should have prior leadership experience and be company-oriented rather than focused solely on individual quotas.
  • The right candidate should be experienced but still willing to engage directly in sales activities.

"The next one could be a player coach who can roll up his or her sleeves, do the selling, while simultaneously taking the lead on hiring the next four account executives."

This quote outlines the dual role of the subsequent head of sales, stressing the need for a balance between direct sales involvement and leadership responsibilities.

Transition to a Chief Revenue Officer (CRO)

  • A CRO is needed when the company moves past the startup phase and the sales formula is ready to scale.
  • Hiring a VP or SVP allows room for growth in earlier-stage companies, whereas later-stage companies can hire an experienced CRO.
  • The CRO will significantly influence the sales culture and should be hired thoughtfully.

"You need a CRO when you're past the zero to one phase."

This quote identifies the stage at which a company should consider hiring a CRO, linking it to the company's growth and readiness to scale.

Characteristics of Exceptional Sales Leaders

  • Exceptional sales leaders have a genuine love for selling and are natural connectors.
  • They should have a track record of people willing to follow them to new roles.
  • A good sales leader is unafraid to challenge the status quo and debate healthily.

"I want someone who breaks glass."

This quote describes the desired characteristic of a sales leader who is proactive and willing to disrupt the norm to achieve results.

Internal Promotion vs. External Hiring for Sales Leadership

  • Both internal promotions and external hires have their place, but the first senior sales leadership role may benefit from external expertise.
  • Hiring externally should not be done at the expense of internal promotion culture.
  • External hires need to adapt to the new company's culture and not just replicate past playbooks.

"So should you create a culture of promoting within? Yes. But for first senior leadership, higher in sales, should you necessarily do that from within the company? No, not necessarily."

This quote discusses the balance between fostering internal growth and bringing in external expertise for critical sales leadership roles.

Integrating External Sales Leaders Without Demotivating the Team

  • Cultivate a culture where employees take pride in building and handing off responsibilities.
  • Ensure new hires are flexible and understand what practices will not transfer to the new company.
  • Transparency and clear communication are key when bringing in external leaders.

"I think you need to make that a part of each employee's personal brand."

This quote suggests that embracing change and growth should be part of the company culture, easing the integration of external hires.

Structuring the Sales Hiring Process

  • Founders often lack experience in hiring sales roles.
  • A sales interview process should be structured around a scorecard with key must-have attributes and skills.
  • Interviews should reveal a candidate's thought process, business acumen, and decision-making patterns.

"We start by creating a scorecard. That scorecard has no more than five must-have attributes and skills, and we figure out what those are, and then we start structuring the questions around them."

This quote advises on a structured approach to sales interviews, focusing on essential attributes and skills relevant to the role.

Evaluating Sales Candidates

  • Avoid hypothetical questions as sales candidates are adept at selling themselves.
  • Instead, ask questions that require candidates to demonstrate their knowledge and thinking in real-time.
  • Use work samples and strategic problem-solving sessions to assess candidates' capabilities.

"For a sales rep, I want to hear what it sounds like when they sell."

This quote highlights the importance of practical demonstrations of a sales candidate's skills, ensuring they can perform effectively in their role.

Sales Rep Evaluation Criteria

  • Assessing sales reps involves observing their ability to ask open-ended questions.
  • Handling common objections with thoughtful questions is critical.
  • Avoiding immediate discounting or transactional responses is a positive sign.
  • Evaluating craftsmanship in presentation, such as slide quality and absence of typos.
  • Understanding the product and customer base, as well as doing homework on the company, is essential.
  • Watching company-related YouTube videos and podcasts is part of the preparation.

"And what you're listening for is do they ask open-ended questions."

This quote emphasizes the importance of a sales rep's ability to engage in a conversation that elicits detailed responses from potential clients.

"Are they putting together one or two slides that don't have any typos?"

The attention to detail in a sales rep's presentation materials reflects their professionalism and dedication to quality.

Importance of References in Hiring

  • References provide crucial insights into what it's like to work with a candidate.
  • A diverse range of references from peers, subordinates, and superiors is valuable.
  • The reference check is a critical step, not just a formality.

"There is no more important step in the process than understanding what it was like to work with this person."

This quote highlights the significance of reference checks in the hiring process, as they offer a realistic view of a candidate's work ethic and interpersonal skills.

Conducting Effective Reference Checks

  • Start by asking the reference to share positive experiences with the candidate.
  • Use a scale of 1 to 10 to gauge the strength of their recommendation, probing on any score less than 10.
  • The addition of the word "blindly" can reveal hesitations and provide context-specific insights.

"On a scale of one to ten, would you blindly recommend this person into a vp of sales role?"

Asking for a "blind" recommendation can uncover reservations the reference may have, offering deeper insight into the candidate's suitability.

Interpreting and Valuing References

  • A tenacious sales hire may not always have universally positive references.
  • Negative feedback should be weighed against the candidate's overall fit for the role.
  • Trusting one's intuition is important, alongside considering references.

"References are critical, but they aren't everything."

This quote suggests that while references are important, they should be balanced with personal judgment and other factors in the hiring decision.

Hiring Based on Respect Over Likability

  • Respect is prioritized over personal likability in hiring decisions.
  • Candidates should be capable of earning respect from their colleagues.
  • Being liked should not overshadow the ability to challenge and ask difficult questions.

"I would hire someone if I didn't like them, so long as I respect the way that they think."

The speaker expresses a willingness to hire someone they don't personally like, provided there is professional respect for the individual's abilities and integrity.

Overcoming the Need to be Liked

  • Being respected should take precedence over being liked in a professional setting.
  • Accountability partners can help individuals focus on being respected.
  • Reflecting on the unconditional love from close ones can provide courage for tough conversations.

"I think if you make it a priority to be respected versus liked. It will inch you in that direction."

This quote advises focusing on gaining respect rather than likability as a means of professional growth and effectiveness.

Onboarding Sales Leaders and Reps

  • The first month for a sales leader should involve a customer tour and extensive listening.
  • Reps should listen to sales calls and practice with discarded leads to improve their skills.
  • Proactive engagement and understanding of the product are necessary for success in a PLG company.

"So a sales leader should go on a customer tour, ideally meeting some of the customers in person."

The quote suggests that personal engagement with customers is a crucial part of a sales leader's onboarding process to understand the product's real-world application.

Red Flags During Onboarding

  • Lack of product knowledge is a concern, especially in PLG companies.
  • Inaction or lack of a formulated action plan can be warning signs for new leaders and reps.

"A good candidate will use the product and perhaps deliver some of the interview unprompted by utilizing the product itself."

The speaker indicates that a candidate's proactive use of the product during the interview can be a positive indicator of their initiative and understanding of the product.

Customer Orientation in Leadership

  • Importance of new leaders engaging with customers from the start.
  • A leader's lack of customer interaction is a red flag.
  • Optimal leaders are proactive and dive into sales opportunities.

If a leader had not gotten in front of a customer, if he or she was sitting in virtual or physical conference rooms for their first two months and wasn't talking to one new customer, at minimum every single week, that is a major flag for me about customer orientation and the health of the that they were going to build on the seller side.

This quote emphasizes the significance of leaders actively engaging with customers early in their tenure to establish a customer-centric approach and to gauge the health of the sales side they will build.

Building Confidence in Sales Reps

  • Confidence is crucial for sales reps, especially younger ones.
  • Strategies to foster early confidence in sales reps.
  • Celebrating small wins and creating a supportive culture.

I think confidence is such an important part of sales, especially on the rep side, when they're maybe a little bit younger.

This quote addresses the importance of instilling confidence in younger sales reps, which is key to their performance and development.

Culture of Experimentation and Failure

  • Founders and CROs should encourage a culture where experimentation and failure are acceptable.
  • New reps should be given manageable leads to build confidence.
  • Positive reinforcement is preferred over fear-based motivation.

Part of it is the culture that the founder sets and that the CRO sets within the company. So if there is a culture where experimentation is welcome and failure is okay.

This quote highlights the role of company culture in fostering a safe environment for sales reps to experiment and learn from failures without fear of repercussions.

Sales and Product Relationship

  • Aligning incentives between sales and product teams.
  • Regular meetings and personal relationships are key for alignment.
  • Product teams should be involved in sales QBRs and customer calls.

Within your number one incentives should be aligned.

This quote suggests that for effective collaboration, the sales and product teams need to have aligned incentives, ensuring they work towards common goals.

Sales Leader and CEO Relationship

  • Trust and mutual respect are foundational in the sales leader-CEO relationship.
  • Regular communication and inclusion of the CEO in sales processes are recommended.

It is a critical relationship, and I think my answer here is the same answer as I would give for any ideal relationship, which is there should be a sense of trust and a sense of mutual respect.

This quote underscores the importance of trust and respect in the relationship between a sales leader and the CEO, which is essential for the success of the business.

Sales Tactics and Strategies

  • Timeless sales skills: asking good questions, listening, and connecting.
  • Outdated tactics: long slide deck presentations.
  • The importance of early investment in revenue ops and sales enablement.

Asking good questions, listening and connecting are timeless skills of a sales professional.

This quote identifies the fundamental, unchanging skills that are essential for sales professionals to master.

Sales Leader Advice

  • Sales leaders should deeply understand their customers.
  • Personal branding and proactive outbound approaches are beneficial.
  • Setting ambitious goals can drive personal and professional growth.

Get to know the customer, meet them where they are, fly out, see where they work, understand the full context, and show them that you care.

This quote advises sales leaders to immerse themselves in their customers' environments to build meaningful relationships and show genuine care.

Personal Life Influences

  • Service industry experience teaches valuable life skills.
  • Personal relationships and proactive life approaches are impactful.
  • Balancing family life and work is essential for personal fulfillment.

I got the job at HubSpot because I was a waitress.

This quote connects the speaker's experience in the service industry to the development of skills that contributed to their professional success.

Sales Strategy Admiration

  • Community-first strategies like those of Figma and Notion are commendable.
  • Sales assist from passionate user bases can drive growth.

Well in that Figma and notion community. First, welcome sales assist impassioned user base.

This quote praises the community-first sales strategies of companies like Figma and Notion, highlighting the effectiveness of leveraging a passionate user base.

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