20 Sales Three Reasons Why Sales People Fail The Two Things That Matter When Hiring Sales Leaders Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

Summary Notes


Harry Stebings interviews Jordan van Horn, a seasoned revenue leader at Monte Carlo, on his podcast "20 Sales." Van Horn, who previously excelled in sales roles at Segment and Dropbox, shares insights on scaling sales teams, emphasizing the importance of simplicity, clarity, and hiring top talent. He also discusses his journey from the wine industry to tech sales, the evolution of sales playbooks, and the necessity of product-market fit before hiring salespeople. Van Horn stresses the significance of founders in shaping sales strategies and the value of understanding customer needs and qualification in sales tactics. Additionally, he highlights the transformative sales approaches of companies like Retool and MongoDB. Throughout the conversation, Stebings and van Horn explore the nuances of sales leadership, onboarding, deal reviews, and fostering a culture of openness and learning from failures.

Summary Notes

Introduction to Jordan Van Horn

  • Jordan Van Horn is a revenue leader at Monte Carlo, a data observability company.
  • He has a background in sales with previous roles at Segment and Dropbox.
  • His experience includes leading a sales team of 50+ account executives and spearheading international expansion.

"Today I love doing these episodes because I simply learn so much today. More so than ever. Get your notebook out and be ready for Jordan van Horn, revenue leader at Monte Carlo, the world's first data observability company."

The quote sets the stage for the interview, emphasizing the learning opportunity from Jordan Van Horn's insights on sales strategies and his background in leading sales teams at tech companies.

Jordan's Journey into Sales

  • Jordan entered the sales world by chance, starting in the wine industry with Gallo Winery.
  • His move to tech sales was influenced by relocating to San Francisco, leading to a role at Dropbox in the early 2010s.
  • The transition from wine to tech showcases the diversity in sales career paths.

"I just kind of wandered into it, to be honest... I ended up at Dropbox maybe back in the early 2010s from there. It's just an amazing experience."

Jordan describes his unconventional path into sales, highlighting the serendipity of his career trajectory and the positive impact of his time at Dropbox.

Learning from Early Career Experiences

  • Selling to a broad range of people, from grocery store managers to U.S. senators, provided Jordan with invaluable experiences.
  • These experiences taught him how to connect with people from different walks of life and understand their priorities.

"One day you're selling to grocery store managers, and the next day I had this job where I was selling to U.S. senators... it gives you a perspective on how to connect to people in different walks of life."

Jordan reflects on the variety of his early sales experiences, emphasizing the importance of adaptability and understanding diverse customer needs in sales.

Key Takeaways from Dropbox and Segment

  • Dropbox taught the importance of simplicity and clarity of thought, as well as the challenges of identity in a company.
  • Segment highlighted the critical role of hiring and maintaining a high talent bar.
  • Jordan credits his success in talent evaluation and hiring to his experiences at these companies.

"I think startups live and die by simplicity and clarity of thought... Segment was really different... I think I learned in that role the importance of becoming really great at hiring."

Jordan compares his learnings from Dropbox and Segment, noting the significance of company identity and the impact of effective hiring practices on business success.

Defining the Role of a Revenue Leader

  • The title of "revenue leader" encompasses sales, development, customer success, and partnerships.
  • Monte Carlo does not have formal titles or levels, so the exact title for Jordan's role is flexible and not yet defined.
  • The discussion reflects the evolving nature of roles in fast-growing startups.

"It's not different than a CRO. So my remit is sales, development, sales, cs, customer success, partnerships, bunch of broad functions."

Jordan clarifies the scope of his role as a revenue leader, equating it to that of a Chief Revenue Officer (CRO) and outlining his broad responsibilities.

The Sales Playbook

  • A sales playbook consists of steps to help customers understand the product, evaluate its impact, gain consensus, formalize the relationship, and ensure customer success.
  • The playbook should be initiated by the founder, with later versions becoming more detailed and prescriptive.
  • Founders are responsible for defining the core market pillars, documenting wins and losses, and establishing reasons for immediate action.

"So a sales playbook is discrete steps that you take to accomplish five things."

Jordan provides a succinct definition of a sales playbook, outlining its purpose and components in the sales process.

Founder's Role in Sales Playbook Creation

  • Founders should create the initial sales playbook, focusing on who the product is for (and not for), key factors for success, and reasons to buy now.
  • The playbook evolves over time, with sales leaders refining it to onboard and guide sales teams effectively.
  • Founders must continually answer core go-to-market questions at every stage of the company's growth.

"I think 100% a leader of an organization, a founder, is accountable for that v zero of that playbook."

Jordan emphasizes the founder's responsibility in establishing the foundational sales playbook, which sets the direction for the sales team.

Documenting Points of Resonance

  • Recording sales calls and having salespeople shadow founders are effective ways to document what resonates with customers.
  • Founders should ask customers why they took the call and categorize their reasons into a few broad archetypes.
  • This documentation helps salespeople understand customer motivations and tailor their approach.

"The best gift you can give to a salesperson coming in is a subset of recorded calls."

Jordan advises on the best practices for documenting points of resonance, highlighting the value of recorded calls and direct customer engagement for sales personnel.

Addressing Urgency in Sales

  • Understanding a customer's pain points is essential to creating urgency for a purchase.
  • Sales teams must make the consequences of not addressing these pain points clear to the customer.
  • Discounting strategies, like exploding discounts, can be detrimental to the customer experience and should not be the primary method to create urgency.

"If you deeply understand a customer's pain, then you know why they have to solve it... and why do they need to solve it right now?"

Jordan discusses the importance of aligning sales strategies with customer pain points to naturally create a sense of urgency for closing deals.

Importance of Early Customer Acquisition

  • Early customer acquisition is crucial for startups, focusing on learning and product improvement.
  • Good early customers drive product forward through positive market advocacy or valuable feedback.
  • Initial revenue amounts from early customers are less significant compared to long-term growth potential.
  • Discounting practices should be carefully considered, emphasizing price-to-value communication.

"I think the only thing that matters is that you're learning and that you have good customers who are good fits that are going to drive your product forward."

This quote emphasizes the importance of having customers who contribute to the startup's growth either through feedback or by advocating for the product in the market.

Pricing and Discounting Strategy

  • Pricing discipline becomes crucial as a company grows and acquires more customers.
  • Customers seek fair pricing and want assurance they aren't being overcharged.
  • Over-discounting can lead to customer experience issues and undervalue the product.
  • Aligning price to value is critical, and some customers may not find value at certain price points.
  • Pricing and packaging should be addressed instead of resorting to excessive discounting.

"Aligning price to value is really critical."

This quote highlights the importance of setting prices that reflect the value provided to customers, ensuring they feel they are getting a fair deal.

Multithreading in Sales

  • Multithreading involves engaging multiple stakeholders within a customer's organization.
  • It is crucial for larger, complex deals to mitigate churn risks if a single champion leaves the company.
  • For smaller deals, compressing deal cycles is more important than multithreading.
  • An enterprise sales rep's role is evolving to include managing relationships with multiple champions.

"You have to multithread, you have to have multiple stakeholders, you have to have a person."

This quote stresses the need to engage various stakeholders to secure the deal and maintain customer relationships, reducing churn risk.

Timing for First Sales Hire

  • Hiring a sales leader depends on luck, timing, and business needs.
  • Founders must identify the problem they aim to solve by hiring a salesperson.
  • Sales hires should not be used to address product-market fit issues.
  • The right timing for a sales hire depends on the founder's capacity and the type of business (transactional vs. enterprise).

"What problem are you trying to solve with hiring a salesperson?"

This quote prompts founders to consider the specific challenges they aim to address by bringing on a sales hire, ensuring alignment with business goals.

Signs for Hiring a Sales Leader

  • Founders should look for signs like successful customers, lead generation, and lead progression.
  • Hiring a salesperson can be beneficial when the founder needs to focus on other aspects of the business.
  • The decision between hiring a head of sales or junior reps depends on deal complexity and go-to-market confidence.

"If you have a transactional business, yeah, you're probably ready."

This quote suggests that for businesses with a straightforward, high-volume sales model, it may be time to hire a sales leader to manage the process.

Choosing Between Head of Sales and Sales Reps

  • The complexity of the sale, go-to-market confidence, and founder involvement determine the type of sales hire.
  • For simple, low-cost deals, junior reps may suffice; for larger volumes, a head of sales might be needed.
  • A senior head of sales might not be hands-on in selling but can be valuable for team growth and talent attraction.

"If you go too senior on ahead of sales, they don't know how to sell anymore."

This quote warns that highly senior sales leaders may be removed from actual selling, which could be a mismatch for startups needing hands-on sales efforts.

Common Mistakes in Sales Hiring

  • Founders often mistakenly hire salespeople to solve product-market fit issues.
  • Evaluating sales and marketing talent is challenging due to the difficulty in attributing individual excellence.
  • Founders should deeply understand a candidate's past experiences and contributions beyond brand names on resumes.

"What problem you're trying to solve is probably the biggest one."

This quote reiterates the importance of hiring with a clear understanding of the problem that needs to be addressed, rather than expecting sales hires to fix underlying product issues.

Structuring the Sales Hiring Process

  • Salespeople may fail due to cultural misfit, lack of motivation, or skill set misalignment.
  • Founders should define cultural fit and motivation expectations before hiring.
  • Transparency about company challenges during interviews helps candidates self-select based on alignment.
  • In-depth questioning about past performance helps assess a candidate's true contribution and potential fit.

"Let me walk you through all of the things that are wrong at Monte Carlo."

This quote demonstrates the strategy of being upfront about company challenges to ensure candidates are willing and able to contribute positively to the organization's growth.

Interview Process and Hiring Criteria

  • Jordan Van Horn discusses the importance of examining candidates' relevant experiences and patterns in their background.
  • The interview process at Monte Carlo is broken down into motivation, historical track record, and skills assessment.
  • The initial interview screens for motivation to determine if the candidate is a fit for the company's challenging environment.
  • The second interview with the hiring manager assesses the candidate's history of excellence and deep dives into their success.
  • Onsite interviews involve three different interviewers focusing on specific competencies needed for the role.
  • The presentation at the end of the process is a test of motivation and hard skills, and gives candidates a taste of working at the company.

"90% of our interview is looking back at relevant experiences and trying to find patterns in that person's background and how they perform, how they relate to others, and how they use the experiences that they have to acquire the skills that we know that they need to be successful in our company."

This quote explains that the majority of the interview process is dedicated to understanding a candidate's past experiences and how those experiences have equipped them with the necessary skills for the role at Monte Carlo.

Presentation Evaluation in Interviews

  • The best presentations are characterized by the candidate's discovery process and ability to ask questions and engage the audience.
  • The worst presentations are compared to book reports, where candidates focus on showing knowledge rather than engaging in a dialogue.
  • Jordan Van Horn criticizes the pitch presentation interview format but acknowledges its usefulness in gauging a candidate's curiosity and communication skills.

"Discovery makes the best. Someone's curiosity, ability to ask questions and hold court."

This quote highlights that the most effective presentations during the interview process are those that demonstrate a candidate's curiosity and ability to lead a discussion, rather than just presenting information.

Hiring Mistakes and Lessons Learned

  • Jordan Van Horn reflects on hiring mistakes such as deviating from a structured process, inadequate reference checks, and not having a clear idea of what is needed for the role.
  • He emphasizes the importance of sticking to a structured hiring process, conducting thorough reference checks, and having a small, decisive hiring group.
  • Harry Stebbings notes the similarities between these hiring mistakes and his own experiences with investment decisions.

"The first one is veering from a very structured hiring process and letting bias creep into the process is always number one."

This quote captures the significance of adhering to a structured hiring process to prevent bias and ensure the best hiring decisions.

Post-Hiring: Management and Onboarding

  • Jordan Van Horn uses a public document called the "Jordan Van Horn User Guide" to communicate his work style, expectations, and important values to his team.
  • He discusses the importance of setting clear boundaries and providing a framework for communication.
  • Jordan Van Horn believes in nurturing talent by understanding what employees care about, being direct about their strengths and weaknesses, and revisiting these points regularly.
  • The ideal onboarding process reflects the stage and maturity of the company, with more structured programs as the company grows.
  • Managers play a crucial role in onboarding, and the biggest mistake they can make is not being close enough to the new hire's work.

"What I found is two things. Like one working remotely and then having larger teams. It's harder and harder for people to understand my motivations and why I do what I do."

This quote emphasizes the challenge of communicating one's motivations and working style in a remote work environment with a large team, and how the "User Guide" helps mitigate this challenge.

Onboarding Process and Identifying Fit

  • Effective onboarding is achieved through pattern matching and recognition.
  • Managers should focus on the best onboarding examples and emulate key aspects.
  • Monitoring and supporting new hires closely is crucial for their success.
  • Determination of a new hire's fit should be possible within 30 days.

What I always say to managers is pick out one or two people that you think had the best onboarding.

This quote emphasizes the importance of using successful onboarding examples as a benchmark for new hires.

And then you should know within 30 days about whether someone's going to be a fit or not.

This quote suggests a timeline for assessing a new hire's fit within the organization.

Identifying Red Flags in New Hires

  • Impact should be noticeable within the first 30 days, even if it's not in the form of major deals.
  • Red flags include lack of tangible impact and focusing on less relevant tasks.
  • New hires should demonstrate progress and engagement with the organization.

If you're not seeing that, but you're seeing maybe people are like, oh, I developed five x pipeline coverage or all of these very soft things that TBD about whether they're high impact or not.

This quote highlights that superficial achievements are not as valuable as actual impact on the organization.

Assessing Sales Efficiency in Long Sales Cycles

  • Sales efficiency should not solely focus on revenue as it's a lagging indicator.
  • A well-designed sales process with measurable events allows for early assessment of a salesperson's performance.
  • Even with long sales cycles, early interactions can provide insight into a salesperson's fit and potential.

But a ton of stuff happens up until that revenue point.

This quote acknowledges the various activities and milestones that precede revenue generation in the sales process.

Example of Assessing Sales Performance

  • New hires should be evaluated based on their performance in initial tasks such as pitch presentations and setting up calls.
  • Failure to progress in these early stages can be a red flag.
  • It is essential to understand the underlying issues behind poor performance.

There's a very clear indicator that something's not going right in the onboarding with a person of that level of experience, and you have to understand what's going on there.

This quote illustrates the importance of identifying and addressing issues early in the onboarding process.

Timing of Reps Meeting Customers

  • New sales reps should meet customers early but under close supervision.
  • The primary goal is for reps to learn and develop, even if these meetings don't result in sales.
  • The ideal timing for reps to run deal cycles is still being optimized.

I think people should meet a few customers in their first month on the job under close supervision from a buddy or a manager.

This quote suggests a strategy for integrating new sales reps with customer interactions.

Deal Reviews and Postmortems

  • Regular deal reviews and postmortems are essential for rapid learning and improvement.
  • Creating a safe space for sales reps to share failures is crucial for a learning environment.
  • Reps leading the postmortems can foster ownership and openness.

Because the only thing that matters early on in your company's life is how quickly you learn.

This quote highlights the importance of learning from every business interaction to improve future performance.

Creating a Safe Space for Sharing Failures

  • Sharing failures should be seen as a strength, not a weakness.
  • Leaders should be transparent about their own mistakes to encourage openness.
  • Trust is built when team members are willing to discuss what they need to work on.

I try to communicate to people that sharing your failures and your mistakes is a sign of strength and not a sign of weakness.

This quote stresses the value of vulnerability and learning from mistakes in building a strong team culture.

Unchanging Sales Tactics

  • Understanding customers and qualification remains crucial in sales.
  • Sales should be viewed as an engine, focusing resources on likely buyers.
  • Discipline in qualification is increasingly important.

Understanding your customer will always be the most important component of sales.

This quote reinforces the timeless importance of customer understanding in sales success.

Outdated Sales Tactics

  • Top-down sales approaches have become less effective.
  • Decision-makers now require evidence of team adoption and impact before committing.
  • Sales strategies must engage both executives and practitioners.

Pure tops down sale. I will never be able to go into a CIO's office and show them a really spiffy deck and give them a customer reference and get a deal.

This quote indicates the shift away from traditional top-down sales strategies towards more inclusive approaches.

Advice for Sales or Revenue Leaders

  • Choosing the right founder to partner with is critical.
  • Open dialogue about strengths, weaknesses, and expectations is necessary.
  • Understanding the complementary skills between a founder and sales leader is vital.

Today it's all about your founder. You're picking a partner.

This quote advises sales leaders on the importance of selecting the right founder to work with.

Sales Strategy Impressions

  • Customer-oriented sales strategies should prevail.
  • Companies like Snowflake demonstrate the importance of customer impact.
  • Trust between sellers and buyers is key to successful sales.

I'd like to see customer oriented sales win out.

This quote expresses a desire for sales strategies that prioritize customer success and value.

Challenges in Rapid Scaling

  • Rapid growth in revenue and team size presents significant challenges.
  • Maintaining simplicity and focus during complex organizational growth is essential.
  • Communication and maintaining core values are the first aspects to be challenged during scaling.

Maintaining simplicity and focus when an organization is becoming much more complex is a huge challenge.

This quote acknowledges the difficulties faced when a company experiences rapid scaling and expansion.

Sales Strategy Admiration

  • Retool and MongoDB are admired for their nuanced sales strategies.
  • Adapting sales approaches to complex problems and transitions is impressive.
  • Product-led but sales-assisted growth models are noteworthy.

MongoDB has always impressed me. But to go from tops down enterprise led to product led sales in the last couple of years, that's a really hard transition.

This quote praises MongoDB for successfully transitioning to a product-led sales approach.

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