20 Sales How To Create and Execute a WorldClass Sales Playbook, Why You Should Do Both PLG and Enterprise Sales at the Same Time, Three NonObvious Qualities the Best Sales Reps Have & The Four Steps To Sales Team Onboarding with Oliver Jay, Former CRO



In this episode of "20 Sales," host Harry Stebings is joined by Oliver J, a seasoned sales leader with a track record of scaling sales teams at Asana and Dropbox. Oliver shares his insights on the importance of product reverence and the ability to make those around you better as key traits in sales hires. He emphasizes that sales teams should be seen as equal to product teams, helping customers solve problems. He also discusses the pitfalls of premature sales commission plans, the necessity of a dynamic sales playbook, and the critical relationship between a sales leader and the CEO. Oliver advises that sales leaders need to manage up effectively, especially in today's challenging environment with inflated valuations. He also touches on the importance of onboarding, advocating for product-first, market-second, and sales-last approach, and the value of agility over rigid playbooks in early-stage startups.

Summary Notes

Introduction to the Podcast

  • "20 sales with me, Harry Stebings" is the podcast's title.
  • The podcast aims to provide insights into the strategies of top sales leaders.
  • Oliver J is the guest, known for his success in sales leadership.

Welcome to 20 sales with me, Harry Stebings. And I'm so thrilled to be joined today by Oliver J. One of the most successful sales leaders of the last decade.

The quotes introduce the podcast and its purpose, as well as the guest, Oliver J, who is recognized for his expertise in sales leadership.

Oliver J's Background and Success

  • Oliver J's tenure at Asana as the first revenue leader.
  • His role as CRO involved both product-led and sales-led revenue growth.
  • At Asana, he grew the sales team from under 20 to over 450.
  • Oliver's experience at Dropbox during a period of rapid scaling.
  • As head of APAC and LaTAM at Dropbox, he expanded the sales team and tripled ARR.
  • Oliver's position as an independent board member at Grab.

Most recently, Oliver spent six years at Asana, where he was hired as the company's first revenue leader. Before Asana, Oliver spent four years at Dropbox in a period of hyperscaling for the business where OJ was head of APAC and LaTAM.

These quotes outline Oliver J's impressive career achievements, highlighting his roles and the significant growth he accomplished at both Asana and Dropbox.

Sales Tools and Technologies

  • Dooley, a tool for sales reps to input data into Salesforce efficiently.
  • Sales Loft, a sales engagement platform for prospecting and managing deals.
  • The importance of accurate deal data and forecasting in sales.

Dooley is what top performing sales reps use day to day... It's the fastest, easiest way for sellers to input deal data in real time... Sales Loft is the leading sales engagement platform, helping sales teams drive more revenue with the modern revenue workspace...

These quotes explain the functionality of Dooley and Sales Loft, emphasizing their roles in improving sales processes and data management.

Oliver J's Journey into Sales

  • Oliver's initial career in finance, covering tech companies at Morgan Stanley.
  • His venture experience at NEA and the influence of investors with operating backgrounds.
  • The decision to pursue sales based on the advice that operating involves building or selling a product.

First couple years of my career was in finance... I really saw how amazing some investors were sort of leveraging their operating background to help founders... you either build product or you sell product.

This quote provides insight into Oliver J's career path and the rationale behind his move into sales, influenced by the operational aspect of investing.

Key Takeaways from Dropbox and Asana

  • The changing landscape of technology adoption in businesses.
  • The rise of product-led growth (PLG) and its difference from traditional B2B sales.
  • At Asana, the combination of product growth sales and traditional enterprise sales was successful.
  • The possibility and challenges of integrating PLG with traditional sales approaches.

So Dropbox, I think for me, number one is technology is just fundamentally adopted differently in businesses... PLG is fundamentally is a very different kind of go to market than traditional B2B sales... At Asana we pioneered and we try to do both at the same time.

These quotes summarize Oliver J's reflections on his experiences at Dropbox and Asana, focusing on the evolution of technology adoption and the innovative approach to combining different sales methodologies.

Founders and Sales Playbooks

  • The importance of founders in creating the initial sales playbook.
  • Defining what a playbook is and its role in the sales process.
  • The distinction between the initial playbook (identifying personas and value proposition) and the repeatable sales process.
  • The necessity for founders to engage with customers to achieve product-market fit.

If that playbook hasn't been written, founder must be involved... The reality is, in your first two AES, there is no playbook. Your hire, your first head of sales, you're piloting it.

Oliver J emphasizes the critical role of founders in developing the foundational sales playbook, which involves understanding the customer and the product's value, before a repeatable sales process can be established.

Agility Over Playbooks

  • The preference for agility and nimbleness in the early stages of sales.
  • The focus on learning and adapting to different personas and sales approaches.
  • The idea that a true playbook cannot be established until there are at least 20 ramped Account Executives (AEs).

I'd rather focus on agility... I'm not telling them to come back with a playbook. I'm telling them to come back with learnings and insights... I don't think you create that playbook until you have at least 20 ramped AES.

Oliver J advises against rigid playbooks in the early stages and advocates for a flexible approach that prioritizes learning and adapting to the market and customer needs.

Importance of a Sales Playbook

  • A sales playbook is essential for a company's sales team to hit numbers and maintain high morale.
  • Without a playbook, companies risk high churn rates and a toxic work environment.

"They don't hit numbers because they don't have a playbook to work against. They churn and morale sucks."

The quote emphasizes the negative consequences of not having a structured sales approach, highlighting the need for a playbook to guide sales teams effectively.

Creation and Evolution of Sales Playbooks

  • Start with an initial playbook based on traction gained to raise seed or Series A funding.
  • Playbooks should be dynamic and continuously improved.
  • Encourage sales teams to contribute to the playbook's evolution by testing and providing feedback.

"I think playbooks should be dynamic, and so it should be something where, hey, I hired my first two, three AES. They may be junior people. You're going to start with this, but I also expect you to make it better."

This quote suggests that playbooks are living documents that should evolve with the sales team's experiences and insights, starting with what has been successful so far.

Hiring Sales Team Structure

  • The decision to hire a head of sales or sales reps first depends on whether the product is in an existing or new category.
  • For existing categories with clear buyers, hire a head of sales to accelerate growth.
  • For new categories, hire customer-facing people first to determine the best sales motion before hiring a head of sales.

"If you're trying to actually create a new category... I think you're better off with hiring some hungry and smart customer facing people first."

The quote indicates that when creating a new product category, it's beneficial to start with versatile, customer-facing team members who can help define the sales strategy.

Sales Team Competition

  • Hiring sales reps in batches can be beneficial for A/B testing and onboarding.
  • Early-stage companies should foster a culture of collaboration rather than competition.
  • Ideal sales hires are intrinsically competitive and collaborative.

"I want us to learn. I want us to co-create that playbook together."

This quote reflects the speaker's belief in the importance of teamwork and shared learning in the early stages of building a sales team.

Timing for Hiring a Head of Sales or Sales Reps

  • The first hire doesn't necessarily have to be a sales-specific role but should be customer-facing.
  • Hiring early, especially with substantial funding, can provide valuable market insights.
  • The goal is to learn about the market and potential buyers, not just to drive immediate sales.

"If you're not that resource constraint, spending that much money to hire like a junior customer facing person as early as you can is actually would be my advice."

The quote advocates for hiring customer-facing personnel as soon as financially feasible to gather market insights and feedback.

Structuring the Hiring Process

  • Establish a clear hiring process to avoid unconscious bias and promote diversity.
  • Define the competencies and traits required for the role.
  • Develop interview questions that assess these competencies and traits.

"Be really clear about what are the competencies and the behavioral traits that think the characteristics that you want to test for."

This quote underscores the need for clarity in the hiring process to ensure candidates are evaluated based on the specific needs of the role and company.

Traits to Look for in Sales Reps

  • Look for reverence for the product and the ability to convey passion to customers.
  • Assess whether the candidate has a track record of making people around them better.
  • Use specific interview questions to gauge these traits.

"I think the things that I always look for in whether you're a leader or just any of my customer facing folks. Number one, reverence for the product."

The quote highlights the speaker's priority in finding candidates who genuinely appreciate and can advocate for the product.

Interview Process

  • Map out competencies and design interview slots to test specific ones.
  • Optimize for a manageable number of key competencies (around four to five).
  • Involve different team members in the interview process to assess different aspects.

"My first step is I'm going to map out the competencies."

This quote indicates a structured approach to interviewing, where each part of the process is tailored to evaluate a specific competency or trait.

Interview Process: Competency Testing and Final Round Demos

  • Interview process includes meeting multiple people, each testing a different competency.
  • Final round often involves a demo or pitch to assess preparedness and potential.
  • Candidates may perform differently when given time to prepare versus on-the-fly interviews.
  • Prepared demos can reveal a candidate's potential and areas for improvement.
  • Interviewer diversity is crucial to reflect the desired team diversity.
  • Cross-functional partners should be included in the interview process.

"Each person tests a different competency. So that's one dimension. Second dimension. The final round for me has always been for someone to give a demo."

This quote emphasizes the importance of assessing various competencies and the value of a final round demo to gauge a candidate's preparation and potential.

"I want to give people a chance and see how do they act. If you give the time to prepare, someone may bomb their on the fly interviews, but they may crush their prepared demo."

This quote suggests that giving candidates time to prepare for a demo allows a better assessment of their true abilities and potential growth.

"I think it's important to make sure your interview slate represents the kind of diversity you want on your team."

This quote highlights the need for a diverse set of interviewers to ensure the team's diversity goals are met.

Sales Compensation Plans: Common Mistakes and Lessons

  • Early-stage companies should be cautious about implementing sales commission plans due to potential legal repercussions and difficulty in setting targets.
  • Variable compensation can be structured in various ways besides commissions, such as bonuses or team competitions.
  • It's essential to consider different metrics for variable compensation, such as logos or deal sizes.

"Putting in place a commission plan when you're really young and early in your lifecycle, I think is very potentially very detrimental."

This quote advises against early-stage companies hastily implementing commission plans, indicating potential negative consequences.

"There are many, many different forms of variable compensation. Doesn't have to be just commission you can do a bonus structure, you can do team comp, you can do team competitions."

This quote suggests alternative forms of variable compensation, providing flexibility for early-stage companies to motivate their sales teams.

Equity for Sales Teams: Building Long-Term Relationships

  • Not offering equity to salespeople can be a significant mistake.
  • Early hires, including salespeople, are integral to the company's culture and growth.
  • Salespeople who feel foundational to the company are less likely to leave, maintaining the team's cohesion and knowledge.

"I think it would be a mistake not to give equity. I think sometimes, I don't know why, but sometimes I talk to founders and I feel like they treat salespeople as second class citizens."

This quote stresses the importance of granting equity to salespeople, warning against undervaluing their contribution to the company's success.

"If you lose your initial batch, what you have is you have your playbook that you know is somewhat going to be outdated within the next quarter, and it's really going to be transactional."

This quote explains the risk of losing early sales hires, which can lead to outdated sales playbooks and a lack of deep team connections.

Onboarding Sales Reps: Ideal Processes and Stages

  • Onboarding should prioritize product knowledge, market understanding, and then sales training.
  • Early-stage companies should involve new hires in support to gain technical product knowledge and understand sales obstacles.
  • Market knowledge can be imparted through fundraising decks before a formal sales pitch is developed.
  • Sales orientation involves shadowing founders, developing customer relationships, and eventually presenting a product demo.

"We're talking about like you're still early stage. So I would do product first, market second, and sales last."

This quote outlines the recommended sequence for onboarding sales reps, emphasizing the importance of product knowledge before market and sales training.

"You're going to present your demo of our product and we are going to actually role play."

This quote describes the culmination of the onboarding process, where new hires demonstrate their product knowledge and sales skills through role-playing scenarios.

Ramp-Up Time and Customer Engagement

  • A two-month ramp-up period is reasonable for new sales reps to become solid in their roles.
  • New reps can engage with customers earlier than two months, especially in PLG companies, to gather feedback and experience.
  • The difference between PLG and non-PLG companies affects the timing and manner of new reps' customer interactions.

"I feel like two months is reasonable at this stage to get to a point where they're really, really solid with a great demo."

This quote provides a timeline for new sales reps to reach a level of proficiency where they can effectively demonstrate the product.

"You can actually start doing that, and it helps with accelerating the ramp."

This quote suggests that early customer engagement can help accelerate the ramp-up process for new sales reps.

PLG vs. Outbound Sales Approaches

  • PLG (Product-Led Growth) relies on inbound interest, while outbound sales target a different buyer with a different value proposition and messaging.
  • Transitioning from PLG to outbound sales requires adjustments in strategy, messaging, and expectations for conversion rates.

"I love PLG. I breathe and bleed PLG at the same time. I love outbound. Outbound's way easier."

This quote reflects the speaker's enthusiasm for both PLG and outbound sales approaches while acknowledging their differences.

"For outbound to be successful, generally speaking, you're selling to a different buyer, probably a more senior Persona, probably selling a different value, and so therefore, you need different messaging in terms of the sales process."

This quote highlights the distinct requirements for outbound sales success, including targeting senior decision-makers and crafting appropriate messaging.

Plateauing Growth and Shifting Sales Strategies

  • Companies often experience an initial surge in growth, followed by a plateau.
  • The common reactive strategy is to shift from inbound to outbound sales.
  • Outbound sales require different talent and a restructured conversion process.
  • Marketing must align with sales to develop messaging for a new customer persona.
  • Product augmentation may be necessary for larger deal sizes.
  • Outbound efforts should be a company-wide initiative, not just a sales task.
  • Companies should explore ways to revitalize their inbound funnel before relying on outbound strategies.

So what I see a lot happening is people's initial inbounding. It's like you hit that s curve, it's amazing. And then suddenly it just starts plateauing.

This quote highlights the common pattern of rapid growth followed by a plateau, which companies often face.

You're just going to get some salespeople to go buy some lists and just start cold emailing LinkedIn bombing people, it won't going to work because your entire conversion process is designed around a different buyer, articulating a different value, converting at a higher speed and a smaller deals.

This quote underscores the inefficacy of simply switching to outbound tactics without considering the need for a different sales approach and conversion process tailored to a new type of buyer.

The CEO and Head of Sales Relationship

  • The relationship is a partnership focused on bringing in revenue and aiding the CEO's decision-making.
  • The head of sales must provide the CEO with relevant feedback for informed decisions.
  • Avoiding recency bias and understanding what's working is crucial.
  • Regular, ideally weekly, meetings between the CEO and head of sales are recommended.

My job, I got to bring home the bacon. I got to get the cash in. I get that. But there's a bigger play here that I have in my head, which is I see an equally important part of my responsibility as a CIO, head of sales, whatever, is to help my CEO make the best decisions that he or she can.

This quote illustrates the dual role of the head of sales in both generating revenue and assisting the CEO with strategic decisions by providing accurate and comprehensive feedback.

Sales Performance Analysis Techniques

  • Regular deal reviews and post-mortems are essential, even for small teams.
  • The "Five Whys" technique from Toyota is used to uncover root causes of failures.
  • It's important to go beyond surface explanations to understand deeper issues.
  • This method fosters meaningful discussions to identify and address core problems.

Five wise is really not about getting to the answer. I think it's about really creating the right level of discussion. It's a framework to create the right conversations so that you will, through that process, find one or two big core root problems that you can address.

This quote explains that the "Five Whys" technique is not just about finding an answer but about facilitating the right conversations to uncover and solve fundamental issues.

Sales Tactics and Industry Changes

  • Articulating business impact and value remains a constant necessity in sales.
  • Mass emailing and marketing automation tactics have become less effective.
  • Founders often overlook the importance of integrating customer feedback with product development.
  • New sales leaders must manage expectations and communicate clearly with executives and boards.
  • The perception of sales as less prestigious than product development needs to change.
  • Sales should be viewed as problem-solving for customers, on par with product management.

What salespeople do at the core is they help customers solve their problems. They happen to do that sometimes because your product actually does that really well. But that is what sales is about.

This quote redefines the essence of sales as problem-solving for customers, emphasizing its importance and value in the business ecosystem.

Sales Tools and Platforms

  • Sales tools like Dooley and Sales Loft can improve data input and forecasting accuracy.
  • These platforms save time for sales reps and provide managers with more reliable deal data.
  • The right tools can support sales teams in driving more revenue and improving performance.

Dooley is what top performing sales reps use day to day instead of Salesforce.

This quote highlights Dooley as a tool that enhances the efficiency of sales reps by simplifying Salesforce data entry, thereby improving the sales process and forecasting.

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