20VC The Memo What is a Sales Playbook Does the Founder Need to Create It Should the First Sales Hire Be a Leader or a Rep

In this episode of "20 VC: The Memo," host Harry Stebbings explores the pivotal question of whether a startup's founder should create the initial sales playbook or delegate it to a head of sales. Sales leaders from top companies like Dropbox, Loom, Asana, Zoom, Sequoia, and Stripe weigh in on this debate. Jordan Van Horn of Monte Carlo Data argues that founders are responsible for the foundational sales playbook, emphasizing the importance of defining the target market and understanding customer resonance. Oliver Jay of Asana and Janya Loganov of Miro discuss the significance of identifying the right customer personas and value propositions, while Danny Herzberg of Sequoia and Carl Parrish of Figma stress the founder's role in early sales to gain customer insights and set the sales culture. Sam Taylor of Loom and Gene DeWitt Grosser of Stripe suggest that while founders should be deeply involved in early sales, professional sales skills are crucial for scaling, and Mitch Tariqa of Zoom advocates for hiring a head of sales first to establish the playbook and team culture. The consensus indicates that while the founder's involvement is essential in the early stages, a skilled head of sales is critical for developing a scalable sales strategy and fostering the right team dynamics.

• A sales playbook consists of discrete steps to accomplish five main objectives.
• The playbook evolves over time, starting with version zero and potentially reaching version twenty or beyond.
• Early playbooks should be open-ended to accommodate unknowns, while later versions become more prescriptive.
• The founder is responsible for creating the initial version of the playbook, which should document foundational go-to-market pillars.
• Founders should outline the problem being solved, the target audience, and who is not being targeted.
• Key factors for success in the sales process and reasons for customers to act immediately should be clearly understood and documented by the founder.
• As the company grows, sales leaders refine the playbook, adding details and improving discovery questions.
• Founders remain accountable for the foundational aspects of the sales playbook throughout the company's lifecycle.

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

This quote outlines the core purpose of a sales playbook, which is to guide the sales process through five key objectives.

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

Here, Jordan Van Horn emphasizes the founder's responsibility in creating the initial version of the sales playbook, underscoring the importance of founder involvement in early sales strategy.

"What problem are you trying to solve and who are you trying to solve it for?"

This quote highlights the first foundational go-to-market pillar that a founder must document in the sales playbook, focusing on the problem and target audience.

• The founder must be deeply involved in the initial creation of the sales playbook.
• Direct engagement with customers is crucial for the founder to understand their needs and feedback.
• The founder's involvement ensures that the product evolves towards achieving product-market fit.
• Founders should identify the target personas and the value proposition of the product.
• The first sales hire should be made when the company is ready to address big open questions about sales strategy.
• The founder's role is to determine the "who" and "what" of sales, while the head of sales can later focus on the "how" of the selling process.

"Founder must be involved. You have to talk to the customer to hear the feedback firsthand so that you can then incorporate it into your product and eventually get to product market fit."

Oliver Jay stresses the necessity for founders to engage directly with customers, which is critical for refining the product and sales approach based on real feedback.

"The harder part is the who you sell to and what are you selling."

This quote by Oliver Jay captures the essence of the initial challenges in sales strategy, which involve identifying the target customer and clearly articulating the product's value.

"I don't think you create that playbook until you have at least 20 ramped AES, where you have the right to say, this is a playbook."

Oliver Jay provides insight into when a sales playbook can truly be considered established, indicating that a significant number of successful sales staff are needed before a process can be deemed repeatable and scalable.## Scalability and Agility in Early Sales Strategy

• In the initial stages of a business, the concept of a sales playbook may not be practical or scalable.
• Identifying the primary persona for the product is crucial and may require different approaches.
• Agility is preferred over repeatability, focusing on adapting and learning rather than following a set playbook.
• Early sales efforts should aim to answer key questions about customer engagement and the product's resonance with different personas.

"It may be repeatable for the next month. It will not be scalable as you build more people, because you have to figure out a lot."

This quote emphasizes the limitations of a repeatable sales strategy when scaling a business, as new complexities arise that require attention and adaptation.

"Instead of like, hey, trying to get people to write up some playbook, hey, actually be really nimble."

Here, the speaker advocates for flexibility and responsiveness in early sales strategies, rather than rigid adherence to a predetermined playbook.

• The decision to hire a head of sales first or sales reps depends on the nature of the business and product.
• For businesses targeting an existing category with clear buyers, hiring a head of sales may accelerate growth.
• In cases where a new category is being created, starting with customer-facing individuals can provide valuable insights for establishing sales strategies.
• The first sales hires should return with learnings and insights, not necessarily a playbook.

"So hiring ahead of sales can really accelerate things."

This quote suggests that in certain business scenarios, bringing in a head of sales early can speed up the company's growth trajectory.

"I think you're better off with hiring some hungry and smart customer facing people first."

The speaker advises that for companies creating a new category, beginning with eager and intelligent customer-facing staff can be more beneficial than starting with a head of sales.

• Initially, the founder acts as the head of sales and must understand the customer's needs and objections firsthand.
• Through early sales experiences, the founder develops empathy for future sales hires and gains insights that inform product direction.
• The founder may transition from being the primary salesperson to hiring a player-coach who can sell and lead the hiring of additional sales staff.
• The founder's involvement in early sales is a critical input mechanism for the business.

"So day one, founder equals head of sales."

The quote asserts that at the inception of a company, the founder should take on the role of head of sales to intimately understand the sales process.

"Say the first head of sales is the founder."

This statement implies that the founder's initial sales experience is integral before delegating the role to a professional head of sales.

• Sales playbooks should be considered at the customer, team, and market levels.
• The customer level addresses immediate problem-solving with the product.
• The team level involves organizing the sales team for effectiveness over a six to twelve-month period.
• The market level focuses on long-term strategies to dominate the market over a span of five years or more.
• Founders should be involved in creating the sales playbook but not necessarily run the entire process.

"I think about sales playbook on 3d FNF levels, the customer level, team level and market level."

The speaker breaks down the sales playbook into three distinct areas of focus, each with its own set of considerations and timeframes.

"It's very helpful for them to be deeply involved in creating this first sales playbook."

This quote underscores the importance of the founder's involvement in the initial creation of the sales playbook, linking it to the company's vision.

• The consensus among sales leaders is that while founders are often the first sellers, they should not create the sales playbook alone.
• Sales is a deep area of expertise, and founders may lack crucial knowledge that a sales professional would bring to the playbook creation process.
• Empowerment and enablement are key; salespeople should have ownership and feel empowered to execute the playbook.
• There's a debate on whether founders or heads of sales should create the sales playbook, with implications for the order of sales hires.

"And I think that, no, the founder shouldn't, and it's better that they're not."

The speaker argues that founders should not be the sole creators of the sales playbook, highlighting the value of sales expertise in the process.

"I think if the founder sort of hires salespeople who he gives the playbook to that the founder developed, it's going to be less effective and less efficient."

This quote suggests that salespeople are more effective when they contribute to and feel a sense of ownership over the sales playbook, rather than simply being handed one developed by the founder.## Hiring the Right Sales Role

• Hiring a head of sales is preferable to hiring just sales representatives initially.
• A head of sales is recommended after achieving initial product-market fit or reaching around 1 million in revenue.
• Junior sales representatives may require significant guidance from the founder, consuming valuable time.
• A head of sales can create bandwidth for the founder to focus on other areas of the business.

"I think that if you can at all afford it, then I think go and hire your first head of sales."

This quote emphasizes the importance of prioritizing the hiring of a head of sales when financially feasible, as it can be beneficial for the growth of the company.

"The head of sales will instead create bandwidth that the founder can use to go solve other problems to go, like build a product, to go hire finance person, to go do something else."

This quote highlights the strategic advantage of hiring a head of sales, which allows the founder to delegate sales responsibilities and focus on other critical aspects of business development.

• The CEO's involvement in early sales and understanding customer interactions is crucial.
• CEOs should contribute to shaping the sales playbook but not necessarily create it.
• A sales playbook signifies a move towards a repeatable sales process, indicating readiness to hire a sales team.
• Founders should remain involved but not be bogged down by the details of sales management.

"But does the CEO need to build the playbook? I don't think that's the best idea."

This quote suggests that while the CEO's involvement is important, they should not be the primary creator of the sales playbook, which is better left to sales professionals.

"Founder led sales isn't scalable. It's not repeatable."

This quote underscores the necessity of transitioning from founder-led sales to a structured, scalable sales process as the company grows.

• The decision to hire a head of sales or sales representatives first depends on the company's stage and market fit.
• If there is a clear market opportunity and capacity to hire a sales team, it is advisable to hire a head of sales first.
• A head of sales can bring valuable experience in leading and building sales teams, which most founders lack.

"Go and get that head of sales. Go and get that frontline sales manager."

This quote advises founders to hire a head of sales or a frontline sales manager when ready to build a sales team, rather than starting with individual sales reps.

"Most founders that come in, they don't have experience in building or growing sales teams."

This quote points out a common gap in founders' expertise, which can be filled by hiring an experienced head of sales.

• The term "playbook" may imply a rigid approach, whereas "frameworks" suggest adaptability and customization.
• Sales frameworks should include storytelling and relevant customer anecdotes.
• Sales strategies should be tailored to different verticals, personas, and company strategies.

"I don't love Playbook as a term because it sounds rigid."

This quote reflects a preference for the term "frameworks" over "playbooks" due to the flexibility and adaptability it conveys.

"How do we have relevant stories that customer facing teams, regardless of if they're quota carrying?"

This quote emphasizes the importance of equipping all customer-facing team members with compelling stories and narratives to enhance sales effectiveness.

• Founders are inherently involved in sales by pitching their company to investors and early customers.
• Founders should ensure that the sales messages they create are transferable and credible when delivered by the sales team.
• Early sales hires should have access to the founder's sales experiences to integrate that knowledge into their sales approach.

"I'd kind of call bullshit on the founder can't create it."

This quote challenges the notion that founders cannot create effective sales frameworks, arguing that founders are already engaged in sales when starting their company.

"Don't discount the special sauce that you've practiced in terms of the person that we bring in."

This quote advises founders not to underestimate the value of their unique sales insights and to share this "special sauce" with new sales hires.## Sales Team Composition

• The composition of a sales team can vary depending on the company's stage and the nature of the product or service being offered.
• Early-stage companies may benefit from hiring more junior, versatile sales reps to handle both inbound and outbound sales and learn from customer interactions.
• More mature companies or those with a clear value proposition and buyer persona might consider hiring seasoned sales leaders to build and manage a sales team.
• The importance of customer insights is emphasized, especially in early go-to-market phases, to inform broader market strategies.

"You can make the argument, let's get some junior resources in and let's start seeing if you can scale to the next level."

This quote suggests that at certain stages of a company's growth, it may be beneficial to hire junior sales reps to help scale the business and handle customer interactions.

"Err and insights. And the insights are almost as important, if not more important, the earlier you are on your go to market journey, because that helps inform where do you want to resource and how do you want to go to market more broadly?"

This quote emphasizes the dual role of early sales teams in generating revenue (Err) and gathering insights, with insights being crucial for shaping the go-to-market strategy.

• Founders play a critical role in determining product-market fit through direct conversations with customers.
• Sales is seen as both a revenue driver and a research and development activity, particularly in the early stages.
• Founders are encouraged to recognize sales as a specialized skill and consider hiring experienced sales professionals to take over sales activities at the right time.
• The timing for hiring a sales team is crucial and should align with the founder's capacity to manage customer interactions and focus on the product roadmap.

"Sales is one part revenue and one part R and D."

This quote highlights the dual role of sales in generating income and contributing to the research and development of the product through customer feedback.

"I think a founder needs to be really core to determining initial product market fit."

This quote underscores the importance of founder involvement in the early stages of sales to establish the product's fit in the market.

• The founder sets the tone for the sales culture within the organization, which can range from caring to competitive.
• A strong head of sales is essential for creating a sales playbook, hiring the right team, building a sales culture, and aligning sales with other functions like marketing and channel partnerships.
• The head of sales should be capable of operating in an environment with some ambiguity and be able to drive ownership within the sales team.

"Founder may not create the first sales playbook per se, but they are certainly leading by example on what they want done."

This quote illustrates the founder's influence on the initial sales approach and culture, even if they are not directly creating the sales playbook.

"First, they create that sales playbook... Second, they can hire the team... Third, they can build the culture... And then finally... that head of sales can be very, very well aligned cross functionally."

This quote details the four key responsibilities of a head of sales, highlighting their multifaceted role in shaping the sales organization and its integration with the broader company.

• Hiring skilled developers is a challenge, and companies may need to look globally to scale their engineering teams effectively.
• Terminal is a platform that connects companies with pre-vetted engineers from around the world, supporting the hiring process and legal aspects of international employment.
• Proper management of equity is crucial for motivating and engaging teams and having transparent conversations with investors.
• Legi is an equity management product that provides employees with dashboards and scenario modeling tools for understanding their share options and collaborating with investors during fundraising.

"With four open positions for every one developer in the US, it's no wonder why this challenge persists."

This quote emphasizes the high demand for developers in the US and the resulting difficulty in hiring domestically.

"When you really understand your cap table and share ownership, you motivate and engage your team and have more transparent conversations with investors."

This quote highlights the importance of transparent and well-understood equity management for team motivation and investor relations.