20 Sales The Ultimate Guide to Sales Onboarding for New Sales Reps and Sales Leaders, The Biggest Red Flags in the First 30 Days & What Can Be Done to Set Them Up for Success with Leaders from Figma, Dropbox, Miro and more



In this episode of "20 Sales" with host Harry Stebbings, the discussion revolves around the critical topic of sales team onboarding, a common challenge for founders. The episode features insights from top sales leaders like Oliver J., Jordan Van Horn, Danny Herzberg, Jenya Loganov, Lauren Schwartz, and Carl Parrish, who share their experiences and strategies from companies like Asana, Dropbox, Slack, Miro, and Figma. The conversation delves into the importance of product knowledge, customer engagement, and practical experience for new hires. The speakers emphasize the need for new sales hires to immerse themselves in customer support, understand market dynamics, and practice sales pitches using real-world scenarios. They also discuss the role of sales leaders in fostering a culture of customer understanding and the significance of immediate impact and proactive engagement, even in a product-led growth environment. The episode underscores the importance of a structured onboarding process, tailored to the company's maturity stage, and the necessity for new hires to deliver value early on while building solid foundations for long-term success.

Summary Notes

Introduction to "20 Sales" Podcast Episode

  • Harry Stebbings hosts "20 sales," a monthly show featuring sales leaders' insights.
  • The episode focuses on sales team onboarding, a common challenge for founders.
  • The episode includes insights from sales leaders at Figma, Notion, Loom, Zoom, Miro, etc.
  • The discussion covers the first week in a sales role, setting up for success, and measuring success.

This is 20 sales with me, Harry Stebbings. Now, 20 sales is the monthly show where we take you inside the minds of the best sales leaders to unpack their tips, tactics and strategies when it comes to scaling the best sales teams in the world.

Harry Stebbings introduces the show and its purpose, which is to offer insights from top sales leaders on building and scaling sales teams.

Importance of Sales Team Onboarding

  • Onboarding is critical for setting up sales teams for success.
  • The process involves product knowledge, market understanding, and sales skills.
  • Founders often struggle with how to structure the onboarding process effectively.

And today we focus on sales team onboarding an area where founders universally struggle.

Harry Stebbings highlights the significance of sales team onboarding and acknowledges the difficulties founders face in this area.

Sales Onboarding Structure by Oliver Jay

  • Oliver Jay suggests a three-stage onboarding process: Product, Market, Sales.
  • Stage 1: New hires should start with support to understand technical aspects and customer issues.
  • Stage 2: Market knowledge is gained through fundraising decks and understanding competition.
  • Stage 3: Sales skills are developed by shadowing founders and engaging with top customers.

Like you're still early stage. So I would do product first, market second, and sales last.

Oliver Jay proposes a sequential approach to onboarding, prioritizing product knowledge before market understanding and sales training.

Product Knowledge Acquisition

  • New hires should delve deep into the technical side of the product.
  • Exposure to customer support tickets reveals common sales obstacles.
  • Understanding the product's technical aspects is essential for customer-facing roles.

In the beginning, I think it's super important that whatever customer facing people you hire, they have to play that role.

Oliver Jay emphasizes the importance of product knowledge for customer-facing employees, particularly in the early stages of a company.

Market Understanding

  • Market knowledge involves learning about the competitive landscape and the company's mission.
  • Founders often lack a sales pitch, so fundraising decks can be a resource for market education.
  • Understanding the market is crucial for high performance and should precede sales training.

Why I think it's important to do market first is I think I want to put the sales stuff last because that's the stuff that the team will hone in on forever.

Oliver Jay explains why market knowledge should come before sales training, as it provides a foundation for understanding the company's position and mission.

Sales Skills Development

  • Sales skills are honed by shadowing founders and engaging with friendly top customers.
  • New hires should conduct demos and role-play with the team as a form of certification.
  • This stage is a high-stakes presentation that simulates real customer interactions.

So you basically shadow the founder for a little bit and then what I do is, it culminates for me. Absolutely. I want someone to demo the product at the end of whatever onboarding period.

Oliver Jay describes the culmination of the onboarding process, where new hires demonstrate their product knowledge and sales skills through role-playing demos.

Onboarding Duration and Customer Interaction

  • The three-stage onboarding process can reasonably take two months.
  • New hires may interact with customers within three weeks, initially focusing on existing customers rather than selling.

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.

Oliver Jay provides a timeframe for the onboarding process, indicating when new sales reps might be ready to engage effectively with customers.

Customer Engagement and Readiness in PLG Companies

  • Oliver Jay (OJ) emphasizes the importance of customer interaction for PLG companies.
  • Engaging with customers helps in understanding their love and issues with the product.
  • Repetition (getting more reps) is crucial but not an indicator of readiness to scale.

What do you love about the product? What do you like about the product? What's your issues? Is like get more reps?

The quote highlights the need for companies, especially those with a Product-Led Growth (PLG) model, to engage in conversations with customers to understand their preferences and problems with the product. This process is essential before considering scaling up operations.

Onboarding Sales Hires Reflecting Company Maturity

  • Jordan Van Horn suggests onboarding should mirror the company's stage and maturity.
  • In a small company, onboarding is informal and requires new hires to learn on-the-fly.
  • As the company grows, structured and rigorous onboarding becomes necessary.
  • Frontline sales managers are responsible for onboarding in the early stages.

I always think that onboarding should reflect the stage and maturity of your company.

Jordan Van Horn stresses that the onboarding process for new sales hires should be appropriate for the company's current stage of development, with more structure added as the company matures.

Managerial Involvement in Onboarding

  • Proximity is key; managers must be close to new hires' work.
  • Managers should distinguish between inexperience and skill gaps.
  • Successful onboarding involves identifying key skills and supporting new hires intensively.
  • Managers should assess new hire fit within 30 days.

It's incumbent on the manager to go spend third of their time with new hires in the first month.

Jordan Van Horn underlines the importance of managers dedicating significant time to support and assess new hires, as this is critical to their successful integration into the company.

Identifying Early Impact and Red Flags in New Hires

  • Impact should be visible within the first 30 days, regardless of the magnitude.
  • Lack of tangible impact is a red flag.
  • Managers should look for contributions to customer interactions, sales processes, and onboarding improvements.

Everyone can make an impact in 30 days.

Jordan Van Horn asserts that all new hires should be able to demonstrate some form of meaningful contribution within their first month, which is indicative of their potential success within the company.

Sales Leader Onboarding and Customer Engagement

  • Danny Herzberg emphasizes that the first month for a sales leader is about listening and understanding customers.
  • Sales leaders should communicate insights back to the company, fostering a customer-centric culture.
  • Reps should practice selling by engaging with leads and refining their approach.

Month one as a sales leader is about listening and engaging.

Danny Herzberg highlights the importance of a sales leader's initial focus on understanding customer needs and experiences to effectively communicate these insights to the company's founders and team.

Proactivity in Product-Led Growth (PLG) Companies

  • Reps in PLG companies should not solely rely on inbound leads.
  • They should actively engage with users to gather insights and communicate them to decision-makers.
  • A tenacious seller synthesizes user feedback and proactively reaches out to higher-level executives.

Loving to sell does not mean sitting back in your chair and waiting for product qualified inbounds to fall into your lap.

Danny Herzberg emphasizes that true sales professionals are proactive and do not wait passively for leads but engage actively with potential customers to drive sales.

Red Flags in Candidate Interviews and Early Employment

  • In PLG companies, reps and leaders must be knowledgeable about the product.
  • Candidates should demonstrate product understanding during the interview process.
  • Post-hire, a lack of product knowledge or engagement is a concerning sign.

A good candidate will use the product and perhaps deliver some of the interview unprompted by utilizing the product itself just to show that they know how to geek out in there and that they've taken the time to understand the user journey.

Danny Herzberg points out that during the interview process, a strong candidate for a PLG company will showcase their familiarity with the product, indicating their potential for success in a customer-facing role.

Onboarding New Reps and Leaders

  • Onboarding should be action-oriented, with new leaders developing a POV on key deliverables for the year.
  • Leaders need to combine insights from founders and customers to form their action plan.
  • A leader should engage with customers regularly, with a lack of customer interaction being a red flag.
  • New reps should actively engage with users, leads, or create opportunities rather than getting stuck in research.

"So I did talk about the listening tour for a leader, and on the leader side I would look to see whether they've developed a point of view about what are the one to two things that are most important to deliver on over the course of this year and what's their action plan for doing that."

This quote emphasizes the importance of new leaders having a clear perspective on their priorities and a plan to achieve them, highlighting the balance between learning and taking action.

"If a leader had not gotten in front of a customer...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."

The quote stresses the significance of new leaders interacting with customers as an indicator of their customer focus and the potential success of the team they will build.

"You want someone who is diving in...so that they can start working out the kinks and figuring out how to sell this thing."

This quote underlines the need for new reps to be proactive and hands-on from the start to quickly learn and adapt to the sales process.

Onboarding Process for Leadership Hires

  • The initial months for a leadership hire should be free from deliverables to focus on understanding the product and building relationships.
  • Leaders should connect with key company figures they'll work with in the future, not just immediate colleagues.
  • Early projects should be small but valuable, establishing credibility and facilitating larger future changes.
  • CEOs should invest time in new hires to ensure their success.

"I try to free up their first months as much as possible...I'm hiring them for the next five years plus with the company."

The quote indicates the strategic long-term perspective taken when onboarding leadership hires, focusing on their long-term integration and success within the company.

"I'd like them to have one low hanging fruit in their area...that delivers value too."

This quote suggests that new leaders should quickly demonstrate their value to the company through achievable, impactful projects.

"It's your mutual job to make them successful. It's their job and it's your job."

The quote highlights the shared responsibility between the company and the new hire in ensuring the success of the onboarding process.

Identifying Successful Leadership Hires

  • Signs of a problematic hire include a lack of tangible results in the first three months and an overemphasis on strategy without action.
  • Early contributions and delivering value are critical indicators of a successful hire.
  • New hires should be accepted by their initial team, with early rejection being a concerning sign.
  • CEOs should proactively seek feedback from the team about new hires and their impact.

"If you don't see any results delivered in the first three months...that's a big red flag for me."

This quote conveys the expectation that new leadership hires should start contributing to the company's success within the first few months.

"You need to start delivering value on your month's number two or number three. And you need to ship something."

The quote stresses the urgency for new hires to deliver value early on, reflecting the fast-paced nature of small companies.

"When your initial team starts to reject the person you just hired...you need to dig deeper and figure out can you enable this person to be more successful or do you need to part ways?"

This quote points out the importance of team acceptance and the CEO's role in addressing any early signs of team rejection of a new hire.

Onboarding Sales Reps

  • Exposure to customers is crucial for new sales reps to understand the product's impact and value.
  • Learning from recorded sales calls and post-mortems of wins and losses can accelerate the onboarding process.
  • New reps should be given access to materials that help them understand what has worked and what hasn't in past sales efforts.

"I think the most important thing you can do when you're starting your sales role is getting exposure to customers."

The quote underscores the importance of customer interaction as a key component of effective onboarding for sales reps.

"Having like a library of recorded calls is really valuable as people ramp."

This quote suggests that providing new sales reps with a repository of recorded calls can be a helpful resource for learning and ramping up.

"I'm really big on running deal reviews and making sure that we capture learnings that we can then amplify when people are joining the team."

The quote highlights the value of reviewing deals and sharing the insights gained with new team members as part of their onboarding.

Onboarding New Hires in Sales

  • The process of onboarding new hires in sales is crucial, especially in enterprise settings.
  • New hires need to learn about the company, the pitch, the customers, and the value drivers.
  • There's a structured onboarding plan that can span up to 90 days.
  • The onboarding process includes listening to recorded calls, reading company materials, and engaging in pitch practice before speaking to customers.
  • The timeline for allowing new hires to speak to customers varies based on how quickly they ramp up.

"Right now at Fivetran, we have, like, a full 90 day plan of onboarding where you come in and you have very structured. These are the things you're learning about the company. This is what you're learning about our pitch. This is what you're learning about our customers, our value drivers, et cetera."

This quote explains the comprehensive onboarding plan at Fivetran, which is designed to educate new hires about various aspects of the company and sales process over a period of 90 days.

Building Sales Teams from Scratch

  • Carl Parrish built the sales engine at Figma from the ground up, overseeing the growth of the sales team.
  • In the early stages of building a sales team, one might have to take on multiple roles due to the absence of specialized functions.
  • Hiring key leaders in sales operations and enablement is a milestone in the development of the sales team.
  • The initial focus is on team bonding and trying different strategies to see what works.
  • Early on, sales reps are encouraged to shadow calls, absorb resources, and learn about the product and market.

"So my happiest day is when we hired a sales ops leader, and then we hired someone to lead enablement."

This quote highlights the significance of hiring specialized leaders in sales operations and enablement, which marked a pivotal moment in the development of the sales team at Figma.

Sales Onboarding and Ramp-Up

  • Sales onboarding involves a period of observation and learning before actively selling.
  • New sales reps need to understand the product, market, competition, and customer personas.
  • The onboarding phase includes shadowing calls, learning from documentation, and receiving feedback.
  • It's important for new hires to have a growth mindset and to continuously incorporate new learnings.

"Early on, shadow as many calls as you can. Here's all the documentation we have access to. Here's how we think about the space."

This quote emphasizes the importance of shadowing calls and utilizing available documentation as part of the onboarding process to understand the sales space and product.

Sales Performance Review and Metrics

  • After three months, sales performance is reviewed based on metrics such as the number of discovery calls and pipeline added.
  • Closing deals and generating revenue are key indicators of a sales rep's performance.
  • Reviews consider both quantitative data and qualitative feedback from different departments.
  • The goal is to provide sales reps with clear direction and motivation for their continued success.

"By three months, you've been closing deals, you've been bringing on revenue. And so we've got a body of work to review and we have some data to see."

This quote explains that by the three-month mark, there should be tangible results in terms of deals closed and revenue generated, which are used to assess the sales rep's performance.

Sales Planning and Engagement Tools

  • Sales planning and engagement tools are essential for managing sales teams.
  • Pigment is a platform that helps with sales capacity planning, quota management, and maintaining pipeline health.
  • Sales Loft is a sales engagement platform that supports prospecting, deal management, and performance insights.
  • Chargebee is a subscription revenue and billing management platform that automates the lead to ledger workflow.

"Pigment is an integrated planning platform that helps sales leaders bridge the gap between strategy and execution."

This quote describes Pigment as a tool that assists sales leaders in aligning sales strategy with execution, highlighting its role in sales planning and management.

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