20Sales Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Summary Notes


In this insightful conversation, Harry Stebbings welcomes Matt Rosenberg, Grammarly's Chief Revenue Officer, to discuss the nuances of building and scaling effective sales teams. Rosenberg, with a diverse background including roles as CRO at Compass and Eventbrite, shares his journey from an accidental sales leader to a seasoned executive. He emphasizes the importance of hiring beyond prestigious company alumni for the first sales executive role, advocating for individuals with active listening skills and analytical thinking, such as ex-bankers or lawyers. Rosenberg also highlights the significance of thorough discovery processes in sales, the strategic involvement of CFOs in deals, and the careful management of discounting practices. Additionally, he touches on the challenges and strategies for transitioning from a product-led growth model to enterprise sales, the role of data in guiding sales processes, and the need for more women in sales leadership roles. The discussion also covers the effectiveness of prospecting and the importance of customer expansion, with Rosenberg praising companies like Gong for their market-creating sales strategies.

Summary Notes

Hiring Philosophy

  • Matt Rosenberg advises against hiring individuals who prominently feature their past employment at major tech companies like Google, Amazon, or Facebook on their LinkedIn profiles.
  • He suggests that these individuals may be trying to leverage the success of those companies rather than their own merits.
  • Matt recommends hiring ex-bankers, consultants, or lawyers as the first sales executives, implying they may have more to contribute individually to a startup's success.

"Don't hire anybody from Google. Don't hire anybody that says on their LinkedIn, ex Google X, Amazon X, Facebook, when they put that on their LinkedIn, they're associating themselves with the success of the business."

The quote highlights Matt's belief that past affiliations with successful companies do not necessarily translate into individual competence or success in a new role, especially in a startup environment.

Matt Rosenberg's Introduction

  • Harry introduces Matt Rosenberg, praising the quality of the sales advice he provides.
  • Matt is currently the Chief Revenue Officer and head of Grammarly Business.
  • He has a history of significant contributions to companies like Compass and Eventbrite, leading to substantial business growth.

"This is one of the best 20 sales episodes we've ever done. This guest was phenomenal. He did not hold back and there's so much goodness here it and so I'm thrilled to welcome Matt Rosenberg."

Harry's quote indicates that the information provided by Matt in the episode is particularly valuable and actionable, making it a must-listen for those interested in scaling sales teams.

Sales Execution Platform: Outreach

  • Outreach is described as an AI-powered sales execution platform that enhances seller productivity.
  • The platform supports various stages of the sales process, from prospecting to deal management and forecasting.
  • Outreach is unique in offering sales engagement, revenue intelligence, and revenue operations in one platform.
  • The platform is trusted by over 6000 companies, including high-profile names like Zoom and Siemens.

"Outreach is the only aipowered sales execution platform that unlocks seller productivity to help sales teams efficiently create and close more pipeline."

This quote underscores Outreach's role in boosting sales team productivity by leveraging AI, which is an important tool for modern revenue-generating activities.

B2B Data Platform: ZoomInfo

  • ZoomInfo is presented as a platform that amplifies a company's revenue potential by providing efficient access to quality B2B data.
  • The platform offers insights to identify and engage the right prospects, which facilitates customer conversion.
  • ZoomInfo is used by over 30,000 customers, including prominent companies like Snowflake and PayPal.

"Zoom info helps companies supercharge their revenue potential. Landing your next customer. It's really freaking hard, but it doesn't have to be."

The quote emphasizes the challenges of customer acquisition and how ZoomInfo's data and tools make the process more manageable and efficient.

Matt Rosenberg's Background and Entry into Sales

  • Matt Rosenberg describes his path into sales as accidental, following a stint in law school and working as a lawyer.
  • He moved to California during the dot-com boom and joined a startup as the head of business development, pivoting into sales after several business failures and pivots.
  • Matt's love for sales developed from the intellectual and emotional aspects of the role.

"I moved to California. I joined a startup as the second employee, and along the way joined them as their head of business development."

Matt's quote narrates his career transition from a lawyer to a sales leader, highlighting his decision to embrace the startup world and the different roles he took on that led him to sales.

Career Pivots and Lessons

  • Matt believes that making career pivots requires courage and conviction.
  • Remembering the reasons behind a career pivot can serve as an anchor during moments of insecurity and doubt.
  • Celebrating small wins and building momentum are crucial for navigating career transitions.

"One of the big lessons is when you make that pivot, just remember why you made it."

This quote reflects on the importance of recalling one's motivations during a career change, which can help maintain focus and drive through challenging times.

Building Momentum in Sales Teams

  • Momentum in sales can start with small actions like securing a meeting or translating feedback to the product team.
  • Celebrating small victories is important for building confidence and maintaining a positive trajectory in sales.

"Momentum could be you have a first meeting and you're able to translate that meeting back to the product team to help them understand what it is. You heard."

Matt's quote illustrates how seemingly minor achievements in sales can contribute to overall momentum and success, which is vital for sales team morale and progress.

Sales Playbooks

  • Matt Rosenberg defines a sales playbook as a set of repeatable processes that lead to the best outcomes.
  • He debates the effectiveness of rigid playbooks, preferring to tailor strategies to each company's unique circumstances.
  • According to Matt, the nuances and flexibility within the 20% of a playbook that is tailored to a specific company are what lead to sustained success.

"While certain processes may be repeatable, there's 80% of commonality. It's that 20% that actually is the difference between winning and losing, and that 20% of the Playbook that you really have to build."

The quote emphasizes that while there may be common strategies in sales, the unique elements tailored to a company's specific needs are critical for achieving consistent wins.

Flexibility vs. Rigidity in Sales Leadership

  • Matt encourages flexibility over rigidity in sales leadership.
  • He believes that a great sales leader should deeply understand their market and adapt processes to maximize team success.

"I would encourage a lot more flexibility than rigidity."

This quote suggests that adaptability is more valuable than strict adherence to previous methods when it comes to leading sales teams in different companies and markets.

Role of Founders in Building Sales Playbooks

  • Matt disagrees with the idea that founders should build the sales playbook, suggesting that it is a task better suited for the first sales hire.
  • He believes that founders have their own superpowers, while sales leaders bring unique perspectives formed from diverse experiences.

"Let's call this our first point of divergence. I think founders, they have superpowers in lots."

Matt's quote indicates a differing opinion on the responsibilities of founders and sales leaders, highlighting the importance of leveraging each individual's strengths in a startup.

Building a Sales Playbook

  • Founders are often too close to their business to effectively build a sales playbook.
  • Sales leaders can provide a beneficial layer of abstraction.
  • Translation between company language and customer language is key.
  • Product-market fit is influenced by understanding customer perspectives.
  • Founders excel at positioning but may not best construct the sales process.

"I think you need a level or a layer of abstraction to be great at building a playbook." This quote emphasizes the need for a perspective that is somewhat removed from the founder's intimate knowledge of the product to effectively build a sales playbook.

Hiring the Right Sales Leader

  • Founders should have a clear point of view on the type of sales leader needed.
  • Hiring based on pedigree can be misleading.
  • The ideal first sales executive should be a great listener and critical thinker.
  • Lawyers, bankers, and consultants can be good first hires for their probing questions and pattern recognition.

"The first sales executive you want to hire, an ex banker, an ex consultant, an ex lawyer." Matt Rosenberg suggests that the skills possessed by professionals from these backgrounds are beneficial for building a sales playbook.

Sales Team Structure

  • Starting with a sales leader rather than a junior rep is advised for scalability.
  • Sales leaders can mentor and develop junior reps.
  • A sales operations lead is crucial for building out the sales process.

"I think you should be sales leader. I really do." Matt Rosenberg advises hiring a sales leader first to build a scalable sales team.

Role of Sales Operations

  • Sales operations is often neglected but is vital for establishing the sales process.
  • Hiring a sales operations lead to work with the first sales executive is ideal.
  • Sales operations and sales executive roles require different skill sets.

"Everyone always neglects sales ops, but sales ops is sitting in the background figuring out the process, the motion, the stages." This quote highlights the importance of the sales operations role in defining the sales process.

Hiring Sales Reps

  • Hiring two sales reps at the same time is recommended.
  • Collaboration is more valuable than competition in early sales hires.
  • The goal is to optimize the sales process and best practices through collaboration.

"You want collaboration, not competition." Matt Rosenberg stresses the importance of collaborative efforts in the early stages of building a sales team.

Transfer of Learnings

  • Every sales call should be recorded and reviewed collaboratively.
  • The three by three framework helps identify what went well and what could improve.
  • Optimal processes and best practices emerge from pattern recognition.

"There is no reason every call shouldn't be recorded. There is no reason that every call shouldn't be listened to together." Matt Rosenberg emphasizes the importance of collective learning from sales calls to refine the sales process.

Challenges with Remote Sales Teams

  • Remote work makes it more challenging to share learnings among sales team members.

"It becomes more challenging because the level of conversation amongst your peers is just different." Matt Rosenberg acknowledges the difficulties that remote working conditions pose for sales team communication and learning.

Effective Discovery in Sales

  • Deals are won or lost during the discovery phase.
  • Research and understanding customer priorities are crucial.
  • Mapping solutions to the customer's challenges is essential for sales success.

"It always comes down to discovery. And deals are won and lost in discovery." Matt Rosenberg asserts that the discovery phase is critical in determining the outcome of a sales process.

Alignment with Client Success Priorities

  • Identifying client success priorities is the first step in understanding their needs.
  • Alignment with these priorities is crucial for a successful business relationship.
  • Asking about how success is measured and what the client cares about most can reveal key insights.

"The next set of questions is, how is your success measured? Like, what do you care most about?"

This quote emphasizes the importance of understanding the client's criteria for success and what they value in their business operations, which is essential for tailoring a sales approach.

Effective Discovery Process

  • Starting with what the client is doing well encourages open communication.
  • Inquiring about areas for improvement and listening carefully to the response is key.
  • Understanding the impact of fixing issues can lead to a strong business case and reduce the need for discounting.

"If you were to fix those things that aren't going so well, what impact would it have for you, for your business, for how you're measured?"

This quote highlights the importance of understanding the potential positive outcomes of addressing a client's issues, which is a critical component in building a compelling value proposition.

Prioritization of Issues

  • Clarifying how the client would prioritize their issues helps in creating a strategy to win the account.
  • Understanding the client's pain points and their significance is essential for a swift and successful closure.

"How would you prioritize those issues? Because you need to know what they care most about."

This quote underscores the necessity of grasping the client's prioritization to effectively address their most pressing concerns and align sales efforts accordingly.

Encouraging Openness and Honesty

  • Establishing trust and demonstrating insight can encourage clients to be more open and honest.
  • Salespeople should do their research and use insights to resonate with potential customers.
  • Being relatable and showing empathy can lead to better issue identification.

"People will feel comfortable expressing themselves more openly if they believe that you are a trusted partner and have some insight to share."

This quote suggests that trust and perceived expertise can facilitate a more transparent dialogue with clients, which is essential for uncovering their true needs and challenges.

Creating Urgency in Sales

  • Great discovery can lead to urgency by linking the resolution of pain points to business outcomes.
  • Quantifying the economic benefit of solving an issue can motivate clients to act quickly.
  • Without understanding the value to the client, creating urgency is challenging.

"Every unit of delay is equal to some value."

The quote implies that by quantifying the cost of inaction, salespeople can create a sense of urgency that motivates clients to move forward with a solution.

Painkiller vs. Vitamin Sales

  • Selling a solution that addresses a pain point (painkiller) can make it easier to create urgency.
  • Selling a nice-to-have product (vitamin) is more challenging and requires understanding client goals and timelines.

"It's a lot harder when you're selling vitamins, you could do it."

This quote acknowledges the difficulty in creating urgency when selling products that are not seen as immediately essential by the client, as opposed to those that solve a pressing problem.

Engaging the CFO in the Sales Process

  • Salespeople should involve the CFO early in the process as they are key decision-makers.
  • Presenting demonstrable value is crucial to persuade CFOs to invest in a product or service.
  • Transparency and a clear process can facilitate the involvement of the CFO without alienating other stakeholders.

"You have to get this to their desk in front of them and understand what they care about."

This quote emphasizes the importance of engaging CFOs in the sales process by addressing their interests and demonstrating value, which can be pivotal in securing their approval for a purchase.

Handling Discount Requests

  • Ideally, a strong business case would negate the need for discounts.
  • Realistically, traditions of discounting can set expectations that are hard to overcome.
  • Discounting should be principled, controlled, and communicated clearly to the customer.

"Ten to 15% discount or more is a problem."

This quote suggests that while some level of discounting may be inevitable, it should be kept within reasonable limits to avoid devaluing the product and to maintain profitability.

Data-Driven Sales Leadership

  • Data analysis can help identify gaps in the sales process and individual performance.
  • Sales leaders should use data to coach their teams and improve overall success.
  • Data can also guide strategic decisions on pricing, discounting, and sales motions.

"Data will tell you all of that. It'll even tell you your sales motion."

This quote conveys the comprehensive role of data in informing and guiding sales strategies, team development, and process optimization.

Prospecting Effectiveness

  • Prospecting is often not done well, as evidenced by ineffective outreach like LinkedIn messages.
  • Exceptional prospecting involves strategic use of data and insights to identify and engage potential customers.

"No, it is not done well. If you just check my LinkedIn messages, it is done very poorly."

This quote criticizes the common prospecting practices and suggests that there is significant room for improvement in how salespeople identify and connect with potential leads.

Effective Prospecting Techniques

  • Personalized outreach based on recipient's background can lead to successful engagement.
  • Understanding the message and the recipient is crucial.
  • Doing homework on the prospect can make cold outreach work.

ith a very precise message around his interest in talking to me because of a number of different reasons based on my background, and it was a cold outreach and I read the email and I was like, wow, that's a very interesting approach.

The quote emphasizes the impact of a well-crafted, personalized message in cold outreach, highlighting the importance of tailoring the approach based on the recipient's background.

CEO Humility and Leadership

  • The CEO of Grammarly reached out personally, which is seen as a display of humility.
  • This approach is uncommon among CEOs, especially for a company of Grammarly's size.

I loved it for so many reasons, not the least of which is the humility and the non alpha nature of that leader to be able to be like, hey, I'm looking for assistance here.

The quote reflects admiration for the CEO's humility and willingness to seek assistance, which is considered a strong leadership quality.

Customer Expansion in Business

  • The importance of customer expansion has resurfaced.
  • It is easier to expand and retain existing customers than to acquire new ones.
  • Customer expansion can lead to reduced discounting and easier new customer acquisition.

Customer expansion is hot again. How do you view this?

The question introduces the theme of customer expansion's renewed importance in business strategy.

Transition from Consumer to Enterprise

  • Transitioning from a consumer product to an enterprise sales-led product is challenging.
  • Everything from language to pricing is different in enterprise sales.
  • Founders need to understand that enterprise requires different staffing and capabilities.
  • Data from product-led growth can guide the enterprise motion.

Grammarly was the ultimate PlG... Making that transition. What do founders not know about moving from consumer to enterprise that you just really think they should everything.

The quote discusses Grammarly's transition from a consumer-focused product to an enterprise solution, highlighting the differences and challenges involved in such a shift.

Timing the Enterprise Transition

  • Founders should wait until they have control and visibility into their product-led business before transitioning to enterprise.
  • The transition shouldn't be rushed but should not be delayed too long either.

There's a point where you really understand your product led motion... That's the time.

The quote advises on the optimal timing for a business to consider transitioning to enterprise sales, emphasizing the importance of understanding the existing product-led business first.

Organic Testing for Enterprise Readiness

  • Testing for enterprise readiness happens organically through data.
  • The use of a product by large organizations or within enterprise environments indicates readiness.

The testing happens organically, like the testing is already there. It's in the data.

The quote explains that the data already available to a company can naturally indicate whether a product is ready for enterprise adoption.

Incentive Mechanisms in Sales

  • Incentive mechanisms must be carefully considered to avoid cannibalization.
  • Selling enterprise licenses and expanding them requires specialization and warrants compensation.
  • Each stage of the value chain from acquisition to enterprise expansion has its complexities.

Cannibalization is the trickiest of all issues... that warrants that kind of compensation.

The quote addresses the complexity of designing incentive mechanisms in sales, especially when transitioning from product-led growth to enterprise sales.

Sales Tactics and Advice

  • Great discovery in sales remains unchanged and is always important.
  • Cold calling has declined as a tactic.
  • New sales leaders should ask a detailed set of questions to accelerate learning and understand the organization.
  • There is a need for more diversity in sales leadership roles, particularly for women and parents.
  • Efficiency in sales can often be found by hiring parents who are adept at multitasking and driving behavior.

Well, great Discovery never changes... Hire a mom because they know how to multitask.

The quote touches on the timeless importance of discovery in sales and suggests that hiring parents, especially mothers, can bring efficiency and empathy to sales leadership roles.

Sales Strategy Impressions

  • Creating a market and owning it is impressive in sales strategy.
  • Gong is recognized for creating a market around call analysis technology and brand building.

I'm always impressed by companies that make markets... I think they've done an exceptional job.

The quote praises Gong for not only developing innovative technology but also for successfully creating and dominating a new market segment.

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