Matt Rosenberg on Sales Hiring, Discovery and Building a Repeatable Playbook

Grammarly chief revenue officer Matt Rosenberg tells Harry Stebbings that he entered sales accidentally. After law school and a legal job in Chicago, he moved to California during the late-1990s technology boom and joined a startup as its second employee, taking a substantial pay cut.

He began in business development, drawing on his experience with fundraising, contracts and partnerships. As the startup pivoted, he helped sell its first major solution and discovered that he enjoyed the intellectual, emotional and competitive aspects of sales.

For anyone changing careers, Rosenberg recommends remembering why they made the move when doubt appears. He also suggests recognizing small wins along the way. Those wins do not remove the difficulty of a transition, but can create momentum.

At an early sales organization, a first call, a second meeting or useful feedback for the product team can be a meaningful step. Rosenberg says the eventual customer win is built from many such actions. Leaders can help new hires build confidence by noticing progress rather than waiting only for the final contract.

He defines a sales playbook as repeatable processes that lead to the best possible outcome. He rejects taking an identical playbook from one company to another: product, market, pricing and culture differ. His “80% common, 20% different” distinction is a heuristic for the importance of company-specific details.

Rosenberg prefers flexibility to rigidly importing a past process. A sales leader should listen to the market, identify patterns and adjust the motion as evidence accumulates. He says his own career across different industries has helped him combine ideas rather than rely on one template.

Stebbings argues that a founder should build the first playbook. Rosenberg disagrees: he believes a sales leader can provide useful distance and translate between the founder’s language and the buyer’s needs. He still wants founders in customer meetings because they understand the product deeply.

Stebbings responds that without some initial clarity on the motion, a founder may not know which sales leader to hire. Rosenberg agrees a founder needs a view of the type of leader and market, but distinguishes that choice from documenting a repeatable process for winning an account.

Rosenberg warns against hiring solely on a large-company name. He argues that a famous employer does not by itself show what a candidate contributed or whether they can build a new motion. His broad comments about particular employers are a hiring opinion, not proof that their alumni cannot succeed at startups.

For an early sales hire, he values active listening, probing questions, analytical thinking and the ability to spot patterns in customer conversations. He suggests people with banking, consulting or legal backgrounds may have those skills, while acknowledging that his own transition from law shapes his view.

He prefers hiring a sales leader rather than only a junior representative, so the business can build around someone able to coach and scale a team. A junior hire can grow with the right leader. This is his preference; it depends on the company’s needs and resources.

Rosenberg recommends following the first commercial hire quickly with a strong sales-operations partner. He sees the roles as complementary: one discovers customer needs and develops the selling approach, while the other documents stages and process. Hiring both immediately may be difficult for a cash-constrained startup.

Both guests like hiring two early salespeople, but for different reasons. Stebbings wants a comparison that might distinguish a weak seller from a weak product. Rosenberg values collaboration more: two people can test questions, share findings and develop the motion together rather than compete.

Rosenberg cautions that two representatives are too small a sample to draw confident conclusions about the market. Even a strong seller may struggle when product-market fit is poor. The point is to compare what is working, learn from different styles and build shared patterns.

He recommends recording and reviewing early customer calls together. His three-by-three coaching exercise asks the person on the call, a peer and the leader each to identify three things that went well and three they would change. The aim is shared learning and a repeatable approach.

Rosenberg believes deals are often won or lost during discovery. Poor discovery can produce a long, slow loss, while good discovery clarifies whether a solution fits. He starts before the call by researching company priorities and what the buyer and their manager are likely trying to accomplish.

He asks how a buyer’s success is measured, what is going well, what could improve and what is not working. Then he asks what solving those problems would mean for the individual and the business. He says sellers often rush past this payoff question as soon as they hear a problem.

The seller should repeat back what was heard and ask the buyer to prioritize the issues. That creates a map of the customer’s actual needs and whether the product addresses them. Rosenberg argues that without it, a team may spend a long time pursuing a deal it cannot win.

Stebbings asks how to get honest answers when a prospect is guarded. Rosenberg recommends arriving with relevant research and an insight from similar customers, then asking whether it resonates. In his view, showing understanding and empathy can make it easier for the buyer to explain their own situation.

To create urgency, he tries to quantify the benefit of solving a problem with the prospect. If both agree on the value, they can discuss the cost of delaying a month and set a realistic timeline. He says urgency is harder for a desirable but nonessential product, where budget and process may matter more.

When a CFO controls the budget, Rosenberg advises demonstrating value and bringing that person into the process early. He views many CFOs as rational decision-makers, though his claim that a compelling case will lead to purchase is his experience-based view, not a guarantee.

He suggests explaining the approval process transparently to the initial contact instead of treating them as less important. If CFO approval is essential, the seller can say so and avoid dragging both sides through a process without the necessary decision-maker. He calls this a difficult but useful position to take.

On discounting, Rosenberg describes an ideal in which discovery and a clear return on investment support the stated price. In practice, end-of-quarter habits and business pressure can lead to concessions. He has discounted when a deal was important, but recommends clear reasons and limits.

He regards a discount around 10% as a ceiling to watch and says 10–15% or more can become problematic in his experience. That is his rule of thumb, not an industry standard. Repeated discounts can signal a pricing, product or sales-process issue worth investigating.

Rosenberg says sales leaders should use data to coach individuals rather than merely report totals. Conversion, deal duration, win and loss rates, transaction size and expansion can show where a representative or the broader process needs help. His stated goal is to develop people for their next career opportunity.

At Compass, he used public real-estate transaction data to identify prospects and possible introductions from existing customers. Those signals could be surfaced to the sales team in Salesforce. The example shows how data can narrow prospecting, although each business needs its own relevant signals.

He criticizes generic prospecting messages that assume a recipient has a problem without knowing them. By contrast, Grammarly’s CEO contacted him with a tailored cold email explaining why his background was relevant. He says that message led to the conversation that brought him to Grammarly.

Rosenberg argues that retaining and expanding existing customers deserves sustained attention, even when incentives reward new customer acquisition. Existing users have already demonstrated interest, and their references can help establish value for new prospects. His claims about reduced discounting are his sales judgment.

He says more than 50,000 teams and roughly one-third of Fortune 500 companies used Grammarly at the time, figures presented as company claims. He describes adoption beginning within one function and expanding through introductions to other departments and enterprise agreements. As Grammarly’s revenue leader, he has a direct commercial interest in these claims.

Moving from consumer product-led growth to enterprise sales changes messaging, customers, pricing, staffing, product and security requirements, Rosenberg says. He had worked on a similar transition at Eventbrite. The new motion must complement the existing one rather than create conflicting incentives.

He recommends beginning an enterprise motion when the product-led business is understood well enough to see and influence acquisition and retention, without waiting for perfection. Usage within large organizations can provide an early signal, although it does not by itself mean the product is ready for enterprise-wide deployment.

Stebbings asks how to compensate product-led acquisition, enterprise sales and customer-success expansion without cannibalization. Rosenberg says each stage involves different work: landing a sanctioned enterprise agreement and expanding it across the business are difficult in distinct ways and can warrant separate incentives.

In quick-fire advice, he says good discovery remains essential while cold calling has become less effective in his experience. When joining a new company, he asks people across functions the same detailed set of questions to spot patterns in strengths, weaknesses and risks.

He wants more women in sales leadership and argues that parents of young children can bring empathy, multitasking and efficiency. These are his observations about skills, not guarantees about any individual or a substitute for assessing candidates fairly.

Rosenberg praises Gong for building both a call-recording product and a market around sales coaching. The guests close by thanking each other for the conversation.