Authors: Bojan Stojkovski and Bogdan Iordache

With over a decade of experience helping startups grow in the US market, Jen Abel is one of the most opinionated and unique voices on the founder-led sales topic. And that makes sense because she has guided more than 350 B2B enterprises towards early sales success. 

Jen earned her knowledge by working with multiple startups early on as a sales exec. She was one of the very first hires on the enterprise sales team at General Assembly, and later the first sales hire of the  YC-backed startup called The Muse. Each of these roles allowed Jen to gain insights into how startups operate and understand the unique challenges founders face in setting up and scaling sales processes.

Now, as the co-founder of JJELLYFISH, Jen advises startups and Fortune 500 companies on refining their sales strategies and optimizing their go-to-market approaches to achieve early revenue growth.

The Zero-to-One Stage Gap 

“If the founder is not leading sales from a visionary perspective, every salesperson is set up to fail.”

The zero-to-one stage sales process is a distinct stage with specific rules: if the founder isn’t actively involved and provides visionary leadership, every salesperson is set up for failure.

“A founder’s day one vision on a given market is never the same vision that’s going to take them to product market fit – it requires so much iteration. So, we saw that there was a massive talent gap in the zero to one stage. Honestly, there is no such thing as sales talent in the zero-to-one stage because it needs to be led by the founder. However, significant fine-tuning is necessary to ensure their vision aligns perfectly with market reality,” Jen explains.

Founders generally don’t want to handle the heavy execution work, as they prefer building products over sales processes. However, according to Jen, sales are at the heart of everything. “Whether you’re dealing with investors, employees, or customers, it’s all about selling.”

“A founder’s passion drives them to dedicate their life to their business. But, this passion can also be a double-edged sword, bringing with it a sense of blind confidence. To fully commit to such an endeavor, a founder needs to possess an almost excessive level of confidence,” she explains. 

Then again, blind confidence should also come with some type of reality check or grounding to ensure that it does not lead to unrealistic expectations or decisions.

“It’s challenging for a full-time employee to provide this kind of insight, which is why we saw a major opportunity for founders to have access to a resource that offers honest feedback. I found myself in a position where I was handling 90% of the execution behind the visionary, and I had this realization. This process is called facilitating learning, ensuring that founders stay focused and don’t fall victim to their own biases,” Jen says, describing how her own business operates.

The Product Is the Founder

“Only a founder can identify an opportunity forming in the market.”

In the early days, the product is the founder. At the beginning of every startup journey, the early adopters are buying into the founder and his expertise because the product is still in its early stages and not yet a polished technology.

“They’re buying access to this founder. And if the founder cannot or is not willing to go out and learn and get rejected and go through that process, they are setting everyone up to fail,” Jen points out. 

Hence, this is what sales actually is—constantly facing rejection and then shifting your focus to areas where the market shows enthusiasm, she explains. 

There are many bad habits among salespeople, with some merely pushing a product rather than genuinely engaging with customers. So, having a founder at the forefront provides a significant competitive advantage, as everyone wants to learn from a visionary.

“Only a founder can recognize emerging market opportunities that weren’t apparent from day one. Achieving product-market fit can take years—some of the biggest companies took two to four years because their initial market vision wasn’t accurate. It’s the founder’s unique perspective that allows them to spot these opportunities,” Jen emphasizes. 

Understanding Market Feedback

“The only person that’s incentivized to learn is the founder.”

Many founders are seeking validation, believing that actions such as warm introductions signal momentum and confirm their assumptions. This often leads them to stop questioning or testing their ideas further.

“Warm introductions are often seen as favors and rarely align perfectly with your ideal customer profile (ICP). The chances of finding someone who fits your ICP through these introductions are quite low. Additionally, most people who agree to a call are doing so on behalf of someone else, which means their interest might not be genuine,” Jen explains.

Therefore, it’s essential for founders to remain critical and continue validating their assumptions, rather than relying solely on early positive feedback. 

“When they hear 5 to 10 people say, “Yeah, this is a great idea,” someone with limited sales experience might take that as enough validation and dive straight into building and selling the product, bypassing the entire customer discovery phase,” she adds.

As she further points out, early-stage sales are extremely challenging and here, the founder is the only one who is truly motivated to learn and figure things out.

“The first two years are a huge learning sprint, refining the vision and getting specific on who you want to serve, understanding if those people churn or not, and so on. The founder needs to lead sales until product-market fit is achieved. Product-market fit means not only acquiring customers but also retaining them. Simply closing 10 customers who then churn doesn’t signify product-market fit; true fit requires ongoing customer satisfaction and retention,” Jen says. 

Many founders will engage with the market by asking questions like, “Hey, what are your priorities?” or “What keeps you up at night?” They might even ask obvious questions like, “Are you looking to drive more revenue?” These types of questions are ineffective because the answers are obvious—of course, everyone wants to drive more revenue, Jen explains.

Instead, what founders should be seeking is the key discovery, which she describes as the “AHA moment,” a vital step in the sales process. It occurs when a founder tests their vision against market problems and gets a response like, “How did you know that?” or “We’re facing that issue too.” This reaction indicates that the founder has tapped into a significant insight, prompting deeper engagement.

“To achieve this, conversations with the market must be consistent. Inconsistent discussions lead to noise rather than valuable feedback. To unlock unique insights and ensure repeatability, it’s essential to keep conversations focused and specific on the problems customers are experiencing, not just the abstract solutions. This specificity helps elicit genuine AHA moments, making customers more engaged and willing to discuss their issues,” Jen adds.

Such market feedback essentially becomes the biggest gift the market can provide even before revenue because it helps founders further understand where to double down and where to pivot or adjust their approach. 

“Fear of rejection is common, but not seeking market feedback early on is a major red flag. No one is right from day one, and market invalidation is vital. It shows investors and your team that you’re avoiding bias and learning from feedback,” Jen points out.

What Sets Your Product Apart

“The demo is showing them where they are today and where you can take them tomorrow.”

The value proposition is the key incentive of understanding what sets a product apart. It should directly stem from the specific problem being solved. Simply stating that something is faster, better, or cheaper doesn’t differentiate a product if competitors can claim the same. Effective value propositions highlight unique solutions to clearly defined problems.

“Starting with the value proposition and then searching for the problem is the wrong approach. It should begin with identifying the specific problem your audience is trying to solve and understanding their journey toward a solution. Only then can you demonstrate how your offering moves them from their current state to their desired outcome. Additionally, this solution must be both digestible and believable, so make sure the solution isn’t overly ambitious to the point where it seems unbelievable,” Jen suggests.

The demo is another crucial segment in the sales process, since everyone appreciates a great presentation. However, it should focus less on the product itself and more on understanding the customer’s problem. 

For high-value deals, it’s important to gather detailed insights into the customer’s challenges before the demo. For higher-velocity deals, one likely already has some understanding, but the demo should still highlight the current state and the future possibilities that their solution offers.

“The demo isn’t about showcasing the product itself. Instead, it’s about illustrating the buyer’s day-to-day experience. It’s an opportunity to show how you understand their specific challenges and how your solution addresses those problems, essentially demonstrating the gap between their current state and where you can help them be,” Jen emphasizes.

The First Sales Hires

“The first sales hire is hard because you need to bring them in at the right time, after the key issues have been figured out.”

Most importantly, before hiring anyone, it’s crucial to determine if the founder knows how to hold team members accountable, Jen says.

“Often, founders will hire salespeople and then express frustration that the team isn’t moving as quickly as they’d like. When I ask what the team is doing, they might reveal that 50% of their time is spent handling and converting inbound leads, while the other 50% is unproductive because no one is pushing them to generate demand and engage in outbound activities,” she points out.

Jen’s experience shows that getting the timing right for hiring the first salesperson is very challenging. It’s often less about hiring too late and more about hiring too early, which is a common mistake.

“Sales success is often a 50/50 shot. Many believe you need two hires to find what works and where strengths lie. Sales expertise varies widely: inside sales focuses on high-velocity deals with leads driven by marketing, typically in the $1,000 to $15,000 range. In contrast, field sales involve creating opportunities, driving leads, and managing larger deals, often over $50,000, requiring more consultative efforts,” Jen explains.

Another common mistake is hiring someone from a big, well-established company that’s several stages ahead of your startup. These candidates often benefit from brand equity, case studies, and substantial marketing budgets, making their previous success less about their individual skills and more about the advantages provided by their former company. 

“When they join your startup, they may find it much harder to sell, as they lack the same level of market trust. In the early days, trust comes from the founder and the salesperson’s deep understanding of the problem,” Jen says. 

What she suggests for making sales hires depends on the sales model. For high-volume, marketing-driven sales, hiring one or two inside sales reps is usually sufficient, as it allows for a quick assessment of what works and what doesn’t. In contrast, enterprise sales have a longer feedback loop, often taking three to nine months to evaluate a rep’s effectiveness.

For enterprise sales, it’s essential to hire reps who can manage the entire funnel, from generating demand to validating market problems and converting leads into sales-qualified opportunities. Experienced senior AEs are preferred, as they should be capable of creating new demand, validating key issues in the discovery phase, and effectively handling the sales process.

“The founder can’t completely step away from sales initially. They need to stay involved in each stage of the sales funnel until salespeople prove their effectiveness. Once the sales team demonstrates success, the founder can gradually step back. However, the founder will likely remain involved to some extent, though their role should become less demanding over time,” Jen notes.

On sales metrics, Jen explains that conversion rates vary by sales type. Inside sales, driven by marketing and inbound leads, will have different rates than enterprise sales, which rely on outbound efforts. Founders typically achieve higher conversion rates than non-founders because they are visionaries and experts, and people are more eager to talk with them.

“Founders’ conversion rates are usually slightly higher, though not dramatically so. For instance, if a founder achieves a 15-20% blended win rate, a sales rep’s rate might typically range from 12-15%, covering both inbound and outbound sales,” she says.

The Mid-Market Does Not Exist

“The mid-market doesn’t exist; it’s a mix of two different markets.”

The mid-market is not a single segment but a blend of two markets. It lies between small business and enterprise levels, Jen points out. 

“When someone says that they are going after the mid-market, that delta is so wide, and not only that, that delta has two radically different go-to-market motions sitting in it. One that requires high volume, the other one that requires high value,” she says.

Landing a single go-to-market strategy is challenging enough, yet many founders attempt to manage two distinct strategies without realizing the complexities involved. The go-to-market space is risky because it often involves navigating dramatically different approaches, and many founders struggle by trying to balance both.

Then, there is the notion that mid-market roles are less consistent compared to small business and enterprise roles. 

“Unlike enterprise, where expansion opportunities are more evident, the mid-market lacks this level of consistency. However, if used strategically as a stepping stone to move into the enterprise space, it can still be valuable,” Jen emphasizes.

And if more reasons were needed for why founders should do sales, here’s another from Jen: only a founder can spot emerging market trends or opportunities that weren’t apparent from the start.