We spoke to 200 B2B Sales Reps, here are 10 pains we learned

Nov 30, 2023

Hey there 👋🏻,

Welcome back to the third episode of my monthly newsletter: 'build together.' To quickly warm you up, I am Ludo, co-founder and CEO of Leadbay, with the aim of empowering the next generation of B2B sales champions through technology. Alongside my co-founder Milan Stankovic, PhD, a small tech team, and a community of 200 B2B sales reps, we started working on the future of Sales last August. We quickly arrived at our initial hypothesis, which I shared in my first newsletter, 'Manifesto: B2B leads search sucks, so leadbay will make it magic.' In september, we learned a lot about our target market “Target the next generation B2B sales”. In October I will tell you what we learned from 200 B2B Sales Reps interviews.

In this article, I will cover:

  1. My methodology for learning from B2B, including the mistakes I have made,

  2. 10 pains I listed from from our interviews,

  3. 3 prediction I will bet on for the next 5 years.

1. Market research methodology: don’t be salesy, record, listen & interpret results

Don’t be salesy, set guidelines to yourself

My first mistake was being too salesy. I am the business profile of the team, so I like persuading, selling, and closing deals. After the first interviews, I came back to the team saying “Everyone wants to buy my product!!” but we learned nothing from it. Therefore, it's crucial to establish guidelines for yourself, including:

  1. Clear goals

  2. Types of users to interview

  3. Defined interview techniques

  4. Listing your questions & scenarios

  5. Pitching your product (ONLY at the end)

Effective questions could be:

  • Recall the last deal you successfully closed → Can you walk me through the steps? How did the customer feel? What tools were involved? What were the time and cash you spent in the process?

Most valuable insights are discovered within interview recordings

It’s super difficult to capture everything during an interview. Most valuable insights are often feelings, which can be seen only during records. So record all market research interviews.

Interpret results

After each video, share it with your team, extract outputs, and draw conclusions. Sometimes, the interpretation of the results surpasses initial expectations. For instance, If someone tells you “I am already paying for it, I have a whole team dedicated to that pain, so we are the best at it”. It means that what you want to offer if so painful that people are actually spending time and money on the solution to solve this internally. It doesn’t mean there are not interested.

Reaching out to interviewees

To secure interviews with 200 B2B sales reps willing to dedicate 20 minutes of their valuable time, I employed several methods:

  1. Contacted friends working in B2B sales (10 responses).

  2. Utilized LinkedIn Sales Navigator to select a diverse group of B2B sales reps (approx. 500 identified for 100 responses).

  3. Leveraged interviewed sales reps to recommend me to their friends.

  4. Published a newsletter featuring my monthly output to drive more interviews.

A valuable tip: quality supersedes quantity. I conducted multiple rounds of interviews with the most relevant B2B sales professionals I initially met, allowing for multiple rounds on different topics.

Interviews phases

As your comprehension of pain points and value propositions advances, your guidelines must evolve too. In my case, I conducted three types of interviews:

  1. General market research (being impartial, asking questions, identifying pain points),

  2. Surveys validating value propositions and pricing,

  3. Product demos and feedback sessions.


Today, we continue to adhere to this methodology, consistently learning and evolving based on market feedback. Our current pace involves releasing a new version of the product every Wednesday, recording a weekly product demo, and 1-2 new user demos each week. We record these sessions, initiate discussions within the team, share insights, and integrate improvement suggestions into the product roadmap.

2. 10 pains I get from speaking to 200 B2B Sales Reps selling the mid-market (50-500 employee companies):

#Pain1: Too much time spent on listing leads

B2B sales reps targeting mid-market companies (50-500 employees) encounter a vast market with inadequate data. Consequently, it's challenging to compile a list of leads and determine which ones are most likely to make a purchase. The most common methods used include Google search, LinkedIn search, and networking within the industry.

#Pain2: Hard to say it’s qualified, hard to score the lead within the pipeline

Due to the lack of insights into leads and difficulties in accurately assessing product-market fit, qualifying a lead within the pipeline becomes challenging. Sales reps invest time in contacting leads for qualification and cash of software to access the data. In tech sales organizations, this role is called “sales development representatives"

According to Zippia research done on this US market, 67% of lost sales are due to sales reps failing to properly qualify potential customers before beginning the sales process.

#Pain3: Massive entry of leads, resulting in a massive drop of leads

One current practice involves contacting a large number of leads to yield very few “Yes”. It entails reaching out to leads through various channels (email, LinkedIn, phone calls), identifying the most interested prospects, and closing a small percentage of them. However, this approach might appear as spam to the potential buyers.

While some tactics focus on personalizing this quantitative approach, the lack of data in the mid-market makes it difficult for sales reps to be relevant.

#Pain4: The Pricing page makes leads drop, not close

Each company react differently to pricing. Most of the time public pricing become a deal-breaker. Lack of transparency in pricing is neither the good way to not having leads drop.

Startups working on it:

  • https://www.hyperline.co/

  • https://www.getlago.com/

#Pain5: The button “talk to sales” doesn't work

The "talk to sales" button is often a result of companies' unfamiliarity with their sales funnel. Many leads refrain from clicking on "talk to sales" as they prefer trying and using the product immediately. This step is seen as inefficient, even by those working in sales.

#Pain6: Right lead into the right funnel

Redirecting the right client to the suitable funnel poses a significant challenge. Some leads prefer a self-serve funnel, while others favor being contacted by outbound teams. The choice often depends on the company's size, pricing, and the product or service's self-serve nature.

Startups working on it:

  • https://www.mutinyhq.com/

  • https://www.userled.io/

#Pain7: Get a reco is not easy for everyone

They allow B2B sales reps to approach prospects with the recommendation of a similar company already using the product. The prospect, in turn, anticipates that the service/product might align with their organization, particularly when introduced via a friend's advocacy. However, the network of Sales Reps is limited; they need to map out their relatives' network, and it is not an easy task.

Startups working on it:

  • https://www.commonroom.io/

  • https://reveal.co/

  • https://www.refer.social/

#Pain8: B2B Sales Reps exhausted for non-value tasks

B2B sales reps prefer to focus on sales rather than performing non-value tasks such as listing leads, contacting leads, qualifying leads, writing emails, internal processes, and other administrative work. Additionally, they express discontent with the tools they use, preferring more effective tools that match their pace and professionalism.

One segmentation we can have here:

#Pain9: Still difficult to understand what works and what doesn’t

Most of the B2B sales teams don’t have proper dashboard to understand the whole workflow performance.

Startups working on it:

  • https://www.actiondesk.io/

  • https://growblocks.com/

#Pain10: GenZ's different approach to work

The new generation of B2B sales professionals seeks job changes frequently, causing talent and knowledge turnover within sales teams.

3. Hearing 200 B2B sales, here is my 3 predictions how the B2B sales market will evolve in the next 5 years

#Prediction1: B2B buyers seek the B2C experience

B2C sales are so advanced compared to B2B. B2C sales have accustomed customers to highly targeted and customized sales experiences, secure transactions, one-click checkouts, and excellent customer success. Especially with the new generation, customers will demand a much smoother experience than what B2B sales currently offers.

#Prediction2: Transitioning from mass personalization selling to qualified & personalized selling

Everyone faces an abundance of spam across multiple channels (email, mail, LinkedIn, phone, SMS), mostly failing to address what the buyers truly seek. This mismatch often includes the wrong value proposition, mistimed communications, improper channels, and inadequate context. B2B buyers are in search of supporters and partners. They are seeking the right B2B sales reps who can engage at the right time with the right value proposition and pricing. Moreover, B2B buyers anticipate being able to start using the app or service the day after the purchase.

Promising startups:

  • https://www.mutinyhq.com/

#Prediction3: New generation of tools offering higher value (AI native) and better experience (so desired by the next generation of users - GenZ & Millenials)

This one is my favorite. 40% of the B2B sales reps are tech native (GenZ & Millenials), they will be 80% in 10 years. It s approximately 2,000,000 B2B sales reps today in the EURO & US and 4,000,000 B2B sales reps in 10 years. All of them are telling me “B2B sales tools user experience suck”. This new generation of sales is born with intuitive app, taking into account their low attention span, they want 1 click, not 2. They ask for immediate high value now, not tomorrow. They are boring on non-value tasks and won’t do it. They are familiar with platforms like Instagram and TikTok, not hubspot and salesforce. It means than UI/UX will have to be radically different to be used and AI can help with that.

Promising startups:

  • https://attio.com/

  • https://www.folk.app/

  • https://www.unifygtm.com/

Good readings:

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