What Are the Biggest Challenges and Priorities of Entrepreneurial Sellers in 2024? [Analysis Based on 100+ Sellers]

Author's avatar Sales Mar 13, 2024 22 minutes read

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    Peter Caputa

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    What are the biggest roadblocks with entrepreneurial selling that companies run into? And what are the needle movers that they prioritize?

    Entrepreneurial selling is usually the go-to approach for early-stage businesses that can’t rely on established products, markets, or customer bases.

    But things can get really complex, real quick.

    Filling your pipeline with qualified leads, getting through to decision-makers, building trust with bigger organizations… these are just some of the challenges you can run into.

    So, what’s the solution, and what should entrepreneurial sellers focus on to continuously increase sales?

    That’s what we set out to find out in partnership with Rick Roberge. Together, we surveyed 108 companies to better understand both the challenges and priorities of entrepreneurial sellers.

    We received a lot of valuable insights from them about their specific challenges, how they address them, and what tactics they employ to continuously increase sales in their businesses.

    So let’s dive in and see what they had to say.

    Who Did We Survey

    For this report, we partnered up with Rick Roberge and surveyed 108 companies since August 2023 – and we are still collecting feedback. Approximately one-third of our respondents belong to SaaS, Software, or Technology.

    When it comes to the size, most of our respondents belong to small businesses (as expected):

    • 20.37% have only 1 employee
    • 27.78% have 2-10 employees
    • 26.85% have 11-50 employees
    • 15.74% have 51-200 employees
    • 9.26% have more than 200 employees

    “Extraordinary companies are driven by extraordinary leaders that think ‘scale’ and make headlines, but within those companies are extraordinary individual producers that look at the data, compare it to their own behavior and ask, ‘What can I do differently to grow my sales?’”

    Rick Roberge

    Rick Roberge

    Founder at Sales Rock Stars & RainMakers

    Want to get highlighted in our next report? Become a contributor now

    If you’re an individual producer (owner or representative) who is responsible for one-on-one customer acquisition and/or retention, you can join the exclusive Entrepreneurial Selling (1:1) Benchmark Group for free. All benchmark data from contributors is anonymized.

    But even if you’re not an entrepreneurial seller and want to gain access to your industry benchmarks, don’t worry. You can still join Benchmark Groups and find the group most relevant to your business. It’s free, and you get instant access to how your business compares against similar-sized niche competitors.

    Entrepreneurial Selling 1:1 Benchmark Groups

    Over these past few months, we collected a ton of valuable data, both by survey and through the Benchmark Group – here are just some of the insights that you may find interesting.

    Let’s talk about lead generation numbers first.

    When it comes to generating leads in your business, who do you rely on?

    For 54.37% of our respondents, Marketing is responsible for creating leads in their company. 41.75% of respondents opted for Sales instead. However, over 40% of the respondents think that both marketing and sales are responsible for creating leads.

    Marketing is responsible for creating leads in a company

    But when talking about lead quality, it looks like marketing takes the top spot. Around 36% of respondents stated that marketing generates the most leads that close.

    Marketing generates the most leads that close

    We also asked them about lead gen channels – and for about 23% (biggest cohort) of the respondents, most leads come from the company’s blogs, newsletters, and ads. 

    Now, according to data provided by Benchmark Group Entrepreneurial Selling (1:1), companies with 1-250 employees and up to $50M revenue have 124.5 new leads added in January 2024 (median, 282 contributors).

    However, the top quartile of these companies is doing substantially better in lead generation, with almost 4 times more new leads added in the same period – 491 new leads (also median), which indicates that there’s room for growth.

    New Leads Added

    Similar results can be observed for Deals Closed Won. The median value is 8 (667 contributors), while the top quartile reports 31 deals (also median) closed won in January 2024.

    Deals Closed Won

    And this is just scratching the surface of what we found in the Entrepreneurial Selling (1:1) group. To get more insights like this, you can join it for free and get instant access to all of our data – it only takes a couple of minutes.

    PRO TIP: Do you want to have a comprehensive overview of your sales leads in one place? And stop worrying about compiling data from several reports? You can download our free HubSpot CRM Overview Performance Dashboard and have your first dashboard ready in just a few minutes. Stay on top of all of your most relevant lead data in one view.

    HubSpot CRM Overview Performance Dashboard

    The Biggest Challenges Entrepreneurial Sellers Face When Selling

    We know that entrepreneurial selling comes with its own set of challenges… but which are the biggest ones that companies face?

    When we asked our respondents these questions, we found that for about 40% of them, the most challenging is forecasting deals.

    The Biggest Challenges Entrepreneurial Sellers Face When Selling

    We also wanted to know what challenges are currently in the way of their progress.

    For 60% of the respondents, the main challenge currently hindering their progress towards achieving their goals is Quantity/Quality of leads. Despite participants having the opportunity to select multiple options, this choice stood out as the predominant concern.

    Main challenge currently hindering sellers progress towards achieving their goals

    Now, let’s go through all of these challenges specifically to see what our respondents had to say about them and what they’re doing to address them.

    Getting People to Commit to a Product

    New enterprises often lack the reputation and credibility of their more established counterparts. And without a proven track record of success, it leads to customers being more hesitant to commit to a product.

    But this is just one of the potential underlying issues.

    Many markets are also saturated with similar products, making it difficult for new entrants to stand out.

    When customers have numerous options, convincing them to commit to one particular product and get them to the “AHA” moment can be challenging.

    Michaela Zammuto of FinOptimal is one of our respondents who talked about this challenge.

    “Opportunities stall. People on demos love the product, but getting them to commit has been a challenge. We’ve tried tightening the demo and providing materials for internally socializing the product. We created a mentality of ‘if you don’t have the next meeting booked you’ve lost the deal’.”

    PRO TIP: Want to keep a steady record of what’s happening with your leads in one place? Check out our free HubSpot CRM Deals Performance Dashboard. You can connect all of your most relevant deal metrics and track what’s happening in your pipeline in a glance, instead of manually scrambling through different reports in HubSpot.

    HubSpot CRM Deals Performance Dashboard

    Building Trust with Clients When Competing with Larger Companies

    This is a common challenge as larger companies often have well-established brand recognition and reputations that come with a perceived guarantee of quality.

    This makes it that much harder to compete with them when you’re new in the industry.

    They also have more resources, including financial, human, and technological, allowing them to offer more competitive prices, higher quality products, or services, and better customer support.

    Case studies, testimonials and LinkedIn recommendations are important, but nothing beats having a prospect’s trusted advisor introduce the rep as someone that’s helped others.

    Rick Roberge

    Rick Roberge

    Founder at Sales Rock Stars & RainMakers

    Want to get highlighted in our next report? Become a contributor now

    Eddie Kingsnorth of NoTriangle Studio shares that “as an entrepreneurial seller, the biggest challenge has been building trust with clients when competing with larger, established firms.”

    “To address this, we’ve focused on showcasing our expertise through case studies and client testimonials, demonstrating our ability to deliver outstanding results. Additionally, we emphasize our agility and personalized approach, highlighting that we’re not just another corporate entity.

    Building genuine relationships with clients and consistently exceeding expectations has been key to overcoming this challenge and establishing our reputation as a trusted partner in the highly competitive world of 3D architectural visualization.”

    Knowing When and How to Scale Your Business

    When it comes to scaling, there are several challenges that companies can run into.

    First, you have to properly assess market demand to scale effectively. Scaling too soon or too aggressively without sufficient demand can lead to increased costs without corresponding revenue growth.

    On the other hand, scaling too slowly can lead to missed opportunities and allow your competitors to capture market share.

    The complexity of your operations also increases. Systems, processes, and technologies that work well at a smaller scale may not be adequate for a larger operation.

    That’s why you need to both find and implement the right infrastructure to support your organization’s growth.

    Andrew Meyer of Arbor shared that one of his biggest challenges has been “knowing when to scale and how to scale. We grew fast and it was challenging to keep up with our growth.”

    His solution was “hiring a larger customer service team which allowed us to respond faster to customer inquiries and concerns. This has increased our customer satisfaction immensely.”

    What’s more, the scaling process also gets that much harder if you’re a one-person-shop.

    Kenny Lange of Kenny Lange Coaching says that “being a one-person-shop means that I’m always deciding between activities that generate awareness and relationships, move opportunities through the pipeline, deliver on what I sold, and everything in between.”

    “In my current lifecycle stage, I’m focusing more on how many conversations I’m having daily and simplifying how I measure success on a day-to-day and week-to-week basis in order to make progress instead of just having a bunch of random activities.”

    Building a Pipeline While You’re Also Taking Meetings and Progressing Deals

    Entrepreneurs often wear multiple hats and juggle various responsibilities – from product management to marketing. Selling is just one piece of the daily puzzle. 

    So when you’re prospecting and building a sales pipeline while also attending to current deals, it can quickly stretch your schedule thin.

    My mentor told me “Prospecting is like shaving, you might not want to do it everyday but if you don’t, it doesn’t take long for you to become a bum.” So, as long as you are open to taking new clients, block off a chunk of time every day to reach out to ‘x’ number of people that you have never spoken to before and don’t let anybody schedule over it.

    Rick Roberge

    Rick Roberge

    Founder at Sales Rock Stars & RainMakers

    Want to get highlighted in our next report? Become a contributor now

    James Arnold of HubSpot talked about this and said that “creating enough pipelines whilst also executing meetings and progressing deals to a standard I’m satisfied with is a big challenge.”

    James says he addressed this issue by “shortening by prep and process for prepping for meetings and progressing deals by having more of a repeatable process, freeing up more time for prospecting.”

    Remi Bazille of Mentore also faces a similar issue with organizing his calendar.

    “The biggest challenge as an entrepreneurial seller is organizing my calendar to get enough time to do everything… everything is time-consuming so it’s really important for me to never lose time ever, in a sales process or other tasks.”

    And when talking about building a pipeline, it’s important that we don’t leave out how many calls you have to make as an entrepreneurial seller each day.

    When it comes to making these calls, Mathilde Bonard says that “contacting decision-makers is one of my biggest challenges. Usually, I get intermediates, assistants that filter calls.”

    PRO TIP: Check out our free Pipeline Performance Dashboard if you want to track your pipeline metrics and KPIs in one place and see changes as they occur in real-time. You’ll see how healthy your sales and marketing funnel is, what the key conversion rates between lifecycle stages are, how well your landing pages are performing, and more.

    Finding and Keeping a Steady Customer Base

    With so many markets saturated with competitors, it’s difficult for new companies to gain visibility and attract customers – especially the first batch.

    And even when you do find a customer base, you need to continuously work on retention. This is especially an issue if you’re an independent seller, like Luke Van Der Veer.

    Luke explains that to combat this challenge, he “concentrated on fostering long-lasting connections with my current clients through thoughtful personalization and top-notch support.”

    “Additionally, I’ve made investments in marketing plans that cater to my ideal clientele and use online communities and social media to increase my reach. I strive to consistently evaluate customer input and modify my strategy to deliver value that both retains existing customers and draws in new ones, eventually sustaining and expanding my business.”

    Having an Open Mentality

    Unlike our previous challenges, this one is more internal – but it’s just as important.

    Having an open mentality as an entrepreneurial seller can help you in several ways. For starters, you’ll be able to spot new, potentially lucrative, approaches quicker than your competitors.

    Jonathan Palley of QR Code Generator Hub explains that “an open mentality is one of the major challenges in entrepreneurial selling and is sometimes underestimated.”

    “The mindset is the most important component of the entire entrepreneurial selling strategy. Customers cannot be approached in a predetermined and scripted manner in order to offer them something.

    Entrepreneurs must approach clients with the idea of jointly creating something new in mind. The most crucial thing to keep in mind is that customers are not in the business of buying; rather, they are in the business of profitably providing their clients and consumers with value and superior experiences, and to do that sustainably, they must innovate. I have therefore made it a priority to encourage my clients to innovate, which in turn encourages them to buy from us.”

    Lead Nurturing

    With limited budgets and manpower, it’s not a huge surprise that many entrepreneurial sellers struggle with maintaining a consistent lead nurturing strategy that includes regular content creation, communication, and follow-up.

    James McNally of Self Drive Vehicle Hire says that he’s faced the challenge of lead nurturing plenty of times.

    “It’s a vital aspect of business as it helps customers to make the best purchasing decisions. If one properly proceeds it, one can effortlessly convert prospective customers into loyal customers. For efficient lead nurturing, one has to collect customer engagement data and feedback regularly. It’s a tiresome process.”

    PRO TIP: Does YouTube play a role in your lead nurturing strategy? If so, you’ve probably seen first-hand how unintuitive the main interface can be for reporting and analytics. You can simplify things if you download our free YouTube Channel Performance Dashboard. Track your most relevant YouTube lead nurturing metrics in one place.

    YouTube Channel Performance Dashboard.

    What do 100+ Entrepreneurial Sellers Do to Continually Increase Sales

    When it comes to sales, increasing sales is a top priority for the next 3-6 months for over 70% of respondents.

    But what exactly can you do to increase your sales? Which tactics and strategies can you follow?

    Here’s what the 100+ entrepreneurial sellers we talked to had to say about it:

    Use the GAP Selling Method

    GAP selling is one of the most popular sales methodologies in the industry – it focuses on finding and addressing the gap between your customer’s current state and the desired future state.

    By focusing on the gap between where a customer is now and where they want to be, sales reps can better understand their actual needs and pain points. And if implemented properly, sell more products.

    It also encourages sellers to create better relationships with their customers, instead of only focusing on “closing the sale”.

    But this is just scratching the surface of the methodology – it’s a lot more comprehensive than just a few tips and tricks.

    Mohamad Saab of Growth Automated even decided to hire a sales coach to better understand the method and apply it:

    “I hired a sales coach to help me better understand the gap selling methodology and how to apply it in real life. Discovery calls haven’t been an issue since then though the problem was with companies being serious or not about going a step further and signing. So I can’t really say I increased sales that way but I do believe I just wasn’t lucky with the SQLs I had.”

    Improve Your Tools Based on Audience Feedback

    Are you asking your customers what they would change in your tool? And are you implementing these changes?

    When it comes to building tools, what you want doesn’t matter – your user’s opinion is the only one that matters.

    And if you manage to align your product’s features with what they need – selling the product gets that much easier.

    Alex Ebner of Ace Medical is one of our respondents who uses this strategy.

    “We manufacture new tools that we offer to recurring and new customers. We use feedback and survey answers to decide what our next medical tool should be, and then we share the new developments with the audience that it would appeal most to. I think of it in revolutions.

    We market to a general audience, draw out the specific requests, take feedback from the sales process, and then start over again with a new tool while maintaining rapport with customers purchasing other inventory.”

    Focus on Building Relationships with Clients

    You’re not just closing the sale – you’re opening a relationship.

    If you’re continuously focusing on building relationships with your clients, you’re not only getting more repeat business – you’re also getting a lot more referrals your way.

    This helps you expand your customer base without always relying on direct marketing and sales.

    What’s more, in markets where products and prices are similar, strong customer relationships can be a decisive factor in a customer’s choice.

    Michal Kierul talked about using this method at his company, INTechHouse.

    “To continuously increase sales at INTechHouse, I actively foster strong relationships with our clients, ensuring we understand their needs and provide tailored solutions.

    This approach not only secures repeat business but also encourages client referrals. Quality assurance plays a pivotal role; by delivering high-quality services, we earn client satisfaction and positive word-of-mouth, driving sales growth.”

    Natasha Rei of Explainerd also focuses on “maintaining strong client relationships and exploring upselling opportunities. Furthermore, referral programs and regular follow-ups encourage word-of-mouth recommendations and repeat business.”

    PRO TIP: Want a better way to track your conversations with clients and keep a steady eye on how you’re developing relationships? Download our free Drift Conversations Insights Dashboard to simplify the process. Monitor new contacts, existing contacts, conversations made, and more – all in one comprehensive dashboard.

    Offer a Free Trial

    A free trial lowers the barrier to entry for potential customers and reduces the perceived risk of trying a new product.

    This means it’s great for getting your users to experience the value of your product first-hand and then try and persuade them to stay after the trial ends.

    Max Wesman of GoodHire talked about dealing with rejections as an entrepreneurial seller and how offering a free trial helped him sell more products.

    “As an entrepreneurial seller one of the biggest issues that is faced is requiring to constantly follow up with potential customers and handling the rejection. When you’re an entrepreneurial seller, the rejection is more personal, and putting yourself out there can sometimes be damaging to the company’s image.

    That’s why the first thing I do is offer a free trial service for companies to see for themselves the positive impact and value of our services and how beneficial they will be for them. It’s difficult for a company to say no to a free trial, as they have absolutely nothing to lose. That’s why we let our service do the selling itself, so they can determine its immense value without putting themselves in a tough spot during sales.

    Focus on the Top-of-the-Funnel (TOFU)

    Your TOFU activities are designed to create awareness about your product among a wider audience – this involves targeting people who may not yet be familiar with your brand but have the potential to become customers.

    It’s also the starting point for nurturing leads. By providing valuable content, you can keep potential customers engaged over time and gently guide them through the buyer’s journey.

    This long-term relationship building is crucial, especially in markets where the buying cycle is longer.

    Matthew Sullivan of Akumina, Inc. recommends that you should “open up the TOFU as much as possible.”

    “As actual buying may be 24-36 months out from initial contact, we are trying to get leads in the door with the hopes of nurturing until they have been given a green light for a project.”

    PRO TIP: Are you using Instagram as a part of your TOFU strategy? If you are, here’s an easier way to keep track of your most important metrics – download our free Instagram Business Profile Overview Dashboard. Track everything from followers and post shares to reach and website clicks, all in one place.

    Instagram Business Profile Overview Dashboard.

    Don’t Cut Off Communications with Lost Deals

    Even if a deal doesn’t close, it doesn’t mean you should completely give up on them.

    Maybe it just wasn’t the right moment for them – and if that’s the case, you’ll be glad you kept a relationship with them when they are in the market for your product.

    What’s more, a prospect who wasn’t a good fit for your product might know someone who is.

    As Anna Lopez-Ratouis of Dropcontact puts it, “make sure not to cut off communication with lost deals and know why a deal has been put as a close lost.

    Use Databox to See Where You’re Falling Behind in Your Entrepreneurial Selling Efforts

    It’s true – entrepreneurial selling is harder than ever.

    And even if you implement some of the strategies we’ve discussed in this report, there’s one puzzle piece you shouldn’t go without – data.

    Sure, you might be continuously adding new leads to your pipeline and closing deals… but how do you compare to other entrepreneurial sellers in your niche? Are your numbers up to par with the best of them?

    This won’t be a guessing game once you join our Entrepreneurial Selling (1:1) Benchmark Group. You’ll have instant, real-time insights into how your competitors are performing and see which areas you’re falling behind in.

    And you don’t have to stop at just one group – we have benchmark groups for 50+ most popular tools, ranging from sales and marketing to finance and accounting.

    You can join Benchmark Groups for free and start comparing yourself to competitors in just a few minutes.

    P.S. You’ll also get free access to our Databox Dashboards tool. Here, you can compile all of your most relevant sales insights in one place and get a birds-eye view of your performance. The best thing is, you can set up your first dashboard in literally minutes.

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    Filip Stojanovic

    Filip Stojanovic is a content writer who studies Business and Political Sciences. Also, I am a huge tennis enthusiast. Although my dream is to win a Grand Slam, working as a content writer is also interesting.

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