Sales Habits of Successful Small Business Owners and Entrepreneurs (Based on 180+ Expert Responses)

Author's avatar Sales UPDATED Jul 11, 2024 PUBLISHED Jul 4, 2024 25 minutes read

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    Peter Caputa

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    Small businesses live and die by their sales strategies.

    But what is it that sets highly successful small business owners and entrepreneurs apart in their sales approach? Are there specific habits or strategies they employ that drive their success?

    the nuanced approaches that successful entrepreneurs use can provide a roadmap for others looking to improve their own sales processes.

    To get a comprehensive understanding, we partnered with Unbound Growth to survey 183 successful small business owners and entrepreneurs. We wanted to uncover the habits, strategies, and tools that contribute to their impressive sales performance.

    From leveraging AI technology and automation to mastering the art of personalized customer engagement, the insights we gathered offer a valuable look into what truly works when it comes to small business sales.

    Check out our findings to learn the secrets of these top-performing entrepreneurs and see how you can apply their habits to your own business:

    Who Did We Survey

    For this report, we partnered up with Unbound Growth and surveyed 183 small business owners and entrepreneurs since July 2023 – and the survey is still open.

    The companies we surveyed shared the following employee numbers:

    • 48.72% are companies with 1-10 employees
    • 25% are 10-25 employees
    • 26.28% are 25-50 employees
    small business sales habits - number of employers

    And for most of the companies we surveyed, the approximate annual revenue per employee is under $100,000. 

    small business sales habits - annual revenue per employee

    If you’re a B2B business owner, you can join the exclusive Sales Benchmarks for B2B Business Owners who Sell benchmark group for free. All benchmark data shared within the group is anonymized.

    And if you’re interested in other benchmarks aside from just sales, you can join Benchmark Groups for free and find the groups most relevant to your company and niche. We have insights on everything from sales and marketing to finance and accounting.

    Sales Benchmarks for B2B Business Owners Who Sell

    During our research, we received a ton of valuable insight from our respondents – both direct feedback on certain strategies and through surveys (which we’ll go over below).

    But first one question – what is sales even?

    Almost 70% of the surveyed companies agree that “sales is about collaborating with a prospect to identify whether and how my solutions can address their needs.”

    small business sales habits - sales beliefs

    Now, one of the first things we wanted to know was how much time these entrepreneurs spent on sales, and we found that most of our respondents personally spend between 6 and 20 hours per week on sales activities.

    small business sales habits - time sales activities

    For the majority of our respondents, the biggest chunk of their selling time is spent on marketing activities.

    small business sales habits - percentage of time spent on sales activities

    What about their goals?

    Well, about ⅓ of the respondents agreed that they have personal, business, and sales goals that motivate them. On the other hand, about 22% of the respondents stated that they have defined and written down their personal, business, and sales goals. 

    small business sales habits - managing sales goals

    When it comes to parts of the sales process respondents have documented with a full description of how they execute it, most of them selected:

    • Prospecting to connect with potential buyers (54.2%)
    • Definition of your ideal customer profile (52.67%)
    • Presentation to demonstrate how your solution addresses your prospects’ needs (51.91%)

    Almost 10% haven’t documented any of the processes we listed.

    small business sales habits - selling time

    We also presented several statements to our respondents and asked them to choose which one was the most accurate for their business.

    Most respondents selected this sentence as the most accurate for their business: My clients/customers know they need a product or service like mine and are in the process of choosing one.

    small business sales habits - customers knowledge

    Interestingly, we found that there’s only one activity most of our respondents are very confident doing – discovering a buyer’s needs!

    small business sales habits - confidence graph

    Lastly, we talked about lead generation activities and which ones they’re investing the most money in currently.

    Most of the surveyed companies are currently investing in the following lead-generation activities:

    • SEO (71.76%)
    • Website (67.94%)
    • Social media posting, commenting, direct messaging (61.83%)
    • Email marketing (61.07%)
    small business sales habits - lead generation activities

    We also pulled up a few interesting sales insights from our benchmark groups for you to check out.

    According to data provided by Benchmark Group Sales Benchmarks for B2B Business Owners who Sell (the group is for companies with 1-10 employees), there were 51 leads on April 24 (median, 279 contributors). However, top performers had 299 new leads in the same period (also median).

    small business sales habits - sales benchmarks new leads

    According to the same group, there were 19 deals created on April 24 (median value, 134 contributors). The top performers had 101 deals created in the same period (also median).

    small business sales habits - sales benchmarks deals created

    Want more sales benchmarks like these to compare your performance with? Then make sure you join our exclusive Sales Benchmarks for B2B Business Owners who Sell benchmark group for free.

    5 Go-To Sales Habits for Closing Deals

    OK – so we’ve covered some of the most important survey findings and sales benchmarks from our survey.

    Now, it’s time we talk about the specific sales habits our respondents use to close deals successfully.

    Reaching Out to Prospects Directly on LinkedIn

    LinkedIn provides direct access to key decision-makers across various industries.

    By reaching out directly, sales professionals can bypass the “gatekeepers” and connect with those who have the authority to make purchasing decisions.

    This direct line to decision-makers significantly shortens the sales cycle and increases your chances of closing deals.

    Farhan Siraj of OSHA Outreach Courses says that he’s experienced “a great degree of success by approaching prospects through LinkedIn messages”

    “I reach out to fellow business owners or managers who may need our online courses. Even if I don’t secure an immediate sale, I focus on building a connection and sharing some free resources with them, such as study guides. In many instances, I receive word from them after a few months, expressing their interest in signing up for my platform.

    Offering Free Consultation Calls to New Prospects

    Free consultation calls provide an opportunity to demonstrate your expertise and show the prospect that you really do understand their needs. This way, you’re building trust and establishing credibility which is essential in getting them to convert.

    What’s more, you get a personal interaction, which is often more impactful than using email or some other form of digital communication.

    Alex Williams of The HubSpot Expert shares his approach:

    “I offer a free 30-minute consultation to all new prospects, during which we explore their challenges and how my services can help address them. I also use these sessions to offer any advice that might be immediately beneficial to them, even if it doesn’t result in a sale. I’ve found that even if a prospect doesn’t choose to work with me at that moment in time, they come back to me later because they know I’ll offer them value.”

    Alex Williams

    Alex Williams

    Founder at The HubSpot Expert

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

    Building a Presence on LinkedIn

    A well-crafted LinkedIn profile, coupled with regular content sharing, is one of the best ways to establish yourself as an authority in your field.

    You can share industry insights and thought leadership articles, and engage with relevant content you’re your connections to demonstrate your expertise. This makes prospects more likely to trust your recommendations and consider your offers.

    Chris Lloyd of Chris Lloyd Marketing is one of our respondents who talked about this strategy:

    “LinkedIn – generated content marketing opportunities and leads in less than 2 weeks of building my presence. I comment on others’ posts 3x a day and post 3x a week. Other people’s posts need to have been posted within the last 24 hours, had a lot of engagement and the author responds to comments.”

    PRO TIP: Are you active on your LinkedIn’s company page? If so, you can download our free LinkedIn Company Page Engagement Dashboard to track all of your most relevant engagement metrics in one place. You’ll have everything from clicks and comments to impressions and followers on one simple dashboard.

    small business sales habits - LinkedIn Company Page Engagement Dashboard

    Data-Driven Insights Combined with Personalized Client Engagement

    Data-driven insights help you gain a deeper understanding of your clients’ behaviors, preferences, and pain points.

    You can analyze this data from various sources – such as CRM systems, social media, and website analytics, to identify patterns and trends that reveal what your clients truly need.

    And when you combine data-driven insights with personalized engagement, you can create highly relevant interactions that resonate with your clients. Personalization can range from addressing clients by their names to offering customized solutions based on their past interactions and preferences.

    Here’s what Dominik Maka of TOP10 Agency had to say about this sales strategy:

    “One part of our sales and marketing process that has proven exceptionally effective is our data-driven approach combined with personalized client engagement. Given my extensive background in SEO/SEM, I’ve always believed in the power of data to guide decisions. We utilize advanced analytics to identify potential leads and segment our audience based on their specific needs and preferences. Once we have this information, we tailor our pitches and marketing materials to resonate with each segment. This personalized approach has not only improved our conversion rates but has also fostered trust and loyalty among our clients. A testament to its effectiveness is the consistent 300% average ROI we’ve been able to deliver, especially for our client campaigns.”

    For personalized engagement, another tactic you can use is personalized email outreach.

    This is what helped Simon Brisk of Click Intelligence increase response rates:

    “One part of my sales and marketing process that works well is personalized email outreach. By crafting highly tailored and relevant emails to potential clients, I’ve achieved a significant increase in response rates. This approach involves thorough research on each prospect’s needs and pain points.

    This enables me to create compelling messages. As a result, my email campaigns have consistently outperformed industry averages. It has an average open rate of 40% and a conversion rate of 15%. This personalized outreach has boosted sales. It has also fostered stronger client relationships.”

    Carole Mahoney of Unbound Growth emphasizes the importance of researching buyers to enhance personalized interactions:

    “Research, research , research! Don’t assume you know everything there is to know about your buyers. Research their LinkedIn profile for their educational background to get a sense of how they think. Look at the recommendations they have given for others, what traits and characteristics do they value in those that they work with? What articles, posts, and interviews have they given, where do you have something in common, or something that intrigues you? Check the LinkedIn Insights on their company, what jobs are they posting? Which departments in the company have seen attrition or growth? What new hires have come on board?”

    Carole Mahoney

    Carole Mahoney

    Founder at Unbound Growth

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

    Create Niche Webinars for Your Industry

    With niche webinars, you attract a highly targeted audience interested in specific topics relevant to your industry. This way, you draw in prospects who are genuinely interested and invested in the subject matter, which leads to more high-quality leads.

    Niche webinars also allow you to highlight your unique value propositions in a more detailed and focused manner.

    Declan Flaherty of Soone Agency says that deep-dive niche webinars tailored for the tech sector are one of their “standout sales components”:

    “One standout component of our sales and marketing process at Soone Agency is our deep-dive niche webinars tailored for the tech sector. We host monthly webinars discussing real-time challenges and innovations in tech marketing. This approach not only positions us as thought leaders but also captures high-quality leads genuinely interested in our expertise. As a result, we’ve seen a 25% increase in client onboarding from these webinars alone, with clients citing our niche expertise as a major deciding factor.”

    Key Tactics to Implement for Scaling Small Business Sales

    OK – so we’ve covered some of the main sales habits these successful small business owners and entrepreneurs have in common.

    But what’s their plan going forward?

    Below, you’ll find the key tactics our respondents are using to scale their small business sales:

    Using AI Technology for Better Insights and Analytics

    AI technology is helping businesses gain a deeper understanding of their customers by analyzing vast amounts of data faster than ever before.

    Through machine learning algorithms, AI can identify patterns and trends in customer behavior, preferences, and buying habits. This allows you to tailor your marketing strategies and sales pitches to better meet your customers’ needs.

    Predictive analytics is especially popular since AI can forecast sales with higher accuracy through historical sales data and market trends.

    Jason Tebeau of Da Vinci Medical is one of our respondents who “intends to launch an AI-driven predictive analytics tool to anticipate client needs within the next six months.”

    “We will provide personalized product recommendations by analyzing historical data and client behaviors. This proactive approach is consistent with our commitment to innovation and customer focus. Upsells and cross-sells are expected to increase by 15%, resulting in stronger client relationships. This tool not only complements our Superhuman Protocol® offerings, but it also places Da Vinci Medical at the forefront of anticipatory and tailored solutions in the wellness technology sector.”

    Karl Robinson of Logicata also mentioned using AI to obtain better insights and expand sales.

    “Leveraging AI-driven insights is our go-to tactic. Our next six months are laser-focused on utilizing AI-driven insights to expand our sales. We’re looking to implement advanced AI tools that can assist in analyzing current and potential clients’ needs, pain points, and industry trends. This will allow us to craft highly targeted marketing campaigns, and personalized offers and more effectively anticipate the needs of our audience. We’ve chosen this approach due to the immense potential AI holds in dissecting and understanding large sets of data, which can provide invaluable insights for refining our sales and marketing strategies.”

    Using AI Technology to Create Marketing and Sales Content

    Even though they still might not be up to par with the “human touch”, AI-powered tools can generate quality content quicker than ever before.

    You can automate the content creation process and use AI to produce a large volume of marketing materials, such as blog posts, social media updates, email campaigns, and product descriptions, in a fraction of the time it would usually take.

    Jason Toy of 88stacks shared his plans for leveraging generative AI to craft personalized marketing content in the upcoming period:

    “In the upcoming six months, I’m strategically harnessing advanced technologies, specifically generative AI to amplify our sales growth. By employing generative AI algorithms, we’re set to craft personalized marketing content and tailor product recommendations. This aims to elevate customer engagement and drive conversions, ultimately leading to a projected 15% increase in sales over the next six months. I’ve chosen this path due to the proven effectiveness of generative AI in enhancing customer interactions and sales performance. I’m anticipating stronger customer loyalty, solidifying our brand’s position in the market through generative AI.”

    Stephen Beach of Craft Impact also talked about “using AI to help us execute our content marketing plan at a larger scale than we ever could have done before.”

    LinkedIn personal content creation and engaging on other LinkedIn creators’ posts… a la Pete Caputa who does this really well! Launch a new website with revised niche messaging Use AI to help execute our content marketing plan at a larger scale than we ever could have before We’re already seeing good results with a deeper, more qualified pipeline than we’ve had in the last 10 years of doing business.

    PRO TIP: Google Analytics 4 is an indispensable tool for gauging your content marketing efforts – but it’s not exactly the most intuitive. If you want all of your key Google Analytics 4 insights without the hassle of scraping them from the main interface, you can download our free Google Analytics 4 Website Traffic Dashboard.

    small business sales habits - Google Analytics 4 Website Traffic Dashboard.

    Build a Referral Program

    Are you using referrals from your existing customers to grow your base?

    Referral programs can significantly reduce customer acquisition costs. Especially today, when traditional advertising is getting increasingly expensive and time-consuming.

    What’s more, referred customers are more likely to convert into paying customers. Recommendations from friends, family, or colleagues carry a higher level of trust than generic marketing messages, and this trust translates into higher conversion rates.

    Andre Oentoro of BreadnBeyond says that “in the next six months, we’re launching a referral program to boost sales at my explainer video company. This approach involves incentivizing existing clients to refer new business, leveraging trust and credibility. Anticipated benefits include expanded leads, higher conversions, and deeper client engagement, fostering organic growth and stronger relationships.”

    Michael Chien of 101Karaoke plans to do the same:

    “I am planning to implement a targeted referral program to further boost our sales. I believe that word-of-mouth recommendations from satisfied customers hold immense potential for driving new business. To execute this strategy, I will initiate a structured referral program that rewards both existing customers and their referred contacts. First, I will create an enticing incentive structure, offering exclusive discounts, free upgrades, or other valuable rewards to customers who refer friends or colleagues to our services. I will promote this program through various channels, including email campaigns, social media posts, and our website.

    Additionally, I’ll provide customers with easily shareable referral links and personalized discount codes to track referrals accurately. I chose this approach because referrals often come from a place of trust, and potential clients are more likely to engage with our services when they receive a recommendation from someone they know. I anticipate a noticeable increase in leads and conversions, ultimately contributing to substantial sales growth over the next six months.”

    Leveraging Newsletters and Email Marketing

    Newsletters and email marketing provide you with a direct line of communication with your customers.

    Unlike social media posts, PPC ads, or advertisements that might get lost in a crowded feed, emails land directly in the inbox of your audience. This makes it a highly effective way to stay connected with your customers.

    Furthermore, regular newsletters help in building and nurturing relationships with your audience. By consistently providing valuable content, updates, and offers, you keep your brand top-of-mind and create a sense of loyalty among your subscribers.

    Kyle Vamvouris of Vouris shared his newsletter sponsorship strategy for scaling small businesses:

    “One strategy I plan to implement in the next six months is sponsoring more newsletters. We recently ran a test campaign where we sponsored a large newsletter, and the results were promising. We had a 1% click-through rate, which may not sound like much, but the newsletter has a large audience. Of those who clicked, 35% filled out the form, and 3% booked a meeting with us after watching a video we sent them. This ended up being a profitable campaign for us. So, my plan for the next six months is to identify a handful of newsletters that are a good fit for our target audience and sponsor them regularly. I expect that this will get us in front of a larger audience and drive sales.”

    We also talked to Calan Breckon of Calan Breckon SEO about his plan to grow an email list:

    “I’m currently focused on growing my email list. Email lists still have almost a 40% higher ROI than any other marketing options today. Through growing my email list I’ll work to push listens to the podcast as well as some affiliate products. I also have an online course for new entrepreneurs teaching them the fundamentals which I include in my weekly emails once and a while to help drive sales.”

    PRO TIP: Is Klaviyo your go-to email marketing tool? If so, you might’ve noticed how complex it can be sometimes to collect and compile all your most relevant email data. That’s why we recommend checking out our free Klaviyo Email Performance Dashboard where you can monitor all of your key metrics like open rates, email CTR, received emails, and more – all in one place.

    small business sales habits - Klaviyo Email Performance Dashboard

    Creating an Online Community for Your Brand

    An online community provides a platform for customers to interact with your brand and with each other. When customers feel connected to a community, they are more likely to engage with your content, participate in discussions, and become advocates for your brand.

    Also, an online community serves as a valuable source of customer feedback. You can observe discussions within the community to get a deeper understanding of your customers’ needs, preferences, and pain points.

    Emily Onkey of Aplós says that building an online community is “especially important with the customer acquisition costs soaring each year.”

    “The number of businesses heading online has continued to climb since the pandemic. And more entrants into the eCommerce space mean more competition for ad space, driving the cost of advertising skyward. The 60% increase in CAC over the last 5 years correlates to so many DTC brands relying heavily on Facebook’s robust databank to help them reach their target audience. People want to feel a part of something. But your brand’s ‘why’ alone won’t sustain a community. So we’ll focus on strengthening emotional resonance by encouraging our audience members to share their own stories about rethinking their drinking habits. Making your community less about your brand and more about your customers shows how much you value them. It also inspires greater engagement, repeat purchases, and long-term loyalty.”

    Investing More in PPC Advertising

    PPC advertising gives you immediate results. Unlike organic search efforts that take time to build, PPC ads can place your business at the top of search engine results pages or across various digital platforms instantly.

    This is especially important for smaller businesses that want to drive quick traffic and sales for newer products or time-sensitive promos. 

    And the best part is, you can track every aspect of your campaign, from impressions and clicks to conversions and revenue. This allows you to analyze the performance of your ads in real-time, make data-driven decisions, and continuously optimize your campaigns for better results.

    Andrew Dunn of Zentro Internet shared his plan to invest more in PPC in 2024:

    “I plan on increasing my investment in PPC. I believe PPC can get even more leads. So for the next six months, I will boost my PPC efforts and target a 200% increase in lead generation.”

    PRO TIP: Are you planning to increase your PPC investments on Facebook? You can download our free Facebook Ads Campaign Performance Dashboard for a better way to keep track of your most important metrics, like ad spent, clicks, impressions, CTR, and similar ones.

    small business sales habits - Facebook Ads Campaign Performance Dashboard

    Focusing More on Existing Clients to Increase Retention

    It’s no secret that acquiring new customers is more expensive than retaining existing ones.

    Retaining existing customers and consistently overdelivering is cost-effective, as it leverages the established relationship and trust you’ve already built. This also translates into a higher return on investment for your marketing and sales efforts.

    What’s more, these clients are more likely to make repeat purchases, upgrade to premium offerings, and explore additional products or services.

    So, while it’s important to focus on getting new business, don’t overlook the lifetime value of your current customers.

    Lyndsey Maddox of Digital Third Coast follows this principle:

    “Our focus is on clients that we can make a measurable difference for. We are having thorough discovery conversations and conducting research and competitive analysis in order to ensure our solutions will be effective and efficient for them. While new business will always be part of our growth, our focus is on getting the right clients on board who will stay with us for years. Our vision is that every client can be a case study.”

    Lyndsey Maddox

    Lyndsey Maddox

    CEO at Digital Third Coast

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

    Changing Your Team Structure and Bringing More Help

    Restructuring your team allows for more specialization because you can define roles more clearly and ensure that each team member is operating in their area of expertise.

    And if your budget can support it, it’s always a good idea to bring in additional help so you can distribute workloads more evenly and prevent burnout in your team.

    With a larger, well-structured team, you can also provide more personalized service to your clients.

    John Reinesch of Asset Growth is one of the respondents who plan on building out his team more:

    “We are building out the team more so I have some support. We are bringing on a prospector and an SDR and then I will be focusing on just the sales calls and closing. We are also creating quarterly plans and reporting that we review each week and then make adjustments in real-time throughout the quarter. We used to be more reactive at the end of the quarter and now we are creating processes to make sure we can adjust at a faster rate so we achieve our goals.”

    Nathan Bliss of Kinsta talked about restructuring to a different function type:

    “We are changing our structure from being based on position type (SDRs and AE’s) to function type (inbound and outbound). We are following OKR methodology to execute a plan against this transition, all driving towards an end goal of growing revenue and increasing our growth rate.”
    Nathan Bliss, Kinsta,

    As for Ben Donahower of No Bounds Digital, he plans to “get an SDR agency to focus on our more productized services.”

    Stay on Top of Your Sales Strategies and KPIs with Databox  

    When it comes to scaling small businesses, having a firm grasp on what drives success can make all the difference.

    And from our extensive research based on the insights of over 180 experts, it’s clear that the most successful small business owners and entrepreneurs share certain habits that set them apart.

    Some of these things include personalizing your sales and marketing efforts, using artificial intelligence for more granular insights, producing content at scale, and doubling down on channels like email marketing and social media.

    But how can you make sure your approach is on par with these high achievers?

    Well, this is where Databox comes in.

    With Databox’s Benchmark Groups, you can instantly access real-time insights into how your business measures up against the best in your industry. Whether it’s sales performance, marketing effectiveness, or operational efficiency, you’ll have the data you need to identify gaps and opportunities for growth.

    And the benefits don’t stop there. You also get Databox Dashboards which allow you to visualize your most critical metrics in one place, making it easier than ever to track your progress and adjust your strategies accordingly.

    Join a Benchmark Group today to see how you compare, and start using these powerful tools to drive your business forward. The path to success is clearer with the right data at your fingertips.

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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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