15 Expert Tactics for Engaging Hard-to-Reach Prospects in B2B

In business-to-business (B2B) industries, hard-to-reach prospects are some of the most valuable leads you can contact. You might work in a high-value niche where clients are hard to find because there just aren’t many. Or, maybe you target C-level executives who have a lot of spending power but not so much time.

At Databox, we’re currently partnering with SpotOn Agency to learn how B2B companies connect with hard-to-reach prospects. While SpotOn specializes in healthcare, we’re trying to identify best practices for B2B companies in any industry. We’ve collected insights from 72 companies so far. (And, by the way, you can still become part of our next report by taking part in our survey.)

Even partway through this research, we have plenty of tips from experts who handle hard-to-reach prospects. So, we thought we’d share some of these insights to tide you over until we release the full report. The sales and marketing experts who took part in our current survey data had these tips for reaching, engaging, and closing hard-to-reach prospects:

1. Create Personalized, High-Quality SEO Content
2. Research Your Prospects In-Depth
3. Offer a Personalized Sales Experience
4. Build Relationships With Your Prospects
5. Use a Casual Tone in Your Outreach
6. Guide Your Sales Process With Customer Profiles
7. Check Out Your Prospect’s Online Profiles
8. Run Targeted Ad Campaigns
9. Perform Thoughtful Cold Outreach
10. Solve Your Prospect’s Problem
11. Count on the Right Tool Stack
12. Send Tailored Emails
13. Network In-Person
14. Start With a Solid Multi-Channel Marketing Strategy
15. Offer Branded Gifts

1. Create Personalized, High-Quality SEO Content

According to our preliminary survey data, search engine optimization (SEO) is the top tactic for reaching, engaging, and closing hard-to-reach prospects for B2B businesses.

One of the most popular ways to use SEO as a channel is to create and execute a content marketing strategy. You can put your content to work in your sales strategy by creating content that meets your prospects’ needs, as two executives shared with us.

At Userpilot, Emilia Korczynska develops personalized content to build audience trust. Korczynska says, “One strategy that’s been particularly successful for me at Userpilot in reaching hard-to-reach prospects is to create highly personalized content. This wasn’t easy, but it began with a deep dive into understanding our prospects, their pain points, desires, and the industry landscape they operate in. We conducted market research, customer interviews, and mined existing customer data to really get a grasp on what makes our prospects tick.”

Korczynska continues, “Then, we took this understanding and translated it into content – be it educational blog posts, case studies, or webinars. The key was ensuring this content spoke directly to their needs, showed an understanding of their industry, and demonstrated how our product could solve their challenges.”

Some companies, like Olive & Company, start by developing an in-depth content strategy and find that it serves them well in their sales endeavors. Erik Norsted explains how content aids in the sales process:

Note that Olive & Company’s content strategy now includes topics mentioned in interactions with prospects. Content and sales can work together to better serve your prospects, giving them a better chance of becoming customers.

2. Research Your Prospects In-Depth

Successful engagement with your prospects requires you to know your prospects in the first place. Your prospects’ pain points and preferences will teach you what aspects of your product to emphasize in your sales outreach.

The SponsorCloud team performs individualized research on each prospect to tailor their sales process. According to Ameet Mehta, “One thing that has significantly helped us effectively reach, engage, and close hard-to-reach prospects is our relentless focus on understanding their pain points, offering proof-of-concept and value demonstrations based on that, and building genuine relationships with them. We recognize that hard-to-reach prospects may have unique challenges and concerns that prevent them from readily engaging with sales pitches. Therefore, we invest time and effort into conducting thorough research on each prospect before initiating any outreach. This research helps us gain insights into their industry, specific pain points, business objectives, and even their past interactions with similar solutions.”

Evergreen PR’s Leigh Greenwood takes a similar approach. “If a prospect is hard to reach, it’s likely that you haven’t yet identified the most effective route to engaging them yet. In the healthcare space that we target, right now demand is high and capacity is low, making it harder to cut through the noise. However, in these challenging times, people will turn to experts that they believe can help them with their biggest and most stubborn challenges. The key is to really understand your audience, what action you need them to take, and what their barriers and drivers are – as well as who might influence or block them on their journey to your particular outcome,” Greenwood says. So, Evergreen PR uses a framework called MERTO to coach clients into offering personalized content and sales themselves.

3. Offer a Personalized Sales Experience

After you put so much work into researching your prospects, make the most out of that knowledge by providing a personalized sales process to your prospects. Among the experts who shared their experiences with us, personalized sales tactics were one of the most popular.

“Personalized outreach is a tactic that has been successful in attracting, holding the attention of, and closing hard-to-reach prospects. I can adjust my approach and messaging to more deeply connect with the prospects by taking the time to learn about and comprehend their unique requirements, issues, and interests,” says Melissa Caverly of Imagine Maids. “This entails creating tailored emails, texts, or pitches that express your understanding of their problems and provide original solutions. Utilizing social media platforms and business networks also enables me to interact with prospects in a more casual and personable way, fostering connections and trust over time. I can successfully overcome obstacles and build deep connections that result in successful closures by exhibiting a sincere grasp of their position and offering insightful advice.”

“We invest time and effort in researching and understanding our prospects’ pain points and challenges, allowing us to craft tailored and compelling messages that resonate with their specific needs. By demonstrating a genuine understanding of their unique circumstances and offering customized solutions, we have been able to establish trust, engage effectively, and successfully close deals with these challenging prospects,” Click Intelligence’s Simon Brisk says.

GR0’s Jonathan Zacharias suggests a community-focused approach that starts from the bottom up: “To connect with hard-to-reach prospective customers, a personalized approach is needed. Instead of mass marketing, targeted ads and social media outreach can be effective. In 2023, people are overwhelmed with impersonal ads and crave personal connections. By using personalized messaging and outreach, businesses can stand out and build meaningful relationships with their target audience. This approach takes more time and effort, but it can pay off with loyal customers who feel seen and heard. Creating a community around your brand can be a powerful way to connect with hard-to-reach prospects.”

Personalized sales outreach gives you a chance to get creative. VEM Group’s David Reid has a story involving an out-of-the-box tactic. “As a sales director, I understand the challenges of reaching, engaging, and closing hard-to-reach prospects. One strategy that has helped me effectively connect with such opportunities is personalized outreach. I recall a specific instance when I had been trying to reach a key decision-maker in a large organization for weeks, but my emails and calls went unanswered. Realizing that a personalized approach might be more effective, I researched the prospect’s background and interests. During my research, I discovered that the decision-maker was actively involved in a local charity.”

Reid acted on this knowledge. “Inspired by this information, I donated to the charity and sent a personalized email congratulating them on their involvement and expressing my support for the cause. To my surprise, I received a response within hours. This small act of personalization helped break the ice and led to a productive conversation, eventually leading to a successful deal closure,” Reid says.

Some companies go so far as to develop an account-based marketing (ABM) program. ABM involves creating personalized campaigns for prospects that could be a good match for your company.

“One thing that has helped us effectively reach, engage, and close hard-to-reach prospects is implementing account-based marketing (ABM),” says Derrick Hathaway of VEM Medical. With ABM, we identify high-value, hard-to-reach prospects and create personalized marketing campaigns tailored to their specific needs and pain points.

Hathaway continues, “We leverage multiple channels, including personalized emails, targeted social media ads, and custom content, to capture their attention. Additionally, our sales team takes a highly personalized approach in their outreach, focusing on building relationships and understanding the prospect’s unique challenges. By providing valuable insights and solutions tailored to their business, we have been able to break through barriers, gain trust, and successfully close deals with previously elusive prospects.”

At Recommended Home Buyers, Ben Gold also relies on ABM as a sales strategy. Gold says, “One strategy that has been highly effective in reaching, engaging, and closing hard-to-reach prospects is implementing an account-based marketing (ABM) approach. By identifying specific high-value target accounts and tailoring personalized marketing campaigns for each account, we have been able to break through the barriers and connect with key decision-makers.”

Here’s how the ABM process works at this company: “With ABM, we conduct extensive research to understand the challenges and pain points of the target companies. Then, we create compelling content and messaging that resonates with their specific needs. Personalized emails and direct outreach are utilized to establish genuine connections with the prospects. Furthermore, our sales and marketing teams collaborate closely to provide a seamless experience throughout the buyer’s journey. By aligning our efforts, we can deliver consistent messaging and targeted content at each stage, which has led to increased engagement and higher conversion rates from hard-to-reach prospects.”

Related: SMART Sales Goal Examples from 30+ Sales Professionals

4. Build Relationships With Your Prospects

During the sales process, you likely notice that most prospects aren’t a “one-and-done” deal. It can take multiple follow-ups for them to decide if they want your product or service. Rather than a hard push for conversion, most prospects need support as they consider what you offer. You can more effectively serve this role by viewing the process as building a relationship.

Resolute Technology Solutions’ Colton DeVos checks in with prospects throughout the sales process. “It can be very difficult to engage hard-to-reach prospects. They are typically hard to reach intentionally whether it is because they don’t like engaging in sales conversations, they receive too many inquests, or they simply have too many things on the go and no time to respond – let alone look into your pitch. It’s also important to understand your buyer’s journey – what stages do they have to go through to learn about a product or service, compare it against other options, and come to a final decision on what direction they will go,” DeVos says of the barriers that hinder the sales process.

DeVos proposes these solutions: “To effectively work through these hurdles, leverage a number of tools to connect and stay in touch with prospects as they work through their decision-making process. Find out what communication channel works best for each individual prospect (phone, email, LinkedIn, etc.). Set a cadence of follow-ups and check-ins through your CRM or personal organization tool so you stay in touch but don’t spam the people you are trying to connect with. More than all the above – make your offer clear, concise, and targeted to your prospect. They should see the value in what you are offering even if they don’t have the time or budget to engage with it. Keep notes on their account as to what aspects of your pitch the prospect has been most interested in. If any news or developments arise surrounding those topic areas, you can use that as an ice breaker to get a conversation going at a later date.”

Nate Nead of Marketer.co comes from a human perspective. “A strategy that has proven highly effective for me is cultivating strong relationships with my potential prospects. That means spending a ton of time really getting what they’re all about – what kind of challenges they’re facing, what their goals are, you name it. Then I show them how my product or service can make all those issues disappear!” Nead says.

Nead continues, “Once you take this personal approach, potential prospects tend to be way more excited about hearing from you! They become more inclined to engage with my outreach initiatives, such as reading my emails, paying heed to my calls, and investing their time in understanding the benefits of the products or services I provide. So by treating potential prospects like actual humans instead of cash sources, we get better results all around in terms of connecting with each other and seeing success.”

Avinash Chandra of BrandLoom Consulting takes a relationship-first approach to sales: “Based on my experience, I have always encouraged my team to form a strong relationship with the prospects, which helps them to close hard-to-reach prospects. The main goal is to understand our prospects and develop a solution that meets their expectations and requirements. Moreover, we always try our best to provide the best services so that we can build trust with our clients.”

At Custom Neon, Clare Jones keeps up with industry news to build meaningful relationships with prospects. “One strategy I use is keeping abreast of industry news, award ceremonies, tenders won, etc. Reaching out to cold contacts, congratulating them on their accolades, or pitching when you know tenders have been won, is just putting yourself in the right place at the right time. People are inundated, so tell them something they want to hear or something that is of use to them. Just being super personalized, authentic, and genuinely happy about someone’s successes, differentiates from the rest of unsolicited emails hitting their inbox and definitely equates to higher response rates,” Jones says.

Lydia Sugarman from Venntive has simple advice to share about what the company did to succeed in engaging hard-to-reach prospects:

5. Use a Casual Tone in Your Outreach

The tone you use in your sales outreach matters in your chance of persuading prospects. The rise of AI-generated sales outreach makes this principle more important than ever.

According to Victoria Yu’s experience with handling sales for Making That Sale, “A trend we’ve noticed in the past few months is that leads are less likely to engage with materials and pitches that seem AI-generated. Instead, they’re more drawn to things like personal anecdotes and opinions, and more casual, conversational tones. As such, we’re focusing on developing that sort of tone in all our communications, rather than trying to be strictly ‘business formal.’”

6. Guide Your Sales Process With Customer Profiles

So far, we’ve focused on tactics that take time and effort. It’s a lot of work to meticulously personalize every bit of sales outreach you perform. Customer profiles give you a starting point so you already know some facts about your prospect and can have customizable templates on hand to try the personalized tactics you’ve learned about.

The SwagMagic team deals with multiple people within a company, making it critical to reference customer profiles. Jas Banwait Gill explains, “We have been working on narrowing down our ideal customer profile to create a robust message map. As a B2B company, we must reach out to multiple individuals within a company’s buying center rather than just one stakeholder who determines whether the company will purchase your product or service. This group consists of individuals who are first introduced to your product, those who will utilize it, the purchasers, decision-makers, and administrators.”

Gill continues, “Each of these personas may have distinct pain points and priorities that you can target with contextualized content. For example, a Buyer will be more interested in downloading a cost analysis report, while a User will be more likely to click through to a how-to guide. The more targeted your content is, the higher the engagement for that segment of customers.”

Customer profiles can also serve you well when you work with multiple industries, as Sumeet Anand discovered at Marveta. Anand says, “I operate a B2B marketing agency that serves various industries, each with its own Ideal Customer Profile (ICP). When working with small and medium-sized businesses (SMBs), we follow a specific set of steps: Once we receive the specifications and ICP from the client, our Data Analyst extracts relevant data using various tools that align with the client’s ICP. This data is then utilized to run targeted email marketing campaigns while tracking open rates. Our telemarketing team reaches out to prospects to confirm their presence in the company. If confirmed, we proceed to send additional engaging content such as eBooks or whitepapers to build brand awareness. Following this, our appointment-setting telecallers contact these prospects using a script designed to generate appointments. In summary, if your company falls under the SMB category and lacks sufficient marketing awareness, we can help create brand awareness by syndicating your content through email marketing. This approach maximizes the potential for successful closures when we secure appointments with your target clients.”

7. Check Out Your Prospect’s Online Profiles

When you perform personalized sales outreach, you may have more information on your prospect available than you think. With personal branding becoming a must for many leaders, many prospects already share valuable information about their business values in their profiles.

Here’s how Ninja Transfers’ Tom Golubovich puts it: “Take the time to do a deep dive into their online presence to learn more personal details about them. Doing this helps you send more compelling outreach that’s tailored to their interests. It’s particularly helpful for cold outreach and can be a good nudge for a warm lead too. Taking the time to make the outreach truly personal shows the prospect that you are invested in building a relationship and are willing to go the extra mile, which helps paint your company in a good light and make a good impression.”

At Alta Technologies, Corey Donovan turns to LinkedIn for insights. “When trying to connect with a hard-to-reach prospect, it can be helpful to explore their LinkedIn activity. A prospect’s LinkedIn profile can give you insight into their preferences, which can help you make a more targeted and effective connection. Before reaching out to a prospect, spend some time on their LinkedIn profile to learn more about them and also to browse their posting and sharing activity. This gives you valuable insights into the kind of content they are interested in and the topics they engage with the most and can help you better personalize your outreach,” Donovan says.

8. Run Targeted Ad Campaigns

To get prospects in your sales pipeline in the first place, you need to bring them in with compelling marketing. Ads allow you to choose exactly who sees your marketing, helping you reach specific groups of prospects.

Balance’s Daniel Osman explains what makes this an effective tactic: “One way to connect with hard-to-reach prospective customers is through targeted online advertising. By leveraging data and analytics, ad campaigns can be tailored to specific demographics, interests, and behaviors, ensuring that your message reaches the right people at the right time. Plus, you can actually learn more about your target base in the process.”

If you already use Google Ads for this purpose but don’t see the results you want, check out our list of Google Ads industry benchmarks. You’ll see how other companies perform on average to find areas of your advertising that could use improvement.

9. Perform Thoughtful Cold Outreach

While sales practices have less of a focus on cold outreach than they did in the past, cold messages still have a role to play. But, you’ll need to consider the needs of today’s prospects as you send them out.

Ditto Transcripts’ Ben Walker gets a lot of value out of old-fashioned cold calls (yes, over the phone.) Here’s how:

At Reporter Outreach, Brandon Schroth performs cold outreach through social media. Schroth says, “I present an elevator pitch through social media channels. I take the time to craft a short, concise message that clearly outlines my expertise and what I have to offer prospective customers. Then, I invite potential clients to book a consultation with me where I can better outline our services, address any concerns they may have, and demonstrate my knowledge and expertise in a way that makes them feel comfortable making an investment. It is important to approach these people with their needs, interests, and challenges in mind, so they feel as though you understand their unique needs and can provide the solutions they’re looking for.”

ReloadUX’s Ali Husnain uses a similar tactic with LinkedIn specifically. “In a recent scenario, I implemented personalized direct outreach through LinkedIn messages. By researching and understanding the prospects’ pain points, I crafted tailored messages that demonstrated how our product could solve their specific challenges. This approach helped me grab their attention, initiate meaningful conversations, and ultimately close deals with previously hard-to-reach prospects,” Husnain says.

Whatever platform you use, implement a sales call reporting system to track what tactics work. Our guide to this process focuses on phone calls, but you can adapt it to any type of communication.

10. Solve Your Prospect’s Problem

Your goal is to meet your prospect’s needs with your product or service. Why not give them a taste of that experience by doing some of the work in advance?

The FirstPrinciples Growth team provides a complementary solution by performing basic keyword research. “From our experience, when it comes to hard-to-reach high-ticket prospects, personalized marketing that reflects that you’ve done extensive research about their company usually works the best,” says manager Pushkar Sinha. “That includes writing hyper-personalized sales emails — while selling our SEO services, we search for keywords they can rank for and get more organic traffic and subsequently more MQLs. We mention those keywords in our first sales email to make the outreach more personalized.”

The SEO professionals at RegexSEO research each prospect’s needs in advance to demonstrate how they can solve their problems. According to owner Dmitrii Kustov, “Prior to meeting with a prospect, we conduct a thorough analysis of their business and market position. We request a list of previous marketing agency engagements and carefully evaluate the outcomes they achieved. Additionally, we assess the performance of their existing marketing channels. This comprehensive analysis allows us to identify areas for improvement and develop a tailored plan that outlines the potential market reach achievable through our strategies.”

Kustov adds, “By providing prospects with a clear overview of their current situation and a calculated projection of the results we can achieve, even the most discerning customers are able to grasp the bigger picture. They can evaluate the potential outcomes and determine the return on investment they can expect. This approach helps build confidence and trust, as prospects can visualize the possibilities and understand the value we bring to their business. Ultimately, our success in effectively reaching, engaging, and closing hard-to-reach prospects lies in our commitment to understanding their unique needs, aligning our strategies with their specific situation, and providing a clear roadmap for improvement. By demonstrating our ability to deliver tangible results and showcasing the potential growth opportunities, we can engage even the most skeptical prospects and increase the likelihood of successful partnerships.”

Laimonas Jurgaitis works for a B2B company and as an independent consultant, where they put a problem-solving approach to use for multiple companies. Jurgaitis gets a lot of mileage out of this technique: “First of all, we contact the department head by offering to meet and share the latest technological (if it’s a manufacturing company, for example) or management (if it’s a service company) solutions/trends. During the meeting, we offer a free audit or ask the manager to share what their objectives are and what problems they are solving. We then list solutions and insights to solve the problems with potential benefits from the information gathered. (Even in the first meeting, we try to find quick wins for the potential client). After this meeting, we share the solutions and ask if we could meet and share our insights with the top managers. Nine out of 10 said yes.”

11. Count on the Right Tool Stack

A well-curated selection of marketing and sales tools makes it easier to turn hard-to-reach prospects into customers at every step. Customer insights, lead generation, and prospecting tools help you find prospects in the first place. Then, customer relationship management (CRM) software takes you the rest of the way.

At Wiserbrand, Eugene Koplyk uses a variety of platforms to make it easier to handle hard-to-reach prospects. “One thing that has been really helpful in effectively reaching, engaging, and closing hard-to-reach prospects is leveraging the right tools,” Koplyk says.

Koplyk then lists the tools Wiserbrand uses: “HubSpot is a versatile tool for lead generation, B2B data management, and sales growth. Hotjar and Google Analytics provide valuable insights into user behavior and website performance, enabling improvements to the customer experience and lead generation. Clutch, GoodFirms, and Design Rush are useful for lead generation and reputation management. LinkedIn Sales Navigator and LinkedIn Helper are valuable for finding and engaging with relevant leads.”

“It’s important to explore these tools to enhance B2B outreach and achieve success in reaching, engaging, and closing challenging prospects,” Koplyk concludes.

Confection’s Quimby Melton automates most of the company’s lead generation so the sales team can invest more critical thinking into the rest of their jobs. “Tools like Seamless, Apollo, and LinkedIn Sales Navigator make it easy to generate B2B leads quickly and inexpensively. In a matter of minutes and for < $100/mo, we can generate lists that contain thousands of qualified business professionals,” Melton says.

With that time freed up, Confections’ salespeople can put more effort into important sales tasks like persona definition and development, messaging, systems engineering, and data analysis. Melton says, “Making these four elements work harmoniously ensures that leads who enter the top of our funnels move through constructive, results-oriented, well-defined nurturing processes and toward positive revenue outcomes.”

Looking for more marketing and sales tools to try? Our list of the best free options works for businesses with any budget. 

12. Send Tailored Emails

Email can serve you well in engaging hard-to-reach prospects — if you know how to use it properly. Consider how people use email and integrate that knowledge into your communications strategy.

Paige Arnof-Fenn of Mavens & Moguls shares her knowledge on the subject: “E-mail has been a big part of my communications strategy. Here are a few tips that have worked successfully for me:

• If you have a contact in common who mentioned the person to you I start the e-mail with a subject line of “XYZ suggested we connect” so that even if they do not recognize my name in their inbox XYZ should ring a bell. If you saw them speak at a conference or read an article they wrote you can tailor the subject line to that such as “Loved your piece on ____ in HuffPo!” or “Great talk at the conference this week!”
• Then I check them out on LinkedIn and let them know in the e-mail that “I see we also have # connections in common” to make me seem more familiar to them.
• Then I explain why I would like to connect to bridge the intro and suggest we set up a call at their convenience. It usually works and it shows I have done my homework and am respectful of their time.”

Arnof-Fenn adds, “Another tip is that the worst time to make a cold call to prospects in any region is 8-10 am when everyone is rushing to work and preparing for the day, but the worst time to call is the best time to e-mail. Once employees are at work, the first hour is generally spent checking e-mails and organizing the day. During this hour, your e-mail has a higher chance of visibility. Sending an e-mail during their transit period places your e-mail on top, and would be among the first they see as they open their inbox. E-mails that are sent late in the evening or early morning have a chance of being buried/missed.”

Related: 8 Sales Prospecting Email Examples to Help You Come Up with Yours

13. Network In-Person

With so many online options for interacting with prospects available, it’s easy to overlook the way we originally did it: networking in person. InfraCloud’s Faizan Fahim uses conferences and events to get in touch with hard-to-reach prospects:

14. Start With a Solid Multi-Channel Marketing Strategy

Your prospects need to trust you before they can even consider your offer. Marketing helps you build that trust, especially if you can spread awareness of your brand in multiple places.

Jonathan Aufray of Growth Hackers explains how this works: “To effectively reach and engage with hard-to-reach prospects, the goal is to have a multi-channel approach. You want them to see your content in different places (Social media organic posting, search and social ads, SEO-optimized blogging, and cold outreach). Once they have seen your presence in multiple places, they will trust your brand more and start engaging with you.”

15. Offer Branded Gifts

Sometimes, building trust with prospects is easier than you think. High-effort strategies like personalized outreach have a lot of potential payoff, but you can supplement those tactics with easier tasks.

Trinity Packaging Supply’s Payam Karbalai proposes a strategy that just takes a little extra budget: providing gifts. Karbalai says, “One thing we have done that has helped us effectively reach hard-to-reach prospects is sending them branded gifts. Sending items that provide value such as a beer opener or stress ball goes beyond just a simple piece of paper or email. This has proven to be highly effective in capturing their attention and establishing a relationship that can grow.”

Share Your Experience to Get Exclusive Insights

While we just shared plenty of expert advice, it’s only a part of the research we have in progress on connecting with hard-to-reach prospects. You can still contribute to our final report and get exclusive insights in return by:

• Taking our survey: If you work in B2B and engage with hard-to-reach prospects, take our survey on the subject. You’ll have a chance of being featured in our report and get invites to exclusive Benchmark Groups where you can compare your company’s data to group trends.
• Joining our Benchmark Group: Speaking of Benchmark Groups, we’re also on the lookout for healthcare tech companies to SpotOn’s Benchmark Group to inform our report. In exchange for anonymously sharing your Databox metrics, you’ll see how you compare to the other participants in the group.