Episode 491: Selling with Heart: How Storytelling and Empathy Transform Sales with Tom Jackobs
Can you lead with heart and still drive a massive profit? In this episode of Making Sales Social, host Brynne Tillman sits down with Tom Jackobs, a sales growth coach and creator of the “Selling with Heart” methodology. Tom shares his powerful origin story, from the brink of bankruptcy in the fitness industry to developing a consultative approach that skyrocketed his closing rate to 90%. Together, they explore why storytelling is the ultimate “pattern interrupt” in a boardroom, the shift from outdated sales tactics like BANT to heart-centered frameworks, and how to build radical trust by being willing to tell a prospect “no.”
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Tom Jackobs 00:00
Being social and selling is a human interaction. It’s one-on-one or one-to-many, but it’s coming from your heart to their heart and connecting on a human level.
Bob Woods 00:11
Welcome to the Making Sales Social podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman, Stan Robinson Jr., and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching and using so you can leverage them for your own virtual and social selling. Brynne, welcome to the show.
Brynne Tillman 00:33
Welcome back to Making Sales Social. I’m Brynne Tillman, and I am here today with Tom Jackobs, a sales growth coach, speaker, and trainer who helps health and wellness professionals turn meaningful conversations into confident client decisions without pressure, scripts, or feeling salesy. Tom is the creator of Selling with Heart and the Impact Pilot Framework, a practical approach that helps practitioners guide conversations with clarity, ethics, and intention. Impact Pilot focuses on helping clients make informed decisions while allowing professionals to lead the conversation with confidence, structure, and empathy. Tom, welcome to the program.
Tom Jackobs 01:17
Thanks for having me. I’m really happy to be here.
Brynne Tillman 01:20
Before we jump into your genius, we ask all of our guests the same first question: What does Making Sales Social mean to you?
Tom Jackobs 01:30
To me, social—being social and selling—is a human interaction. It’s one-on-one or one-to-many, but it’s coming from your heart to their heart and connecting on a human level with that prospect. Whether you make the sale or not, it’s so important to make that connection with another human.
Brynne Tillman 01:52
I love that. Connection really is ultimately what we want to achieve in life, right? At least in sales. When I was digging into you, one of the things you talk a lot about is how you help people tell their stories. Tell me a little bit about why that matters, how you teach your clients to do that, and what our listeners can do to tell better stories.
Tom Jackobs 02:25
Storytelling in sales is one of those skills that elevates the entire experience—not just for yourself, but for the prospect as well. People want to do business with other people, and even if you sell B2B, you’re still selling to another person. We all want human connection, and storytelling is a great way to provide that.
I’m sure everybody’s been in a situation where someone is trying to sell to you with just figures and facts, and you’re checked out. But the moment they start telling a story, everyone’s ears perk up and they pay attention. That’s the power of a story. People not only pay attention, but they also retain information better.
There are a couple of stories I recommend every business owner or salesperson have: your origin story—why you do what you do—and client success stories. Your origin story helps people understand your motivation. Client success stories demonstrate transformation. The key is to make it relatable, not braggadocious. It’s not about “me, me, me,” it’s about bringing the prospect into the story so they can envision themselves experiencing the transformation.
Brynne Tillman 05:30
I love that. I’m sure that was a big piece of Selling with Heart. Talk a little about your origin story around Selling with Heart and how that came to be.
Tom Jackobs 05:46
I owned a fitness center for 10 years in Houston, Texas. In the first six months, I almost went broke—physically, mentally, and financially—because I could not sell. One Sunday afternoon, I was in my office, which was really the electrical room with transformers buzzing behind me. I started crying because by Friday, when rent and payroll were due, I was going to be $10,000 short. I had to call my dad and ask for a loan at around 40 years old.
My dad, who had never been an entrepreneur, agreed to loan me the money at 12% interest with my house as collateral. I used the money to cover rent and payroll, and I invested in coaching. My coach told me straight: “Tom, your sales suck. You need to get better at sales.” I didn’t want to sell—I thought people would automatically sign up for personal training—but I dove deep. I read every book, attended seminars, and learned how to communicate appropriately, especially in health and wellness, where you’re selling something people don’t inherently want, like exercise or nutrition programs.
What I learned was people want the result. I redesigned my consultative approach. During my first consultation using this method, I listened to the client’s problems and presented step-by-step solutions with multiple session options. The client chose the option I recommended, and it went through. That moment boosted my confidence. From there, I had a 90% close rate and grew my revenue from $100,000 in the first year to $400,000 the next.
Brynne Tillman 11:58
So now you help other health and wellness professionals do the same thing.
Tom Jackobs 12:03
Exactly. I help them have meaningful conversations at a human level with people who need our help.
Brynne Tillman 12:11
Quick question: How do you get them in the door? These methods are great once they’re in front of you. What strategies do you use to attract clients?
Tom Jackobs 12:24
That’s part of my Heart-Led Growth System: Attract with Heart, Sell with Heart, Keep with Heart.
Attract with Heart can include paid advertising, but I focus on relationship marketing: referrals, networking, and public speaking. Public speaking was the one marketing campaign that consistently brought good clients to my business—webinars and seminars should be a cornerstone for any business looking to bring in new clients.
Brynne Tillman 13:14
I love that. What’s the second part?
Tom Jackobs 13:19
Sell with Heart—that’s the methodology I teach for the sales conversation itself.
Brynne Tillman 13:41
And the third?
Tom Jackobs 13:41
Keep with Heart—how to retain clients, increase their lifetime value, and get referrals.
Brynne Tillman 13:55
So that’s the Heart-Led Growth System. Is it spelled out in your book?
Tom Jackobs 13:55
Yes, the center section of my book covers Sell with Heart.
Brynne Tillman 14:04
That’s awesome. You also host a show called The Heart-Led Business Show.
Tom Jackobs 14:11
Correct.
Brynne Tillman 14:13
Great! Tell me a little about that podcast.
Tom Jackobs 14:17
I want to connect with other heart-led business owners, specifically in the health and wellness space, who have been able to balance leading with heart, having a heart-led business, and making a profit. Many heart-led business owners believe you can either lead with heart and have a heart-led business or make a profit. In my world, it’s not “or”—it’s “and.” You can be heart-led and still make a profit. When you look at it, the stories I get from other business owners on the show—the ones pouring their heart into it—the profit always follows. But when you focus only on the numbers, your head is in a spreadsheet, you’re not listening to your customers or prospects, and your business won’t be as successful as if you balance both.
Brynne Tillman 15:19
I love that. We have 21 tenants of social selling in our company, and one of them is “detached from what the prospect is worth to you and attached to what you are worth to the prospect.” That really brings it together: it’s not about making the sale, it’s about solving their problem—and more sales will come.
In many businesses, trust has been eroded over the years, unfortunately. On the corporate side, which is more my focus than health and wellness retail opportunities, it really comes down to board expectations, management, and KPIs. Often, those indicators encourage the wrong behaviors and activities, creating conversations that feel “icky.” In your world, how do you earn trust?
Tom Jackobs 16:45
You earn trust by doing what you say. It’s okay to tell someone you cannot help them. It’s okay to say no. It’s okay to tell a prospect, “I don’t think you’re ready for this right now. Let’s reconnect in a month or two.” You build trust by being completely transparent and honest.
Many salespeople want to say yes and be agreeable to be liked—but they don’t need to be liked. They need to be known and trusted. You can have a confrontational sales approach and still win when you’re honest. You can give hard truths: “What you’re doing right now isn’t good. This is where you’ll be in six months if you continue. How do you want to handle that?” Having these conversations builds trust. Even if you don’t sell to that person, if they have a great experience, they will refer others to you.
Brynne Tillman 18:28
That’s really important. It’s like detaching from the sale and attaching to the solution. We use an acronym called CHIRP:
- C: Challenge they’re facing
- H: History of trying to fix it
- I: Impact today
- R: Risk tomorrow
- P: Priority in their world
Once we go through CHIRP, we have all the information to identify if a solution exists. I feel like we’re very aligned in our thinking.
Tom Jackobs 19:20
This is the new way of selling. It’s no longer “beat them over the head until they buy or die.” It’s now, “Let’s figure out together—can we help each other?”
Brynne Tillman 19:32
I’ve been through almost every sales training out there. For years, BANT was the top framework: Budget, Authority, Need, Timing. But over time, it became irrelevant—buyers don’t always know their budget, who else is involved, or exactly what they need. That’s why we shifted from BANT to CHIRP. Many outdated sales processes erode trust and make it clear the salesperson is only there for the sale, not to solve a problem. Selling with Heart is under-leveraged, and it works anywhere.
A challenge I see is that leadership often manages to metrics that erode trust. There’s a disconnect: we want to create trust but aren’t measuring or doing the right activities. Many buyers worry AI will replace SDRs. Where do you see AI affecting your ecosystem?
Tom Jackobs 22:18
I see AI as a thought partner—a resource with all the knowledge in the world, though it doesn’t yet know how to use it. Human-to-human selling will always be essential. AI can help with filtering, outbound SDR tasks, inbound calls, FAQs, and scheduling. For example, my AI receptionist, Betsy, is sharp, empathizes, and makes jokes. It’s engineered empathy, but it calms people down and improves the customer experience. Companies need this, especially for after-hours calls.
Brynne Tillman 23:24
Exactly. I’ve experienced this as a buyer—Betsy can handle irate customers calmly, which is invaluable.
Tom Jackobs 23:59
Right. AI can add tons of business if implemented correctly.
Brynne Tillman 24:25
I could talk to you all day—it’s been so fun—but we’re over time. My last question: what should I have asked you that I didn’t?
Tom Jackobs 24:43
You didn’t ask what the HEART acronym stands for.
Brynne Tillman 24:54
Alright, Tom—what does HEART stand for?
Tom Jackobs 24:58
- H: Heart—rapport building, easing tension, allowing the person to relax.
- E: Engage—ask good questions, mirror back what they say, and actively listen.
- A: Ask—the prospect should ask how to start or enroll because they’re ready; you guide them subtly.
- R: Referral—ask for referrals during success moments, not at the sale.
- T: Testimonial—social proof, like video testimonials on your website or socials, helps the sales process immensely.
So HEART stands for Heart, Engage, Ask, Referral, Testimonial. Beautiful.
Brynne Tillman 26:33
I love it. Tom, what a pleasure meeting you. How can people get in touch with you?
Tom Jackobs 26:39
I’m on Instagram as @ImpactPilot, or visit my website at tomJackobs.com. I also have training on the Heart-Led Growth System at tomJackobs.com/watch.
Brynne Tillman 27:03
Great. Tom is also very active on LinkedIn, so go find him there. Thank you so much. To our audience: don’t forget to make your sales social.
Bob Woods 27:18
Thanks for watching. Join us again for more special guests sharing marketing, sales training, and social selling strategies. Hit the subscribe button for the latest episodes of the Making Sales Social podcast. Give this video a thumbs up and comment below on what you want to hear next. You can also listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.