Jason Smallheer Of Smallheer Consulting On Mastering the Art of Remote Selling in a Post-Pandemic World
An Interview With Chad Silverstein
Trust — As a sales leader and former front-line employee, you must be trusted to do the right thing. Some managers, the bad ones, always think we are getting a massage or sitting in the tanning bed if I don’t answer a ping. Again, what if this was a traditional environment and I was not in the office but on client calls? Where would their head be? I had a manager once who always believed someone was off getting their hair done or getting a massage. Deep down, I think she wanted to get out of the office, get a massage, and get her hair done. The person in question was 40 miles away, closing a huge automotive account.
The global pandemic has forever altered the landscape of sales, propelling us into the era of remote selling. Today, businesses and sales professionals face the challenge of connecting with clients and closing deals without the traditional in-person interactions. Mastering the art of remote selling has become not just an advantage but a necessity. From leveraging technology and digital tools to building trust and rapport over virtual platforms, the skills required for effective remote selling are evolving. I had the pleasure of interviewing Jason A. Smallheer.
Jason A. Smallheer, MBA, is a respected leader in the marketing and business sectors, with over two decades of experience spanning diverse sectors, including marketing, digital advertising, cannabis, and academia.
Armed with an MBA from Webster University and a BS in Journalism from Southern Illinois University, he couples academic prowess with SEO, AdWords, and inbound marketing certifications.
Jason’s dynamic career includes teaching roles at Columbia College and Southern New Hampshire University, where he blended traditional education with modern technology to prepare students for today’s workplace challenges.
As the founder of Smallheer Consulting, he guides businesses in mastering digital and traditional sales strategies, leveraging his expertise to drive significant growth and ROI for clients.
Thank you for joining us. To start, could you share your “origin story” with our readers? How did you begin your career? What challenges did you face in the early days? How did you overcome them?
My career started in traditional media as a newspaper reporter. I transitioned to radio and played DJ for 13 years before finding my way into marketing, getting my MBA, teaching, and starting my own consultancy. I began working remotely when my wife was pregnant about eleven years ago. I’ve had a few corporate roles since then, but working remotely was always a part of it. The greatest challenge I’ve had is discipline. It’s easy to stay in bed for 30 extra minutes when my commute is a walk down the stairs or get sidetracked into vacuuming the office when I’m supposed to be working on a presentation. I started chunking my day into eight 1-hour blocks to get past it. I work for 50 minutes and take a 10-minute walk down the driveway a few times (I have a long driveway.) I know. If you do the math, I spend 80 minutes a day walking. If I were in an office, I’d lose that time with water cooler talk, the “hey, ya got a minute” conversations and other noise. I am more productive than ever now.
Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
I’m an avid reader. I have about 330 books in my home office. My favorite is “Building A Story Brand” by Donald Miller. Working in marketing and teaching business in higher ed, knowing how to brand myself and my business, and teaching others, businesses, and students how they can stand out in a noisy world has been imperative. I sneak back to it often.
Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
“Bloom where you’re planted.” All graduating seniors were asked to give inspirational quotes in high school. I had no idea what I was doing, so I asked my mom. I was a military child, and we moved around every two years or so. She helped me come up with it. It’s about finding success no matter where you are. It works for me in a number of environments. Home office. Coffee shop. Vacationing abroad. I feel like I can get it done no matter what soil is under my feet.
How have you used your success to make the world a better place?
I have found myself in the serve-before-you-sell mindset. I want to give as much as possible to my clients, students, and strangers on the street. If I see an opportunity to help a business with a marketing idea, I share it, almost to a fault. It drives my wife crazy when I’m in the car and see a business billboard that makes no sense, and I start analyzing how to improve it. But I hate seeing big or small businesses go out of business because they have noble intentions and no direction. When I go to bed each night, I want to know I made someone’s life a little better. Whether coaching a student on how to brand themselves, helping a team member get used to remote work, or emailing someone about how they can stop competing on price and still earn more business, it’s nice to know I’m helping people.
Ok, let’s now turn to the central part of our interview. In your experience, how has the transition to remote selling altered the traditional sales cycle, and what strategies have proven most effective in closing deals virtually?
I’ve noticed sales cycles are a bit shorter. Traditionally, I would prospect, call, email, visit, call again, maybe text, and juggle this with meetings in the conference room, bathroom breaks, conversations in the hallway, etc. Now, I don’t have those distractions. I walk to my office; there’s no traffic, and I start my day. The new technologies that have fostered a remote environment make reaching decision-makers easier, having thoughtful conversations, and sending proposals at a record rate. Again, I have become far more productive in this environment with discipline. I make it a point to tell my clients that I work remotely and have more flexibility than the average worker. Same for my students. They know I am not on campus full-time, so they can schedule office hours during the day and receive regular, timely feedback on their work.
In what ways do you believe technology will continue to shape the future of remote selling, and what tools should sales professionals be focusing on?
Companies large and small can now compete without having to shell out big bucks for the office space in a prime location. Heck, I worked for a company that had an office in a horse pasture. Getting there could have been better. Businesses now see how their team can be productive and even happier working in their space. Corporate workspace is, for the most part, uncomfortable. Desk. Walls. Hard lines, Bad colors, and so on. Some progressives have opted for the pool table and nap room. I have that at home. I have a futon in my office, a stand-up and sit-down desk, and a recliner. I can change my perspective and crank out a better product. Companies are seeing this. They don’t need to dazzle me with their vast selection of coffees. I have a coffee grinder in my office.
I look forward to going into my space and enjoying the work I am doing so much more.
Professional salespeople should embrace flexibility and drive better results. I can remember the days of the all-day call blitz. We would sit in a room and dial all day. Or send faxes. There would be balloons and pizza, and it was just crap. Now, with discipline, we can do a call blitz from the couch, the kitchen table, coffee shop with noise-canceling headphones and actually enjoy our environment and work.
Today’s sales pros should invest in the tools they need to succeed at home. Good headphones to remove the distraction of the mailman, high-speed internet, and face-to-face conversation tools. Facetime, Google Meet, Microsoft Teams, Zoom are all available. There is no reason we can’t ping a customer or a team member to ask a question and move on. Oddly enough, I had a client taking his Christmas holiday near me in northern Utah. Small world. He knew I was making the drive for 19 hours and called me to discuss his website and some changes we could make after the holiday. The technology we have, cell phones and face-to-face tech, enables us to remove barriers and do more.
How can sales teams maintain and build rapport with clients in a fully remote environment, especially when face-to-face interactions are limited?
Customers know more of us in sales are moving to a remote environment. The win for us in sales is in setting expectations with the client. Telling them we work remotely, stating we may not be in front of them shaking hands in the traditional sense but offering several solutions for the virtual conversations gives us and the clients flexibility. In my first year, it was more challenging because clients expected someone to walk in, interrupt their day, and engage in conversation. Now, I can take clients anywhere from anywhere. I’ve worked with a pharmacy in Utah, a convenience store in Nebraska, and a tech company in Australia. Instead of settling for clients within a radius or territory, we can communicate as long as they are on Earth with some internet. It’s a much bigger pool. Clients appreciate that they can work with various experts who meet their needs instead of settling for whoever is nearby.
Can you share a story of a challenge you faced in adapting to remote selling, and and how you overcame it?
I had a client who was up for an annual renewal, an insurance agent. I called and got the gatekeeper, and he never called back. I went by, and he would tell me he didn’t have the time for me. I was driving almost an hour to get the door closed on me. I sat in my favorite coffee shop, enjoyed a dark roast, and sent a single email. I acknowledged he was busy and maybe working together wasn’t ideal for him or his agency. I informed him his deadline for renewal was that day, and if I heard nothing, I would assume he was canceling his account. I had an email back in minutes. He was a frazzled business owner who couldn’t escape his computer. But I was able to meet him on his terms. I employ this strategy with many customers who ghost me now, and I ask my team to do the same; the single “breaking up email” gets the phone to ring. We can also be more flexible. Historically, if I walk in and get shut down, I must return to my car and drive to my next prospect. Now, I can call, video conference, or email far more people in a day.
Can you share a success story of a remote sale that exemplified innovative tactics or approaches in the post-pandemic world?
We were working with a non-profit organization during its RFP process. They were 100 miles away, so our best option for immediate delivery was virtual. One of the members of my team who was the driving force behind the proposal had a last-minute emergency. And I mean last minute. I was on the video call waiting for the client, and I got a text message asking me if I could lead the proposal as she couldn’t make it. I had the proposal on the cloud, pulled it up on my screen, and when the client logged on, we went through it together and won the contract. They never knew there was a hiccup on our end. If it weren’t for cloud technology, video calls, and remote work, there would have been a no-show at the client’s office, and we would have been fighting for another appointment. Our clients are busy, and we need to meet them where they are with as little friction.
Could you list and briefly explain “5 Key Strategies for Mastering the Art of Remote Selling” based on your experiences and insights?
1 . Time management — You are dead in the water without a detailed strategy. It’s so easy with remote work to get stuck jumping through hoops, walking the dog, answering questions on Slack, teams, etc.; you get lost. I write it all down, I use a Panda Planner, and I stick to it. Nobody needs anything “right now.” What if they came to my office and I was in the restroom? The company wouldn’t implode. I have daily kick-offs and wrap-ups with my team. It’s in their planner, and they fill me in daily. Sure, they can ping with needs, and I can ping them, but we all know we are not sitting on the computer waiting for an alert. We have our daily activities, and we stick to them.
2 . Trust — As a sales leader and former front-line employee, you must be trusted to do the right thing. Some managers, the bad ones, always think we are getting a massage or sitting in the tanning bed if I don’t answer a ping. Again, what if this was a traditional environment and I was not in the office but on client calls? Where would their head be? I had a manager once who always believed someone was off getting their hair done or getting a massage. Deep down, I think she wanted to get out of the office, get a massage, and get her hair done. The person in question was 40 miles away, closing a huge automotive account.
3 . Know when to log off — When we work remotely, it’s easy always to be working. For our own sanity and the sanity of our family, we need to log off and shut down at the end of the day. Working 16-hour days doesn’t make you a hero. It makes you look like you’ve taken on more than you can chew. When it’s quitting time, let’s say after 8 or 9 hours, set your availability away, put an out-of-office reply on your email, and don’t return until the next day. I left a role because a boss needed to email me all day on Sundays and get a response. I was having panic attacks at the end. Just because she wants to work on Sunday, for whatever reason, does not mean I need to do the same. Log off. You’ll be thankful you did.
4 . Be transparent — Make sure your clients know you are a remote worker so they aren’t expecting you to show up for a meeting. Offer to make the relationship as easy as possible. If they don’t know how to work with a remote worker or don’t prefer it, be open to showing them how easy it is. I have a local client whose website I was consulting on. He really wanted a person in his community; there were none. I found him a great Arizona provider with a designer in Arkansas. The client is in Missouri. I got him a webcam and walked him through a software setup process using Facetime, and now he can have conversations with the stakeholders in three states. He loves it. He’s very proud of his out-of-state partners.
5 . Be flexible — As technology evolves and our business grows, we need to be open to adapting to the work of remote work. A few years ago, nobody was thinking about noise-cancelling headphones. Now, it’s almost a requirement. I was having a meeting at a coffee shop. I used older headphones, and my team on the other end said I was hard to hear. It would have been embarrassing if I were on with a client. I ordered noise-canceling headphones from the hotel and had them waiting for me when I got home. As a remote worker, the world will not stop and hush-up if I am on the phone. I need to adapt my business to the world around me.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Be passionate about the work you do. Some choose their roles for the money or the benefits, like working remotely. That’s the wrong reason. Be so excited about what you do that you can’t wait to log on. Your customers and your team will see the authenticity, and they will follow you. Find your passion, and you’ll never work a day in your life.
As we wrap up, how can our readers follow your work?
You can find me online on LinkedIn, YouTube and my webpages: https://www.linkedin.com/in/jasonsmallheer/
www.themarketingprofessor.net — education
www.smallheerconsulting.com — business consulting
www.elevatedgrowthgroup.com — cannabis marketing
Thank you for offering such valuable insights into the art of remote selling. We wish you continued success.
About the Interviewer: Chad Silverstein, a seasoned entrepreneur with over two decades of experience as the Founder and CEO of multiple companies. He launched Choice Recovery, Inc., a healthcare collection agency, while going to The Ohio State University, His team earned national recognition, twice being ranked as the #1 business to work for in Central Ohio. In 2018, Chad launched [re]start, a career development platform connecting thousands of individuals in collections with meaningful employment opportunities, He sold Choice Recovery on his 25th anniversary and in 2023, sold the majority interest in [re]start so he can focus his transition to Built to Lead as an Executive Leadership Coach. Learn more at www.chadsilverstein.com
Jason Smallheer Of Smallheer Consulting On Mastering the Art of Remote Selling in a Post-Pandemic… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.