When COVID-19 first broke out, it was clear that small businesses would have to make a lot of operational adjustments if they wanted to maintain their usual sales quotas. However, what many business owners failed to anticipate were the changes that they’d have to make to their marketing strategies as well. In this episode, Jon Aidukonis and Gene Marks, along with Small Biz Silver Lining Founder Carissa Reiniger, discuss how the pandemic has impacted consumer needs and how small business owners can alter their sales tactics to meet their desired goals.

Executive Summary

2:29—Today’s Topic: How Do I Keep Selling During This Pandemic?

3:17—Because of this pandemic, online accessibility has become a nonnegotiable aspect of every small business. Similarly, offering a wide array of delivery options and platforms to your customers has also become a standard business practice.

4:30—There has been a significant shift in the type of marketing that customers prefer. Nowadays, audiences want their advertisements to seem authentic and genuine; the most compelling brands are those that come from a place of sincerity.

5:58—The decision to let your personal identity define your brand is one that only you as an individual are qualified to make.

10:15—Business owners should only leverage social issues if they genuinely want to take a stand. Doing so merely for the sake of publicity will always backfire on you because customers can sense when a business is just virtue signaling.

13:44—When hiring new sales people, look for individuals who have experience working in another small business; have a proven track record of consistently hitting their sales targets; possess a demeanor that matches your brand image; and can confidently own up to the risks of their position.

16:20—Small business owners should utilize a “hire slow, fire fast” approach when it comes to their sales staff, which means they should hire a lot of salespeople with the intention of weeding out those with a poor performance.

19:02—Your sales team will be more motivated by a cause, not a product. Another way to motivate your sales staff is by offering them the time and support that they need to succeed.

20:59—In order to accurately assess the performance of your sales team, you need to consider both the overall volume of customers they speak to and the conversion rates of those interactions.

23:41—Although technology can certainly help boost your sales, it can never fully replace the human connection that your customers crave.



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Gene: Hey everybody, and welcome to the Hartford Small Biz Ahead Podcast. My name is Gene Marks. I’m here with my formidable co-host Jon Aidukonis. Jon, say hello.

Jon: Good morning, everyone. I like that description.

Gene: Yes. Formidable co-host. I like that as well. I just actually was standing by and listening to another great conversation that Jon had with Carissa. And now I’m back with Carissa as well. It’s Carissa Reiniger, who is the founder and CEO of Small Biz Silver Lining. So Carissa, why don’t you say hello?

Carissa: Hello, hello, hello. So nice to be back with you guys. Thank you for having me.

Gene: Right. And glad to have you on this episode as well. And so listen, I mean as, as I can imagine, everybody is listening to all of the segments that we’ve been interviewing you. We will have to at least give our respect to the people that have not listened to anything. So Carissa, just a quick recap of who you are, and what you do, and what Small Biz Silver Lining is all about.

Carissa: Yeah. Happy to share. So Silver Lining started in 2005, a very long time ago. And we have been on a mission to help more small businesses succeed since then. Our core business is we have a program called SLAP, which is the Silver Lining Action Plan, and it’s based on behavior change science. So we help small business owners build really strategic but really direct action oriented plans to grow their business. And then for the next year, we give them all of the strategy, accountability, training, structure, support that behavior change science says that they need in order to actually implement that plan and succeed. In addition to that, we run a global movement called Thank You Small Business, which is all about acknowledging and celebrating and supporting small businesses, which the Hartford has been a great, great, great partner in. And we do a lot of work around economic justice, really advocating for access and equality for diverse and traditionally underserved small businesses. So that’s what we do.

Gene: That is fantastic. And it makes me laugh because you and I have been dealing with small businesses for a long time. You started in 2005. I started in ’94. That’s just dating-

Carissa: Wow.

Gene: I know. And I have to admit that considering all the business owners and all of my clients I’ve dealt with, if I were going to start a program, I would probably call it SLAP as well. I don’t even know what it stands for, but I don’t care. Because that’s sometimes the way I feel, depending on how I deal with some of our clients. But okay. Listen, this segment, we’re going to talk about sales, which is near and dear to my heart.

So Carissa, as we talked about earlier before, I mean, I want you to view me as a client of yours right now. I’m a business owner. I have 10 employees in my company. I’ve got about a dozen contractors. We have about 600 clients. I’m a CBA so we sell financial services, technology services as well. And like any business owner, I want more clients. So I’m in charge of selling for my business, which is a pretty common role for the principle of business to have.

So I have some specific questions for you because I know this is the kind of thing that you advise your customers on. And I hope that these questions I’m about to ask you are ones that other business owners are also interested to hear. So here’s the first question. We’re emerging from the pandemic as we speak. We’re having this conversation at the end of April so things are definitely brightened up. The economy is growing. So looking back now, tell me a little bit how has selling changed since 2019?

Carissa: That’s interesting. I mean we could talk for 10 hours about that probably. Listen, I think there’s the obvious, and then there’s sort of the psychology less obvious things that are happening. I mean, number one on the obvious category is that being digital is obviously required. So being able to have your customers find you online, buy from you online. The shift from people coming to you and you needing to go to them is significant. So I think delivery. And delivery in every way, right? How you deliver your products or your services. Maybe before you used to travel to a conference, now it has to be on Zoom. Maybe before people came to your restaurant, now more people are doing takeout. Maybe before people shopped in your store, now more people require you to ship your products. So certainly the way that that people find us has changed.

I think the way that we need to deliver our work has changed dramatically. And then I think at a more philosophical level, two or three of the things that I’ve seen really, really sort of strongly are, one, authenticity really matters. I think that after 2020, not just the health crisis, but also the the racial reckoning that was far overdue, and many of the other things that happened in 2020, people are tired. And people are not interested in marketing messages. People are really looking for authenticity.

And so the businesses that we work with, certainly the ones that have sort of tried to be clever versus being really real, the clever ones have done less well than the very real ones. Which I think is really good actually. I think that’s a good shift. Connected to that, because I think that we’ve come out of an era, and I hope we stay out of it, where sort of flashy was important and really polished was important. And I think we’re in a new era where accessibility is really important.

So being able to see the business owner on an Instagram Live without their makeup on in their kitchen talking about something about their business. That’s becoming more compelling from a sales point of view and a connection point of view than having the $25,000 flashy automated website. So I think there’s a significant shift in what customers are looking for, and how quickly and easily they can access someone to buy from them. But also the things that they’re connecting to from a point of view.

Gene: Do you think that identity has become more important in the selling process now? And as an example, I see some people that are female entrepreneurs and business owners. They say straight out, “Hey, I’m a female owned business. That’s a connection you want to make with me.” Then again, I see other female entrepreneurs that say the exact opposite. They’re like, “Listen, it doesn’t make a difference I’m a female owned business. My business is even better for you.” We have some of my clients that are identifying racially, they’re identifying politically, they’re identifying from their area. And when you do that, you create potential sales and relationships with people that identify with you. But then you’re also creating the risk that you’re going to lose customers that don’t identify with what you identify with, if that makes sense. What are your thoughts on identity and sales in 2021?

Carissa: Gene, you are not making this easy. That is a complicated question. Listen, I think… Instead of me saying, I think, let me say, I hope. I hope that-

Gene: I’m going to interrupt you. I’m going to interrupt you. I’m going to interrupt you to help you with this question, also to make it a little bit easier. You’re a female owned business owner. And you’re looking for clients like anybody else. So identify as a female owned business owner, do you think that’s important to you? Do you think that’s important for other people to use that as a potential help in their sales process?

Carissa: I don’t. And in fact the opposite. But again, this is me speaking from a very personal experience. I was 22 when I started my company. I was really young. And I had all sorts of ridiculousness happen to me as a result of that. I am blonde. I looked more like a cheerleader 15 years ago than I do now. And the comments and the things that people said, and the assumptions. The number of people that asked me if my dad owned my business. Or how impressive that, for a woman, I had started this business at such a young age. Basically insinuating that if a man my age had done it, that would just the obvious because they’re a man.

So I actually got so sick of the identity stuff around me being a woman. Both the sexual innuendo, the assumption that I was somehow less capable than a man, all of the things that women often face, that I actually really felt strongly that we needed to get to a point in the business world where everyone was created equally and treated equally. And that that required not being segmented.

And so actually, I was the president of an organization, when I lived in Canada, called Women Entrepreneurs of Canada. And I advocated really hard to actually have men join the board because I felt very strongly that if we as women wanted equality, then we couldn’t do that alone. By nature of wanting equality, we needed everyone at the table. We needed men to support women being equal as much as women were advocating for being treated equal. So I say that to say that that’s my personal journey.

What I also think is true, though, is that there are segments of the entrepreneurial community, and obviously humans at writ large, so we can look at the example of black business owners, black entrepreneurs. They have been so damaged by systemic injustice, and held back in so many significant ways. And all the stats show that to be true. That for there to be a moment in time where there is a strong advocacy and people are proud to say, “I’m a black business owner,” and, “I’m going to buy from black businesses,” I actually think that’s great.

I think I support that entirely because when there are segments of the population who have been so disadvantaged for so long, we do have to do extra work to get them to the table to make sure that there is the beginnings, the breakings open of equality. And so I actually really support identity based identification, and having that be part of the business message. And I am inspired by it, and I try to buy from people who are advocating for themselves in that way. And I think we all need to be at the table together. And so the ideal utopia, which we’re nowhere near, is that that wouldn’t be necessary. But we’re not there. And so here we are.

Gene: That’s a great answer. It’s a great answer. So okay. So besides identity, how about the social warrior entrepreneurs and business owners? And I’ll give you another example. There’s a restaurant near me. It’s a vegetarian restaurant. It’s popular. It’s really good. And they issued a press release recently saying that they are going to be paying their hourly employees $15 an hour. Which I think is great. I mean, that’s fine.

But I did think to myself, geez. Okay, if you’re going to pay them $15 an hour, because that’s obviously a social issue right now, minimum wage, do you have to advertise that, in other words? Good for you that you’re paying your workers that amount of money, but it’s almost as if they were using it as a PR thing. You know what I mean? And because they’re using it as a PR thing, they’re trying to generate more sales.

So this is a conversation about sales in 2021. Do you think it’s valuable? Do you recommend to your clients that if they want to increase their sales that they do leverage social issues that they feel are important? Or do you tell them to just stay out of it because there might be more costs instead of benefits? What are your thoughts on that?

Carissa: It’s a very, again, tricky question. You’re really giving it to me today, Gene. So I think two things. I think that those types of decisions should be made at a moral level, not a sales level. So I think that if you have raised your minimum wage because you are convicted that that is the right thing to do, that’s the role you want to play as an employer, you want to pay what you believe is a fair minimum wage, that’s the reason to do that. And then if you want to talk about it because it comes from an authentic place, because it is what your moral stance is, it does matter to you, you want other restaurateurs to make me do the same, you want to create social change, you want to lead by example, then go for it.

The risk of that, of course, I mean, I’m quite outspoken about my social views, and I do talk about them, and I do lead Silver Lining in a very specific way. And the benefit of that is that people who align with my views believe in us even more, and the people who don’t align with my views find me difficult. But I am okay with that because I’m not doing what I’m doing to drive sales. I’m doing what I’m doing because I think it’s my responsibility as a business owner and a citizen to operate the way I’m operating. And so if it alienates some people, that’s okay with me. And I can give you an example of that in a second.

I think that if you’re doing it for the press release, if you think to yourself, oh okay, if I raise my minimum wage, I’ll be able to do a press release, and then I can do these three things. And that will probably get 20% of the population to kind of do business with me. A, it’s going to ring in authentic, going back to what we talked about earlier. And B, then you actually are running the risk of alienating people, and that might actually not be a solid sales strategy.

So I think from a social issue point of view, I do think that business owners have a significant role to play in justice. I do think that business is actually one of the most powerful forces for justice. And so I think there’s a really compelling opportunity for business owners right now to create a better world. But I think that that has to come from a different place than thinking about sales. I think right beside our morals, we need solid sales strategies, but I don’t know that I would connect them so directly to each other.

Gene: Great. That’s great advice. That’s great advice. Okay. So Carissa, I am hiring a sales person sometime in the next few weeks. So I’ve just begun the process. Again, you’re my advisor here. What should I be looking for in a good salesperson?

Carissa: Great question. So hiring salespeople’s got to be one of the worst things on the planet to do. It’s so hard to pick good salespeople. I don’t know why. It’s confusing to me that it’s so hard. But every business owner I know has struggled to find a good website builder and a good salesperson. Those are the two big things. For me, there’s probably four things. Number one, that they’ve worked in a small business before. I think that we assume that if someone’s gone and worked in a big business, then somehow they’re going to be fancier or better. But culture is so different. If you’re coming from a sales team of 500, and you’re one of 500, your skillset, your work ethic, your point of view is going to be entirely different than if one of your last jobs was with a sales team of three and you had to do everything. So the myth that if they come from a big company, they’re better, I think needs to be shot down. So have they worked in another small business? That’s crucial.

Number two, have they hit sales goals before? I ask our salespeople very literal and direct questions. What were your sales targets the last two years in a row, and what was the exact amount of money that you sold? I mean, to what degree did you miss, hit, or exceed your sales targets? And tell me why. Give me specifics. And if they can answer, I mean, a good sales person knows exactly what their sales targets are, right? And they know exactly if they’ve hit them or not. And so if there’s any vagueness, or a little back and forth, or a little weirdness, you know that there’s something going on there. So that’s number two.

Number three is just demeanor and personality. I mean, when you’re a small business, if you’ve got one salesperson, or two or three, it’s going to be a small team, they’re your voice. They’re as important as your website. They’re as important as your marketing materials. They in fact are your marketing materials. And so do they represent your brand? Are you proud of how they communicate, how they present themselves? I mean, they’re literally representing you. That’s a really, really crucial thing if you’re a small business owner, and you’re a small, small, small sales team.

And then I think number three is just, are they willing to own some of the risk. As a small business, you can’t afford to spend huge amounts on salaries and then have that person not perform. So I’m a really big believer in a fair base pay, and then lots of motivation around performance-based pay. And if they don’t believe in their sales skills, they won’t want to do a deal like that. But if they do, they’ll be excited about it.

Gene: So you’re saying if I’m going to hire somebody, I mean the best way to do it, or what you would recommend, is that I do have a base salary, and then some type of a commission structure above that. That’s really common with salespeople, right? My problem in the past has been salespeople that just don’t perform up to my expectations. A lot of it business owners have that problem.

Carissa: Like every business owner of all time, I’m with you on that 100%. Yeah.

Gene: If a sales person performs super well, the chances are that salesperson’s going to leave me anyway and open up their own business, or sell on their own.

Carissa: Totally, I know, right?

Gene: Because as a a small business owner, you kind of attract people that they’re not small business owners. They just hit this certain plateau. And it drives me nuts, and I know it drives a lot of my clients. How do I motivate them to sell more? Because so many people that run their own businesses are profit driven, you would think, hey man, I’m offering you a 10% commission. I mean, you would think you’d be out there trying to sell more so you can make more money. And it’s a lot of people in this world are just like, yeah, I’m making enough. I’m good. I’ve got Netflix, and I’m going to hang out this weekend and ride my bike. And it’s good. So what advice do you have for me or to your clients to try and motivate salespeople to sell more? What can they do? And do you ever recommend that we just cut people loose if they’re just not performing?

Carissa: Well, definitely. I mean, this is age old. This is not my own wording, but hire slow, fire fast. I definitely, definitely think that with a salesperson it’s pretty obvious, right? Are they performing or not? I mean, it’s pretty black and white. I mean, obviously you need to know what your sales cycle is and give people enough time to… Certainly you need to have reason within that. But with sales, I mean, that’s one of the most clear cut. They’re doing it, or they’re not. I mean, there’s not a lot of room for gray in sales.

So I definitely think we’ve got to get rid of underperformers. I just think that if they’re not motivated to go for it, and they’re not showing any signs of changing. You can teach skills, but you can’t teach hustle. Someone either has it, or they don’t. And I think that you see that pretty quickly. So we actually, whenever we’re hiring for a sales role, we hire three people. We put them all through training, and we assume that we’ll have one of them three months later. So every time we need one, we hire three. Because we are planning for the fact that two that did great in the interview will not do great in real life. We’re actually very formulaic around expecting people to not make it and needing to fire basically two thirds of the people we hire.

In terms of motivating them, I’d say there’s two things that I’ve learned. One is people, and again, this is not necessarily new news, but people are much more motivated by a cause than a product. So at Silver Lining, we’re a SaaS company. We have a subscription-based small business growth program. To come to work everyday and be like, “I sell a SaaS small business growth program,” I mean, that is so boring. I mean, I’m not even motivated by that. I could care less about a SaaS small business program.

But that SaaS small business program helps small businesses accomplish their goals and make more money doing what they love. And when they use it, we can serve them, and we can support them, and we can cheer for them, and we can rally around them. And every small business that we get to work with becomes another person in our global network that gets connected to this incredible community that we have. That I can sell. That I can sell all day long. So I spend a lot of time really focused on what is the message and the cause of what we’re selling, not the product. And we do basic product training. But we do a lot more around mission and cause and big picture, and who the customers are and how we can help them. And that is very motivating.

And then the other thing, which is not fun to hear, and no one wants to do this, including myself, it takes a lot of management. Daily huddles, weekly reviews of the sales goals. Meetings to say, okay, well what went well and what didn’t. And how can we role play this out and come up with a different way to approach it? And I think for a lot of business owners, myself included, we’re busy. We know our business inside and out so it seems so obvious to us. But for other people, they need management. They need support. And so whether it’s you or somebody else in your business, I think a significant part of keeping a sales team motivated is actually giving them enough time and structure to help them succeed.

Gene: So you mentioned earlier about, listen, whether a sales person is succeeding is black and white. Either they’re selling or they’re not. And you’re also talking about how important it is to supervise and manage the salespeople. So what metrics do you recommend, Carissa, for a business owner to target? Because, yes, there is completing a sale. That’s fine. But there’s a lot of other metrics that lead up to a sale that can give a lot of insight as to whether or not a salesperson is performing, or are going to run into any problems. I mean, some companies-

Carissa: Very much so.

Gene: Right? You make a number of calls, and that’s going to generate a number of appointments, a number of visits, and value of quotes that are set up, and what your close ratio is, and what your appointment ratio is. When you’re talking to your clients, what are some key sales metrics that you advise that they should have?

Carissa: So again, this is kind of sales 101. But if you think about, we call it a sales funnel. So a sale doesn’t just magically happen. There’s steps to that sale. So the metrics that we always look at are what are all of the steps to the sale? And then what are the conversion rates that we need to realistically expect at each of those steps? So for example, if you’re doing just pure cold call, right, like hardcore sales, how many calls do you have to make in order to get a certain percentage to actually pick up the phone, in order to then get a certain percentage of those to actually stay on the phone and not hang up on you, to then get a certain percent of those to agree to a follow up call, to then get a certain percentage of those to review the materials, to then get a certain percentage of those to actually purchase?

And so when we look at our sales performance in each of the people that are on our sales team, we’re looking at each of those metrics. And we’re looking at two things. We’re obviously looking at volume. How many people did they call? How many people picked up? How many people didn’t hang up? But we’re also looking at those conversion rates. Because if we start to see, for example, that 94% of, let’s call it, salesperson one’s people hang up on them, but only 23% of salesperson two’s people hang up on them, well, I want to know what salesperson two is saying on the phone that’s resulting in so few people hanging up on them. And I want to know why… Number one might say to me, “But Carissa, I’ve made 10,000 calls. What do you want from me?” But something’s happening at that moment that’s then cutting off the funnel. So we’re looking at every single step that leads to the sale. We’re looking at volume numbers, but we’re also looking at conversion rates for each of those steps. And that gives this very clear view of really what’s going on.

Gene: That’s great. We only have a couple of minutes left, Carissa. And we started this conversation about emerging from the pandemic and what’s changed since 2019. Obviously, and you had mentioned, about digital commerce and just your virtual tools. I mean, technology has been a huge part of a business owner’s life now. And sometimes I feel like we’re losing that personal touch. I mean, I close more deals when I talk to somebody on the phone, and I close even more deals when I literally am face-to-face from a prospect.

But the technology has taken some of that away. Number one, it’s made me more lazy. Well, I’ll just send an email or do a Zoom call, or whatever. And number two, I know it’s also created particularly with, I think, younger prospects, like please don’t call me. Don’t bother me. Just send me an email. It’s taking that personal touch away. What do you think has been that the impact of technology on the sales process, and what is your advice for business owners for sort of balancing technology and personal connections?

Carissa: Oh, such a good question. I think our whole Thank You Small Business movement is all about reinstilling a sense of pride in being a small business owner. And I always say to our businesses, if you’re trying to compete with the big brands who’ve got quadruple bajillion dollar marketing budgets, they can out buy you on SEO, and they can outrank you in everything you try, you are definitely going to fail. But where small businesses will always win is that human touch. Being authentic, being you, showing up when something goes wrong, having your heart and soul out there for everyone to see, that is what makes small business so special. I mean, that’s just why I think small business is big and the best.

And the people that we should be paying attention to, small business owners are not small and tiny and crappy. Small business owners are building businesses that have human connection that can be connected to their customers in a way that is really special and that our communities and our economy needs. So it’s a long and fascinating topic that we could spend, again, hours on.

But the short answer is, I mean, absolutely crucial that we can use technology for automation and efficiency, but we can never give up our human touch as business owners. That’s the magic, that’s the sauce. That’s the thing that keeps people coming back. And so, I mean, we’re a SaaS company. We obviously have a ton of technology in our business, but we use technology to make our human connections more efficient. And so we haven’t used technology to replace our humanity. We’ve used technology to actually allow us to increase our humanity because it’s more efficient, more organized, more things are automated. So I’m a huge believer in technology, and using it to automate and make efficient all the things that a small business owners should not be spending their time on. But there’s a lot of human things that technology will never be able to replace that is absolutely where our time should go.

Gene: Carissa Reiniger is the founder and CEO of Small Biz Silver Lining. Carissa, give me your website again.

Carissa: Just smallbizsilverlining.com.

Gene: Fantastic. Hey, you’ve been fantastic. Thank you so much for spending the time with both myself and my formidable co-host, Jon, who is also still there and hanging out in the background. Great conversations. Jon, I don’t know if you have anything to add before I take things out of here.

Jon: No. Just I think that was a really great session. And Carissa, thanks so much for spending the time with us today.

Gene: Yeah. I really appreciate-

Carissa: Thank you, guys. So happy to be here.

Gene: So that was just great. For everybody listening, if you are interested in more advice and tips and help in running your small business, please visit the Hartford Small Biz Ahead at smallbizahead.com, or sba.thehartford.com. My name is Gene Marks. On behalf of my co-host Jonathan Aidukonis, thanks very much for joining us and we will see you next time.

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