Lead With Empathy – Michelle Accardi


“Feel the fear and do it anyway,” says Michelle Accardi, President & Chief Revenue Officer at Star2Star Communications. Michelle, who has worked in half a dozen different roles in her long career at Star2Star, prides herself on being agile, and says that agility is one of the most valuable skills for aspiring sales professionals and leaders today. She always focused on the rule, lead with Empathy.

And serving as President and CRO of Star2Star is no small feat. The company has a startling 99.4% customer retention rate, has been featured on the Forbes Most Promising Companies List, and was named on the Deloitte Technology Fast 500 five times in the last six years.

Watch or listen to this episode about Lead With Empathy

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Fri, 11/20 2:09PM • 31:07 

people, sales, role, career, crm, thinking, mentor, team, marketing, salespeople, helped, life, michelle, coach, realized, important, communications, sales team, leadership role, leveraging 

Speakers of discussion about Lead With Empathy

Michelle Accardi, Christopher Smith  

Welcome to the Sales Lead Dog Podcast hosted by CRM technology and sales process expert Christopher Smith, talking with sales leaders that have separated themselves from the rest of the pack. Listen to find out how the best of the best achieve success with their team and CRM technology. And remember, unless you are the lead dog, the view never changes. 

Christopher Smith  01:24 
Welcome to Sales Lead Dog. Today, we have a guest I’m very excited to have on the show, Michelle Accardi of Star2Star Communications. Michelle, welcome to the show. 

Michelle Accardi  01:35 
Thanks for having me, Chris. 

Christopher Smith  01:37 
It’s great to have you on here. Michelle, tell us a little bit about your, yourself and your company. 

Michelle Accardi  01:43 
Sure. So I am again, Michelle Accardi. I’m the President and Chief Revenue Officer of Star2Star Communications. Star2Star is a leading communications collaboration and contact center and integration solution provider. We have been in business since 2006. And rapidly growing, we are really proud of the fact that we have one of the highest customer retention rates in the industry, people come to Star2Star and they stay with us for a very, very long time. We’re 100% channel-focused. So we sell our solution through our channel partners. And we pride ourselves on being one of the easiest and friendliest companies in the channel to do business with.  

Christopher Smith  02:34 
And I just want to clarify there you said talked about your customer retention rate. For everyone listening. It’s 99.4%. That’s pretty impressive. I’m gonna throw out some other little factoids about Star2Star communications. They have been in the Gartner Magic Quadrant seven times. They’ve been named to the Forbes most promising companies list, Deloitte Technology Fast 505 times, and The Inc 506 times. So fast growing. You guys are crushing it. That’s awesome. 

Michelle Accardi  03:13 
Thank you. 

Christopher Smith  03:14 
So, Michelle, thinking back about your entire career, which you’ve had a very impressive career. Tell us about the person who’s had the most impact on your success? 

Michelle Accardi  03:26 
Well, I’d like to say that it’s one person, but it’s really a myriad of people. I mean, it starts from having really great family support when I was a kid, to having a wonderful husband and great kids. And then in my career, I’ve been really lucky to work with some of the most talented executives, and people like the CEO of Star2Star, Norm Worthington, who, ironically enough, when I was 20 years old, gave me my first start in technology at another company that he owned, and really cut my teeth at that company. And that got acquired by CA technologies, where I like to say that I grew up, so I spent 17 years at CA and then came to start a store about eight years ago and Norm was a just a tremendous influence on my career and life. 

Christopher Smith  04:18 
That’s awesome to have someone like that in your life. That’s tremendous. What are the top three things that helped you the most in your career? 

Michelle Accardi  04:29 
Well, I will say that the things that I feel like help anyone and that are the ability to have perseverance, and resiliency because you’re not always going to have good times and in whatever you do, but if you have the grit and perseverance to see things through and the resiliency, you’ll do really well. The other, the last one I’ll say is agility, the ability to adapt. Things are always going to change. And I find that for me, you know, while I certainly have loved many of the different roles I’ve had, in my past, what has really worked for me is the fact that I wasn’t just stuck to saying, “This is all I can do.” I had adaptability. So I started out as, for example, Star2Star’s Chief Marketing Officer, helped to build our marketing framework and team and then realized, “Hey, we needed, we had some operational challenges we needed to work on.” So jumped in and became our Chief Operating Officer, and really worked on our back-end systems and processes, and then was asked to take on the presidency and chief revenue officer role. So those roles may not all seem, obviously, they’re not all the same. So the ability to be adaptable and agile, super, super important skill. 

Christopher Smith  05:49 
Did you have any hesitancy at all about shifting into the CFO role? 

Michelle Accardi  05:54 
You know, I think I did for like 30 seconds. And then it’s a it’s a field of fear and do it anyways. 

Christopher Smith  06:02 
It seems to be a theme in your career, just looking over at all the different things you’ve done, you don’t seem to have much fear. 

Michelle Accardi  06:09 
It’s true. I just think life you have to take risks, as long as they’re calculated risks. I think you just do it. 

Christopher Smith  06:17 
That’s awesome. That’s awesome. Thinking back to when you were first starting out, in this path you’re on, what do you think or what do you wish you would have been taught?  

Michelle Accardi  06:32 
Well, I wish I would have been taught that this was even an option. Frankly, I’m very lucky to be in the career that I’m in. Because when I was in college, and I really had no thought of technology as an industry, even as marketing and sales as something that I could do, I was a political science major thinking I’m going to go to law school. I also had was into theater and I was at, so sn actress. So I was like, well, I’ll do something in entertainment law. And that’s going to be what what my option is if I want to be in corporate America is law. I didn’t really realize how important sales is, to every industry, there’s not. And it’s mind boggling to me that colleges don’t, they teach marketing to some degree, but there is no course catalog, or university program that’s around selling, ethical selling. And so to me, that’s just mind-boggling, because every industry requires someone to sell something in order for you to do anything else. So, to me, I wish that I had realized much earlier, you know, how important sales as a skill is, and been taught more about it in my formative years.  

Christopher Smith  07:56 
It is mind-boggling that you can’t major in sales. 

Michelle Accardi  08:01 
Yeah, it is. 

Christopher Smith  08:02 
It’s so fundamental.  

Michelle Accardi  08:04 

Christopher Smith  08:06 
Wow. That is crazy. What’s your best advice for someone thinking about a sales career? 

Michelle Accardi  08:14 
Well, first of all, go out and take a sales role, whatever sales role you possibly can get into. Or if you can’t find your way can’t get your foot in the door to a sales role, and you’re in a different role in your in your company, asked to go on sales calls with the salespeople learn what they’re doing, see how they communicate, see what their challenges are. Because ultimately, that helps you build a repository of knowledge in your own mind so that when you can make that leap into a sales role, you sort of know what it’s about, because so much of sales is just active listening. And if you can start doing learning by going out with salespeople who are really good at that, you’ll be miles ahead when you get into your own role. 

Christopher Smith  08:58 
I love that answer. Active listening is such a critical, it’s actually one of our core values. I think it’s just so important in in really any role, but especially in sales. Do you think people are afraid to go into a sales career? 

Michelle Accardi  09:16 
I think so. I think I think people obviously see that, you know, salespeople have to take on a lot of risk, right on a monthly basis, they have a revenue target that they have to hit. And if they don’t hit it, they may not have a job. But to me, that’s the opportunity because I don’t know about you, but I don’t like feeling like I’m just a cog in the machine. And I don’t know what my value is. I love being able to every month sort of put up on a board and say this is what I and my team were able to deliver. And you know, I think when when you get good at putting up numbers if you have a month or two where the numbers don’t, people understand, but the ability to be, show value is incredible. And I would say even if for a person who’s not in sales, that would be my advice to them is make sure that you’re always putting up what your value is. It’s incredibly important. 

Christopher Smith  10:19 
Do you want your sales team to be open enough to ask for help when they’re struggling? 

Michelle Accardi  10:24 
I think it’s really important that they ask for help when they’re struggling, first of all, your bosses don’t know what you might be struggling with, if you don’t tell them. You know, I think a lot of times people think their their management is, are mind readers, or that they have or they think that they have all the answers. I’m the first to tell my sales people look, I’m not on the, you know, you’re on the front line, you have to tell me what your partners and your customers are asking for. I may or may not be able to give them what they’re asking for. But I won’t know unless you tell me. 

Christopher Smith  10:55 
Besides the lack of production, is there something you look for, to see if someone’s struggling as a sales leader? Are there clues? Or, 

Michelle Accardi  11:03 
I think, you know, I found in my career that salespeople are natural cynics, and it you know, and if I if I start to not get a level of pushback on things, or if they’re not engaged, that’s how I can tell, right? I mean, if I’m not hearing them speak up on a call. And, you know, and question me harder or, you know, that’s what I’m going to dig in and say, “You know, what’s going on? Is there something personal is there, you know, are you having a challenge?” But it’s really again, it goes back to that active listening, you just really have to see the cues within your organization of, of where engagement is happening or not. 

Christopher Smith  11:46 
Let’s talk about your transition to Chief Revenue Officer, that that’s a huge responsibility for any organization. What was your thought process? After those 30 seconds, say yes, I’m gonna do it, what were you thinking about then? 

Michelle Accardi  12:02 
Well, I’m, I am always about how do you break things down into their smallest parts in order to be able to accomplish a goal? And so for me, it was thinking about, “Okay, do I have the right team in place with the right skill sets in the right areas? Oh, gosh, I might have some gaps, how am I going to fill them?” Thinking about that, and who else I needed to pull in to help us be successful. Because no matter what role that you’re filling, it’s generally bigger than any individual, it really takes the whole team to make it successful. So for me, it was, “Do I have the right team to make me successful in this role and to make the company successful overall?” 

Christopher Smith  12:49 
So if you don’t have the right team, what do you do? What did you do? 

Michelle Accardi  12:53 
Well, you have, you have two options, you either coach up or your coach out. And so for me, if I am very transparent in my management approach, I let people know whether or not I felt like they were the right team members for what we were trying to build. And I gave them a chance in terms of to prove that they were or they weren’t, and put personal, individual action plans in place where necessary, and move people out if they needed to be moved out. And then started to also work the network that I have of really great relationships over a 24 year career to, to bring in some really great talent to help scale up my entire team. 

Christopher Smith  13:41 
That’s terrific. What do you think some of the common mistakes people transitioning into asleep sales leadership role make? 

Michelle Accardi  13:50 
I think they, I think often it’s thinking it’s all on you. It’s all on you as the individual and not asking for help. I have to tell you, partnering for me with the different executives around my business and with some of my my, my team members, and members of the different executive teams, whether that was my Chief Financial Officer and and saying, “Gosh, is there a creative way for us to help get this customer what they need that meets our targets that I’m not thinking about,” and things so not just imagining that you can do everything on your own, but pulling in the people around you to help. 

Christopher Smith  14:30 
I know you love where you’re at. But for people that are considering, “Hey, I, you know, may not be thrilled with the opportunity in front of me, I’m looking for a new opportunity.” What should they be looking for to say, “This is the role I want, if I’m going to leave and join another or organization?” 

Michelle Accardi  14:49 
Well, I’m going to guess so I’m a long time or I don’t I don’t jump around a lot. And so one of the a piece of advice first of all that my father gave me early on in my career, when I had come into some challenges, he said, you know, the grass isn’t always greener someplace else. And if it is, it’s likely because they have a problem with their septic system. So don’t be careful of what appearances are on the surface. Go ask additional questions to any of our past employees, current employees, go do your own research and remember that you are interviewing them as much as they’re interviewing you. And and don’t expect perfection anywhere. If someone’s telling you this all rainbows and unicorns in any business, that’s a red flag to me. And so it’s really about do you like the team that you’re going to work with? Can you be open, honest and transparent? Can you communicate the way you like to communicate? And will that be effective within that environment? 

Christopher Smith  15:55 
Right. What do you do to cultivate your team for leadership roles? 

Michelle Accardi  16:00 
Well, for my team, it’s certainly about where the talent rises to the top. And people who are already high performance that don’t necessarily have a leadership title, but are exhibiting like they’re helping their peers, and really taking the extra initiative, that’s going to get noticed. And when that gets noticed, that gives me an opportunity to evaluate and think about where I may have gaps that I need to fill with, with with an employee. 

Christopher Smith  16:31 
Right. What do you do, like so you have someone who’s transitioning into a leadership role, and they’re, they’re not performing as you wished? How do you approach your, your coaching in that scenario? 

Michelle Accardi  16:45 
Well, I’m extremely direct. So you know, and and I believe in sort of continuous feedback. So it’s not something where you just have one discussion. For me, it’s about “Hey, this is where you’re falling short. I need you to pick this up.” I’m also talking to them about are they happy in the role, but there, is this something that’s going to be a fit, because I think oftentimes, people get put into things or asked to take on roles that may not be, I say, it’s like a fish climbing a tree. So you know, asking again, “Is this really what you’re looking for? Is this what you want to be doing?” If not, let’s figure out where it makes the most sense for you. But I think that open conversation about here’s my expectations, how are you going to meet them, and if you don’t think you can meet them, you don’t have the skill set, or okay, what is it that you think you can do and where is your value? Again, showing where that value is. 

Christopher Smith  17:42 
Do you use third party coaches or anything external? 

Michelle Accardi  17:45 
I personally have, and in different times in our in our history of Star2Star we have as well. 

Christopher Smith  17:52 
Yeah. So you’ve, have you ever had a personal coach or mentor that’s helped you a lot? 

Michelle Accardi  17:56 
Oh, absolutely. I have a woman by the name of Joanne Muready, who is a personal friend, but has become a, just a tremendous mentor to me. And I’ve also leveraged a woman named Katie Temple, who’s also done a lot of great coaching with me. 

Christopher Smith  18:15 
That’s awesome. Do you coach anybody or mentor anyone? 

Michelle Accardi  18:18 
I do. I have a few people whom I work with very closely. And, and again, it’s really comes out of a, I’ll say, a trust relationship, right? I’ll be working with someone and they’ll say, “Hey, would you mind mentoring me or giving me feedback?” And my answer is always a resounding yes. As long as the person’s willing to put in the work and isn’t afraid of feedback and isn’t afraid to give feedback because I don’t think coaching relationships can ever be one way. You really can learn from just about anyone. If you’re open to it. 

Christopher Smith  18:56 
Is there a right way for someone to approach to say, “Hey, could you be my mentor?” Or wrong way, I guess is maybe a better question. 

Michelle Accardi  19:04 
Well, I think if if, if you think that someone’s, if you just go to someone that you don’t have a relationship with, and you haven’t built that trust with, I think that’s, that’s hard. Because you don’t know where to start. I wouldn’t know where to start if it’s someone who I haven’t had some business dealings with. So I would always suggest that anyone that you’re going to go to to be a mentor, be someone that has some interaction with you and has could at least start from a place of perspective. 

Christopher Smith  19:36 
Is there something that you used to believe, you know, when you got into your role as a sales leader, you went into it thinking, “Hey, I know this is right,” but now that you’ve been in it for a while, you realize, “I was flat out wrong?” 

Michelle Accardi  19:52 
Yes, I think I think too, I think there are a lot of areas where I might have had a perspective coming in and it you know, it, it and I was wrong, I don’t know that I can think of specifically one in this in this instance. But I will say the thing that I’ve learned is to take a step back and stop thinking about how you see something, but to try to think about how the person you’re trying to sell to, or coach or manager, how, what their perspective is, you know, put on those shoes versus your own, and stop with the story in your own head, because you have to sort of tell yourself a different story sometimes. And remember that everybody’s got a different story going on in the back of their, their minds, sort of play multiple possibilities. 

Christopher Smith  20:41 
That’s awesome. So it sounds like lead with empathy is a pretty important aspect of how you work with people. Is that correct? 

Michelle Accardi  20:49 
Absolutely. I try, at least I try to be. 

Christopher Smith  20:55 
How did that develop for you? Or did you always have that? 

Michelle Accardi  20:58 
I think that was fairly innate, in me, but I also had some time periods of challenge in my life at different at different stages. And, you know, I can tell you as a child, and I was pretty precocious, and I didn’t have a lot of kids who just loved me when I would, because I was very direct. And, you know, children don’t tend to know how to process some of that. And as I matured, and I found in some instances that, you know, that that could be misinterpreted. And then as I got into my 20s, and into a relationship, I was I, I was about to be married. And my fiance was in a terrible accident, broke his neck, and became a vent-dependent quadriplegic. So that was the first time I was working in corporate America at CA at the time. And that was the first time that I had really thought I, you know, I had thought about what my life would be, like, by myself without Yeah. And had to make some very tough choices. So all of a sudden, you know, I could start to see how other people might have, make difference. You know, I was all work, work, work, work, work. But then when you have something like that, that happens and jolt you, you realize, “Oh, my God, you know, people have lives outside of their offices, they have things that they’re dealing with.” So that was the first time that that and that was I was in my late 20s. At the time when that happened. In my 30s you know, that that certainly was a cathartic moment, I’ll say, you know, and, and when I got into my 30s, and I, you know, got married again, and I was working, I’ve got back into my work, work, work, work, work mode. And I woke up basically, when I was about 38, or 39, and realized, gosh, something else is missing here in my life. And I realized I hadn’t married the right partner, and I decided to get divorced and met someone else and got married. And now have I have six children, three, three stepchildren, and a foster, foster son and two twin toddlers, all within the last five years. So I’ve got six kids, if that doesn’t teach you lead with empathy, I don’t know what will. 

Christopher Smith  23:25 
Oh, I hear you. I hear you. Tell us about your success habits? 

Michelle Accardi  23:33 
Well, again, I think I’m just being open to things is how I make success happen, right? I don’t say no, a lot. And when I say no, it’s generally “No, but you know, this is what I can do.” And I just think being open, I think a lot of people close themselves off to what opportunities and success can be. Because there, there’s just this innate fear. And I just step into that. And I, I just think people need to sort of step forward and not be so afraid, because I find the things that we’re afraid of aren’t the things that happen anyways. And again, you know, maybe my life experiences, the tragedies and the and the, you know, the needing to be resilient in personal relationships, etc, has caused me to be less fearful because I know that there’s good things on the other side. But that’s what’s made me successful. 

Christopher Smith  24:33 
When it comes to, you know, a key part of being a leader is keeping your team focused and motivated. What are some of the tips you have for people around in that area? 

Michelle Accardi  24:45 
Well, you know, I really prescribe to an agile methodology. I believe that doing sort of stand up calls with your teams every day, even if it’s, you know, 15 minutes, just sort of temperature checks, are we working on the right deals, are there obstacles you can take out of the way? Being a help, and always being a service to your team. I think that is what real leadership is. And that will motivate people the most. The only caution I have for you is don’t always give the answer or the solution. That’s something in my career I’ve had, you know, I tend to jump forward want to help solve every problem for every person. And I’ve learned I’m, I should say, I am learning to step back from that, and letting people solve some of their own problems. But being there as a guidepost for them, what when, if they want to talk about those things. 

Christopher Smith  25:45 
I can relate to you on that one, I have to pull my reins, my persona back and say, woah, give them a chance. Let them do it. Let’s shift topics here and let’s talk about CRM. I always start this off with the same question when it comes to CRM: Do you love it? Or do you hate it? 

Michelle Accardi  26:05 
Well, it is a love and hate relationship. I think on one end, I love, I love the fact that I can get really good visibility into my business and what’s going to happen, what’s happening. And what I hate about CRM is it’s still too manual of a process with people having to you know, put information in and I think that’s getting better. There’s more automation that’s happening in the back end of different CRMs. But that’s, that is still tends to be the challenge. 

Christopher Smith  26:34 
Do you think that’s your biggest struggle, or the biggest struggle most people have? 

Michelle Accardi  26:39 
I think that is probably one of the biggest struggles because that’s, you know, that’s where the adoption struggle of CRM is, right, is in getting people to use it. Now, I’m very lucky that it’s the corner, CRM is the cornerstone of most of what we do at Star2Star, you know, it, quote doesn’t come in, an order doesn’t get processed, a support ticket doesn’t get done unless we’re leveraging our CRM. So people are, I want to say forced into adoption within our environment. But I would rather that be a, “Oh gosh, it’s great.” I want to I want to be leveraging a CRM to and and I think in many cases, again, we focused a lot on usability in our CRM, to make it so it’s not so painful. But again, in my vast career, whether you know, regardless of what CRM tool people are using, and it could always be simpler, it can always be, it just if, if I picked up the phone, I want it to be there, the information to be there. I don’t want to have to type in a note. If I sent an email, if I went into another marketing automation system, I want it to be there. I want my emails to be there. I want my calendar to be there. I don’t want to have to do in multiple systems. 

Christopher Smith  28:02 
Right, right. When it comes to you, we’re talking about user adoption, and thinking back, you’ve got a, like you said, a very strong level of experience when it comes to this. What do you think works better? Or how do you approach user adoption? Do you use a carrot? Do you use a stick? What do you do? 

Michelle Accardi  28:23 
Well, I think you have to do both. I don’t think again, it’s like anything else in life. It’s it’s a bit of moderation of both.Certainly you the carrot, first of all has to be making it as usable as possible and giving people access to data that helps them with making decisions and drive. And that can’t just be at the management level, it has to be at the rep level. So I think that that’s, that’s really, really critically important as the carrot. And then the stick is you have to use that because if you don’t, then you may not, you know, keep sales. As long as you still have to put input information into a CRM, you’re going to have to use a stick. If, If CRM matures, the way that I think that industry is going, hopefully that will become less and less over time. But for right now, I think there is a little bit of stick-ness there. 

Christopher Smith  29:14 
Right, right. Because you have had in the past, you know, the head responsibility for marketing and now you’re CRO, what advice would you give to any CMOS that may be listening on what they should be doing to better support sales team? 

Michelle Accardi  29:34 
Well, I think first of all, I think you used really good terminology, better support sales team, I think marketing should see themselves as a as a support center of sales and end at the customer. And so I think if you’re looking at what types of marketing automation tools and such to use, you know, make sure it’s going to integrate well to the sales tools that are in place are going to be used. Because if you’re using something that can’t integrate, then getting a 360 view is going to become very, very difficult, and you’re not gonna get the full value that you could. 

Christopher Smith  30:08 
Right. That’s great. But we are coming up on our time here. So I really, this has been terrific talking to you. It’s been absolutely terrific. If people want to get in touch with you, what’s the best way for them to reach out and connect with you? 

Michelle Accardi  30:24 
Sure. So you can reach out to me at [email protected]. I’d love to get an email from you. And I’ll, would would love to talk more. 

Christopher Smith  30:35 
Should they preface it in any way or, so it stands out? 

Michelle Accardi  30:39 
But well, if they if they want to preface this podcast, I would. That would be wonderful. 

Christopher Smith  30:46 
Sales Lead Dog. That’s awesome. And you’re on LinkedIn as well.  

Michelle Accardi  30:50 

Christopher Smith  30:50 
They can get to you through there. That’s awesome. Michelle, thank you so much for being on Sales Lead Dog. It’s been terrific talking with you. 

Michelle Accardi  30:58 
It’s been great, Chris. Thanks for having me. 

As we end this discussion on Sales Lead Dog, be sure to subscribe to catch all our episodes on social media. Follow us on LinkedIn, Facebook, and Instagram. Watch the videos on YouTube, and you can also find our episodes on our website at Empellorcrm.com/salesleaddog. Sales Lead Dog is supported by Empellor CRM, delivering objectively better CRM for business guaranteed. 


  • “Feel the fear and do it anyways.” (5:59-6:02)
  • “So much of sales is just active listening” (8:46-8:50)
  • “Just being open to things is how I make success happen. I don’t say no often, and when I do it’s generally: ‘No, but…’” (23:33-23:46)


Star2Star Communications Website
Star2Star Communications Partner Website
Star2Star Communications Demo Website
Michelle Accardi LinkedIn
Empellor CRM Website
Empellor CRM LinkedIn

Podcast production and show notes provided by FIRESIDE Marketing


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