Sales Pipeline Radio, Episode 305: Q & A with Russell Benaroya @


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If you’re not already subscribed to Sales Pipeline Radio, or listening live every Thursday at 11:30 a.m Pacific on LinkedIn (also on demand) you can find the transcription and recording here on the blog every Monday morning.  The show is less than 30 minutes, fast-paced and full of actionable advice, best practices and more for B2B sales & marketing professionals.

We cover a wide range of topics, with a focus on sales development and inside sales priorities. You can subscribe right at Sales Pipeline Radio and/or listen to full recordings of past shows everywhere you listen to podcasts! Spotify,  iTunesBlubrry, Google Play, iHeartRADIO, Stitcher and now on Amazon music.  You can even ask Siri, Alexa and Google!

This week’s show is called “Get Inside the Mind of your CFO”.  My guest is Russell Benaroya, Co-Founder and Partner at Stride.

Join us for a great conversation about speaking finance as a marketer, the importance of the sales role in retention, how you are successful as a leader first and much more.

Listen in now, read below, or watch the video!

Matt:     All right. Well, welcome everyone. To another episode of Sales Pipeline Radio. I am your host, Matt Heinz, excited to have you all here. Our very first episode of 2022. Very excited for this year. I feel like we are recording this on Thursday, this is my fourth workday of the year. I do not know about you Russell, but I feel like Monday, we gave everybody last week off and it was awesome. My new yoga move is me, dad splayed on the couch half napping, half watching college football. That was last week. Monday, the RPMs were not firing the way I need them to. But today I feel like between a couple of days of work and a little bit of coffee, we are getting there. But thank everyone for joining us midweek. If you are following us on LinkedIn Live and joining us in the middle of your workday, thanks very much for joining. For 15-20 minutes or so each episode we are featuring each week some of the best and brightest minds in B2B sales and marketing to make all of you better, more successful, more productive, not just as professionals, but as humans. If you like what you are hearing and watching here today, every episode, over 300 episodes of Sales Pipeline Radio, all available past, present, future at We have a lot to cover today, Russell. Very excited to have joining us today on Sales Pipeline Radio, Russell Benaroya, who wears many hats. He is the Co-founder and Partner of Stride. He is a coach. He is a speaker. He is an author. He is a world traveler. What did I miss?

Russell:    That’s enough. That is enough. Thank you. So, great to be here by the way.

Matt:     Thanks for being our first guest of the year and I meant this, we have a lot we could cover here. I like to say the longer I live and the more mistakes I make, and there is a lot that you have learned over time. Not just relative to sales and marketing, I want to talk about finance, but also your book One Life to Lead which talks about, driving success, business success, and life success through better life design. So, I want to get to that as well, even with our audience being mostly B2B sales and marketing folks. I know you have lived that for years in your role at Stride, you are playing a direct sales role, you are carrying a bag. So, just before we get into it, just quick introduce yourself, your background and what brought you here.

Russell:    Yeah, well again, first of all love being on the show. Let us jump in, let us add value. Today, I am the Co-founder and Partner at a company called Stride Services. We provide back-office bookkeeping, accounting, and CFO advisory services primarily to marketing agencies and outsource IT services firms. What I find about those two businesses is they happen to be in the exact same business that we are, they are selling to businesses on an outsourced basis. They are tracking a lot of the same metrics that we track as an outsource provider. So, there is a lot of kindred spirit that comes from that. We have a team of about forty people. We serve a hundred clients throughout the United States. So, that is a little bit about me professionally and yes, Matt as you mentioned, I did publish a book in October, which really has ended up being a field guide for me. The book is titled One Life to Lead and I call it a field guide because it’s not one of those books where it’s like, oh, Hey everybody, I figured everything out. You should read the book. You will figure it out too. It is more like, oh, these are the patterns of how I operate in my life, and this is how they have or have not served me in business. I need to keep referencing that book because it is hard to break tough habits.

Matt:     Oh yeah. No, I highly recommend the book. We are going to get more into that One Life to Lead. And the question that I know you have associated with a book that it continued to not me, is until you can lead yourself, how can you expect to lead and manage others? And that is not an entrepreneur question, that is not a CEO question. You do not even have to have direct reports, if you are trying to coordinate efforts among us or people, if you have children, if you have a partner or spouse, this actually is highly relevant. But I wanted to start with our guest today, Russell Benaroya, talking about the finance side because you mentioned sort of your focus is on sort of marketing agencies. And I mean we are good at the sales and marketing consulting, but not always good at the back end. There is an analogy there for in-house marketers as well, right? Who are good at the marketing, good at creative, good at campaigns, even good at designing demand generation programs, but do not always know how to speak the language of finance. Talk a little bit about that gap. What you have seen in your experience with in-house marketers and marketing agencies and what are some of the keys to bridging that gap? Not so that we do not need marketers to know everything about finance, but there is a basic foundation that needs to be in place.

Russell: Yeah. And just so I am clear because I want to bifurcate is it sales and marketing talking about finance internally, so that they are attuned to the economics of the organization that they are part of and or talking about finance as it relates to client sales and integrating finance related conversation in the sales process?

Matt:     Yes. Yeah, I think all of that applies, right?
No matter which conversation you are having to understand the economic component of that story is really critical. And I do not know that I mean I speak for myself like I do not have an MBA. I do not have a finance background. It was well late in my career that I started to feel like I understood even the basics of finance in a way that I could not just grow a business, but also have that conversation external. No matter which conversation you are having to understand the economic component of that story is really critical. And I do not know that I mean I speak for myself like I do not have an MBA. I do not have a finance background. It was well late in my career that I started to feel like I understood even the basics of finance in a way that I could not just grow a business, but also have that conversation external.

Russell: Where I have felt the most rewarded by sales and marketing people in my businesses and certainly what I see in agencies is when there is a curiosity to understand things like customer acquisition cost. How much does it actually cost us to acquire a customer or payback period? How quickly do we recover that cost when I sign a new client or lifetime value? How long is this client expected to stay on board for us to be successful and profitable as an organization? And when you have a finance partner that you can go and ask those questions to, that’s super powerful in helping you orient as a salesperson to where you spend your time, what types of prospects you’re willing to engage with, how you price that service, and maybe most important what is the role of the salesperson in lifetime value, right? Retention is so important, does sales have a role in that? Well listen if I understand the economics and I am mapping my compensation to those economics, it is such a beautiful symmetry that often fails because sales doesn’t know the right questions to ask and often finance does not have the answers to those questions.

Matt:     Right. I love the way you characterize that. I had a friend of mine, Andy Crestodina, who runs a web marketing firm in Chicago. He said, “the easier the metric is that you can report on, the less impactful it is.” And I was thinking about that as you were mentioning some of these finance measures of like customer acquisition costs. You ask a lot of CFOs, what is my all-in acquisition cost? That is actually a really hard calculation to come up with because it is not just what you are doing in marketing, it is what you are doing in sales and who else is involved in getting that sales deal across the line. But the key here is not necessarily to have the right answer, it is to know that that is an answer you need to seek. And that is a metric as a marketer, as a go to market, as a sales leader, as a member of the revenue team, you need to understand it is important. So, there is a bit of  an intent component here. There is a port of just a culture around knowing and understanding and valuing that, that I think gets you closer to where the CFO is, so that there is a level of trust and alignment there.

Russell: It is awareness, it is connection to the mountain that we are collectively aiming to climb together, and not necessarily knowing all the answers, but at least knowing what the important questions are to ask that helps make my position more strategic than just transactional. On the other side of the equation, when you are guiding clients in a sales process, what is the role of finance? I usually use this very simple four quadrant mechanic and it works something like this. Client has a problem or goal that they are trying to accomplish. We have to be unambiguous together with that prospect in understanding what that problem or goal is number one. Number two, they have faced challenges or obstacles in achieving that objective and we want to very clear with them the prospect on what are those challenges.
And here’s where the finance comes in, number three, if we were able to overcome those challenges, what would be the value of overcoming those challenges and the work of a savvy go to market marketing and or salesperson is to help the prospect calculate that value of overcoming the challenges and that value could be in, well I’m going to free up my time to sell more business. Oh, really? You are going to sell more business. Let us talk about that. Like how many more deals would you sign? Oh, how profitable are those deals? Like you are really helping the client, or the prospect think about their financial impact of you solving their problem. And then the fourth quadrant is okay, so if you are recognizing that there is a lot of value to be created, what is the next step that you are willing to commit to on this journey with me to further or toward that objective?

Matt:     How important is precision in those answers? I mean I think about this relative to the idea of the proverbial ROI calculator, where you say, oh, like here is how much you could potentially save versus how much you could potentially make. And the variables that go into a lot of ROI calculators, like too often we get of the weeds of oh, is that really valuable? Is that really accurate? Is that really precise? To me it is less about being precise and more about getting in the ballpark, right? If I can take something from being an obtuse benefit to at least a band of benefit, right? To say, okay, like let us say the low end of this if that happens, is that still useful? And do we agree these are the right variables to go into that? But even that level of halfway math, right? It gets you in the right direction and allows you to get to quantifiable benefits that your prospect CFO can appreciate and understand as well.

Russell: Totally, like this is where your EQ comes into play because it is not about being super analytical in that inquiry. It is about meeting the prospect where they are at psychologically in what is the relief that they are trying to achieve. Some of the relief could be, hey, I just want to spend more time with my family, right? And that is super valuable to them, and you do not necessarily need to quantify it. It is just helping them see that you are going to unlock whatever they perceive the value to be. And what I find is prospects love when you are curious in wanting to understand what value looks like, even if it is not perfectly quantified. Just the fact that you are asking that without trying to close a deal, you are really curious is so awesome because listen, you don’t want to sign a client for which they can’t at some level calculate value.

Matt:     Well and if you are selling something that you have defined and valued one way and they are buying it based on some different calculation that you cannot stand up to, you are not positioned, your product or service cannot deliver, you are setting everybody up for failure at that point, right? So, defining that upfront, defining it and talking about those as values, more I than having the precise number at the end of the equation. Talking on Sales Pipeline Radio with Russell Benaroya, he is a Co-Founder and Partner at Stride. Check them out stride.service, great content, doing some really great work. Before we get into life design, my follow up question is around sales and marketing professionals listening to this, whether they are early in their crew career or even CMOs, senior marketing leaders who just do not feel like they really understand finance. I have been there. I quite frankly I am still there. It is a journey, not a destination, but there can be a level of just kind of apprehension around who do I ask? Where do I learn? I do not necessarily want to admit that I do not understand what different versions of margin mean or what margin means in general versus gross versus. There are all kinds of financial literacy that marketers do not necessarily have. Who should they ask? Where should they learn? Where are some safe places and ways that sales and marketing professionals can start to increase, improve their financial literacy?

Russell: Yeah, great question. And I know you did tee this up for me, but about a year and a half ago, I published an eBook titled Free Yourself to Work On Your Business: A Journey Into Unit Economics. Free Yourself to Work On Your Business, we can put it in the show notes. But the reason that eBook is useful is it is specifically designed in an approachable way help professionals understand things like, oh, what is EBITDA margin? How is profit calculated and most important, what is gross margin on a customer, right? Because again, customer level profitability is the most important thing. That is the value that you create in your business. And so, I architected it so that it is very understandable, very approachable. And other than that, I mean there is so many approachable resources online to ask what sounds like simple questions, like I should know that, but no, you should not necessarily know that. Just be willing and curious to get a bit more informed. I tried to create one way to do it. There are a lot of ways.

Matt:     Yes, and we will put a link to that eBook in our show notes for sure. Yeah, I would also add on to that no matter where you are at, just go to your CFO and just start saying, just asking questions, like what are the metrics that are most important to you? What are the financial metrics that are most important to you when you go to the Board, when you have your quarterly earnings calls, when you report to your peers, are the financial metrics that you would like to see from marketing moving forward? And I will guarantee you that a good CFO is not going to see this as, oh my God, my CMO does not understand this. Oh, my marketing. They are going to be like, thank God you are finally asking this question. I am so excited to sit down with you and make sure that we are aligned around this because even if you cannot precisely measure all that, the idea that you will start to make priority and initiative and budget decisions based on the answers to those questions is a very exciting thing your CFO and your CEO and your board.

Russell: Still comforting.

Matt:     I want to shift and talk about life design. So, your book, One Life to Lead talks about making better business success through life design and through deciding how do you lead. How are you successful as a leader first? How are you leading yourself before you can lead others? There are so many things that when I think of you, I think of your expertise and experience around so many things. Why this topic? Where did the passion come from to create this book first?

Russell: The passion really originated from a snowy drive in 2016, coming back from a ski trip in Bend, Oregon, where my wife and I were listening to a Tony Robbins podcast, and it triggered a question for me that created a moment in my life. And the question when I turned down the radio and I asked my wife, I said, “where do we want to be in five to 10 years?” Why haven’t we ever talked about that like in this critical questioning way? And she kept the radio dialed down and she looked at me and said, “oh, it’s because it’s never really been about us. It has been about you. You are an entrepreneur. We’ve just kind of been along for the ride.” And interestingly enough, that moment began a journey that ultimately crescendoed in my family and I moving abroad for a year. But really more than anything else that that was a metaphor for, hey, let us get in control of the life that we are trying to create rather than having a life created by others to us, right? We tend to put ourselves in our own cages of self-limiting beliefs, when we actually have a lot of opportunity, but we are not exercising it. And so, I tried to put my life on a new trajectory. We moved abroad. And when I was finally able to step back and observe some of my own patterns and behaviors that weren’t necessarily serving me, I could see that the impact that I was having on the businesses that I was leading was not a circumstance of the business as I was leading, it was a circumstance of the way that I was approaching leading the business. And so, the phrase here is how you lead your life is how you lead your business. And where we all really want to get to, I think I would challenge everybody to want to get to this place of freedom, right?

We all define freedom a different way, but for salespeople and marketing people and entrepreneurs, we want to be free. Free might be making the impact that we want in the world, it might be spending time with the customers that we want, it might be financially free, but many of us are in this state of what I would call frazzled, right? And we want to move along is journey from frazzled to freedom and much of that journey is a function of how we are approaching the life we are creating. And so, what I determined is that there are about five areas in my life that were creating the greatest obstacles. So, one was shall I go through those Matt?

Matt:     Yes, let us do it.

Russell: Okay. Great. So, one was grounding stories with facts. We live in a world of storytelling and certainly as marketers and salespeople, we spend a lot of time spinning stories, but in our lives, we sometimes spin stories that are not really good for us, stories about a thing that happened or a thing that has not happened yet. And, oh my gosh, if it doesn’t happen, what’s going to happen to me? And it is all drama, but it is not grounded in low. What are the facts? Ground stories with facts, number one. Number two, establish your principles. We all operate with some code of integrity, but most of us have not written down those principles as the non-negotiables for which we use to make decisions. And when we do not have good principles written down, we end up succumbing to other people’s desires of us and often compromise decision making because we do not have our own principles, that’s number two. Number three is being attuned to where you get energy. Energy from certain people or energy from your job or energy from your geography. And when you know what gives you energy and what drains your energy, and you are open to talking about it, you can move to what it is that gives and drains your energy, number three. Number four is get and stay in your genius zone. I spent a lot of time outside of the thing that I was uniquely qualified to do. And when I am outside of my genius zone, I am stepping on other people’s toes and I am suboptimized. Own your genius zone, strive to stay in it, acknowledge when you are out of it, and plan to get more time inside of it, number four. Number five is execute and take action. Having the courage to of leap and know in all areas of your life, you have always figured it out. Why would this time be any different? But for some reason, as we get a little bit older, we get a little bit more successful, we become more risk averse. We do not want to leap because we are not sure what is going to happen. We do not want to run the experiment. And so, we end up retreating to safety. So, that the book really lays out those five steps, punctuated with stories from other entrepreneurs and a bunch of exercises to help people get in control of architecting a life by them.

Matt:     It is such a great book and I think especially here at the beginning of the year, I think sometimes we treat New Year’s resolutions in the beginning of January, this annual opportunity to reset and recommit to things. No, you can do it this afternoon. You can do it tomorrow. You can do it any day you want, but it is more than just clearing your calendar, more than just tactical things. But the five areas you just pointed out, those have been instrumental in my continued journey to try to better lead myself, better be responsible for myself. And I have directly noticed the more I feel in control and feel comfortable and feel successful there, I am a better father, I am a better husband, I am a better leader. And it is very much a journey, and it is not just one directional it is forwards and backwards. But we got to be intentional about it. So, highly recommend this book, One Life to Lead. You can learn more about it at Go there, you can learn more about the book, click on the blog link on You will see many of the interviews Russell has done with other entrepreneurs as part of their journey as well. Little over today, but worth it. Russell, thank you so much for joining us today.

Russell: Oh my gosh, Matt. I have been looking forward to this, such a pleasure. You have a great show and excited to reach your audience. Thank you.

Matt:     Awesome. Russell Benaroya again, Co-Founder Partner of Stride. Stride Services.

Matt:     One Life to Lead: Business Success Through Better Life Design. Thank you everyone for joining us today. First episode of the year Sales Pipeline Radio, we will be here each week, next week, every week at 11:30 Pacific on Thursdays. My name is Matt Heinz. Thanks, joining us again. We will see you next week on another episode of Sales Pipeline Radio.

Sales Pipeline Radio is produced by Heinz Marketing.

I interview the best and brightest minds in sales and Marketing.  If you would like to be a guest on Sales Pipeline Radio send an email to [email protected]. For sponsorship opportunities, contact [email protected] 

Republished with author's permission from original post.

Matt Heinz
Prolific author and nationally recognized, award-winning blogger, Matt Heinz is President and Founder of Heinz Marketing with 20 years of marketing, business development and sales experience from a variety of organizations and industries. He is a dynamic speaker, memorable not only for his keen insight and humor, but his actionable and motivating takeaways.Matt’s career focuses on consistently delivering measurable results with greater sales, revenue growth, product success and customer loyalty.


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