Ep. 97 – Driving Symbiotic Outcomes in High-Stakes Sales with Josh Hoffman - Part 1
Ep. 97 – Driving Symbiotic Outcomes in High-Stakes Sales with Josh Hoffman - Part 1  
Podcast: Selling Intelligence (formerly Selling the Cloud)
Published On: Tue Oct 14 2025
Description: In this episode of Selling the Cloud, we sit down with Josh Hoffman, a seasoned go-to-market leader who has guided sales transformations at Dell, Avaya, Poly, Datto, and now ControlCase. Known for his “sell-with” philosophy, Josh shares what it really means to drive symbiotic outcomes, where sellers, partners, and customers win together.He unpacks lessons from decades of leading in high-stakes environments, including mergers, market pivots, and rapid scale, and makes the case for consistency, humility, and emotional intelligence in modern sales leadership. From shifting away from zero-sum thinking to building customer-aligned mutual action plans, this episode is a masterclass in outcome-based selling and team-driven success.What You’ll LearnSell-With vs. Sell-To: Why Josh believes the most successful sellers don’t “close deals”, they solve problems alongside the customer.How to Build Mutual Action Plans: Practical ways to bring partners and clients to the same side of the table from day one.The Role of AI in Sales Coaching: How Josh’s teams are using AI for prompt writing, context synthesis, and deal prep, without losing the human element.Coaching Through Change: Why consistency, not charisma, helps teams thrive through high-pressure acquisitions and pivots.From Manufacturing to CRO: Josh’s story of going from putting screws in motherboards at Dell to building global GTM teams, and what shaped him along the way.Key TopicsTransforming sales cultures from transactional to consultativeTeaching sellers to ask better questions, and when to talk lessWhy top sales leaders reduce the distance between themselves and the AECoaching through ambiguity and building career-defining momentsWhy consistent behavior builds trust in times of changeUsing AI to augment, not replace, frontline coaching and prepGuest Spotlight: Josh HoffmanJosh Hoffman is the Chief Revenue Officer at ControlCase and a proven sales leader with over two decades of experience building high-performance teams. With a track record of leading in moments of transformation, Josh is passionate about coaching sellers to exceed what they thought was possible, through shared success, customer obsession, and scalable systems of growth.Resources & MentionsBook: The Qualified Sales Leader by John McMahonBook: FYI: For Your Improvement by Korn FerryCompany: ControlCase (compliance & audit automation)AI Tool Mention: Grammarly, prompt engineeringLeadership Inspiration: Todd Abbott, Mike Jenner, Mark Anderson🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.Mark Petruzzi (00:34)Welcome to today's episode of Selling the Cloud podcast. We're excited to welcome Josh Hoffman. Josh has built his career leading sales and go-to-market strategies at some of the most iconic companies in tech. He started in Dell's early inside sales organization and went on to senior leadership roles at Avaya, Poly and Datto, often stepping in during times of transformation.Along the way, Josh has become known for his self philosophy and his passion for helping people build careers and outcomes they once thought were completely out of reach. At the heart of that philosophy is symbiotic growth. The idea that sellers and customers succeed together. Instead of pushing a deal across the line, Josh frames selling as sitting on the same side of the table with a customer.tackling the problem on the other side and building shared wins that last. We'll cover four themes today. The sell with era that we feel like we're in today, lessons from a career across Dell, Avaya, Poly and Dotto, leading times in a time of change. We certainly have that world amongst us today. And the future of go-to-market in the age of AI and ecosystems.John, us again, welcome to Selling the Cloud.Joshua Hoffman (01:47)Thank you so much for having me here today, Mark. I'm so appreciative of you and the team and all that you've done to help us all grow. And so it's a pleasure to be here.Mark Petruzzi (01:56)Excellent, thanks again. All right, Josh, so you often talk about creating symbiosis in selling. What does a sell with model look like in practice?Joshua Hoffman (02:05)That's a great question. For me, it's about helping people understand that we're not here to pick up a PO. We're not here to get a credit card number. We're here to solve something together. We're here to deliver something that's gonna help all of the organizations be better off. And in a lot of those environments, I've worked in direct sales, I've worked in partner sales, and I've worked in hybrid sales. They all have a slightly different meaning.But when I think about it the most, you described it at the beginning. It's about making sure that all of us that are solving the problem together, we're all on one side of the table. Sales is not combat. Giving somebody a product or a service that they need is helping them be successful. And if we all focus on what that means, if we're all laser focused on the outcome that we're trying to deliver, then we're all in it together. We're all with each other in that.KK Anderson (02:56)could not agree with you more, Josh. And my question is, so how do you help your sellers make that shift from quota-driven, transactional, I need to educate, I want to talk about my product mindset to one where they are the problem solver sitting on the same side of the table. How do you do that?Joshua Hoffman (03:16)Yeah, Kristen, thanks for the question. I appreciate it. There's a couple of things. First of all, I do want sellers to be quota driven. I do want them to be successful. They have goals to meet also. And part of leading a team is making sure that everybody succeeds company, people, internal, external companies that you're working with. And so there is definitely a part of me as a leader of revenue that says that we need to make sure that they are quota driven.But the shift comes when you help people understand that the more that they listen and the more that they ask questions, the better they're going to understand why are they in the room today? ⁓ Why are they a part of this conversation? And if you can get them into that mode where they care in a way that allows them to open themselves up to different possibilities. And I know that's a very EQ set of statements.but you want them to be sitting there thinking that I'm here to help somebody else succeed today. And the way that I phrase it, for example, with partners is if I focus 100 % on your growth, then it's going to work out. If you grow, we grow. If you succeed, we succeed. And getting that mindset to take place.It's a big shift for people, especially people that have come out of a transactional sales environment or have come out of something that's maybe a little bit more cutthroat. I live and breathe this idea that consultative sell with strategies make a difference. they not only build a better business for the client, for us, for the partner, it does help us build a better world. And that might sound a little bit kind of hippie-ish.But the reality is that I do want the world to be better. And if we all work together, it's going to be.KK Anderson (04:56)It reminds me of, you said hippie-ish, I love that, my Austin, keep Austin weird roots, but one of the things, one of the tactics that I've used in my 20 years of sales training has been, as soon as you feel the compulsion to start talking about your product, ask another question.Joshua Hoffman (05:11)That's a really interesting way of phrasing it. know, Kristin, I've had the benefit of seeing the outcome of the good work that you provide and how you help enable other people to get better and grow. And that goes a long way. It's really well put.Mark Petruzzi (05:25)And with both of those examples, we're hitting on things that I hold near and dear to my heart. And we're living in a world that's not really built that way anymore. Everybody kind of looks at things. We look at it in politics, for one, that you have to win. And then you really have to make somebody else lose, too. And that's not the way I look at it.I've always been someone who's used the term win-win and that's something I always want to do. And then it's nothing in what I do, at least in sales. Maybe there are parts of sales that is closer to a zero-sum game. But when you're looking at the value you can bring for clients and the return on investments and the business cases you can build for your clients, that's not zero-sum. You really can look at it from a solution standpoint.and allow that to really hit home and work to your advantage, not against you. So we love stories here at Selling the Cloud. So can you give us an example, a story, where this approach has created an outcome that wouldn't have been possible in a traditional sell-to model or just a mindset of win-lose?Joshua Hoffman (06:36)I have a lot of stories and so I'm going to generalize just a little bit so I don't name names, but I'm going to use an example where there was a partner engaged as well, where we were the provider of the product or service, but there was a partner that had a client that was involved. And the way that things had traditionally operated at this organization is that the sellers were consistently focused on selling to the partners.You've got to buy this. You've got to buy this. And then you got to go sell it. You've got to go figure it out. You need to internalize and ingest all this information and data. And you got to figure out how to go make it happen. And we changed our approach dramatically. One of the first things we did is we actually brought partner salespeople and SEs into our new hire training. And we said, you're part of the team. we're not trying to sell to you.And sure, you might actually be the ones writing the PO for it, but we're in this together. And so we're going to enable you the same way that we enable our people. We're going to speak the same language. We're going to talk about the same benefits. We're going to learn together. We're going to grow together. And as that shift took place and people started to see ⁓ their cohorts that were on the other side of the table before, I'm trying to get a PO from you.Now they're saying, OK, we're on the same side of the table right now. We're in this together. And once we had crossed that chasm, we now had the opportunity to say, you know what? There's another chasm to go across. Now let's get the customer to be a part of this. Let's get the client to be a part of this. Let's put them on the same side of the table with us. And let's take the approach that we're here to deliver an outcome. And we're going to co-strategize. I'm going to use the word co- bunch right now.We're going to co-strategize, we're going to co-create, we're going to co-decide what the solution is. And when we get to the end of the line, we're actually sitting in that mode of getting a PO, getting a check, getting a credit card, whatever it might be, given the different organization. We're not closing a sale. We're solving a problem. And that became a constant driving force.in the approaches that, that candidly I was able to take, but really organizationally that we were able to take, because we're a team. It's not just me. ⁓ Whether it was at Palo Alto networks, whether it was at Avaya, whether it was at Datto, Poly, whether it's here at Control Case, where we view things the same way. We're here to solve a problem. We're here to create an opportunity. We're here to create an outcome together.and having a collaborative environment makes all the difference in the world.KK Anderson (09:08)win together, right? And I know exactly who you were talking about, Josh. And you're right, you get to a point where all of a sudden your customer is calling you and saying, hey, I've got this client call. Can you help me prepare for it? And then you're building pipelines.Joshua Hoffman (09:10)Yeah.That's right.multiple organizations. I've had the chance tell our team, look, go put on their shirt for the day. You don't have to wear a Control K shirt. You don't have to wear a Datto shirt or a Palo Alto Network shirt. Go put on their shirt for the day. You guys are part of a team. And that team mindset, it solves problems so much faster. And that's what we're really here to do. As long as you're working for a company where you believe in the product or the service that you're selling,KK Anderson (09:34)Put on their shirt. I love it.Joshua Hoffman (09:47)and you're not working for something that's trying to gouge people or trying to do something nefarious. I happen to have been fortunate, the companies that I've worked for for my entire career, maybe minus one or two at the early part of my career, we were really trying to solve something important. And it was something that I believed in. That's an important part of that as well. You've got to and I tell this to people all the time, you got to be happy. Part of being happy is making sure that when you go to work every day, it doesn't always feel like work because you believe in what you're doing.KK Anderson (10:14)Yeah, 100%. And it absolutely applies in the COCEL environment, but even in direct B2B, you at Control Case, are you more direct B2B, or are you more channel partner?Joshua Hoffman (10:26)we do business in 73 countries right now. Not every country has the same kind of partner model. so depending on where we are in the world, it could be direct sales. It could be consultancy partners. It could be referral partners. It could be technology partners. And in the case of one of the missions that we have, it's using MSPs and ITSPs. So I have a vision thatMSBs and ITSBs should be a bigger part of the compliance journey. It's using partners that are actually part of the technical journey that the client's about to go on. so depending on where we are in the world, it could be any one of those things.KK Anderson (11:00)But you know it's one of the ways that we met previously Josh I've got a lot of experience in assessing sales organizations and going through this whole you know sales effectiveness and improvement process and almost always out of hundreds of organizations almost always the sellers come back as they're good at hunting getting the meeting and thenthe next best skill that they have is presentation approach or going into like sell value. And I think they get so comfortable in learning the value proposition, learning the talk track, learning about the features, advantages and benefits of the product that they're trying to sell. And they get that word sell so stuck in their mind that I'm a salesperson, just Mark, we were earlier talking about that very thing.There are so many people that don't even like the word sales. And so it's almost transitioning their mindset from I'm a salesperson to I'm a problem solver. So my question for you, Josh, would be like for the CROs that are listening, and that's probably most of our audience, what's one thing they can do now to help start to drive that culture of ask more questions, solve more problems?Joshua Hoffman (12:05)Well, part of coaching is spending time with people. And in any sales leadership role, you see people get their time pulled in multiple directions. Should I be working on this Excel spreadsheet? Should I be working on this report? Am I spending time in an operational meeting? Am I spending time doing X, Y, or Z? When one of the biggest opportunities that people have is to spend time with people in the environment where they're talking to customers or partners.and having the chance to talk about it afterwards, to talk about what went well, what didn't go well, what would you keep, what did you change, what did you learn? There's all kinds of cliche phrases around that. But that kind of coaching environment is what helps people get better. Now, of course, you have to be a sales leader that believes in this model, and not every sales leader does. And so you have to be a little careful about that. But assuming that you do, that time that you spend with people is one of the most valuable things you can do.The other thing that you can do is model behavior. And I'm the first one to say, look, I screw things up all the time. I'm not perfect. I don't always get it right. But what I do try and do is when I'm sitting inside of that environment, when I'm with the client, the partner, the salesperson, the account manager who's leading that account, is I do try and model that behavior and make sure that they're seeing what, at least what I hope good looks like.Again, said with a little bit of humility, it's not always great, but I try and be very consistent in my approach and it served me well. That's the advice that I give, spend time with your people. there's nothing more valuable than that. That's how you help people get better. And one of the ways that I've branded myself throughout my career is that helping people find a career they only thought aspirational.is a motivator for me, helping people learn and grow and develop into something that they never expected. And you can't do that if you don't get to know your people, if you don't get to spend time with them, if you don't get to coach them along the way.Mark Petruzzi (13:56)Very, impactful. Everything that you just said there. All right, let's switch over to the second topic. know, and this is a perfect build on where we've started, like lessons from a career in tech. So you have been through multiple transformations in your career and transformations within the companies that you've worked within. From being within Dell's Inside Sales team,to intern CRO at Poly, Dorn, what turned out to be a very turbulent year. What experiences has shaped your leadership style the most?Joshua Hoffman (14:29)good gosh. Let me start with, I feel so blessed because I have been shaped more times than I can count. I've been shaped by great leaders. I've been shaped by great situations of growth. I've been shaped by times of, as you said, turbulence where things are not always going well. And I've done my best to learn from each one of those situations.Picking one out of the group is a little bit challenging to consider, but I look back on my early career at Dell. My first job at Dell was putting screws in motherboards. Candidly, I had tried sales, I failed. It wasn't going well for me, and I said, I'm gonna go do something different. And getting the opportunity to walk into an environment at Dell is probably 1992. They said, the phone's ringing off the hook.We need more people in sales. came onto the manufacturing floor. Who wants to come to sales? me, so they chose about 25 of us raised our hands and me and Rick. So Rick knows who I'm talking about. We were the two that were selected and we end up, sitting on the phones for four hours a day and going back to our manufacturing job or vice versa, depending on what day it was. And I got to be part of an environment that wasgrowing like a rocket ship that was also going through challenging times. This was the time of the exploding laptops. And so not exactly one of the best moments in that company's history. And I got to learn from some amazing leaders. Now that carried on. I had leaders at Dell consistently, actually throughout my career, I could probably call out 10 leaders easily that have made a difference in helping to shape who I am.Almost all of it leads back to a common theme, which is being given the opportunity to step into a situation and learn on the fly. I wasn't always put into places where I knew what to do. I wasn't put into places because I had the experience. I was put into situations where I had the opportunity to learn, to grow, to be creative, and to help come up with what are we going to do to solve this.And I give a lot of thanks to people that were willing to put trust into me at various points in my career. And that's what's shaped me the most. That's the consistent theme throughout all of those organizations is let's let Josh do it, which by the way, wasn't always perfect. It didn't always succeed, but I've been fortunate more times than not. It's been a successful.KK Anderson (16:53)You need to screw the tight, the screw is a little tighter on those laptops so they don't explode.Joshua Hoffman (16:57)Yeah, well, okay. It's a funny story when you look back on it now. It was unbelievably stressful at the time. Dell grew so much over so many years. when I started, it was a thousand people. When I left, I think it was 70,000. And, but they gave me opportunities to go learn on getting to move to China, getting to move to India, getting to lead the first services organization, doing things thatKK Anderson (17:05)totally agree.Joshua Hoffman (17:21)that I hadn't done before, but also that the company hadn't done before. And so we got a chance to make things happen along the way. It was pretty spectacular.KK Anderson (17:29)Really cool, and I like what you were saying about trust. That's so important. So you worked under our mutual friend, Todd Abbott, and he's such a strong, awesome leader. I know that he had a strong style and impact on you. What would you take from that relationship specifically, just out of curiosity, that influences you today?Joshua Hoffman (17:37)did.⁓ look, I love Todd. I had this amazing experience with him. I think it was three years or so that I had the opportunity to work for him. And ⁓ during that time, I got to experience a different type of rigidity and approach that I had experienced other times in my careers, but never with the clarity that Todd uses to set expectations.to create an environment for people to succeed, to approach things both analytically and with creativity at the same time. He was a champion of the people on his team and you always knew that Todd had your back. And by the way, I have actually been very focused in my career of finding people to go work with and for that are like that.that provide that kind of environment. It's not always easy, by the way. My CEO today, Mike Jenner, has many of those same qualities. And he has other great qualities too. So it's not like Todd and Mike are twins, they're not. But Mike provides that same kind of environment. And I feel fortunate to be in a place where accountability is sacred. And there's never a moment that you're confused aboutwhat needs to happen and what the outcome needs to be. I've worked for other leaders in my career where there was ambiguity all the time. And candidly, that's really hard to be a part of. And I do my best to make sure that I'm modeling that behavior that I get out of folks like out of Todd, out of Mike, out of other folks in my career. Mark Anderson at Palo Alto Networks is a great example. Earlier in my career, David Lockett at Dell.with somebody that had that same approach. And I've had other leaders too, so I could probably name 20 names and so forgive all the people that I didn't just mention. But these ones jumped to mind because of that approach and combining analytics and behaviors is a lot of what leading a successful revenue organization is about. You have to have both. And so thanks for asking that question. So I'll make sure and call Todd.Mark Petruzzi (19:44)Yeah, you described that really well. So Joss, through many of your companies you've worked with, you've lived through significant change and cultural shifts as well and acquisitions and putting companies together. What did you learn during those times about keeping teams motivated and effective during times of change?Joshua Hoffman (20:04)Well, there's a couple of things. Now I have been fortunate. Most of those times of change have been about rapid rocket ship kind of growth and how that impacts an organization. I know that one of the lessons that I've learned and one that I try and live, although again, not always perfectly, is my behavior doesn't change ⁓ almost no matter what the situation. The message may change. The requirements or the outcomes may change.but my behavior doesn't change. Nobody has to worry about schizophrenic Josh. There's an opportunity to know that there'll be a level of consistency there. The other thing is about making sure that people understand that change isn't necessarily bad. If you go back to the days of like corn fairy and FYI and the introduction of these competencies into the corporate world, I got to live through being one of the guinea pigs for that.One of the competencies was dealing with ambiguity. And getting the chance to teach that, to share with people the sort of the pieces that fit into dealing with ambiguity ⁓ is helpful. And giving people a future that makes sense to them, that change can lead to better things, you have to be consistent in that message. Now,by the way, there's times where change doesn't lead to that. I've been parts of organizations that did layoffs. I've been parts of organizations that were bought. And maybe that wasn't the best thing in people's eyes at the time. But it doesn't mean that the culture of the organization has to change. Candidly, everybody has to be a part of that. And that's one of the other key messages is that change doesn't have to happen to you. You can be part.of what makes things better and that you should feel empowered, you should feel emboldened, you should feel like you have a voice, you should feel listened to. And the other skill that I think comes with that is having compassion. You have to have empathy to be successful in any leadership role. If you don't have that, one, you gotta go find it. Two, you really do have to be able to put yourself in their shoes and say,What are they feeling based on this message? What are they thinking right now? How do I answer questions before they're even asked? And the more you can get ahead of things, the better off things will be.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.