In this episode, Mark Phinick, a fractional B2B deal coach, shares his insights and experiences in the sales industry. He discusses the changes he has witnessed over the past four decades, including the shift from initial public offerings to selling organizations to private equity firms. Mark emphasizes the importance of empathy in sales and the need for sellers to understand their clients’ goals and challenges. He also highlights the role of a deal coach in helping sales reps navigate complex deals and close them at higher margins. Mark encourages sellers to focus on the why behind a client’s purchase and become trusted advisors.




Introduction and Background


Changes in the Sales Industry


The Evolution of Organizations


The Role of AI in Sales


Nurturing and Developing Sales Reps


Empowering Clients to Buy


Becoming a Trusted Advisor


The Importance of Being a Top Vendor


The Role of a Deal Coach


Transitioning from Selling to Buying


Understanding the Why


Empowering Sponsors to Translate Technology


Conclusion and Contact Information

Connect With Mark



Connect With Wesleyne




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Twitter –  


Email- email…  


Wesleyne (00:00.816)

Hello and welcome to another episode of the Transformed Sales Podcast. Today I am so delighted to have Mark Phinick How are you Mark?

Mark Phinick (00:08.822)

I'm great Wesleyne Nice to see you again.

Wesleyne (00:11.116)

Nice to see you too. Let me tell you a bit about Mark. He is a fractional B2B deal coach and he boosts immediate sales by coaching reps on active must-win deals, freeing up leaders to focus on strategic imperatives and internal processes. His clients report an increase in deal conversions, ACV and ARR. All right, Mark, tell us how did you become the first fractional deal coach that I've ever met before in my life?

How did you start your career and how did you get to where you are today?

Mark Phinick (00:43.63)

Sure, thanks, Wesleyne, and thanks again for having me. It's a timely call because a lot of software companies are just not attracting the venture money that they need to grow, and we're gonna help solve some of that today. So you asked me how I started. It certainly wasn't in sales. As a matter of fact, I had it in my mind to be a programmer. I got a bachelor's in computer science long, long time ago.

And ironically, in my very, very first interview, they whispered in my ear, you need to be in front of these things, selling them as opposed to using them. So I took that as a compliment and went down the path of selling enterprise software, which I'd been doing for the last 40 years.

Wesleyne (01:35.504)

Wow. So you are like me, a technical person, went to school to get a degree in a very technical area, got into the world and said, yeah, nope, I'm not using my degree for that. So as somebody who had a degree in computer science, but you never actually used it in the field, how did those skills that you attained in college help you in your sales career?

Mark Phinick (01:59.742)

Yeah, it was all about empathy. And I speak from the heart, my very first sales roles. I put myself in the shoes of my clients and simply asked, what are you trying to accomplish? And it worked. And I gained a reputation for being an empathetic seller, which leads you to words like trusted advisor. And

I've tried to coach my teams to do the same thing throughout my entire career.

Wesleyne (02:35.164)

So tell us what was young Mark, brand new sales person, what was he like?

Mark Phinick (02:43.37)

Young Mark had a Sears suit that was reversible, that probably burned, or probably melted instead of burned. It was a very, very interesting time. We all wore suit and ties. I had a briefcase with seven habits of highly successful people, people poking out of my briefcase everywhere I went. And I was...

going to be there to fake it till I make it. And one thing led to another and started helping clients accomplish what they wanted to accomplish using the technology that my customers were selling. I certainly wasn't the sharpest knife in the drawer. I certainly wasn't the best. But I did take it upon myself to focus on

what was the client trying to accomplish? If they were clearly able to identify a business problem, we would focus on that. We would pull that thread. But it really was about empathy. I come from very, very good stock. My father was the world's greatest salesperson. And I would watch him in action. And I learned quite a bit. And I applied a lot of that.

What's really fun is the fact that many of the people who were my clients Literally 40 years ago are still people who I maintain contact with They've been references for me. They've been repeat clients with me We exchange holiday cards. We exchange. I don't know how or why they do this But right before New Year's they call me they should be focusing on their kids on their family, but we have very strong

long, long lasting relationships as a result of me helping them with their upward mobility and in turn them helping me with my career.

Wesleyne (04:48.104)

Mmm, that's so good. So I know, you know, after four decades in a, in the workplace, you see a lot of change. So talk us through some of the big changes, the big milestones that you experienced in your career over the past four decades.

Mark Phinick (05:07.054)

Just hearing you say four decades, I felt that much older. So going forward, I'm just gonna say decades, but I literally aged. So there's been a lot of changes and I'll think through. So the biggest change that I experienced is how organizations grow.

Wesleyne (05:12.552)

Don't feel old.

Wesleyne (05:17.596)

Ha ha!

Mark Phinick (05:38.41)

I always paid very, very close attention to how the executives of my employers planned on growing the company. And I learned at a very, very young age the meaning of exiting the business, of taking a business, growing it, and bringing in the liquidity, bringing in equity, or investments to actually take the company.

to something much, much larger. Very simply put, I learned that everything is for sale. Everything is for sale, especially the company. The biggest difference in that mindset and in that trajectory was when I started in the business, the way that we would attract capital was through initial public offerings. And I was very, very fortunate. I had been part of four.

IPOs and four more acquisitions. So a multitude of successful exits. The reason I bring this up is, around 2000, Sarbanes-Oxley, I think it was 2000, maybe a little later. Sarbanes-Oxley emerged as regulatory mandates and required everybody to open the books. It's fascinating how the number of companies who went public.

stopped going public and instead started selling their organizations to private equity firms, to other larger organizations. So materially, that's probably the biggest change is instead of doing road shows to Wall Street, we were always trying to impress VC firms and private equity firms. In terms of technology, I've seen

You know, I worked on mainframe technology, and then when mainframe gave way to client server and then distributed object computing, and then the world has changed, and now we're in a world of artificial intelligence, and I've become quite proficient in chat CPT and in Bard, and I'm learning how to use it to complement what I deem to be

Mark Phinick (08:03.886)

uniquely human skills in the sales cycle. There's a role that AI plays. Um, but I have yet to hear of enterprise, um, negotiating with a chatbot. I have yet to find an app or a GPT that gets a customer to return your phone call. Right. People buy from people.

Wesleyne (08:07.737)


Wesleyne (08:13.284)


Wesleyne (08:20.079)


Mark Phinick (08:31.374)

And so this mindset that I have of empathy has carried me through my entire career, including working with all of my reps who, I think many of whom are quite successful. I have a lot of former reps who are now CROs, they're venture capitalists, they're CEOs, they're retired on boats, whatever. But these are the same people that are nice to their clients and are always seeking to do the right things for them.

Wesleyne (09:01.212)

So tell us about, you mentioned your reps and you've mentioned empathy a lot and the changes that you've seen in the world over the past couple, couple years, just a few years. And what I want to ask you is, how do you take a rep who may be fresh out of school, who may have come from a...

toxic work environment and how do you nurture them and help them perform at their best and then go on to see them doing amazing things in the world.

Mark Phinick (09:33.206)

Yeah, and it's a real timely discussion because, so we're, you know, we're a year plus coming out of the pandemic where a lot of sellers...

never had the experience, never had the exposure to face-to-face meetings in their career. They're used to Zoom interactions. And this is quite candidly one of the things that was behind me launching Make It Rain, my new company, where I'm doing deal coaching and helping reps on individual deals. What I started seeing was a lot of reps were...

directed to libraries of curated videos that were recorded during the pandemic. Let's record a video of the features and functions of our technology and we'll send it out to a bunch of people and we'll get attention. And that's good and that will get attention. But what I focus on with my efforts and what I've always focused on is helping sellers.

empower their clients on how to buy the solutions that will derive, that will drive the value that they're looking for. Clients are looking at technology to increase efficiencies. They're looking at technology to disrupt the status quo, but they have relationships with larger vendors. So it's not uncommon for a newer seller.

to attract attention in our organization. And we're talking larger enterprises. It's not uncommon for them to get attention based on features and functions and do a demonstration, respond to an RFI, respond to an RFQ, really establish rapport with their sponsors, submit pricing, and then get totally ghosted.

Mark Phinick (11:42.078)

and not understand why, why am I not getting a call back? Well, there's only two reasons that a customer ever needs to talk to a salesperson, that's to get a demonstration or to get a price. And when you give those two and you haven't demonstrated any real value in helping the client improve their business.

Wesleyne (11:52.113)


Mark Phinick (12:08.394)

you're gonna get ghosted. And this is quite candidly why so many deals are stalling, they're slipping quarter after quarter. Unfortunately, sales organizations are, you know, forcing or faced with reduction to enforce. If you get to a certain size startup, a series B company, for example, you'll see constant turnover, not only in sales organizations, but in the sales leadership itself. Well.

The investors need execution from these startups. So one of three things is going to happen at that stage. If the sellers are not trained to empower their clients on how to buy and how to navigate through the complexities of their organizations, one of three things are going to happen. The CEO is the next person to go. The organization will be flipped to a private equity firm.

or that organization is going to run out of runway. And this is one of the biggest challenges in the VC community right now. People do want to invest, but they need organizations who will execute. And it really does come down to the sellers learning not only features and functions about the technology that they're selling, but how to empower their clients on how to articulate to higher ups.

Wesleyne (13:11.302)


Mark Phinick (13:36.83)

in a language that they understand. Not technology, not features and functions, not acronyms, but how do we increase sales? How do we reduce costs? How do we innovate to improve the business? That's the language of the business. So that's what I've always done throughout my career is help the sellers that work with me. I ultimately work for them. So we work with one another.

and that's what they focus on. Those that understand that mindset are wildly successful in their lives.

Wesleyne (14:14.157)

Yeah, it's really about getting out of your world, stepping into your perspective buyer, stepping into your customer's world. And you mentioned like, hey, here's a video on our features, on our benefits. And I'm a field salesperson, so I didn't have the luxury of sitting behind a desk and sending emails, videos, doing demos. I had to get out. And so even today, I tell people, I'm like...

You gotta do some territory planning. You gotta get out and see people and ask them questions. Like, well, why did you buy this? Go talk to your existing customers. Why did you buy this from us? What about us stood out from the competitors? And you learn the language of your customers and then you use that for your prospects. And when you can do that, that really helps you develop that true expertise in that subject matter.

Mark Phinick (15:02.382)

So spot on, but we're gonna change that word prospect and we're gonna agree not to use that anymore in this conversation or any others. How would you like it if you were a future customer and somebody called you a prospect? That's an off-word, so shame on the both of us if we've ever used it. I know that was a slip of the tongue. You're spot on, you're spot on. And the language of the client is everything right now. Once again,

Wesleyne (15:30.876)


Mark Phinick (15:31.47)

The people who are evaluating technology don't buy it as much as we sell it. So they're always going to have a difficult time translating that into a very, very dynamic set of requirements that if the CEO is evaluating things or the CFO or the board, you know, gone are the days where vice presidents have significant budgets. Most don't have a budget, you know, more than their monthly salary.

Wesleyne (15:38.061)


Mark Phinick (16:00.374)

So everything has to go higher and higher. There's IT boards, there's security boards, there's technology boards that have to meet. And not only do sellers have to factor in these types of meetings and their sales cycles and factor in the time in terms of close dates and such, they have to speak in that language. They have to speak in the language that's going to improve the business or else that money is going to go to another.

priority. This is particularly important in 2024 when software margins will begin to decline in a very significant manner because there's just going to be more competition. There's just going to be more technology. It's going to cost more to go reach a customer. It's gone are the days you can call.

you know, a central location in a customer and find somebody at a desk, it's very hard to find the right people in an organization. So software margins are going down. Organizations are going to have to figure out more effective ways to engage with clients, demonstrate their unique value, and then ultimately land business in a large enterprise.

then through iterative ROI and trust, expand so that they become a top three vendor. That's another thing that I've always strived for throughout my career is always being a top vendor for a client.

Wesleyne (17:44.72)

I love that. I love that being a top vendor being their go-to resource their go-to Authority and I love to say when I have Someone a client who comes to me and asks me for my recommendation on something that is so outside of my sphere I know that I've become a trusted advisor they trust my opinions they trust the people that I do business with to send it to them and as a salesperson as a CEO if you're

an entrepreneur, that is what you want to achieve, that trusted advisor status.

Mark Phinick (18:18.41)

Yeah. And so one of the things I always encourage my reps to do is ask the question early in the relationship. Tell me about your top three vendors. They, everybody knows who they are and they may not always be the biggest companies. You know, the Microsoft's and the IBM's and the Google's and such AWS. I don't mean to ignore anybody to leave anybody out, but all the big guys, they all have relationships. But.

Then there's significant relationships because of how an organization has helped the business. I'll give you a great example, CrowdStrike. CrowdStrike, from an XDR standpoint, has helped so many organizations stay out of the newspapers for the wrong reasons. One of my former employers, BigFix, has helped empower IT systems people.

to do so much more than those that are using other technologies, driving automation, increasing productivity. So it's a big deal to earn the right to call on a client of a large enterprise. It's game changing when you can say, I'm a top three vendor for this particular organization. That's a lot of work.

Salesforce has done a magnificent job over the years of earning that status much to the credit of some really, really top sellers.

Wesleyne (19:57.124)

Good. So you call yourself a B2B deal coach. What is a deal coach?

Mark Phinick (20:02.794)

Yeah, that's a great question. So, um, there's, there's a movement underway, um, that I first learned about last year known as fractional, um, fractional COO, fractional CIO, fractional CTO, they're fractional officers. And the notion is for a fraction of the budget, an organization can hire a very, very experienced.

executive who, by the way, offers a fraction of their time to multiple organizations. So, there's this world of fractionals that are out there. When I decided that I wanted to be on my own, I wanted to no longer have a boss,

I've worked with some and I've learned from some of the greatest sales leaders in my career, but there comes a time where you just, it's my time. So in May of last year, I chose to do this and I reached out to pretty much everybody who I've ever worked for in my career. These are people who are very accomplished in their life. They're the smartest people that I've met. And it was fascinating to hear them describe.

When I asked them, what do you think my superpower is? What are organizations trying to accomplish that you think I can do better than others? I was fascinated and humbled and gratified. I even brought my wife into a couple of these calls to hear how great of a person I was. They're not talking about me. They can't be talking about little or me, but in all candor, they all said the same things.

Wesleyne (21:52.97)


Mark Phinick (21:59.594)

And they said, Mark, you've been an individual contributor. You were always number one. You've been a global vice president of sales. You were always number one. Your teams were always the top producers, but you know, Mark, and this is my, my former employers and peers and partners and customers telling me, Mark, where you really succeeded the most was when you helped reps go from floundering and getting ghosted and.

and struggling to becoming a rainmaker themselves. Getting to President's Club, helping their clients increase productivity and profitability, showing them things that you didn't know. So instead of being a fractional chief revenue officer and focusing on go-to-market strategies and pricing and hiring and sales kickoffs and all the things that are necessary for a sales leader to do.

I compliment that world by focusing on deals. I work with sellers on individual deals. And since I launched the business, I guess we've been very fortunate, I launched the business in May. My first client has already been acquired. My second client closed their largest deal to date.

And then a third client, we thought that they were going to be closing business in April or May of 2024. And we brought all that business forward into 2023. So what I'm doing now is what I've done throughout my entire career. I just came up with the term deal coach and it's nothing that I invented. There are people doing this. And, and I learned from some of the best.

Wesleyne (23:52.856)

I love it, I love it. A deal coach, a deal coach. So really helping people, reps, get out of their head, step into their client's brain and bring business forward. So not just closing business, closing it faster, closing it for higher margins, just really helping move people through that sales funnel.

Mark Phinick (24:12.362)

Yeah, and Wesleyne it's really fun. This is what I'm really passionate about. Those that know me know this is, I mean, this is what drives me. This is, I haven't worked a day since I launched this company. I go to camp every day. It's fantastic. I get paid to go to camp. Um, but what's fascinating is watching somebody. And I was on two calls today with individuals where both of these individuals have been selling a solution for.

X amount of money. But by helping them transition and helping them pivot their approach to the value that they're delivering to the client, I showed them that it's possible to sell it at a premium price. And oh my goodness, were they afraid to do that? Oh my goodness, were they afraid to ask for this?

when they've been selling for this. And I explained to both of them, it's two completely different people, different organizations. And I said, you can do it because you're delivering this much value. If the value that you're delivering is a billion dollars and you're charging $3,000 for it, shame on you. The customer wants to sell that billion dollar problem.

Well, I share this with you because in both situations, they called me, Mark, I did it. Mark, I did it. I asked and we're proceeding. And literally it'll be the largest deals that both of these individuals have ever closed.

Wesleyne (25:46.34)


Wesleyne (25:53.948)

That's amazing, that's amazing, that's amazing. Really having the power, the strength, the courage, the confidence really to understand that your price is a direct reflection of the impact, the ROI that you're giving the client. And if you take the conversation away from your price and start moving into the impact.

and moving it to how you really are going to help them achieve their goals, whether it's revenue or it's status or whatever the thing is, then you start winning more. You start winning bigger. You start winning by higher margins, right? And so really helping reps understand that there aren't enough people that are focused on that specific thing. And I think as leaders, it's something that we need to ensure that we're developing within ourselves because that is what the focus should be. And that's how we should be coaching.

Mark Phinick (26:49.734)

So if we were to summarize what we've covered so far, it's about transitioning from what we sell to why clients buy. It's a simple word, why. And behind everything is a why. Why is somebody interested in a demo? Why is somebody interested in buying technology? And there's going to be a functional requirement.

Wesleyne (27:03.377)


Mark Phinick (27:17.442)

And I'll give you a good example. So many, many years ago, everything in my life is many, many years ago. I used to say a hundred years ago, but now I'm getting too close to reality. So many, many years ago, I was demonstrating a piece of technology to a client. And they explained that they needed to accomplish something. And I said, why? They said, well, we have to...

secure these various things, we have to keep these machines compliant, continuously compliant with a vendor or with a client. And it wasn't clicking. So when it came to the break, what I learned was this organization was hit very significantly with ransomware in 2017. A piece of software known as WannaCry, which hit hundreds and hundreds of thousands of computers all over the world.

And it basically bricked them, right? Manufacturers were not able to use their computers to process orders. Products sat in warehouses and couldn't get to distribution centers, let alone the shelves. Well, for this particular client, they were given the mandate by their largest client, their largest client. You need to be fully patched, fully compliant with, you know,

regulatory standards, regulatory mandates within 30 days. And I said, well, that doesn't sound like that's a big deal. How long does it take you today? Six months. Oh, so it's taking you six months to do what your largest client is required and you need to do in 30 days. How big of a client is it? Well, it's about half of our revenue. Half of your revenue, you're a $4 billion company.

Wesleyne (28:58.002)


Wesleyne (29:04.537)


Wesleyne (29:09.979)


Mark Phinick (29:14.922)

So, Wesleyne, this became a $2 billion problem. Now, obviously, we couldn't charge $2 billion. I can assure you, we did not discount any more than we needed to, because we were focusing on the why. We were focusing on the business outcome. We were focusing on the hole that needed to be dug.

Wesleyne (29:20.87)


Wesleyne (29:26.506)

Ha ha!

Wesleyne (29:31.536)

Right. Yeah.

Wesleyne (29:37.52)


Mark Phinick (29:44.522)

not the shovel. And that's what I try to get my reps to focus on each time. So when I'm coaching my clients reps, they already know I'm going to ask why a thousand times. And we're ultimately going to get to the why, which is always money. It's not the money, it's the money.

Wesleyne (29:46.501)


Wesleyne (29:59.396)


Wesleyne (30:04.261)


Wesleyne (30:08.664)

I love it, I love it. Oh, yes, I often say the why is, equivocates to the biggest business problem, biggest challenge that your client is having. And when you understand that, then it's like, okay, where do I sign? And you take the conversation away from the money that they're having to pay you to solve their problem.

to give them their solution. And it's the whole, literally, in that case, the whole that they're having to patch, right? So it doesn't matter the cost, because it's a $2 billion client, or if it's a $20 million client, or even depending on how big the cost is, it could be a $2,000 client, and your other clients are $2 clients, you know what I mean? So you really have to focus on stepping into that customer's world and asking the why. Ah, Mark, this has been

Mark Phinick (30:59.246)

Asking the why, I'm sorry to interrupt you, asking the why, but also empowering that sponsor to translate the technology they're evaluating into the why, because that's what the business executives understand. Chances are not everybody has access to the CEO, the CFO of a global 2000 company. Those senior executives have people to talk with.

So the vendors have to come, they have to teach the sponsors how to translate this into what's important to the business. And that's largely what I do every single day with my clients.

Wesleyne (31:46.909)

That's awesome. I love it. You have definitely enlightened me and enlightened my listeners. If people want to reach out to you, what is the one best way?

Mark Phinick (31:56.63)

So I would say LinkedIn, Mark Phinick, M-A-R-K, last name is P-H-I-N-I-C-K. There's a lot of client success videos, there's some success stories, there's my story, but I'm here to help.

Wesleyne (32:16.36)

Awesome, well thank you so much Mark for sharing your time, your talent and your expertise with our audience today. It's been a great pleasure to chat with you.

Mark Phinick (32:25.026)

Thanks, Wesleyne. It was a pleasure.

Wesleyne (32:27.704)

And that was another episode of the Transformed Sales Podcast. Remember, in all that you do, transform your sales. Until next time.

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