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In this episode of Selling Intelligence, Todd Cassler, Chief Revenue Officer at Wilshire, joins Mark Petruzzi and KK Anderson to explore the fundamentals that drive trust, stronger relationships, and sustainable revenue growth.
Todd explains the three questions every buyer is trying to answer: Can I trust you? Do you add value? Will you put my interests ahead of your own? He shares how preparation, thoughtful follow-up, and consistent execution help sellers earn that trust over time, especially in complex enterprise sales where relationships can take multiple interactions to develop.
The conversation also introduces Todd’s concept of “Network Alpha,” the ability to activate the right relationships at the right time to create favorable outcomes. Todd explains why having a large network is not enough, how sellers can create “presence in their absence,” and why leaders should deliberately train teams to build and activate stronger professional networks.
Todd also breaks down why sales teams need focus when managing a broad portfolio. Rather than expecting sellers to master everything, leaders should identify the few opportunities that are truly sellable while training their teams to recognize signals and uncover opportunities that may be hiding on the margins.
What You’ll Learn:
- The Three Questions Every Buyer Asks: Why trust, value, and alignment of interests shape every sales relationship.
- Building Trust Through Execution: How preparation, responsiveness, and following through on commitments strengthen buyer confidence.
- Understanding Network Alpha: How activating the right relationships at the right time can create new opportunities and accelerate growth.
- Creating Presence in Your Absence: Why referrals, advocates, and strong professional relationships can extend your influence beyond direct conversations.
- Focusing on What Is Sellable: Why salespeople can only deeply focus on a few priorities and how leaders can distinguish between what is sellable and what is simply tellable.
- Finding Opportunities on the Margin: How curiosity, observation, preparation, and better questions help sellers uncover needs buyers may never state directly.
Key Topics:
- Building buyer trust in complex sales
- Trust, value, and customer-first selling
- Network Alpha and relationship-driven growth
- Turning professional networks into business opportunities
- Creating advocates and referral networks
- Building networking skills across a sales organization
- Sales preparation and follow-up discipline
- Prioritizing three to four key sales opportunities
- Sellable versus tellable products and solutions
- Asking better questions and identifying hidden opportunities
Guest Spotlight: Todd Cassler
Todd Cassler is Chief Revenue Officer at Wilshire, where he leads global growth and distribution across wealth management, retirement, alternatives, and data and analytics. With more than 20 years of experience across wealth management, asset management, and institutional advisory, Todd brings a relationship-driven approach to building sales organizations, developing networks, and creating sustainable revenue growth.
Resources & Mentions:
- Book: Never Eat Alone
- Wilshire
🎧 Listen now and follow Selling Intelligence for more insights from revenue leaders on building trust, strengthening sales organizations, and driving sustainable growth. Subscribe wherever you get your podcasts.
Disclosures:
Recording Date: August 10, 2026
This does not constitute advice or a recommendation or offer to sell or a solicitation to deal in any security or financial product. Except where otherwise indicated, the information contained in this presentation is based on matters as they exist as of the date of preparation of such material and not as of the date of distribution or any future date.
The views and opinions expressed are those of the speaker and do not represent Wilshire as a whole.
Mark Petruzzi (00:29)
Welcome to Selling Intelligence, the weekly conversation for chief revenue authors and the leaders who build revenue teams.
I'm Mark Petruzzi here as always with my co host KK Anderson.
KK Anderson (00:41)
Thanks, Mark. Here's the number that frames today's conversation. It takes six to ten interactions to build trust with someone before you can sell them anything. Six to ten. Now think about how most teams are running outreach right now, and you can see the gap.
Mark Petruzzi (00:58)
Our guest today has spent more than 20 years building distribution across wealth management, asset management, and institutional advisory. He is the Chief Revenue Officer at Wilshire, a firm with more than one and a half trillion dollars under advisement. Todd, welcome to the show.
Todd Cassler (01:17)
Mark, hi KK.
KK Anderson (01:19)
All right. Well let's dig right in, Mark.
Mark Petruzzi (01:21)
Okay, let's start off with topic one, the three questions every buyer asks. Todd, you have sold in nearly every market and channel there is. Direct to consumer and enterprise, the US, EMEA, Latin America. You told us that everybody's trying to answer the same three things in the first thirty seconds. Walk us through those three questions and why the answer holds no matter who is across the table.
Todd Cassler (01:46)
Yeah, I think if you start any sales interaction, it's basically three things that people are trying to determine on the other side of the table. first thing is can I trust you? do you add value? And are you going to put my interests ahead of your own? Doesn't matter if it's direct to consumer, enterprise. I think that's just the baseline that everybody's trying to figure out in that first interaction and over the course of the sales cycle.
KK Anderson (02:09)
couldn't agree more and isn't it interesting that in your world with ultra high wealth huge transactions it's the same as in the world of selling something door to door or even selling B2C like it's the same wherever you go it's the fundamentals of sales that never change right
Todd Cassler (02:27)
I mean, would agree with that. you think about when you meet somebody for the first time and you're trying to develop that rapport, you're trying to find commonality, and it usually goes something like this: where are you from? Where'd you go to school? you're trying to figure out whether or not you know that person and where they're from to develop some kind of commonality and trust. I think the next thing that you're trying to do is you're trying to figure out, okay, is this person going to add value to what I'm trying to accomplish, whether that's network, that's business.
And you guys know this. The most of the decisions that people are making are career decisions. they're trying to decide whether or not they're going buy something or make a big strategic change. And then I think the last thing is, does this person add value? And that value comes in the form of the ability to deliver the product, but I think also information on the industry and whatever the the field you're in.
KK Anderson (03:14)
So a question, so for a leader, whose team is measured on activity, which is probably the bulk of our audience, and likely your team as well, like what does a healthy first six interactions look like? Like what does that how do you do that without trying to go in for a sale?
Todd Cassler (03:29)
I think the first thing in any meeting, and if you start with the basic premise that most people don't want to change. And, salespeople have to figure out how to convince someone to change that behavior. And there's really two reasons why they change. One is, money goes to the most attractive place for money, or two, they're trying to solve for some kind of pain that is giving them discomfort in their business or their life. I think the first thing that you're doing is you have to recognize that.
The person typically is not going to see a salesperson. So if you're walking into the room, the first interaction is really an indication that they want to make some kind of change. And so, you're going to start to build that rapport. And then, one of the big things that you have to focus on is okay, how do you move people through that sales cycle and how you do it quickly and efficiently? we talked about six to ten times. And
You guys know this from enterprise sales, it tends to be an eight to twenty-four month sales cycle. So how do you compress that and do it in a way that you demonstrate that you're gonna add value through that process? I think that's really hard. but there's some techniques that you can use in order to do that.
KK Anderson (04:33)
Like, what are some things
that you do? Or that you would coach your
team on? Just curious.
Todd Cassler (04:37)
I think the first thing is preparation. So you're gonna go into that first meeting, you have that first opportunity, you've done your homework around, okay, can I create some common ground with this individual, whether we know somebody in the inner industry together, we went to school together, maybe we grew up in the same town. we talked about the three questions that you're trying to determine at the beginning. Well, you've done a little bit of prep.
I think the second thing that you're doing is in that meeting, you're gonna have the opportunity to do two things. One is through your questions and your answers to demonstrate that you're an expert in that industry in some kind of capacity. So you're using those comments and that feedback to create that value add that I'm gonna add value to the relationship. And then the last thing is you're gonna have the ability to actually create the next action.
At the end of that meeting. And I think one of the things that salespeople tend to forget is okay, it's really hard to get that person on the phone or get them face to face. You have to schedule that next meeting. And you should really follow up within 24 hours. And so that's an opportunity to demonstrate that you are going to be trusted. Cause if I tell you that I'm going to send you information and it shows up within 24 hours, you remember it, but you've now also built a foundation that says,
Well, Todd said that he would send me the information. I got the information. I got it in twenty four hours. And so you start to build that cadence.
KK Anderson (05:56)
Mm-hmm.
Todd Cassler (05:56)
And I think if you start with those three things, you're off to a favorable, potential outcome.
Mark Petruzzi (06:01)
So Todd, when you meet a seller for the first time, and that can be someone that you're hiring and you're evaluating that individual, or that could be somebody who's just selling to your business on some other item? So when you meet that seller for the first time, what tells you that they're going to earn a yes on all of those three initial questions?
Todd Cassler (06:22)
Well, it's hard to earn a three, a hundred percent on all three every single time.
I think the first thing is if you're going through the interview process, and let's say you're hiring a new salesperson onto the team, all right. Well, you're gonna get a first hand look around whether or not that person has the skill set to do the things you're gonna expect on the other side of the table. And if a salesperson can't sell themselves through the hiring and interview process, that's a pretty good leading indicator.
may be a challenge. But there's little things that you could do. And I'm going to date myself a little bit. one of the things that I would do if I was hiring a senior salesperson is I'd look to try to fact check the names and their relationships. And you would do that through, subtle questions and answers. The second thing that I would do is I'd ask them for a copy of their resume. And I had already read their resume and I had already looked at it in advance of the meeting, but
The salesperson should have been prepared to have a copy of their resume no differently than if they would have a pitch book or some kind of materials in the meeting. So if we showed up and they in we're going through the interview process and they don't have that, well, okay, that's a bit of an issue. And then the last thing that I would do is I'd give them a task. I'd say, please send me your top five relationships when you get home tonight or first thing tomorrow morning. And I would watch and see what was the responsiveness.
Well, what was that? That was a test that would be no different than if I was a client and I would expect them, okay, did they, follow up with the right information? Did
KK Anderson (07:39)
Mm-hmm.
Todd Cassler (07:40)
they set it on time? Did they do the different things? And so, those little tests along the way are a pretty good leading indicator of whether or not they're gonna carry themselves the same way when they're engaging with clients.
KK Anderson (07:50)
So true. And, when you get a lot of sellers who are typically talkers, right, who love the relationship piece, they love to have great conversations. They may not be the most organized people on the planet. It's important to have the systems behind you. and hey, I've fallen prey to it myself, right? In my 20 years of selling. and so this is also where AI can step in and help you with, managing
your email, managing your calendar, making sure that you're setting up systems so that you're always following up, pulling your action items out of all of your meetings that you're recording so that you don't end up the day without sending that note or that message, which is heaven sent, to every salesperson out there. If they're not using Claude Co-work to do all of that, then they're missing the boat. okay, Todd, let's move on to talking about network alpha.
and let's start with the term itself. You used it quite a bit with us in our prep session. define, what it means and why it's an important term of art for you and kind of define it the way you would define it for a sales leader who's hearing it for the first time.
Todd Cassler (08:47)
Yeah, I think it's the ability to activate the right relationships at the right time in order to get a favorable outcome. And I think, we've talked a little bit about the sales cycle and how do you create connectivity and rapport. I think, the network is an important component to selling and is only becoming more important, especially in light of some of the things you referenced with AI and the unwillingness of people to see salespeople. And so
how do you use your relationships and your connectivity in order to get things done at the right time to develop the right outcomes? I think that's really what the essence of network alpha is.
Mark Petruzzi (09:23)
So Todd, you made a point that this is not only an executive asset. the network alpha operates at the territory level too. And that when a national sales manager hires someone, they're hiring a network. How do you evaluate that asset when you are making a hire?
Todd Cassler (09:39)
Yeah, I think you start with two things. One is, you're going to have to determine whether or not the individual has a valid network. And some of that's determined with time and experience, and you can validate that by, making phone calls and determining whether or not that person, has the relationships that they say that they do. I think the second thing is, are they able to understand the context and the nuance?
related to the network and how do they connect it together. So it's two parts. One, do you have the relationships? But then the second piece is do you know how to use those connections and relationships in order to achieve positive outcomes? I think, KK, you made a great point that, there's a lot of people that have great rapport, great conversations, like to go see their same relationships on a regular basis, but they don't move the needle from a sales standpoint or they're not unable to
to get the ball across the line. and I think it's the connection of those two things together. Yes, they have the great relationships, but they also know how to use them and monetize them to drive business for the organization.
Mark Petruzzi (10:38)
and Todd, I think this also at least in my career, I've found that sweet spot of what I'm looking for around networks with the people that I hire. And what I mean by that is, the networks that a sales leader or a CEO thought they were hiring and they get ecstatic about the relationships and the network that person has.
so that they forget about everything else that they need as well in that hire, that never works. And there needs to be a process. There needs to be all the things you just described. how do you work that? Do you see it as like a sweet spot like I do or do you have a different view?
Todd Cassler (11:14)
No, I agree with you. if you have a salesperson, we've talked a little bit about this, if they're in a territory, and let's say it's a new salesperson that's coming into a territory, and I think your point is a hundred percent accurate. Just having the network alone isn't gonna generate the results that you're looking for in the territory. You need to have somebody that's gonna be smart, technical driven, they're gonna show up every day, they're gonna look for ways to connect.
their network to the outcomes you're looking to achieve. the other thing is you have to have high quality product and you have to be able to prioritize where you have an opportunity to play and a right to win. I think it's that multidimensional kind of combination of those things coming together. But you're 100% correct. There are plenty of people that go out and hire somebody and they think just because they have a great network and great relationships, that's going to translate into business.
I think you need those other characteristics to go along with it. because the network by itself, again, you have to be able to optimize it at the right time and in the right way. I think there's a bit of a skill to that beyond just having relationships.
KK Anderson (12:16)
So in our call that we had to prepare, you described using the network to create presence in your absence. And I thought that was spot on. And that's what you're describing essentially. what are some examples? Like what does it look like when you have created a network that creates presence in your absence?
Todd Cassler (12:32)
Yeah, I think the first thing is you get referrals. if you've developed a network and you've developed it really well, people know exactly what you do and they send you referrals. And in many cases, they send you referrals that are complex and they're like, you should talk to Todd or you should talk to Mark or KK because
KK Anderson (12:47)
Mm-hmm.
Todd Cassler (12:48)
they may be able to help you. So if you've done a good job building that kind of foundation that people say, this person helps, they'll send them into the right location.
And again, you get back to those three things that we were talking about. They add value and they put the other person's interest ahead of their own. So someone calls you and says, Hey, can you solve this problem? I think the second thing is there are advocates and supporters behind closed doors. And we all know this when someone's sitting in front of you, they'll tell you do a great job, you're the very best. Where you want the advocate and support is when the door is closed and they're not in the room or not present.
And so if someone's talking about how good you are and what you've done, I mean, you both have experienced this. When you're talking to someone, they say, I was talking to such and such, and they were talking about you and singing your praises, and they'll usually will say something like, Well, I hope they're speaking well with me. And they'll usually say, Yeah, that's the case, they are. But that's your network operating while you're not there, that the person while you're not in the room is saying positive things about you and your organization.
And so if you can do that, it creates a one-to-many model, which is very, very powerful when it comes to selling and building your business.
KK Anderson (13:56)
quickly
before Mark, before you ask the next question, what you're saying even reminds me of the power of creating your personal brand and your network even on LinkedIn. Like when you're posting things that are are insightful that others may see or comment on or talk about or forward. Like there are some ways with social media and content strategies, even email marketing, right?
Where you can get a one to many approach and build that network to create presence in your absence.
Todd Cassler (14:22)
Well, yeah, and we talked a little bit about this. when I started in the business, one of the first things I did was a mail merge. And this was this idea,
KK Anderson (14:30)
Mm-hmm.
Todd Cassler (14:30)
okay, I'd read a book and you basically wrote this letter, signed it in green pen and sent it out, and then got some business and response. And then as a follow-up, I knew that certain people were interested in certain things and I would read in an article and I'd rip it out and take a sticky note and write on the sticky note, hey, I thought you would like this.
KK Anderson (14:48)
Love it.
Todd Cassler (14:49)
And then there was this thing called a blind copy email. And so you could put like 10 names in the email. Hey, I thought you'd like this piece. no need to follow up, Todd. And you'd send it out. And sure enough, you would get five or six people that would respond and say, Hey, that was a great piece. I really appreciated it. But you're exactly right. Technology has created this ability to connect with people.
And those are little subtle ways to continue to add value around, particular areas of interest for folks. And so I think you're a hundred percent right.
KK Anderson (15:19)
Yeah. one thing I will say real quick, Mark.
one thing I just want to alert is that for our audience listening, the technology is so tempting. And you may be tempted to try to send a hundred emails at once and use some kind of AI personalization that doesn't work, and you may be tempted to try to really take a big bite out of that apple.
But what you said, Todd, and the fact that you're doing kind of 10 at once and you're doing small groups, like that is key. And actually today, when your humanness is actually your uniqueness, right? Today your humanness is more important than ever. Printing an article, writing a sticky note, putting something in the snail mail is more powerful today than it was back then because of the noise that's out there. But if you're building your network and to act creative.
In your absence, as you say, I think that segmenting and that small groups is so, so, so important.
Mark Petruzzi (16:06)
Todd,
for a leader who wants to build network alpha deliberately across a entire team, rather than just leaving it to the few people who already have it, where do you start? How have you started?
Todd Cassler (16:18)
Yeah, I think the first thing is there's some great books that are out there. Never Eat Alone is a great
KK Anderson (16:23)
Yeah.
Todd Cassler (16:24)
book that you can read that talks about how you build your network and the way that you leverage it. So that there's lots of great material and content out there that people can read and get access to. I think the second thing is you have to train for it. You have to teach people how to do it, you have to show them how to do it. and I don't think that this is a skill that people have
that they're just it you have to have practice in order to do it. I think the other thing is you have to reward for it. And people, whether that's compensation or, the way that you're gonna measure people, but you have to create that behavior around how it works. and then I think the last thing is you have to highlight it when it's successful. And so calling it out and demonstrating it. I think if you do those things,
It creates the ability for those to see it, experience it, and learn how to do it. and then I think the last thing is you have to identify it for them. I don't think most people think about it in the sense of, hey, I'm networking for the purposes of doing this. It you have to do a couple of those different things to create the awareness around it. But if you do that,
they'll have the ability to experience it and they'll be able to incorporate it into their business.
KK Anderson (17:30)
Todd, let's move on to our next topic around focus and expertise inside a wide catalog, which I know is your world there at Wilshire. you told us, salespeople, in your opinion, can really only focus on three to four items. So how do you decide which three to four? And how do you make sure that the rest of the portfolio still gets heard? Like how do you manage that?
Todd Cassler (17:50)
I
think the first thing is you have to have a future back strategy on what it is that you're trying to accomplish. And that obviously that starts at the corporate level. Okay, what are we trying to accomplish from our revenue, sales, distribution? pick whatever the category is, but you have to start with what's the goal that we're trying to achieve. I think from there you start to work backwards and say, okay, well, is this an AUM goal? Is it a revenue goal? Is it a product expansion? Are you trying to cross-sell? Whatever it is that you've agreed upon strategically that you're trying to accomplish.
You're then going to start to line up, all right. Where are you going to focus your sales team from a tactics standpoint? Where are they going to apply their effort and energy? and yeah, then when it comes down to product, the reality is like they can only really focus deeply on three to four things. And I think that there's a bunch of data out there on like if you give people too many choices and options, it's hard for them to make a choice.
But three to four things are kind of the key items that you want them to focus on. And I think you have to have honest reflection. And I'll use that term a bunch, honest reflection about whether or not it's really sellable. And I think sometimes there's a disconnect between management and sales around what actually is sellable versus tellable. And you lose sight of what that is. And so those three or four things have to really be sellable. so they're gonna meet the criteria of the buyer, whether that's size, scale, performance.
Pick whatever the key buying characteristics are, but you start there. And then, to your point, you have those things that are on the margin. Okay, the job of the salesperson is to be able to identify those opportunities when they hear them and be able to action them when they hear them, but not necessarily have to go really deep with the materials and the content.
until maybe the second call or getting a resource into the second call.
Mark Petruzzi (19:33)
So Todd, you talked about opportunities on the margin, the ones a client never says directly that show up in a passing comment or in how they ask a question. How do you treat to train a team to catch those? How do you really pull out the intuitive side of your team members?
Todd Cassler (19:50)
I think it starts with good questions. And some of it's also that preparation in advance that you've come in and you generally know, okay, this buyer looks like this. Okay. And my experience has told me that these tend to be the three or four things that are important to the buyer. these may be three or four things that are an issue. My experience tells me that these may be the places where there are hidden opportunities in the corners of the
I think the second thing is you just have to be observant. And, as I was thinking about the interview here in the podcast, I was thinking about an event, a meeting that I had with a bunch of salespeople. We were sitting down in the office and I started to ask a bunch of questions. And like the questions were, that's one of our key priorities. how did you know that? It sounds like you were just in our meetings. this was a key area we were focused on also. How did you know that?
So when we walked out of the meeting, the other salespeople that were there said, Wow, you really seem to know what was going on with that client. And I said, Well, did you look in the office? And they said, No, what do you mean? I said, on the back of the bulletin board, he had the five priorities for the business written on the bulletin board. I said, I just went right down the list and I said, part of what you have to do is when you walk into the room, make sure you look around the room because sometimes the answers to the test are right there on the wall.
but I think it starts with really good questions. And if you ask really good questions, and what will happen is they will say subtle things that you have to identify. And if you can see that, then you ask the second question, and the second question usually opens it up. But most people don't tell you exactly what their problem is when you walk into the room. You have to kind of uncover that and unpack it.
But it starts with great questions and being curious.
Mark Petruzzi (21:34)
So, Todd, let's conclude part one here. this has been exceptionally insightful, and we're only halfway through. In part two next week, Todd gets into how he builds an organization when the buyer sits at three different levels of sophistication. Also, where AI is actually landing in a regulated business and the advice he gives people at the early part of their career.
KK Anderson (21:58)
All right, Todd, that's it for this week. Thanks for listening, everyone, and we will see you next week.
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