CIO Exchange Podcast

Having a Thick Skin in Executive Search is Critical - Guest: Martha Heller, CEO of Heller Search Associates

Episode Summary

Heller Search Associates is an executive search firm that places technology leaders in the right opportunity for them, nationwide, and across all industries. In this episode we speak with their CEO, Martha Heller, to find out how her team excels at navigating the IT talent market while engaging with high level candidates. She describes what is required of technology leaders to be impactful, how they need to look at their career development, and how roles in technology are shifting.

Episode Notes

Nowadays, technology is a crucial part of every company. Technology leaders need to be capable of more than just supporting their business, they need to be able to help drive it. Heller Search is an executive search firm that places technology leaders in the right opportunity for them, nationwide, and across all industries. 

In this episode we speak with Martha Heller, CEO at Heller Search Associates, to find out how her team excels at navigating the IT talent market while engaging with high level of candidates. Martha explains why working in executive search is so fascinating because she learns so much by engaging with different business models, cultures, and candidates. She sheds light on how the pandemic has changed the rules for recruiters and clients, including what companies have to do now to retain top talent. Martha describes what is required of technology leaders to be impactful, how they need to look at their career development, and how roles in technology are shifting.



Key Quotes:

“If we are all in a company whose products and services are more and more dependent on software and on data, and we all are, that means we all need to be a little bit IT, a little bit data, a little bit business. We all have to be these cyborgs who can be our own data analysts, who can be our own technologists. So the dramatic shift that I'm seeing is CIOs recognizing that they need to get out of the business of delivering data and software unto their users who then consume it and they need to design an organization that democratizes IT and democratizes data.” - Martha Heller

“For a CIO to be considered a highly qualified candidate, they need to be a really good communicator. They need to demonstrate that they're not an order taker, executing on somebody else's strategy that they themselves are strategic thinkers, but it's not my way or the highway. They're really good collaborators, so that business partnership relationship piece is extremely important. They understand how to run a high performing IT organization, and they can prove that through metrics. That's what companies are looking for.” - Martha Heller


Time stamps:

01:15 Approach to Executive Recruiting

04:45 Difference Between Prospects and Clients

07:45 Approach to Candidate Market

11:15 Impact of the Pandemic on Retention and Recruiting

13:45 Shifts in Technology Roles

17:45 Approaching Problems from a Technology Perspective

23:15 Eliminating the Distinction between Inside and Outside of IT

26:45 How Technology Leaders Should Look at their Careers

28:45 How to have an Impact as a CIO

35:15 Best Ways to use a Recruiter



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Episode Transcription

Martha Heller (00:00):

The CIO who says, "I want to have a major impact," the first thing is, look at your resume. Make sure that your resume has business impact, change, digital, data. How have you created data as an asset for your business?

Yadin Porter de Leon (00:19):

Welcome to the CIO Exchange podcast, where we talk about what's working, what's not, and what's next. I'm Yadin Porter de Leon. CIOs and other technology executives are now expected to help drive the business, not just support it. Heller's Search is an executive search firm that places technology leaders in the right opportunity for them across all industries.

Yadin Porter de Leon (00:39):

In this episode, I speak with Martha Heller, CEO of Heller's Search Associates, to find out how her team excels at navigating the IT talent market and connecting individuals to the right companies. Martha sheds light on how the pandemic has changed the rules for recruiting and clients, including what companies have to do now to retain top talent. Martha also describes what is required of technology leaders to be impactful, how they need to look at their career development, and how roles in technology are shifting.

Yadin Porter de Leon (01:11):

Martha, I'm excited to talk to you today, because it fascinates me, the dance between candidate and company. How you talk to individuals, how you make the match between somebody who's looking for a new opportunity, that new next adventure, that new next chapter. And it's not just professional. It's also very personal as well. And then the company who's trying to find someone who's going to add the kind of value that they're looking for, that there's a defensing of culture. There's also a augmentation of culture. It's this really sort of fascinating sort of ritual of bringing two entities and individual personalities together as a part of a team, as a part of a company. Give me a sense of, how do you approach this? How did you get into this? And what makes you passionate about that dance?

Martha Heller (01:50):

So I really appreciate your saying that, because I agree with you. Recruiting is just fascinating, and I'll just, something personal about myself is that every year throughout my career, if I start the year and I say, "I'm not going to learn anything new in this job this year," I'll move on, right? Time for something else. Well, I've been in executive search since 2005. I have one time left a company and started my own, but I've stayed in it, and the reason is because it is so fascinating. You do learn something every single day, because there's a different business model, a different culture. Every candidate has a different story. No search goes exactly the same way, so that it's always fascinating. And then to your point, Yadin, people, as much as I try to change this, people continue to have free will and so if you're-

Yadin Porter de Leon (02:39):

Darn them and their free will.

Martha Heller (02:41):

I know. It's very annoying.

Yadin Porter de Leon (02:42):

What are they thinking?

Martha Heller (02:42):

Or maybe they don't. Maybe it's all just fate and destiny. I'm not really sure, but you can do everything on a search, and then in the 11th hour, somebody's spouse doesn't want to relocate, or somebody got a counteroffer they never expected that they were going to get, and that happens even more so these days, given such a tight market.

Yadin Porter de Leon (02:59):


Martha Heller (03:00):

And so just what makes life interesting is the people in it, and your connection to the people in it, and in executive search, that is pretty much all you do, is connect to people.

Yadin Porter de Leon (03:10):


Martha Heller (03:11):

So just to delve a little bit more deeply into the response to some of the questions that you asked, as a broker, yeah, we get paid by the client, but we still have to make sure that the candidate has not only a good experience with us, but also lands really well in the organization.

Martha Heller (03:32):

So even though the bills get paid by our client, the hiring companies, we have to do right by those candidates. So just going into a new search, it's understanding that this has to be a win-win-win for everybody, and getting to know everybody's agendas, and their culture, and what they're looking for in their career, just got to get really in and get to know people really quickly and really confidently. And that's how you wind up with a successful result. But one thing I will tell you, is we can do all of that right, we place a candidate, and then things change in that organization, and in the end, that candidate doesn't work out. So I think having a-

Yadin Porter de Leon (04:12):

It's changing all the time.

Martha Heller (04:13):

It's changing all the time. And I think having a really thick skin in executive search is one of the probably most critical attributes.

Yadin Porter de Leon (04:20):

Yeah. I think that's really important. One of the things I think that was critical too, was talking about how everyone need to have a good experience. The experience, I think, is a really critical part of that. And so when you're working with a CIO, CTO, a CSO, and you're placing them, and they're the candidate, they're looking to decide whether or not they want to join the company, but also proving to the company that they have what it takes in order to provide value to that company, I think it's a really great perspective for those who are the candidates, to understand that the recruiter's really trying to give them the best experience, not only for that fit prospect that you're talking about, but also, I would imagine too, and you can kind of give me your perspective on this, but some of those candidates are going to be your future clients.

Martha Heller (04:58):


Yadin Porter de Leon (04:59):

They're going to be the ones who are then going to come back to you and say, "I had a great experience. I need to use her again for this other leadership position that we're trying to look for." Is that something you experience?

Martha Heller (05:07):

Well, actually, it's really wonderful, because with executive search, delivery to the client is essentially the same as doing new business development in the market. Because every time you call a potential candidate, you are developing potentially a future client, to your point.

Yadin Porter de Leon (05:23):


Martha Heller (05:23):

So that's why the experience has to be so good. But years ago, one of my very first searches was for a very large media business in New York City, and believe it or not, this was like 10 years ago, and the title of the role I was recruiting actually had the word digital in it. I think of that, digital, as fairly recent, but now I'm remembering about a decade ago I did a role, a digital solutions leader or something. And I called two CIOs I knew in the space who might know somebody, and both of them said, "Actually, we're looking for one of those too." And before I knew it, by the end of the day, I had two new searches. So in executive search, when you're delivering to the client, you're essentially also building a new client list at the same time. So that experience has to be really good for everyone.

Martha Heller (06:08):

And just going back to the experience thing, what I hear, when I hear sort of complaints about other search firms, and recruiters, and that kind of thing, it's a lack of communication. It's if the client is, say, maybe putting that candidate on the back burner because they want to meet a few people, and the recruiter doesn't go and engage that candidate pretty frequently, that's when the bad experience happens. And even worse, that's when the candidate decides to walk.

Yadin Porter de Leon (06:33):

Yeah. [inaudible 00:06:34].

Martha Heller (06:33):

So keeping them engaged in the recruiting process is probably the most important skill when you're recruiting. It's keeping those candidates warm.

Yadin Porter de Leon (06:43):

What really interests me about that piece is the candidates may seem like there's sort of this power asymmetry or information asymmetry when they're looking at these particular opportunities, and they're, "Okay, I'm being evaluated," or there's a very traditional view of, "This is how the interview process, this is how the courting process goes." When in fact, really, especially, like you mentioned, in this market too, that asymmetry is starting to become, in certain circumstances, a thing of the past, and you do need to engage really well with those different candidates and ensure that their needs are being served in a way that ... I don't know if you can give me a perspective on this, but in a way that maybe just hasn't existed in the past. Especially in technology firms. This is a little bit niche here. In technology firms, in this particular market, there seems to be that shift in ... I don't know if you'd say power dynamic, or information asymmetry. What do you feel like that shift, how that shift's happening?

Martha Heller (07:43):

Sure. I would say at this moment, it is absolutely a candidate's market. We'll see what happens, right? With the economy shifting, we'll see. Now, all we do at Heller's Search are technology executive search roles. We're in every industry, but we're only dealing with the technology leadership position, and turns out technology is kind of important.

Yadin Porter de Leon (08:02):

Just a little bit.

Martha Heller (08:04):

So I am optimistic that as the economy shifts here, and there's maybe a little bit of a leveling out, I am optimistic that the technology functional market will not be impacted, because look. In down times, you need analytics even more than you did in up times. In down times, you need really, really good communication technologies more than you did in up times. So I think we're going to stay really strong, but for right now, it is absolutely a candidate market, and I would say the way that changes things for us, one it's client expectations management. "We want someone who costs this much, who will already live in this place, because we don't want to relocate them. We want them to have this kind of experience, this many years of experience, and we really want a diversity candidate." It's like, "Okay. It's a tight market. You can't have all those things. Or you can, but you got to open your wallet."

Martha Heller (09:05):

So in a market, as you point out, where the power dynamic shifts to the candidate, our job is client management, so they really understand what's happening in the market. And then I would say the fundamental shift that we've made for this market, in addition to just moving as quickly as we can, is when the candidate says, "Yes, I will accept an offer from your client for their CIO position, and I will not accept a counteroffer to stay here, because I am ready to leave," you cannot take that at face value. They mean it, but what companies are doing to retain high value candidates today is very different in the past. I'll just, Yadin, give you two examples of that.

Yadin Porter de Leon (09:51):

Oh, no. This is great. See, this is the secret sauce. This is what I want to hear.

Martha Heller (09:54):

One is, we were doing a search for a high tech business, and the CTO, who had accepted the offer, went in to resign. The reason he wanted to move on was because there was a ceiling above his head. The person he reported to wasn't going to leave anytime soon. That person actually resigned in order to retain the candidate. In other words, he said, "You know what? I'll retire early, so that this person, this high value talent, will remove that ceiling, and they can take on this new job." I have never, in my millions of years in this career, seen companies have their senior executives retire early to retain someone. Well, that was a kind of counteroffer I've never seen before. And in the end, that candidate wound up staying. That's something, now what we do is we really drill down more, and we also caution the client that candidates are going to be more susceptible to powerful counteroffers than they have in the past.

Martha Heller (10:51):

Here's one other thing that I think is very interesting right now. In the past, when we are doing a search, and we're reaching out to candidates, if someone's just recently taken a role, say it lasts one to two years, unless we know something, we don't want to reach out to them. We might ask for referrals, but we figure, "They just took a job. They're not going to want to leave anytime soon." And our client is going to be suspicious of someone who's left a role so quickly.

Martha Heller (11:17):

However, in the pandemic, the rules are different. Often people who took roles during the pandemic, so basically from, let's call it April '20 to April '22, are actually more vulnerable to leaving than in the past, because they're working remotely, so they haven't really built a relationship yet. They haven't really become a part of the culture yet. Maybe they took a job under duress, because of the pandemic. So a big shift is, as a recruiter, don't assume that if someone took a job in the last two years, you can't touch them. Those people who took jobs during the pandemic are more susceptible to being recruited than they would have been in the past, if that makes sense.

Yadin Porter de Leon (12:00):

No, that does make sense. That's really interesting too, and maybe even so, and you can give me your perspective on this, they're in this sort of flux period where people left, or people made transitions or changes, because they were looking for something different, a new lifestyle, a new way of working, a different industry. And they might still be in that search, that discovery, that period of discovery. And so they're like, I might see someone for six months, for one year, and they say, "You know what? I don't want to do this. Let me try something else for six months or one year." Are you finding that as well?

Martha Heller (12:30):

What I'm finding is that the whiplash of the pandemic, and its impact on the workforce, on recruiting, and now on the economy, has so many twists and turns that I don't think we're really going to be able to understand the impact until we're able to look back. What I'm seeing now is just things like our time to fill used to be a full three months, maybe a little bit more than three months, from the minute we have an approved position description to when that candidate accepts an offer. You would think in this tight market, everything would take longer. It's considerably shorter now, because all of the first and second round interviews are all happening on Zoom. We used to fly people around all over the place. It would take forever. It could take weeks before you could even get that first round of interviews completed.

Martha Heller (13:19):

Now, we're actually finding that our time to fill is faster, because of the impact of the pandemic, even though you would think that things would take a lot longer because of how tight the market is. So there are so many differences in the market, in how we recruit based on the pandemic, that again, I think in a couple years, we'll be able to look back and say, "Okay, that's how it all shook out." I don't think we're there yet.

Yadin Porter de Leon (13:44):

I see a book in this, Martha. I see a book here.

Martha Heller (13:47):


Yadin Porter de Leon (13:47):

So you can start to write this right now. Put it out.

Martha Heller (13:49):

You got it. You got it.

Yadin Porter de Leon (13:49):

I'm just putting it out there. Excellent. Well, this is a fascinating perspective. Let's shift gears a little bit too, because I want to have some time where we kind of cover what it takes to sort of fill these roles. Because like you said, things have happened in the last decade, you're talking about. The first title with "digital" in it being like a decade ago, and the difference between what was required from somebody back then is just ... There's a massive chasm in those requirements, then versus now. You might have somebody who's far more of an IT functional technologist, who's filling one of these CIO roles or CTO roles, and now you need someone who's a leader, who's a business person, who is all these different things that you never really required of this technology leader before. Could you first just give a little bit of perspective on that journey that you've seen the CIO role and the other roles in the office of the CIO, that shift that's happened historically, and then kind of give me a sense of what's required now.

Martha Heller (14:41):

Sure. So let's think about it this way. In this country, for hundreds of years, we were all farmers. We had an agrarian economy.

Yadin Porter de Leon (14:50):

Back in the good old days.

Martha Heller (14:52):

I don't think I would have been a great farmer, but anyway-

Yadin Porter de Leon (14:55):

You didn't need back office IT back then. Nobody was building exchanges.

Martha Heller (14:59):

No. You do now. You do now. I mean, farming now is highly technical.

Yadin Porter de Leon (15:03):


Martha Heller (15:03):

They're doing a tremendous amount with analytics in farming.

Yadin Porter de Leon (15:05):


Martha Heller (15:05):

But anyway, and then we became an industrial economy in the late 18th century, and that's when we set all this up. We set up our democracy, we set up our companies. We have boards of directors. We have bigger footprints, more train tracks, more ships. Everything bigger, bigger, bigger. Well, we're not in the industrial economy anymore. We're in the digital economy now. We're maybe even the data economy, but we haven't made dramatic changes in the way our companies are organized. But when you think about it, today, every company in one way or another is a technology company. So just as an example, when Cargill, which is like a $180 billion agricultural business or something like that, when they started putting IoT and sensors in their shrimp ponds, in their farms, in order to better predict yield and that kind of thing, the CIO there did not call other food and agricultural businesses to compare notes and to say, "Hey, where does IT stop, and where does this product technology start?" He called the CIO of SAP, and the CIO of Microsoft. So here you've got the CIO of Cargill-

Yadin Porter de Leon (16:19):

A big shift.

Martha Heller (16:20):

... calling software businesses to get their perspective on how you design organizations around this. Because the CIO, he's retired, but the CIO of Cargill just a year and a half ago was thinking like a software company CIO. Not like an agricultural CIO. And you see that across all different kinds of industries. So if we are all in a company whose products and services are more and more dependent on software and on data, and we all are, that means we all need to be a little bit IT, a little bit data, a little bit business. We all have to be these cyborgs who can be our own data analysts, who can be our own technologists. So the dramatic shift that I'm seeing is CIOs recognizing that they need to get out of the business of delivering data and software unto their users who then consume it, and they need to design an organization that democratizes IT, and democratizes data.

Yadin Porter de Leon (17:27):

I love that perspective. Martha, that's just phenomenal, because I've had so many conversations with CIOs who talk about how other people in the organization need to be on the hook for technology.

Martha Heller (17:36):


Yadin Porter de Leon (17:37):

And instead of saying, "I need to then design and innovate and do all of these things," which are part of sort of the charter, but what really makes a big impact, and we're really talking about impact here on the business, and the business value that's created, is creating an organizational, a cultural movement, a way in which you can, programmatize the thought processes of and the strategy around how to approach problems from a technology perspective.

Martha Heller (18:06):

Exactly. And the design of that. But it's more than the design, because you've got to create it. That to me is one of the most important roles of a CIO. More than being very deep technically. More than delivering a piece of software. It's all of that. So a CIO I know from Semiconductor put it this way, which I really liked. He said, "When you take the concept of data," which is of course a huge concept and incredibly important to every company right now, he said, "Think of it this way. In IT, our data engineers are the butchers. They take the big cuts of meat, and they cut it down into the size that customers are going to want. And the customers come in, they choose their meat, and they go home, and they make their own meals. They're not calling the butcher to say, "Deliver a meal to me." So the democratization of data, the democratization of IT, is where IT is creating the environment, the governance, the guardrails, to allow everybody in the company to be their own data analyst, to be their own technologist.

Martha Heller (19:20):

I'll give you one more example to drive this home. This was the CIO of Lear Corporation, Bonnie Smith. When she was there, she found that in all these 270 global manufacturing plants, that the plant managers were doing their own RPA, robotics process automation tools and solutions. And she said, "We're going to be reinventing the wheel all over the place here. Let's try to get organization design down in a governance structure so that everybody can be their own RPA developer essentially, but we are going to put in the tools for them. We are going to inventory what they're doing. So if somebody in a plan in Germany is doing something that somebody in a plan in Brazil is just thinking about, they can be connected so that they can work together, and not have to sort of follow the same ... Stub their toe on the same rock twice." And so what she did is she built an RPA self-service structure. Well, what did it entail-

Yadin Porter de Leon (20:17):

So fantastic.

Martha Heller (20:17):

... for her to do that? It wasn't technology depth. She had to make sure that she could find the vendors that would work in that capacity, which is new. She had to figure out who were going to be the people who were in each plan, who were really going to be her allies, who were going to be the first adopters of this technology. She had to get her team to stop thinking about delivery, and think more about governance and design. Not one of those attributes or skills is very technical. It's influence. It's design. It's strategy. It's relationships. It's leadership. So the move to the democratization of data or the democratization of IT is really about leadership, influence, design, and governance. It is not about being a deep technologist.

Martha Heller (21:06):

Now, that being said, there are many examples of companies that very much need their CIOs to be deep technologists. A lot of it depends on where they are in their life cycle of technology.

Yadin Porter de Leon (21:17):

Yeah. And I think part of that responsibility, like you were talking about before, of the CIO and others within the office of the CIO, is helping others in the organization increase their aptitude when it comes to technology, so that you're not needing a CIO who has all the deep technical skills in order to be the one who has all the right answers in the room, but instead they're enabling others to be able to go off and do those types of, or make those types of decisions on their own, because they're competent in their particular realm, in their business unit, in their capacity, and they have enough technical chops in order to make good, solid technical decisions.

Yadin Porter de Leon (21:58):

And that kind of goes back to that point that I really wanted to dig into, and I love the way that you framed it as a democratization of technology, or democratization of IT, because that really then gives license to the rest of the organization, and also gives a responsibility to the rest of the organization to say, "Look, we need to not just look at this one person, or this one role, or this one silo to have all of technology and applications and services provided to us," but we need to be able to participate in that, and we need to be able to create what you were talking about, which is a self-service platform.

Yadin Porter de Leon (22:27):

And the reason that fascinates me so much is because that's been talked about in so many different ways, but it's usually been talked about within IT. Like, "We need to make a self-service platform for developers." That's a big one. "Applications are key. They're the center of everything. We need to make sure that we increase developer velocity. We need to make sure that we enable innovation, and that needs to be self-service, and all the infrastructure has to be transparent." All that stuff, that conversation's been going on for quite some time, and it's getting deeper and richer. But I think then what you're talking about is coming outside of IT.

Martha Heller (22:53):


Yadin Porter de Leon (22:53):

Having that conversation outside of the technology department, and I'm using air quotes, even though I'm on a podcast here, and saying, "Look it, this is everyone. We are a technology company. Everyone is on the hook for making good technology decisions." And the CIO is going to be the one who's going to be the ambassador for that transformation. And not just the digital transformation, doesn't just mean everything has got IoT, and you've got digital in everything, you've got apps running everything. That transformation really, that idea of digital transformation is really changing to we need to change the way the organization functions, the way the organization is, or literally organized, and that person to be the one potentially in certain companies, when the company's ready for it, to be the champion for that change. Are you seeing that?

Martha Heller (23:33):

That's exactly right. And to pick up what you said is that you've thought of self-service as happening inside of IT, and you're absolutely right. But what we're talking about is happening outside of IT. Well, what CIOs are working hard to do is even eliminate that distinction between inside IT and outside of IT. So take the concept of-

Yadin Porter de Leon (23:54):

I like that. I like that.

Martha Heller (23:55):

... of agile development or product management. So it used to be, we used to do projects. We'd get a project funded at the beginning of a year or what have you, and then we would deliver on that project, and hopefully not run out of money, and hopefully do it on time. And at the end, we would deliver it to our business, quote, "customer." And hopefully, even though the project took three months, six months, hopefully even though we never checked in with one another, and we never really made sure that we were iterating and that we were getting positive feedback the whole way, and then lo and behold, three, six months later, the business partner says, "Oh yeah, I don't even need that thing anymore. That's not at all what I wanted." Now we just wasted a lot of money and a lot of time.

Martha Heller (24:35):

Well, forward-looking organizations are not doing that anymore. They're eliminating the concept of a project, and they're replacing that with the concept of a product and a product leader. And that product can be something that goes out into the market for revenue, but a product can also be an internal system. It's something we're putting out into that market. That market could be internal to the company, like a new video collaboration platform, or the product could be external. It could be a new app or something. But the idea is that there's a product leader, and that product leader isn't managing a project. That product leader is ensuring that a capability gets developed to meet a commercial need. And that product leader is often not in the IT organization. They might come from marketing. They might come from product. They might come from supply chain. They could come from anywhere, but on their team, they've got somebody from development, somebody from security, somebody from operations, somebody from marketing, if it's an external product.

Martha Heller (25:34):

So this design of this new sort of democratization of IT or this new digital organization includes the movement from managing projects in IT, and then delivering them out to the business. And rather than making one cross-functional team that, "Is this in IT or in the business?" The answer is yes. It's in both.

Yadin Porter de Leon (25:54):


Martha Heller (25:54):

So that moving to a product management model, or moving into agile development has been a real tool for CIOs in creating this more democratic organization.

Yadin Porter de Leon (26:07):

And that's such a powerful idea, Martha, because two things. One is, that's shifting the focus of the organization, like you talked about. Fundamentally, organizations have been structured in certain ways for a very, very long time. And some of that, especially in some industries, some organizations, that change is happening very, very slowly. But two, the second piece is that change is happening in some organizations, some much faster than others.

Martha Heller (26:29):

Correct. Yes.

Yadin Porter de Leon (26:30):

And so I wanted to kind of bring it back then to sort of the perspective of the CIO, or the aspiring CIO, or the CIO that wants to move to another company. How pervasive is that idea, and how should a CIO, a CTO, CSO, who is looking to find their next chapter in their career, how should they be looking at this movement with regards to their own experience, their own perspectives, their own vision, and their own skill set, so that when they're talking to another company, they're deciding, "Well, how far along this journey or along this trajectory or transformation is this company that I'm looking at? Should I be looking for a company that's moving in that direction? And what then should I feel like I need to communicate to them in order to say that I have the experience, I have the leadership, I've got the vision in order to help continue that journey?" What should I be looking at as a CIO, if I'm making that move?

Martha Heller (27:16):

So I guess the first thing is, let's start with your own gut check. Are you a business leader who wants to influence and create that kind of change? Were you a technologist who loves the technology, who loves to develop, who loves to lead engineering teams to create new intellectual property? Which are you? And that's the first thing. Because if you're a deep technologist, a real CTO, there's tremendous opportunity for you. You don't have to worry about going to Silicon Valley. There's Silicon Valleys all over the place, but you could go be a deep technology, advanced technology person who does nothing all day but work with engineers to create really, really cool artificial intelligence platforms, either for sale or for your company.

Martha Heller (28:00):

So first decide, if you love the tech more than you love the people, and the influence, and the strategy, and the change management, and all of that, go that route, because you'll have a very rich and highly lucrative career. If you want to be a CIO and eventually a chief digital officer, which is kind of the next rung, although I do believe there will be a point where the concept of digital just goes away. We are digital. How often do we have to say digital? When something means everything, doesn't mean anything?

Yadin Porter de Leon (28:30):

Yeah. Exactly. There's a lot of that. There's a lot of that, and marketing's partially to blame for that.

Martha Heller (28:36):

For sure. Now digital, the concept of digital now connotes change. We're moving from what we were to what we're going to be. And until we get there, we will still use that concept, which is fine. But the CIO who says, "I want to have a major impact," the first thing is, look at your resume. Make sure that your resume has business impact, change, digital, data. How have you created data as an asset for your business?

Yadin Porter de Leon (29:04):

Oh, I love that. Data as an asset.

Martha Heller (29:06):

Maybe you had nothing. Maybe your company had no data anywhere, and you were able to give a modicum of data that allows your company to look backwards in order to make decisions for the future. Great. That's business intelligence. But maybe you've came into an organization that was already pretty mature there, and what you did is you actually put in an artificial intelligence platform that allows your claims processing organization to be that much more accurate and that much more efficient. Get that stuff on your resume. Don't say you rolled out global instance of SAP. That's great, but what was the point of that?

Yadin Porter de Leon (29:39):


Martha Heller (29:40):

What was the business impact of that?

Martha Heller (29:42):

So the first thing is, if you look at your resume and you're like, "Eh, I don't really feel that I had a lot of business impact. That's not really that important to me," then you haven't passed step one. I wouldn't bother. I would go a CTO route. But if you feel that you've done a lot already in that regard, then what you're looking for in an opportunity, in a new business opportunity is you are looking for a culture that is ready for this change. Because if you get in there, and what you see that is right for the company is that we start selling products that have data in them, or we start coming up with new revenue models, or we do something truly transformational that you believe this company absolutely needs, and maybe the CEO agrees with you, but those business partners say, "Hey, I've been doing this this way for 30 years. What you're saying sounds like too much change for me," then you won't be successful.

Yadin Porter de Leon (30:35):

Yeah. That's a red flag.

Martha Heller (30:36):

So you're never going to walk into a new opportunity where everything's lined up perfectly, and everybody's ready for their change, and they're already organized, and they were just ready for you to come in and set the strategy. First of all, that wouldn't be the most gratifying experience anyway. And those really don't exist. So it's to come in and assess.

Martha Heller (30:56):

And I would say some of this, Yadin, also kind of boils down to money. If you come in and you say, "All right, company, you've told me you want to grow X percent. You want to expand into these markets. You want to do more digital engagement," and I have put together a plan and a funding approval request where I have shown you the return on this investment, are you going to say yes, or are you going to say "No, CFO and CEO?" And the worst situation for a CIO to be in is to be accountable for outcomes that the business will not pony up the money for.

Martha Heller (31:32):

So going in, and I wouldn't do this on your first interview. The first interview is, you just want to win the right to come back. That's all you want to do first interview. Just win the right to come back. And how do you win the right to come back during that interview? You're strategic. You're a really good communicator.

Martha Heller (31:48):

Oh, here's a key one. Team development. Because of the tightness of the market now, your ability to go outside of your company and acquire and bring good people in, that's half of what the new company's looking at you for, is, "Are you going to-"

Yadin Porter de Leon (32:01):

I see. See, this is the good-

Martha Heller (32:02):

Yeah. "Are you going to be able to-"

Yadin Porter de Leon (32:03):

These are the goods right here. This is what we want to get into.

Martha Heller (32:07):

But it's, "Are you going to be able to fill these seats? We've got 50 open positions in IT. Are you going to be able to come in, do you have a track record of building that organization?" So let me just put a fine point on this. For a CIO to be considered a highly qualified candidate. They need to be a really good communicator. They need to demonstrate that they're not an order taker, executing on somebody else's strategy, that they themselves are strategic thinkers, but it's not, "My way or the highway." They're really good collaborators, so that business partnership relationship piece is extremely important. They understand how to run a high performing IT organization, and they can prove that through metrics. That's what companies are looking for, and then the cultural fit piece, and that's where we're going way back to the beginning of your and my conversation, where we were talking about recruiting. That's where there's a little bit of matchmaking going on.

Martha Heller (33:01):

It's you want to bring ... You know, if you've ever set anybody up on a blind date, you think, "Oh, these two are perfect for one another," and then they hate each other. There's just a level of cultural fit that has to be there that you cannot really ... You can't fake it. So either you're going to be a cultural fit or you aren't. But then the key thing there is, "Are you a fit for the culture as it is, or are you a fit for the culture as it needs to be in order for the company to be successful in a digital world?" So that's the other consideration.

Martha Heller (33:32):

So those are the things that you need to display in an interview. But for you, the question is, "Are these executive committee members who will be my colleagues, are they the team that is going to be my partner in creating change?" And if you're looking around and you're seeing a lot of people who metaphorically are crossing their arms, and you're thinking, "Yup, that one's not a change agent. That one's ..." You're going to be alone, and you're not going to be successful. So it's a two-way street. They got to evaluate you. You got to evaluate them. But what everybody is evaluating the other one for is, "Is this combination going to help us transform into being a digital business?" Because no business is immune from that.

Yadin Porter de Leon (34:16):

No. So it distills that idea down to one of the really core pillars of what both the company and the candidate need to consider when they're trying to kind of come together and see if something really is going to be created here. I like to talk about that Venn diagram of the crossover of what the company needs, what the company's looking for, and then what the skill of the individual is, and what the individual's looking for. And there's that overlap, that Venn diagram, where those two meet for a certain period of time. Sometimes it's two years, sometimes it's 16 years. One of my other colleagues calls that riding the wave, and that Venn diagram represents that period of time where the wave is, right before the wave breaks, and then rolls back, to make a Hunter S. Thompson reference.

Yadin Porter de Leon (34:59):

And that's that point that you're looking for, and you get to be the one who is just the architect of that Venn diagram, and bringing those together, and seeing if that fit happens. And that kind of brings me sort of to the last point I think is really important to cover, is when you're a candidate or when you are a company, and I guess we're really looking from the CIO's perspective in this, how is it best to use the wonderful talents and experience of the recruiter in order to make sure that your Venn diagram is fitting well?

Yadin Porter de Leon (35:28):

Because I imagine, Martha, that you engage in what I'd like to call therapy, which is in this case candidate therapy, or company therapy, where you're taking them on a journey, where, "Okay, we need to ..." Like you talked about, "What do you really want? What is important to you?" Let's get those straight first, and let's make sure it's realistic. And then let's move you along the journey in order to be able to achieve that. Do you feel like you engage in a little bit of candidate therapy, and should candidates really make sure that they're utilizing that part of your skillset?

Martha Heller (35:55):

Sure. So I'll just ... It's candidate therapy and it's client therapy, but it's very interesting, because early, early on in my career, really early in recruiting, I had a client, and they really liked one of these candidates that I had presented. And the candidate in the 11th hour said, "You know what? I really like my company. I don't think I'm ready to make a move." Well, I wanted to make this placement. So I convinced him. I said, "What are you talking about? My client is great. You want to go here. Blah, blah, blah, blah, blah." Well, he didn't last long. And that's when I realized, you have to be careful in your influence, right? I influenced, he did not want this job, and I put the screws to him, and he wound up taking the job, and then it blew up. He wound up leaving, because he wasn't happy.

Martha Heller (36:40):

So part of it is recognizing what that candidate really wants, not what you want as a recruiter, and not what your client wants. So that's part of it. But I'll tell you one other quick story. I had a search recently where the client had been introduced to a candidate, not through me, through a peer or whatever, and he was a great leader, and he knew the organization well, and he'd be a really good cultural fit, but he wasn't an experienced IT leader. He had some technology acumen, but I said to my client, "Your IT organization is not mature enough for you to have a new CIO who doesn't come out of IT. I understand that you like this person, that he's a good leader and all of that, but the other thing is, he's never going to be in his comfort zone. He's always going to be sort of trying to lead in areas that are his comfort zone, that aren't IT."

Martha Heller (37:32):

So that was, again, and my client listened to me, and they made a great hire, and it's worked out. So I think it's the therapy thing that you're talking about, and as a recipient of many, many years of therapy, I feel that I have a lot to offer.

Yadin Porter de Leon (37:48):

They're professionals. They help you get from A to B. You want to go on that journey?

Martha Heller (37:51):


Yadin Porter de Leon (37:51):

You're stuck in your own head.

Martha Heller (37:53):

Absolutely. Well, no. It's about going through life with eyes wide open.

Yadin Porter de Leon (37:57):

Exactly. Exactly.

Martha Heller (37:58):

That's the idea. But the point being, as a broker, you have to know in your heart what is right for the candidate, and what is right for the client, so that you could use your powers of influence wisely. One example I gave you, I did not use my powers wisely, and it blew up. In another example, I had the courage of my confidence to say, "Hey buddy, I know you like this guy. He's not going to be right for you." So I think that's the most important thing, is to really understand what the right outcome is, and to influence and use that therapy appropriately. I would say I do more therapy with the candidate than with the client.

Yadin Porter de Leon (38:44):

That makes sense.

Martha Heller (38:44):

The client usually knows what they need, but the candidate's, "Oh, I'm not sure. I don't know how it went. I'm not sure what to do." That's usually where the therapy comes in.

Yadin Porter de Leon (38:51):

Well, Martha, this has been absolutely fascinating. I think you provided just some phenomenal perspective. There's so many different ways I could have gone with this, including reorganizing companies, looking to reorganize companies, and how you could do it as a prospective CIO and a new entrance in a company. But we're going to have to unfortunately stop it right there. I appreciate all of the experience, and give the listeners a sense of if they want to learn more about what you're doing or maybe some other perspectives and other places you provide them, can they reach out to you? Can they find you on social media, Twitter? Is there any place that they can find you in the digital world?

Martha Heller (39:23):

The answer is yes. Yes. You'll find me. Go out there.

Yadin Porter de Leon (39:29):

Just go out there. She's there.

Martha Heller (39:31):

Just go out there. I'm out there. I'm everywhere.

Yadin Porter de Leon (39:34):

Oh. That's phenomenal.

Martha Heller (39:36):

All right. And let me say, I started out early in my career. I did something called Talk CIO, or Talk Radio CIO at CIO Magazine. This is early days. I mean, we're talking literally 20, 22 years ago. And I did this. I interviewed CIOs and other people for CIO Magazine, and I was really proud of what I did, but you do a much better job.

Yadin Porter de Leon (39:59):

Thank you so much for the kind words, Martha, especially with your experience. That means a lot to me. But I'm relentlessly curious.

Martha Heller (40:06):


Yadin Porter de Leon (40:07):

And that's just what drives me and I just-

Martha Heller (40:08):

I can tell.

Yadin Porter de Leon (40:08):

... I keep moving. I'll give you one little sort of anecdote too, is actually I literally on my office wall, I literally have pictures and quotes from CIOs. Everyone from Cynthia Stoddard at Adobe to people at Ford, and just what they say. And when I'm talking to people, before I'm interviewing, I'm looking. I'm like, "Will this help them? Will this help them? If they listen to this, is this going to help move the forward?"

Martha Heller (40:28):


Yadin Porter de Leon (40:28):

So getting a little meta there, but that's my perspective.

Martha Heller (40:32):

Oh, that's good. That's great. That's right.

Yadin Porter de Leon (40:34):


Martha Heller (40:34):

It's your North Star. Excellent. All right, Yadin. Thank you so much. Really appreciate it.

Yadin Porter de Leon (40:38):

Thank you. Thank you so much, Martha, for joining the CIO Exchange Podcast.

Martha Heller (40:41):

Okay. Have a good one.

Yadin Porter de Leon (40:43):

Thank you for listening to this latest episode. Please consider subscribing to the show on Apple Podcasts, Spotify, or wherever you get your podcasts. And for more insights from technology leaders, as well as global research on key topics, visit