May 4, 2021

Alternative Job Search Strategies at the Executive Level


Episode Highlights

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Careerwell & Hirewell’s Talent Insights series presents “Adventures in Job Seeking, Episode 5” with special guest Ted Drost.

Finding a job is tough right now, and it’s even tougher at the executive level. Ted Drost is an accomplished sales and marketing leader with a strong background in financial services. Like a lot of people, he realized early on in COVID that his search wasn’t going to be an easy one.

But making a few small changes makes a world of difference. And while applying to job postings is a black hole for most, he actually found a way to be successful with this method by making a few tweaks in his targeting.

Ted joined James Hornick and shared his experiences and job search methods that landed him the VP of Business Development job at Dividend Finance.

Episode Transcript

Welcome to adventures in job seeking, episode five with a Ted drost, alternative job search strategies at the executive level brought to you by Hirewell and Careerwell. I’m your host James Hornick adventures in job seeking is our ongoing series where we talk with people who have been successful, doing some interesting things in their job search with the intention of getting all job seekers out there.

Some actionable takeaways. Today’s guest is an accomplished business development and marketing executive with strong financial services background, experience everyone, please welcome. Hey, thank you, James. Thanks for having me. Yeah. So first things first, I like to always kind of start these off, like tell us about yourself.

 I want your job seeker elevator pitch. So when you talk to companies, what were you telling everyone that you, yeah. Okay. So if you want that 15 second version of who I am and what I do, and typically the way in which I had introduced myself is, you know, I’m, I’m Ted DROS. I am a business development, client partnership and marketing.

Leader 15 years worth of experience in financial services. And I am looking for that next right company that wants to take my skillset and grow and innovate. And that, was it short and simple. Nice. so I wanna give people the perspective, cause I wanna see where you ended up because you had, obviously you got a great gig recently and then we’ll kind of go back to the beginning.

So, not to skip the NFL, but, but where did you end up? What’s the company? What’s your role? Right. And I’ll tell you, I ended up in an organization that is exactly. What I was looking for. This is a, it’s a FinTech firm, based in San Francisco in San Diego called dividend finance. And they’re a FinTech play.

They are focused in on the, solar as well as home improvement industries, providing consumer finance to that sector. And, very digitally progressive in terms of what they do. They have created a platform that is simple and easy to use for the consumers, for the dealers out there. And certainly for the manufacturing partners that we’re looking to do more business with.

But again, grow focused, very innovative and, thrilled that I actually land with with such a, farm. Nice. how long have you been with those guys now? Yeah, so it’s, it’s been about six weeks, so a month and a half drinking from the proverbial fire hose at this point in time and trying to do it all virtually as well.

we’ve got some presence in downtown Chicago. There are about eight other people, in our offices here, but most of the folks are, are out West in San Diego and San Francisco. All right. Let’s get back to the beginning. Let’s get to that, but want to talk about today? tell everyone how you got there.

So when, when did you wrap up your previous job and how long in total were guests, were you looking for a new role? Right, right. So, you know, again, as I shared with you, my, my elevator pitch, 15 years in financial services, Specifically with, big bank, right? Four of them over the course of a decade and a half.

And it was, sometime last year where, you know, there was an opportunity that came around to actually leave financial services. And I always wanted to position myself as more of an expert generalist. Not an industry specialist inside of financial services. So an opportunity arose to join, a management consulting firm and, took that on.

It was a business development role. once we hit 2020, the company announced that they were selling themselves and then we have the effects of COVID couple rounds of layoffs. And I actually got hit in the last round. In may. And so I had been there not, not even a year at that point. And I just, I remember the shock at that point in time.

And usually I’m pretty good with reading the tea leaves in organizations I’ve been in enough of them at this point to know when, things aren’t quite feeling right. But when you’re not working with people and it’s, hard to decipher the signs inside of. A corporate facility to get a call over the phone was, just  little shocking at that point in time.

But I remember sitting there in the middle of may going, how do I do this? I’ve gone through job searches before, but how do I do this in the middle of a pandemic? Right. And, you know, we’ve all been locked down for, at that point. It was two, three months. And it was pretty clear that you weren’t going to be going into offices to actually interview, right.

it was going to be done all through. video conferencing through new technology. And I remember, you know, sitting back and just, just kind of taking it in at that point in time. But, you know, given the fact that I have an incredible network, I started just talking to people right. And getting my head kind of in the game, started applying to things.

And, and honestly I hit some, some success early on. I had, a handful of interviews that were happening within those first six weeks of search, I got to the point, in, it was early July where I had a good, it was two opportunities where I had gone through the fourth round and the third round of interviews for these two individual institutions.

Right. And, I thought, okay, this is it. And James. It was last two rounds of interviews for each of those opportunities actually happened the week after the 4th of July. And I thought, okay, it’s going to happen one of these to this day. I haven’t heard back from either of those opportunities.

Right. Yeah, no, no. Hey, thanks. No, thanks. You’re telling me this when we were kind of talking about it ahead of time, and I want to ask too, like what initial struggles you had? So one is obviously like, just not thought you had something good and then didn’t hear back. You know what I mean? Which. It is odd in normal times, but it’s even more disheartening.

So I guess elaborate on that more like, in terms of like what, because everyone right now is, is seeing a different bag of struggles, you know, with their job searches. I’m kind of curious what things you’ve seen. So that’s one, is there anything else that you want to highlight early on? I, I think the struggle was I was lulled into, I guess it was a false sense of complacency at that point.

I’m thinking, okay, one of these two is going to happen. We’ve gone deep. I’ve had conversations with everybody up and down the food chain. it’s going to happen. I think looking back at that, I really wished that I would’ve continued feeding the top of the funnel. And you know, people say that all the time in, in job search that couldn’t be more true today, even though you are at the brink of getting an offer.

Continue to have those early round conversations because, first of all, it’ll make you feel like you’re doing something while you’re in that waiting game of waiting for somebody to make a decision to contact references, to create that offer. you’ve got to fill your time, right? And if you feel as if you’re being productive, even.

In a beginning stage of a, search with a particular firm do it. and you know,  if you do actually get that other offer or, you know, they’re moving down the path and you know, that offers coming through, you’ll be able to help somebody else out. You’ll be able to maybe pass that lead along.

To another person, you may be able to confer with that HR person and give them, a slate of candidates who, could also fit the bill. So , that was a mistake that I think I made early on. And, I learned from that, and as I progressed through that search process, Yeah, one thing was interesting.

I just kinda wanna interject real quick this year that, even when things like from the recruiting side, even when things started to pick up where, you know, June, July, when we started suffering more things opening up, we still saw like the highest rate of positions just. False starts positions to kind of go away, you know, companies that we’re planning on hiring and then, , either pulled back or so.

And that was frustrating for us. But then we realized we were in for jobs, secrets, even more frustrating because probably what happened in those two positions you were talking about is that like they were serious for a while. And then who knows what they meant negative money for, because that was kind of, that’s been the Mo of this year.

Yeah. Yeah. And, you know, and my response to something like that is that’s. I think we all understand that things happen. Inside of companies, situations change, people leave all of a sudden there isn’t a need for that particular role. That’s all understood, but then communicate, communicate out to the candidates who you are engaged and don’t just do it with an auto gen email.

Thanks buddy. No, thanks. Give him an explanation. Give him a, give him a call. There’s nothing wrong with talking directly to somebody to deliver some not so great news. You know, you can explain it, the honest, be respectful and communicate. That’s all people expect. Yeah, no, a hundred and hundred percent agree.

when did things,  I wanna ask you, like, when did things start to click, so I know you all of a sudden, was there anything else, like, in terms of like a mistake wise or things you want to do over left from the early phase of your search? Or was it just like, was the final kind of the only main thing?

Yeah, I mean, I think it certainly was the funnel that,  you needed to really. Keep filling it. Right. I think I got to the point after. So, you know, if we go back to the story that I was telling about this, this overall journey, you know, it was the weekend or the week after July 4th, when I thought I was going to get offers from those two firms.

And I didn’t hear anything I had about six weeks from that point. Until the middle of August where I thought, and I didn’t have a lead to save my life. At that point, it was the well was dry despite everything that I tried. And at that point in the middle of August, I decided to bite the bullet. And that’s when I created a post that I put up on LinkedIn.

And I said, Hey, network Mike 25, 2,600 people in my network. I’m out there looking for a job, and my strategy up until that point was, I’m going to talk to a few people. Who I know. And, and I’ll tell them that I’m out there looking, I didn’t announce it to the world. And I think, especially given that we’re in the middle of a pandemic, you got to let everyone in your network know that you are out there looking right.

And I put on what they call the collar on LinkedIn that hashtag open to work collar. And that’s when it all really started to click. I had retained search reach out to me for the first time. In a while I had contingence, recruiters reach out. I had a ton of my network connections. Reach out and ask how they could help, how let’s have a conversation.

Let me introduce you to, this person, to that person. And it was from that point on where I had at least six leads in the pipeline to the point where with dividends, I finally got an offer, right? I was out and I don’t know how this happened, but I was actually only out of work in the middle of.

This pandemic for four and a half months. And again, I’ve gone through this before in normal times and it certainly didn’t, it took me much longer than that. Yeah. And for me it was, owning it right. There is no stigma about being between jobs. You’ve got to wipe that away from your mind.

Right. Yeah. This is something that happens actually to most white collar workers in today’s world. And the first time I ever had gone through this, my job coach at the time, Maureen Zabul at alpha at one point was with Kensington outplacement. She looked at me, she sat me down and said, Ted in today’s world, 80% of white collar workers will get laid off.

At least once. In their career, welcome to the majority. Right. And, and those words still ring true to me 20 something years later. Yeah, it happens. But I think times have changed. I think, you know, owning the fact that your auto work there isn’t that stigma anymore. So many white collar workers face this in their careers.

Yeah, this is a mindset change. And it’s, I think it’s like people in our age group, it’s, it’s something that , when we started our career, there always was a stigma, you know? And I think,  you and I have talked before about how. one of the bigger challenges to people in that gen X and above crowd has, is that early in our careers, we didn’t have as much job searching experience because, we would, we were in places where we’d stay for a long time versus people who have kind of come in the younger generations, like job seeking is more part of their DNA.

So. Just getting that mindset that this is not a big deal. There’s nothing to be. You shouldn’t feel shame. And the fact that you were to communicating with people that you’re looking for next job, if anything, it’s just in it at that point, it’s just marketing, you know, the morning, get the word out, let people know, like it’s making any touch points that you can, So there was one thing I want to talk about in terms of, I guess I can make this kind of specific, job boards and stuff like that, because for the last nine months I’ve been telling everyone, I, I still maintain for the most part. It’s true that like job boards, it just can be a source of frustration for most people where you’re gonna apply.

Nuts here a lot back then for black hole, a lot of cases, but you actually had a way where you were successful with this and you did some things are a little bit different than what I normally hear in terms of how you went about things. I think fundamentally different in terms of kind of how you use them.

So tell everyone, because I think this is a pretty actual takeaway. So tell her what your method was. I really have a problem.  when people, speak negatively about things like the LinkedIn job board, I think there’s incredible value on that site and with the postings that they have for, for opportunities that are open.

And in fact, the position that I’m in was actually listed. on LinkedIn. but I took a very different tactic. And so I think for the, I guess this is,  actually a mistake that I made early on and, I discovered it was a mistake. And by adapting my, strategy around job boards, I was successful in terms of locking down some opportunity.

So what I was doing prior to August was I was. Going to that LinkedIn jobs site. And I was typing in a title. So, you know, VP business development, SVP, strategic partnerships, COO, and I was, putting in a location in Chicago and that only garners a limited. Pool of, opportunities. And that’s probably how most people, that’s probably how most everyone does it, by the way.

Yeah. I mean that, because that’s makes sense. It’s grade, you know, Hey, title and location in those, in those two, search, spots. And then I thought I had an aha moment one day and I thought, you know what? I’m in instead of using a title, I’m going to type in a subject. I’m going to use payments as the search criteria and I’m going to leave the location blank.

Right. And my, thought there was so many people are working remotely right now, and companies are getting used to people being remote. At this point, that’s going to open up a world of possibilities. So I did that and that’s when the flood Gates opened up the listings that I then saw were all of a sudden was very plentiful.

Right. And, and I would go through each one to see if there was some kind of applicability to the skill set that I was bringing to the marketplace. And honestly, if I was remotely qualified, I was sending in a resume. Right. And I think that’s the other thing, you know, we are looking so, specific that we are being so specific when we’re actually looking at those postings, we’re looking at every word.

We are dissecting every bullet point. Stop that don’t do that. If you think you are remotely qualified for that opportunity, send in a resume. It’s not going to hurt. Right. And my, my thought around that is it’s so important just to have a conversation. And what I have found with a lot of emerging smaller companies is sometimes they don’t know what they need, but if you can have a conversation with them and demonstrate the value that you could potentially bring to their organization, the light sometimes is going to go on.

And, you know, in fact, with, dividends, the title. Was actually changed based upon the skillset and the experience that I was actually bringing to the organization. They made some modifications to,  the title that they were bringing me in at. So again, change that search criteria just a bit, tweak it a bit.

if there are key words that are used in your industry, Type in those keywords, leave the location blank and see what you can come up with. again, I’m a firm believer in just having conversations with people, right? you want your,  brand and your name out there. So that people begin to think of you.

And that, really changed the trajectory of my search in a very short amount of time. Yeah. And I think it works and I’m trying to like a ways of kind of applying this to people in other industries, but like, Understand your industry. What are a few key words that are specific just to your industry, that you have domain knowledge of that the normal person aren’t gonna have use that as your criteria and just bank on the fact that I think this worked out so well for you because, you know, dividend finance or a small growing startup, they need expertise.

You know what I mean?  I think a lot of companies in that small growing space, aren’t going to care about, I’m seeing this already. Aren’t going to care about location. Like they’re already bought into the fact that we’re in a world where. Things are more remote and you can have the best talent as long as it’s anywhere in the country, or it could be international even that’s going to work.

So it’s great that that worked out well for you. And I think that a lot of people could use that as a, as a better method of kind of using it. Yeah. You know, again, James, I think it’s just important to have the conversation. Right. And, and I was applying to roles. For that van, it had titles that were, that I was overqualified for.

I was applying to things that I was under-qualified for. It’s just important to have the conversations. And, you know, as we talked about before, the whole process of interviewing is so different this year. Than in years past, right? In years past, it was, you get a phone call, Hey, you know, we’re going to do a little screener right now.

Okay. We’re going to think about inviting you in, and then, you’re brought into an office and you’re, , trotted through, few people to talk to and, then you leave every interview that I’ve had through. This process over the last four and a half months, I, through that four and a half months that I was out searching, it’s all over zoom, right?

It’s all video conferences. And that takes on a very different, it’s a different skill set, right? You know, when, when you are in person with somebody, you can pick up the visual cues, you can read faces, you can pick up a vibe. In a room, you can’t necessarily do that over a video conference. And so, my thought is it actually takes more energy to do that.

Right. you’re really seriously looking at somebody you’re focused in trying to pick up those subtle cues as to whether or not you’re resonating with that person. On top of it. You also have the camera pointed at yourself. You’re looking to see how you’re reacting to that person. And so I think it actually takes double the energy, doing a video conference.

It’s great that you’re in the, comfort of your own home or, you know, in an office that is all yours, but I think it’s, it’s given the media that we’re working with here. it takes more life out of you. And you know, one of the mistakes that I made early on, and this was actually, with, my interviews, my interview cycle with dividend, where I had three interviews lined up back to back to back.

And it was with the CEO of the company. The SVP of HR and the chief risk officer. And I thought, okay, three of them lined up, they put in a 15 minute break between the three interviews. And I thought, for sure, that’s going to be enough time. Well, as you can tell, I’m very much a talker, right? They were talkers as well.

And so I ran over time. On each of the interviews to the point where this two and a half hour window, a two and a half hour, interview process became almost three and a half hours. I was so exhausted after those three interviews, I needed an app. After that, I nap, I nap that afternoon. What I learned from that is you’ve got to make sure that you’re building in at least half an hour.

Between video calls. Again, they take so much more energy. Give yourself a break. You know, if they’re trying to get it, if they’ve limited the break to 15 minutes, ask them to move it to half an hour, because things happen. people show up late for video calls as well. Make sure that you build that in there.

And if you think about it, it kind of makes sense because if you’re actually in an office going through, you know, two or three or four interviews during a half day session, you’re being trotted from one office to the next or conference room to conference room. you’re heading to the, the restrooms as well.

You have those natural breaks kind of built in not necessarily true when you’re, sitting at home. So piece of advice for everybody there. Yeah, that’s excellent. And people have been asking me all year, like special advice for interviews and it’s what I’ve been given them. It was a lot of standard.

I mean, vice, but I’m such an AAV nerd. So I’m always talking about like internet connection, camera lighting, all those types of things. But besides that, it’s the same thing, but you bring up a great point cause like, One thing I like about our zoom culture is that you can cram more things in back to back.

You’re not like there’s less wasted time, like going to meetings and stuff like that day. But the flip side is when you’re actually have to be on point. Like you’re like when you’re in a job interview, you know, you need some of that downtime, whereas other parts. And if you don’t, yeah. That, that whole zoom fatigue is very real.

And, you know, I experienced it in the interview process. Thankfully it turned out really well. Right. I ended up getting the job. but, what I learned after that was I made sure that any time I had multiple interviews for one company, I insisted on those 30 minute breaks, whether or not I needed them.

Any other takeaways from the experience, the job searching experience, any of the things you learned that you think would be helpful? Yeah. I was somebody who was always very afraid to ask or I thought it was such a layup softball kind of question, but ask about the culture of the organization, the people.

And the environments, it’s pretty clear that the companies who took the time to interview me, they saw the skill set. They saw the experience that they wanted for their organization. And so from that standpoint, those things were certainly matches, right. But take the opportunity to ask about the people who work there.

the kind of culture that it is. I’m a huge proponent advocate of teamwork and collaboration and diversity. And I wanted to make sure that I was with an organization that matched that because I could do the work all day long. But when, if you happen to be with people who don’t have the same values, the same.

Thoughts around all of that, that, that I do. it could be a rough place to work. And, through my process with, dividend, it was very heartening to hear some of the questions that they were asking me during the, during that process. And in fact, I, I know I shared with you earlier that, No, it was the president of our organization.

I love this one. So I wanna, I wanna lay this one up. So like, I really think this is more of a, something like you learn from your, job search process that you could use as you’re interviewing other people in the future. So there was one thing that stuck out, about these guys in particular, but what, what was that?

So tell us about that experience. Yeah, so I, was having, a typical interview, kind of. Conversation with, the president of the company. And it was the first time ever in my career where the words, empathy and vulnerability came up in that interview process. And, the president of the company shared with me, some facts around.

, his former work life. Right. And because of that, I let my guard down. Right. And, and I felt comfortable in sharing where some of my challenges were inside of the corporate arena. So, that was a great conversation. And I went through a few more rounds of interviews after that. And when it came time to check references, The president of the firm that I’m now working for actually took the initiative to schedule one of those reference check calls with one of my former bosses and in that conversation, which she shared with me after the fact, he asked the question, tell me about a time when Ted demonstrated empathy in the workplace.

And that resonates with me big time. That’s right. Yeah, that’s a question it’s not just kind of stock answer. That’s something you actually have to think about. Well,  it demonstrated to me the kind of organization that he wants, dividend finance to be. And if, yeah, this is a hard charging group.

This is a growth oriented company. They’re doing great and wonderful things for the consumer finance arena, as it relates to payments and they digitize the process, but what do they care about? They care about the people. They want to make sure that you can walk in other people’s shoes in this organization.

And. That’s when I knew that for me, this, this was truly, this was home. it was a home-based moment. That’s awesome. Yeah. I mean, I always talk about  the onboarding process and, you know, you need to make sure those first weeks and whatever go well, but this isn’t even, you weren’t even there yet.

And you already felt better about the decision you made. Based upon a reference check, which is rarely the thing that puts people over the top from like a, the job seeker standpoint. You know what I mean? It’s pretty cool. if you could go back, do it all over again. Anything else? Anything you’d do differently?

Wow. I mean, I think it was a process of discovery. I mean, I don’t think there was one thing that I would do differently. I wish it would have happened sooner, but again, I, can’t complain, a four and a half month job search in the environment that we’re in today is, pretty remarkable.

yeah, honestly, there isn’t much that I would change. I think it all happened at the right time for me. Okay. And I always want to make sure. Is there anything else that we didn’t cover? Anything else you want to share or do you think, yeah, I didn’t get it all out.

what I would say to everybody is you have to keep helping, right? Even after you land, keep those network connections up. help other people, you know, I think empathy goes a long way. If you happen to be in between roles right now, you know how painful it can be, you know that it’s, it’s a roller coaster ride of emotions.

You get one call, you had one interview that went really well. you’re. Feeling like you hung the moon at that point, when you get some negative news, it’s hard to drag yourself out of wow. That one didn’t happen. so remember that, that you will land and it’s important for all of us to help one another.

Find that next right role. So I am, I’m always open to networking conversations, to helping others, whether it’s, you know, introducing somebody to someone else or taking a look at resumes, trying to optimize that, figuring out ways to, Rewrite resumes a little bit differently so that you, you do get the hits.

I think there’s some great tools out there that can help you on the big proponents of, Rezi IO, where you can upload your resume and upload a position description of something that you really want. And take a look at the match between them. You know, maybe it’s an opportunity to tweak your resume and add in a few more keywords, but, you know, again, my messages help other folks and, don’t be afraid to talk to folks, figure out the best ways that you can help.

And I think, well, we’ll certainly all kind of get through this. I have the, it took a while for LinkedIn to get this sorted out, but I can finally see questions. you couldn’t actually see, like people were asking though, we didn’t get one.  different things vice on using the open to work banner, most say mostly not to use it as it comes across desperate.

Any thoughts? No, not at all. I didn’t feel that I don’t think it’s smacks of desperation in any way, shape or form. It’s a way to let people know you are out there and available, so I used every tool at my disposal at that point in time. again, I landed in four and a half months, , I landed in a, vice-president position.

I never felt desperate. I don’t think I ever looked desperate, so, no, I disagree. All right. Yeah. cool. I think we’re this has been excellent. there’s several things in here, which I want to make sure we reshare. I think there’s a lot of value kind of out of people today. Someone else actually recommended they love the remote position, disregarding location idea, and just trying that out.

So I know there’s going to have good itself, Thanks again to everyone out there for listening to adventures in job seeking part of the talent insights podcast, all episodes are available for replay on the higher wall YouTube channel, as well as the talent insights podcast, which you can subscribe to on Apple podcast, Google podcast, Amazon and Spotify.

Ted, once again. Thanks for joining. Hey, thank you for having me. This was fun. Yeah. I never went out there. We’ll see you soon. Sounds good. Thanks. 


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