Strivin & Thrivin E19. Jeff Waldman

Strivin & Thrivin Ep19. Jeff Waldman – Founder & Principal at ScaleHR


Jeff Waldman, Founder of ScaleHR joins us on the Strivin & Thrivin podcast this week all the way from Toronto, Canada, to discuss the career journey that got him to where he is today. 

With over 20 years in the HR industry, Jeff has an HR background that started in business and so has always had a business-orientated mindset. As it stands, Jeff is currently the Founder, Principal of a new company called ScaleHR, a company that works with growing small-medium businesses to help them scale their people operations and brand awareness. 

Jeff isn’t someone who fell into HR or recruitment but rather he pursued it early doors when studying for his business degree. The strategies involved in developing effective workforces and driving good business results is what pulled him in. Retrospectively speaking, he believes his career trajectory hasn’t been based on titles and salary, but rather on the role and responsibilities. 

“Don’t chase money because money will come later on, chase the opportunity”

As we dive into Jeff’s career history, he shares his best and worst moments, encouraging listeners to trust their gut instincts and find companies and environments in which they can thrive. Now working for himself we discuss the importance of structure, staying abreast of everything in your industry and filtering out what’s applicable and relevant to you and your role. 

In the HR industry, things are changing constantly and outdated information can quickly become conflicting with new information. As we learn more about this and the importance of maintaining good relationships with lawyers as you work hand-in-hand so often in HR, we get a great understanding of Jeff’s professional approach to work. 

During this recording, Jeff shares his approach to mentoring, having been a mentor to others for a few years now, and how he aspires to lead his mentees to the best outcomes. We learn how a strategic approach to being a mentor helps drive the best results and how rewarding it is for both mentee and mentor. 

Listen to all this and steal Jeff’s recommended reading list on this week’s Strivin & Thrivin podcast! 


Laura: I’m your host, Laura Johnson. And today I’m lucky enough to have Tim Griffiths as my wonderful co-host. Today we’re thrilled to be joined by Jeff Waldman.

To get us started, can you tell us a little bit about your career background and your current role?

Jeff: How much time do you have?

Tim: 30 minutes to be precise and go.

Jeff: So, career background, I’ve got a background in business. So, I actually started in business, and I’ve been in HR for over 20 years. I’ve led HR, I’m on my third company right now. So right now, I’m a founder, principal of a new company called ScaleHR. So, we work with growing SMBs to help them scale their people operations and we also work with emerging HR tech companies to help them with brand awareness, a bunch of different things, and advisories. So, I’ve been HR Leader I’ve been in-house. I’ve been on my own. I’ve been Head of HR, all these different things. And yeah, it’s been a pretty fruitful career that’s taken me around the world, not physically, but I’ve done lots of work in probably more than 15 countries around the world. Including Australia, which has been great.

Laura: What led you into HR to begin with? What was the first role and what took you there?

Jeff: Oh my God.

Laura: What was the first role and what appealed, I guess?

Jeff: Yeah. So, I used to work for a sports equipment clothing store growing up in Vancouver when I was in high school, and so, we were just selling stuff. Hockey sticks, hockey equipment, running shoes, that type of stuff. And I started getting into product training. So, I actually took over at the age of 16, 17 when you know all about product, all of sales stuff and I absolutely loved it. And then I also started getting into hiring. So, I was actually hiring all of our new sales staff for our busy season.

And then I didn’t really realize at 17 years old, but it was actually part of HR. And so, when I got to business school, in second year, I took a course called organisational behaviour. And I was the only one in my entire class that absolutely loved it while my peers are just dying, just waiting to get to the pub, I was just absolutely loving this stuff. And then I spoke to my boss and he told me that this is actually HR. So that was the first time that I realised the previous three years of doing product training, hiring for this company I was working for and then getting into the psychology of business and people working in groups, but was actually… Been a career in HR. And that’s what I chose to do.

Laura: So, I think you’re the first person we’ve spoke to that didn’t accidentally become a recruiter and then led into HR.

Tim: And you didn’t do a degree in something like butterfly keeping and then become a recruiter, which is the usual one, because most recruiters don’t have a background in… That degree never was in what they’re actually doing. Can you do a degree in recruiting? I don’t know. Maybe you can, but organisational behaviour’s an interesting one.

Jeff: It is. I don’t remember much about the course, you know?

Tim: Yeah.

Jeff: Because I’m old now and it was 20 some odd years ago. But I remember it was pretty interesting. There was something there that I saw. It was something about the psychology of business. In this one class, my prof said, “You’ve got a piece of paper here, this is your strategy? It means nothing unless you’ve got people to do something with it”, and I’m like “Hmm, interesting”, and so I actually got into that and then I realised that unless you hire a company full of robots to do certain things, you’ve got to have people. And I thought it was really fascinating. I didn’t realise how much of a headache it was going to be for the next 20 years of my career, dealing with people, lots of weird and great people.

Laura: What kind of… can you talk us through… I’m trying to think of the right way to put it… how you move from role to role within HR and kind of how your career grew?

Jeff: Yeah. So, I wouldn’t consider myself to be like a true model of someone who kind of moved through my career in a logical in a way. I guess my career has been anything but that. And so, I’m not your typical HR practitioners. So earlier on my first job was in the government and I was there for just about three years and that’s second longest that I’ve been anywhere else. So, after that I was working in Alberta, and I wanted to leave. And so, I basically quit my job, got married and then came to Toronto. And then after that, I guess the progression… I’ve always been driven by work, type of work versus the level. I didn’t care about the level first decade of my career. I really wanted to kind of move around to a different company organisation, get an industry, that type of thing, because to me what more meaningful than staying with maybe one or two organisations and kind of working my way up.

Also, for me, it was always about the opportunity and we’ve always put opportunity first. I spent about four years with the CIBC, which was a major payment bank here. The only reason why that I survive that long is because I moved around to some different parts of the bank. So, you start meeting new people, new challenges, new lines of business, so to me, that was really interesting. If I was there in the same role for four years, I probably would have jumped off the expressway by then.

Tim: Is there something quite nice about working for multiple industries and multiple companies though? Because when you go into a different industry, you can layer some, some things that you’ve seen in other industries across that one and go, “Oh, I’ve seen this one before”, But it’s in a different way. So, it’s quite an interesting.. It’s nice to hear that you took the roles because you wanted to understand how other types of industry did things differently as opposed to going, “Well, I want that role and then I’m going to move to that role, and then I’m going to move to that role”, because it’s very few people actually do that. It’s always… Typically I see a lot of people now that it’s like, “Well, I start at this level and I want to be a manager by that point, and then I want to be C level by that point”, and it’s quite interesting.

Do you find that it’s helped you like that? Did you find that it’s helped you like that? The different experiences you’ve had has helped you on that journey?

Jeff: Totally, yeah, absolutely. Just fast forward to today, I’ve seen pretty much everything, and that depth of experience has really helped me being able to navigate really anything to be quite frank with you. I mean I can go into any organisation. It doesn’t really matter what industry it is or size or challenge. I can probably figure it out now. I’m not to say that others can’t, but there is some value into having that experience and that exposure or diverse exposure, because then I can kind of draw off, I’m probably not going to go down that path because it probably won’t work for me, but there’s organisation. So definitely having that type of exposure has been valuable.

Laura: So, I guess on that, what advice would you give to someone starting out their career?

Jeff: So, this is actually something that I was called that I actually took to heart. When you’re starting out don’t chase money because money will come later on. Chase the opportunity, right? If you’ve gone to school for four years, or whatever. For me, I actually left Vancouver because there was no opportunities. And so, I left the city but, I grew up and I loved and I moved, and that was all because of the opportunity. And it’s worked out well for me. And I know many people who didn’t do that and they stayed and they ended up doing something else and they weren’t really, truly happy.

But I really wanted to explore HR and I wanted… And it’s a very diverse field. So, to get that diversity, I needed to go somewhere where the opportunity was. And I was a HR generalist from whatever school, and they gave me an office and just got to it and it’s through the fire. I did a horrible investigation, I was three weeks into my career, I was 21. I didn’t know what I was doing. And so, I think a bottle of that opportunity, and the second thing is follow your gut. Your gut is always right. If your gut is telling you ‘that it doesn’t sound right to me’, just listen to it. If your gut is saying this feels right.

Laura: I love that. I think I’ve said it more than once the last week to friends that are looking at new opportunities right now. Like what does your gut say? Because I think we do a really good job of ignoring it and then whenever it goes wrong, we go back to it and go like, “Oh yeah, I kind of knew. I just wasn’t ready to admit it”.

Jeff: Yeah. I mean, hindsight’s always 20-20, but you do like a debrief. Do you remember what I had one rule where I was in, I’m not going to say the name of the company, but I knew going in that it wasn’t going to… I just had a bad feeling about it and sure enough, nine months later, I lost 20 pounds, I was quite sick and ill and in poor health. And I had been… I was 25 years old at the time. And while I did learn a lot, I was just in bad shape and I just walked out. I quit. And then I remember walking out of that building in downtown Toronto thinking, “I feel wonderful. I felt great. Now I can sort of go on with my life”. But that was a sort of a moment where I realised that I need to follow my gut from this point forward.

Tim: It’s funny how work environments do that to people. I was only speaking to somebody earlier on this week who had exactly the same story. They’d been having problems with their back and they’d been seeing a chiropractor and an osteopath and could never get it sorted and this was going on for like maybe a year. And she got made redundant and afterwards it all went away… Because it was the stress level of what was going on with the business. And it’s quite interesting, the fact that how sick you can get in… If it’s in the wrong environment and following your gut is probably the… If it isn’t right, it isn’t right.

Laura: Definitely.

Jeff: Yeah. And you know, that environment, I remember my peers some of them loved it. Like they thrive and I just didn’t. It was just not a good environment for me. And that was the turning point for me, I think. And sort of realising that I needed something where I can be creative and have people that I can speak to and going to communicate openly. So, I actually learned a lot about myself and my preferences to work. Although I had to go through a really horrible experience during those nine months of pure hell, but at least I figured it out and I was able to come forward to down the road.

Laura: Do you want to talk to us a little bit about what you’re doing now? Kind of doing your own thing again, going back to what you’ve just said about being able to be creative and kind of following what you want to do.

Jeff: Yeah. You know, the beauty of through working on your own is you get to kind of pick and choose… Well, obviously you have to sell them. That’s a skill that I’ve had to really hone during the past 10 years. But the beauty of my work now, whereas I’ve got such a diverse set of clients that I work with, and projects that I’m working on, it just gives me so much variety of fulfillment to be able to really truly help people. And to me, what motivates me is seeing that I’ve made a difference. A company’s sort of growth or a person’s career.

I actually mentor two people right now. And just having that ability to know that I made a difference is something that I never really had growing up. And I did have a little bit of early on in my career and I just always wanted to like get back. And so now I can do that. I felt that I just couldn’t really do that if I was working for one organisation, although I have gone back to an organisation as recently as last year, but then realised that I need to be on my own. I have to be able to sort of stick to my true self and my values.

Laura: I think it’s tough when you’ve done your own thing to then go back and work for someone else.

Tim: Yeah. Once you’ve seen the freedom and the light, it’s very hard to turn back, especially when the culture and the people in the business is so important. And the ability then to, and especially as you’re saying, the ability to impact many more by doing what you do separately is quite… If you’re that type of person, that’s where you just got to do it and you know it again, it’s not following your gut again. You just got to do it.

Jeff: Yeah, exactly. And I’ve come across many people who thrive in a very highly structured environment and, “I tell them, you need to go work at a highly structured environment. Go and work at a bank or work at a government organisation”. But if you’re truly creative and need that sort of variety, then don’t do that. I mean, you’ll just get stifled and…

Tim: Yeah.

Laura: One thing you did mention there was just around mentoring. So, I wondered if we could talk about that for a minute? So, I guess I’d love to hear kind of any experiences that you’ve had with mentors or what you think you get out of mentoring.

Jeff: I’ve had to be quite honest… I’ve never really had someone that I called a true mentor during my career. I’ve had people that have helped me out so I wouldn’t be on my own and definitely that… I had people that I’ll call up and ask questions, but I’ve never really had anybody that’s been a true mentor me. It didn’t ever really happen that way. I’m not going to force it obviously, but I have mentored quite a few people. I’d probably say about a couple of handfuls of people over the years, and I just absolutely love it. I love giving back to someone, especially someone starting out that. You can see the brightness, thought and the business acumen, which was a huge thing for me. You need a little nudge here and there to make sure that they’ve got that confidence to go down the path.

So, someone right now who was the head of HR right now for a small tech company. She’s 26 years old, she’s really smart. And I’ve been mentoring her for about a year and a half now. And someone her age probably wouldn’t have that opportunity, but she got lucky and she totally owned it. But she also needs some sort of supports and time she sometimes she says to me, “I think I’m doing the right thing. I have no idea, but I have nobody to really talk to”. I said, “Well because that’s why I’m here. Right?”. And so, by the end of the half hour or hour, she feels good about next steps she’ll take and I think that’s what it’s all about.

Laura: I love that. And I think that’s exactly it especially when you’re sat by yourself in like a small business or a growing business, sometimes you just need to say what you’re doing out loud. So, you know you haven’t created this echo chamber or you’ve not gone crazy. You can say it out loud to someone that gets it and just kind of realign and go again. I guess, in terms of when people turn up for a mentoring session with you, what kind of tips or advice would you give people going into those sessions? How can they best prepare?

Jeff: Yeah. So, I think being organised, obviously, then asking what the right question that I think ended up going down the right path. Oftentimes if not always knowing another way to answer everything, but being able to touch, guide somebody down a path, because oftentimes they’ve got the answer, didn’t need it, sort of pulled out of them. Or they got the answer, but they’re not really confident. But I think that probably the main thing is, I don’t know if I answered your question.

Tim: It’s sort of positive reinforcement. So, in other words, it’s really coming to you with an issue or just, this is the way I feel this week. And I feel that I’m not approaching this correctly. And then what you’re doing essentially then is helping them understand what they should be doing as, you said, it’s already within them. And then you just give them that guided path that they follow.

Jeff: Yeah, exactly. Yeah. I mean, there’s especially the world of HR. I mean, there’s so many different paths to get to the end goal and nothing’s really sort of the absolute golden path, got to find that thing. It’s really about trying to look at the situation and sort of see, okay, well, what’s your goal here? What is it, the end goal? And then what are some of the challenges that you’re facing? And you try to put some plans together or some paths and just try to figure it out. And if you screw up, you can just fix it and be on it and then you go back and you try it again.

Tim: There’s so many things changing in the HR world at the moment because the whole, which is a good thing, the whole diversity and inclusion, that’s really, really big at the moment. 20 years ago, that really wasn’t a big thing, which is what’s changing now. And then obviously over in Canada, you’ve got the rule… The legalisation of cannabis as well. And that’s bringing a new, in writing, employment contracts. And how do you keep yourself abreast of all of this? Because obviously it changes so quickly and obviously certain regions of the world, if you’re working with global companies. There’s different rules and regulations, there’s different things that mean a lot in those particular jurisdictions. Do you have a go-to source, or do you literally just ring up a load of people around the world? “So, tell me what’s going on over there. I’ve got someone over here that’s trying to do something”.

Jeff: Yeah. It’s a good problem. Yeah, it really is. In Canada anyway, obviously there are 10 provinces, each province is different. And then some of the workforce is under federal jurisdiction. So, it’s enough to make your head spin, but the good news is that obviously now with the worldwide web and social collaboration, slack communities, and all these things make them much easier to be able to be connected to a certain group of people that have similar challenges. And so, I’m actually a part of just a couple of them. We’re very open and honest about helping each other out and asking questions and sort of getting feedback that way… The other thing too that I’ve done my entire career, just really make sure that I develop my own network and it’s a really a back and forth kind of thing.

And that does include being connected to lawyers as well, as much as I don’t love lawyers, I do have a small network of them that I do like, and so obviously I’m very close with them and I will ask them questions. And then the law industry is one that’s starting to really change a lot and they are now believing in the power of content and videos and all that types of stuff. So, you’re watching a lot of them produce some really excellent articles that can go a long way and actually keeping updated on various things. And I think that mix of having a really solid closed network that you can really lean on as well as making sure that you save time to read some of these things I think is about.

Tim: You finding that time and blocking that time out to keep abreast of things is so important in any career field you’re in, just keeping abreast of what’s going on. In some respects, it gets a bit overwhelming because there’s so much information out there and it’s filtering out the correct information that you need that is certified, for want of a better word. It’s not just random.

Jeff: It’s difficult. I’ve been working for over 20 years now and I’ve seen it all, but now dealing with something about two weeks ago where I really had to dig into some research, and I got some conflicting information. So, I had to double check, even if I’ve done it before. Some things have changed and I’m not confident. So that’s when I had to go back and… Look, we’re not lawyers. I mean, obviously HR practitioners, aren’t lawyers. We have a good understanding of where to look but directly in the question to ask, but at the end of the day there were so many things that go on and each case is different. But one of the reasons why I love HR was because no two days aren’t the same. We’re always dealing with different things.

Laura: I guess just in terms of resources, are there any books or podcasts or go-to newsletters that you always recommend, or you consume regularly?

Jeff: A tough one. I saw the question, I was trying to think about it and I’m not a big podcast person because I don’t have a lot of time, so that’s part of the problem. I think also part of the problem, because of my hearing loss, and so I kind of always fear the podcast, and there’s a whole other of issues, right? But I do read a lot and I’m a big fan of Harvard Business, definitely hands down, or the go-to place for me. I was a fan of until I started getting a little silly-ish. So, I kind of stopped there, but I do have some books. You can see it. This is just some of the books, that I have here. I’m a slow reader, right. But I do have one that I really liked, and it really had nothing to do with HR, but it’s by Daniel Pink.

And so, I love Dan Pink, it’s called Drive. And it’s about selling, but the coolest thing about HR and that thing… My work even I do a lot of selling. So, I’m not talking about used car salesman, sleazy selling, I’m talking about trying to get people sort of on my bandwagon to kind of follow me and… You know what I mean? So, there’s a different element to it. And so, this is one that I really like. So, there was somebody in the US by the name of Laurie who is a good friend of mine. And so, Laurie is going be speaking at the upcoming social HR Social Camp in two weeks, and so she’s probably one of my favourite controversial HR thought leaders out there. I love going to hear her speak and sort of reading her stuff. I think she’s on the ball. And if you ever want her on you show I’ll offer… Get around it.

Laura: I would love that. I’m a big Laurie fan. Just going to go… Last question then. But to pick up on what you’ve just said, other than Laurie, is there anyone that you’d like to hear from on the podcast?

Jeff: Yeah, well Jason Averbrook is another person that I would like. So, I love content that’s about HR technology, business, psychology and all that kind of stuff. And so, I really haven’t found one that I love that’s about psychology work. That just not… Nothing really, unless we have one. But the other one that I really like is a local person by the name of Scott Stratton. So, you’ve probably heard of Scott Stratton. So, Scott to the greater Toronto area, and Scott was a former HR practitioner apparently way back when, which blows my mind. But anyway, he’s a Marketer, Customer Service, and Social Media guy. So, I just love Scott and anything to do with UnMarketing, or UnSelling or that kind of thing. He’s just great.

Laura: When I was in Toronto, I put a picture up of UnMarketing and I think I bought a copy 10 years ago when I was at uni and I posted a picture when I was in Toronto and Scott got into contact and said, “Hey, I’ve actually updated a version. Love that you love the book. Can I send you my new version?”. So just posted me the new version.

Jeff: Are you serious?

Laura: Yeah. What a guy.

Tim: But did he sign it?

Laura: He didn’t. But yeah, it was like one, the fact that he’s paying that much attention to Twitter and two, sent me a free book. I mean, that’s how you can make friends.

Jeff: Yes. Scott’s just one of the guys that’s just really interesting person and he totally gets it. I remember when he spoke at the HRPA conference a couple of years ago and I was sitting at the front table there and he started talking about millennials. I don’t know if you’ve ever seen that clip, but there’s a clip on a YouTube it’s about two minutes long, it’s talking about the pencil jokes. You know how they used to create a playlist with the old tape in a quarter stuff and he pulled out the web and then he’d like, “Can somebody get me a pencil? And if you got that joke, then you became my best friend”. I mean, it depends on what the… anyway. It just, yeah, thank you.

Laura: Yeah. I like him a lot. Thank you so much for that. That was awesome.

Tim: Yeah. I really enjoyed it. Thank you so much for giving your time up to do this. It’s been an amazing chat.

Jeff: So, thank you very much for having me and best of luck to you guys.


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