CallRail VP of Talent & Culture Whitney Bennett

Whitney BennettCallRail VP of Talent & Culture

Today, we have another fantastic guest on the show: VP of Talent and Culture at CallRail, Whitney Bennett! In this episode, Whitney shares her wisdom and expertise regarding the current power shift in favor of the candidate and how companies can and should be responding to new expectations of safety, communication, and psychological support.

Episode Transcript





[0:00:06.1] RS: Welcome to Talk Talent to Me. A podcast featuring the most elite talent leaders on the frontline’s modern recruitment.


[0:00:12.8] FEMALE: We actually want to understand the themes of someone’s life, we want to understand how they make decisions. Where are they willing to take risks and what it looks like when they fail.


[0:00:22.7] RS: No holds barred, completely off the cuff interviews with directors of recruitment, VPs of global talent, CHROs and everyone in between.


[0:00:31.1] FEMALE: Once I went through the classes and the trainings got the certifications through diversity and inclusion, I still felt like something was missing.


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[0:00:53.0] RS: I’m your host, Rob Stevenson and you’re about to hear the best in the biz, Talk Talent to Me.




[0:01:00.4] RS: Joining me today on Talk Talent to Me, after moonwalking into frame, is the VP of talent and culture over at CallRail, Whitney Bennett. Whitney, welcome to the podcast. How are you today?


[0:01:11.8] WB: I’m doing well, Rob. Thanks for having me.


[0:01:13.8] RS: Pleased you’re here. So much I want to talk to you about. Where should we begin, I guess we should begin with the Whitney of it all, right? Would you mind, for the folks at home, sharing some details about your background, how you wound up at CallRail and all that?


[0:01:25.7] WB: Yeah. I actually started my career at a startup in sales, quickly found that sales was not for me, so transitioned to the much less stressful world of HR. I was at a startup that did not have HR at all. I saw a need, I came in at an entry-level role and I was like “Hey, I can do this.” And the beauty of startups, they were like “Yes, you can do this.”


Paid for me to get certified, took a bunch of courses, and I did that and stayed there for about eight years until I moved over to CallRail. Someone I actually worked in sales with was at CallRail and called me and said, “Hey, are you looking to move? We’re looking for someone to head up our HR department” and now, four years later, here I am.


[0:02:12.8] RS: You got all those certifications early on, were you learning recruitment sort of by doing because I don’t know how many certifications there are for sourcing, interviewing, all that stuff, there is only awesome podcasts.


[0:02:24.0] WB: That’s truly all there is. 


[0:02:27.0] RS: How did you kind of fill that into your skillset?


[0:02:29.8] WB: I did get my PHR and the PHR touches like very lightly on recruiting but a lot of it was trial by fire, reading blogs. I don’t feel like when I started recruiting podcast was as popular, I will tell you though, as soon as I was able to make a hire, my first hire as a recruiter was also my first hire at CallRail. My first hire, I think it’s the most important position, it’s always a recruiter if there’s no one else in place.


[0:02:56.6] RS: Interesting, more so than a recruiting coordinator?


[0:03:00.2] WB: Yes.


[0:03:00.2] RS: Just to take all that sourcing off your plate or why do you think that’s the most important?


[0:03:05.2] WB: I think that you should hire in people that are better at you at these. I am okay at recruiting but I think I’m much better at other things so why not have somebody else do that who is very specialized, and then I can focus on the other things and partner with them as they need help and ideas, but really let them do their thing.


[0:03:26.8] RS: Got it. Then, how many roles were there, could you walk me, these are the growth of CallRail once you were heading up the department?


[0:03:33.5] WB: Yes, this year alone, we’ve hired 150 people. We started at 197 and we of course, like everyone else this year had some turnover. We’re going to end around 316. That’s pretty significant growth. When I started, we were about in the 80-employee range and so from 80 employees to now, 300 in about three and a half years.


[0:03:58.4] RS: That’s huge.


[0:03:59.6] WB: It’s a lot. It’s a lot of people.


[0:04:03.6] RS: What have been some of the growing pains you’ve experienced with that scaling?


[0:04:08.1] WB: I think exactly that, it’s the scaling like having to build processes to scale, having to get the right applicant tracking system, having to get the right HRIS so you can keep track of all the people and the things and I think uniquely to this year, 2020 and 2021 were the first years that we ever hired remote positions. Learning how to work in a hybrid environment where you have some people remote, now, people are coming back to the office. How do we make that make sense for everyone and still scale the business?


[0:04:44.0] RS: I’m glad you brought that up because I wanted to make sure we speak about just these changes in work, not just in remoteness but expectations on the part of talent. It feels like recruiters I speak to are telling me that the candidates they are interviewing might have tons of offers, they’re deciding between 10, 15 offers at a time. So there’s demand pent up and candidates can afford to be choosy. And I do wonder how much of that is just an economic reality as supposed to the shifting expectations candidates have for what a job can provide.


For the sake of argument, let’s assume it’s all of the latter. Let’s assume it’s all shifting expectations. Do you see candidates and people who are assessing jobs, having completely different expectations for a company they work for than they work for before?


[0:05:36.6] WB: Yes, I think employees and candidates have much more power now than they ever did before. Not necessarily power to get all the money in the land even though that is currently a thing. Power to hold their employers accountable to do the things they say they’re going to do. I think there are unprecedented expectations from employees now more than ever.


They are looking for their jobs to provide purpose, meaning, passion and fulfillment and then on top of that, to pay competitively in a market that is wide open right now because everyone’s hiring remotely. I think we were trending in this direction pre-pandemic and then the pandemic just accelerated everything.


[0:06:24.9] RS: That’s kind of what I wanted to ask, is it reasonable for candidates to expect all these things? They expect their company, not only to meet all of their financial needs but your physical, your career developmental needs, emotional and mental health needs. A lot of people expect their companies to side with them in an ideological manner when it comes to some sort of political happenstance.


Is this reasonable for the work contract? Do companies just kind of need to meet candidates where they’re already is expectations?


[0:06:55.1] WB: I think the answer is somewhere in the middle, I also think what’s really interesting is we’re saying company a lot, but I do think if the company empowers and enables their employees to foster that sense of community, it can fill the need for a lot of those expectations.


At CallRail, we have a lot of employee resource groups. These are completely employee-led, the company does put money towards them so they can have guest speakers, so they can do donations but it’s completely employee-led. That fulfills the need that candidates and employees want which to be fair, all the company has to do is open the door and say, “Yes, we will support your employees in doing this.”


I think the answer doesn’t have to be, the company has to pay for all the things, the company has to do all the things, hire the right people and empower them to do it on your behalf.


[0:07:47.1] RS: Through ERGs or what?


[0:07:49.0] WB: Through ERGs, I think through having opportunities to volunteer or dominate money and match that. I do think – because we’re talking a lot about what has been labeled the great resignation, right? I think what is being missed in that is the great resignation is not all about money, it’s kind of a shot across the bow at company culture.


Employees need to be included, needed, wanted, heard, understood, all of that. I don’t necessarily know that everybody is like, “Yes, agree with me boss, and what I say.” But they want to be heard, they want to feel psychologically safe to bring up that opinion and have a conversation about it, so expectations are shifting, 


I also think to the financial component, at the end of the day, if the company is not making money, they can’t do all of these things. That’s why it’s a very fine line and balance to “Yes, we want to do all these things but we need you to produce this work so we can continue to make money and you can continue to enjoy all of these things.” Does that make sense?


[0:08:56.1] RS: Yeah, it does. It seems like that is obviously the first box you need to check, right? If it wasn’t, then you would go work for a nonprofit or you go volunteer or what have you, right? it’s like look, I expect to be compensated and on top of that.


Now that that is expected, I want the company to do all these other things for me. And maybe it’s because we just spend so much time, you spend so much time with your coworkers, even in the remote capacity. Or when you were going into the office, you spent so much time in this place, with these people, engaged in this community that you have these other expectations about it because you’re kind of like giving away a third of your life to them.


With the great resignation not being solely about compensation, it’s like look, there’s too many jobs out there or life’s too short for me to have even a mediocre job.


[0:09:45.1] WB: I think it’s a lot of that because we just saw that, we were stuck inside of our homes for what felt like our whole lives, the pandemic is not over. I think people had a lot of time to reassess what they wanted, what they needed. Life is too short to feel like you’re wasting away for some company that doesn’t appreciate you.


[0:10:05.3] RS: Yeah. Doesn’t it kind of come down to motivations in terms of as a candidate, what is it you actually need from a job? I would say, maybe it’s more useful not for us to try, and by us, I mean, you and I, to try and understand where candidate’s heads are at. But can we prescribe an approach for individuals who have participated personally in the great resignation, are now out there looking for a new job and it’s about being honest with your own motivations, what do you really need from a role?


[0:10:35.2] WB: Yes, I think there is a great – just sit down with yourself and “What kind of company do I want to work for? What employee size do I want, yes, what money do I want? Do I want to be super-involved or do I want to do my work and go home and be done?” Those things can build all your interview questions when you get to the culture conversation, which every interview should have some point where you’re talking about the company culture or what happens at the company, ask those questions.


Look at the website, read reviews and then figure out if that’s where you want to be. If you don’t know, to your point, what you want, then you’re probably going to end up in a company very similar to what you left because you don’t know what you want.


[0:11:17.7] RS: Yeah or whichever one kind of comes along at that right moment when you were thinking about looking or you’re like, “I could probably get this job, I will apply for the jobs I think I can get.” As supposed to being very deliberate about the kind of company you want to work with and what’s important in a role. 


I see this all the time in my peer group. People who just sort of float between companies and jobs, without a deliberate sort of approach. Kind of just like, “Oh well, I was not super happy, my job wasn’t that great and then this recruiter came along” Or, and then, “LinkedIn said I should apply for this job and now I’m somewhere else.” This has come up a couple of times in this podcast. I challenge that person and how much free will are they exhibiting in a situation like that.


You have to be deliberate so when it comes to deciding your motivations, you just need to write your priority like, “Okay, for the next year and a half, I just need to make as much money as possible so I can put a down payment on a house” or “I’m about to have a kid so I need flexibility.” Do you kind of have to confront bigger life circumstances when you are picking a job, right? 


[0:12:16.8] WB: Yes, and don’t compromise. I do think we are not in a situation where it’s, “Oh my god, I have to get just any job to put money on the table right now.” I think especially in tech, you don’t have to just take any job. There is a ton of jobs out there that’s why the great resignation is a thing. Don’t compromise on what you want. If it doesn’t have your needs to have, don’t take that job. 


[0:12:45.6] RS: Yeah. 


[0:12:46.3] WB: I don’t know if that just sounds super privileged, I don’t intend it to, but it is definitely coming from a tech mindset. If you are in tech right now, I think you can go get a job and you can be picky. 


[0:12:57.4] RS: Yeah, it’s a privilege in so far as I mean, we’re still telling people to be deliberate about what your immediate needs are, right? If your immediate needs aren’t, “Oh, I need a paycheck two weeks from now or else” then you can afford to run this exercise. Some of these high producer creative spaces, I see these people talking about personal runway, which is basically like how long can I not receive a paycheck before I really start to sweat. 


There is just like a huge amount of freedom with that and people might not quit a shitty job just because a two-week paycheck is addictive but I don’t know, there is not a question there. I’m just sort of adding that. 


[0:13:36.3] WB: Pontificating. 


[0:13:36.9] RS: Yeah, pontificating a little bit yeah. It’s my podcast after all, I will pontificate. No, I will cut all that out. 


[0:13:47.6] WB: But I do think like we’re talking a lot about the only way to get what you want is to leave. And I did say in the beginning, employees have a power now that they didn’t have before. No one can see bunny ears but that is what I’m doing when I say power. Talk to your manager, talk to someone. What is making you unhappy and is there actually a fix that you don’t even know about? 


If it is actually like the function of your job or the work you’re doing, what else could you be doing? Can you transition into another department, another role? I’ve had several conversations with people that say, “Okay, got you. You want to do X, Y and Z. You are not going to be able to end up with that job here but let’s do everything we can to prepare you for that move and then you leave, we help you transition.”


You’re a fan of our business because we helped you, so you’re an advocate on the outside, we still feel good about you because you were transparent and we worked it out. Those are the kind of cultures that you should be cultivating because gone are the days where people work at a role for 20 years, retire and ride off into the sunset. Companies have to be a little bit more open and flexible and not so, “Oh my god, you can never leave me. I’m going to be so mad if you do.” That is just not where we are right now. 


[0:15:12.9] RS: Yeah. In the case where candidates may believe, it is easier to leave and join a new company than it is to affect change or a position. How do you create a culture that teaches them, leads them to believe that that’s not the case? 


[0:15:29.0] WB: I think it is a lot about transparency and willingness to share kind of where the company is at, where we’re going, what we want from our employees but also seeing it in action. Like the situation I have described, we’ve done multiple times at CallRail, so people now know, “Oh wait, they’re not just lying or saying something nice when they say it.” I think there has to be some trust from the employees and some action from the company because it is not going to happen overnight. 


If you are transparent about where you want to go and then also empower your managers, give them the training, give them the skills they need, give them the tools and then let them have those conversations with their people, it will go over a lot better. And then also if it ultimately is “Actually I do need to leave to get what I want,” you’ve been having these conversations and so can start backfilling that role sooner rather than later because you know that person is going to exit. I think it is beneficial for both the company and the employee. 


[0:16:29.0] RS: Is it just on the managers then or can do you employee surveys or how do you kind of take the temperature and surface these individuals?


[0:16:37.6] WB: No, it is not just on the manager but I like to have a lot of the power and influence and stuff like that to be on the manager so they feel empowered to help their employees make decisions. We do engagement surveys as well, we do best places to work surveys, we get a lot of good data and then create kind of action plans around that. People are saying they don’t feel like there’s good growth paths here. I am just using that as an example, we are great at everything we do and so – 


[0:17:05.4] RS: No one has ever written that out in CallRail survey. 


[0:17:08.3] WB: No, never. Okay, you don’t feel like there are good growth paths. Here’s what we’re going to do, we’re going to work with managers to figure out what the paths are for the roles where we have several of them. We are going to publish those paths. We are going to create an environment where employees could raise their hand and tell them, “Hey, if you want to be something raise your hand, tell us.” 


I really think it’s about communication and a lot of companies, to be fair, got burned on transparent communication around politics, around the pandemic, around social justice. So now they’re like, “We are terrified to say anything” and it’s like, let’s get comfortable being uncomfortable, and let’s continue to try to get this right, and let’s just say what it is when we’re not there.


[0:17:51.4] RS: Totally and when you rattled off all of those – 


[0:17:53.9] WB: The big scary things? 


[0:17:55.2] RS: Yeah, all those big scary things, it’s interesting how all of that has fallen on HR and talent, right? That to navigate these things that have never been a work issue before. When has it ever been so important for companies to have a position on social upheaval, and to deliberately support employees personally affected by it. That all feels new, to say nothing of you know, where culture was not a thing. 


The last time, a pandemic forced everyone into quarantine, so is dealing with severe societal crisis part of the gig now? How do you see the landscape of the HR career having changed and continuing to change? 


[0:18:38.9] WB: I think it is part of the gig now. I think the landscape of HR has completely changed. Expectations have completely changed. Along with the employees having the power, a lot of things that they want solved, HR is going to have to lead that charge. I think previously it was, “Keep the wheels on the bus, keep us compliant, do some fun events for employees every once in a while, handle the problems but that’s really our expectations of you.”


Now, we have to address the pandemic, vaccination policies, bringing people back to work, keeping them remote, social justice issues that happened right as the pandemic was getting really bad. So you already had people isolating and scared on top of now our black employees are even more isolated and scared because of everything that’s happening. And I do think in those situations there is an onus on the company, even if you are not going to take action, to acknowledge. 


“I acknowledge right now your work may not be your best work because the world is a freaking nightmare. That is okay, I’m going to give you some grace.” That’s all it takes, give people grace, and that makes people feel safer and better and more apt to want to work at your company. That doesn’t mean you have to go give them a million dollars.


[0:20:03.0] RS: Right. It’s interesting with the shifting landscape, where HR for so long was just compliance and looking out for the best will of the company. And if you were to ask an HR professional, even like 10 years ago. “Is your staff feeling emotionally supported?” they’d be like, “What? That’s not something I ever think about” right?


[0:20:25.1] WB: I always care about personally, me, Whitney Bennett. No, I don’t think, engagement surveys were just, check the box but we’re not going to really do anything with them. we’ll do it so we say we can do it but then, it’s okay, we’ll move on to the next.


I personally, I have always tried to walk the line of what’s best for the employees but also what’s best for the company but there are so many tropes and stereotypes about HR for a reason, those didn’t come out of nowhere. For quite some time, we were seen as the police, not a partner.


[0:20:59.0] RS: The fun killer.


[0:21:00.3] WB: Yes, that’s – hey. We are now transitioning to really partnering with people and executive leadership to get all these things done and figured out and so, I think if people are not engaging with HR right now and asking them for what support they need, what tools they need, what help do they need to get all of this done, it’s a huge misstep.


[0:21:26.4] RS: Yes. Where does this education come from? The people profession were never taught to be therapists, this is not a compliance course you can take. Is it just grace? How do people educate to be able to provide in this new sense of the HR profession?


[0:21:42.8] WB: I mean, I think it’s failing a lot honestly, but failing up and not making the same mistakes twice. I also think it’s about the nature of the people that are in HR. I’m very curious what people are deciding to join HR after watching 2020 and 2021. What are you doing? What did you just see that happened that made you be like, “I want to do that.”


I have always felt like, my whole career genuinely, have always felt like a little bit of a therapist and I think it’s just people tend to want to talk to me, I can help them solve their problems maybe but no, there are no courses. I also think with the landscape of HR changing though, that is catching up I think.


There are certifications, there are other organizations that are catching up and you can take programs to help you with those softer skills that people are now requesting HR to have. I don’t think it’s like a huge black hole where it was before, it’s just going to take a while for them to catch up.


[0:22:40.6] RS: Got you. Well, Whitney, we are creeping up on optimal podcast length here. I think we should probably wind down. At this point, I would just say thank you so much for being on the podcast and for sharing today, I really loved chatting with you and learning from you.


[0:22:54.0] WB: Thank you. Sorry I was tardy.


[0:22:55.7] RS: It’s okay.




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