September 22, 2021

Hiring Well In Sales with Debra Senra


Partner at Hirewell. #3 Ranked Sarcastic Commenter on LinkedIn.

Episode Highlights

Subscribe to the Talent Insights podcast on Apple Podcasts, Google Podcasts, (recommended for Android users), Amazon Music, or Spotify. Watch us on YouTube—and don’t forget to rate us!

When it comes to sales hiring, what are people having the hardest time with that they shouldn’t? 
Answering that question is Debra Senra, the Chief Revenue Officer at Ten Spot. When it comes to hiring sales people, she’s as good as they come.

The short version? A lot.

Hiring manager egos. Not doing the first interview yourself. Saying you want a diverse slate of candidates but showing blatant bias against previous experience. Or schools. Or age.

If you’re hiring salespeople, you’ll want to hear this.

Partner at Hirewell. #3 Ranked Sarcastic Commenter on LinkedIn.

Episode Transcript

Welcome everyone to the Talent Insights podcast brought to you by Hirewell and Careerwell. I’m joined today by the Chief Revenue Officer at Ten Spot, a company focused in employee and workforce engagement solutions. Everyone, please welcome Debra Senra.

Hello! Nice to be here. Yeah. I like going with a really short intro because I’ve been a guest on a few podcasts and people ask me for a bio or whatever and I’m just like, I don’t like it. I’m like, you know what, if you want to do a further intro, you go right ahead. Right now? Off the cuff. No planning.

Yeah I mean, I think you covered it. I’m a CRO at Ten Spots. I spent the last four-ish years at a recruitment software company, a series D startup in Chicago. And then before that it’s like a different world. I spent almost 10 years in the market research industry. So quite the pivot from market research to SaaS. Yeah.

It was funny cause we were talking about, and I think we’ll lay this up- we might do a second show some day, even though we haven’t even done the first one. Because we had a lot of interesting topics and you, you’re a sales professional but you’ve also become an employee engagement expert

or something, right? Yeah. But I was thinking it is kinda funny because I do think that salespeople do end up- like experienced sales people who spend a certain amount of time in a certain industry, they do become experts in different areas just because, they may not have the science and theory background, but they’re usually way better at relating things to people, you know?

So I think if you want to stick around the podcast, we will have a second episode- assuming Debra doesn’t hate this one- where we actually talk more about employee engagement. Because I think that is also kind of relevant to our audience here. But also how we got hooked up. So I feel like we need to give, I feel like we need to get Sales Assembly a shout out. I don’t know.

I think we do, yeah. So Matt green, who has a rip off Peloton somewhere in his house, introduced us. Sales Assembly is a Chicago based organization. It’s actually dedicated towards furthering the sales profession through lots of trainings, through lots of networking. It’s actually a great organization and they don’t have any skin in the game on this podcast per se, but they’re been gracious enough to introduce myself and Debra. And you’re like a celebrity though. We just joined like a couple of months ago and you apparently, you know everybody. So, how long have you been talking with those guys?

So I make, I don’t even pretend to hide it. It was the first purchase I made when I moved to Ten Spot. I find them that valuable. Nice. Back from my time in market research, I used to work for a company called CEB, which is now part of Gartner. And then for the life of me, I cannot remember the research study, but I do remember the fact, which is external networks and the size of your external network is a huge indicator for how successful you’re going to be

at a new company. And so if nothing else, Sales Assembly has helped with that, which is a nice tie into recruiting because having an external network, whether you’re a candidate or a hiring manager is key to finding the right people. Yeah. So what’s funny, because dovetailing once again, there’s a call-

I’m on most Thursdays. I see you pop, you’re kind of big time. So I think you pop in and out because you’re like a celebrity. But it’s funny because there’s a 45 minute call. It’s a lot of this like sales leaders from all the different organizations there and like clockwork, I would say every other week, conservatively sales hiring comes up as like the ongoing topic and it’s like a Groundhog day conversation.

And not just, it’s not repetitive in that standpoint but it’s one of the two things, the other one being what the hell is ever going to do during COVID? That just keeps coming up and that everyone’s struggling with and it very much matches our experiences, what we’re seeing on the recruiting side.

But it’s also why I wanted to have this conversation because like I have a background in recruiting and we have one of our divisions recruits salespeople. You’re obviously a CRO, you hire lots of salespeople. So we kind of come at it from two different areas. And I think that, I would be curious to get your take, what do you think people are having the most hard time with that they shouldn’t? Oh, lots of stuff. I mean the biggest mistake I hear people making when they’re hiring for salespeople is, for lack of a better word, people are gonna get real mad when I say this, but it’s ego. It’s this ego that you are in a position of power and that you are picking someone who should be honored to work for you.

And that’s just not the market we’re in right now. You are a sales person. It is one of your hardest sales jobs ever because you can’t sell the dream and service the nightmare because otherwise you’re going to be in the exact same position. You have to find a way to be really honest about what the candidate can expect, but it is a hardcore pitch to get the right people in your business right now.

And I think I’m seeing a lot of people who are just unwilling to view this as us selling them, not them selling us. And it’s weird because isn’t that their profession is selling, you know? So it’s like the- I see this kind of in all areas of hiring. It’s like when people have their job seeker hat on, they expect a lot.

They get upset when things don’t go their way. They want a certain level of communication, but people always forget- but the irony here is that those same people are also on hiring teams at their own company. And if they feel so passionately about like, “Hey, we need to communicate better or sell better” when you had your candidate hat on, if those same people would just kind of take it, like start with your own company on howyou’re doing things. Because I do think that that is a huge issue, is there’s that feeling that you should be thankful that we’re giving you an offer because we’re the best company out there.

And everyone thinks that, you know? Yeah. And I think when you talk to people they say they don’t do that. When you talk to people, they say, “No I pitch my business hard” and I say, okay from application comes in to first response, how long?

It’s too long. The first 10 minutes of the interview, were you asking them questions versus, them asking you questions? Okay, you’re asking them questions. You’re selling after you know you want someone, but in this market you don’t even have the opportunity to figure out if you want someone, because they’re not interested in talking to you until you sell them on your business.

So at Ten Spot when somebody applies, we have an automatic email that goes out from my inbox, with my cell phone number at the bottom saying, “We appreciate you applied. We know that it’s a hard market. We wanted the actual hiring manager to reach out with my contact information if you have any questions.

And if you feel like I’m taking too long to respond to you now you know exactly who to reach out to.” And I get a response 70% of the time. For people not saying you’re taking too long, but saying “This is really great. I often have three or four conversations before I even meet the hiring manager.

Thank you for this hands-on approach.” And I think that is table stakes right now. Yeah and to be honest, I don’t know many companies doing that. So when you mentioned to me before, that was one of your approaches and it seems like a fairly simple straightforward, automated thing you can do. And it’s again, it’s the ego.

Some people don’t want to be that reachable, you know? Let’s be honest. We’re all overworked. The last thing we don’t feel like doing is taking a few other calls but I think that building your sales, like that is what’s going to help you hit your goal. Like you said, it’s table stakes and something you have to do.

I think it kind of goes even beyond that though leaders who are willing to put themselves out there are having a way easier time. I always do lots of content here obviously, and it’s been good for us. Like we hire recruiters, which are not the same as salespeople but it’s similar.

We’ve hired, we’re about 75 people now. We hired 25 this year. So it’s been really successful and a really hard market to hire these people. And a lot of it’s because not just myself, but others have taken a very kind of public approach in kind of who we are, what we do, what we believe in and that type of thing.

I think that other sales leaders or any kind of leaders need to be not just at the back end of the interview process at that last step trying to close people, but at the front end the process, whether it’s making yourself public or it’s doing what you’re doing.

Because we have done actual surveys on this, like asking people in sales, what do you care about? And it always comes up. Who’s the leadership? What do they believe in? What are they like to work with? Like they want to hear from you. And I think gaiting yourself is a huge mistake. Yeah, and I think

right now, the number one thing sales leaders can do to be successful in their job is to build the right teams. That has always been one of the most important things you can do, but it is super important right now and it’s probably the hardest. And so I think we talked about this before in a previous call. I heard a piece of advice I think on one of the Sales Assembly podcasts where somebody said, if the most important thing I should be doing is recruiting

then my calendar, I’m going to color code every interview I have. And let’s say it’s red, my calendar should bleeding red. If I could say it’s the most important thing, my calendar should reflect that. And so that’s the other thing is that why, if there’s a great applicant, why wouldn’t I take the first call?

Yeah. It’s the most important thing right now. Yeah, I would agree with that. I also, kind of along these same lines because I think the conversation started with talking about egos. Hiring processes themselves, I’m curious how many steps is your typical process? I’m putting you on the spot here.

1, 2- 3 or 4. And it depends on the role. So the first call is with me. It’s 30 minutes and I’m pretty transparent. I say, I’m going to take 15 minutes to try to get to know you better. Then I want you to take 15 minutes to get to know me and the company better. And at the end of this call, we’re going to tell each other, if we think there’s

a possibility of a mutual fit. And this is one thing that I learned. I was a recruiter for a brief moment. and one of my mentors said, “You always reject people on the phone if you know you’re going to reject them. It’s the humane thing to do.” And so I do that at the end of the first call. If it’s not a fit, I say it.

And I encourage them to do the same, and if it is a fit, the next step is me showing them the product. So it’s a 30 minute call where I show them the Ten Spot product. I tell them the good, the bad and the ugly, because I want them to be- you know, we’re an early stage startup and that’s not for everyone.

And the worst thing I could do is oversell what we are, or sell it differently than what it is in reality and have somebody quit two weeks in. So I show them everything. And if they’re still interested, depending on the role, there may be, I call it a homework assignment, but this is not free consulting.

That’s a big thing for me, is that I should not be building your go to market strategy as a part of the-I was going to say we almost weren’t friends there for a second because that’s something I can rant on too, but yeah, the free work. No, I think homework assignments should take maybe five to 10 minutes and it’s things like, let’s say I’m hiring- we do full sales cycle salespeople. I’m hiring an enterprise sales rep and my concern is they’re not going to know how to prospect because they haven’t done that in awhile. So I say, I want you to take five minutes and find somebody that you would want to sell to and then tell me how you would reach out to them.

Don’t write the emails, don’t give me the call scripts, but I want to know which call, which email, which video, how many times, what’s your process? Takes five minutes to prep for that but it tells me a lot about whether or not they’re going to be gritty enough to do that portion of the job. And then the final interview is an hour and that’s where we dig deep into is this person capable of doing the job and vice versa.

At that point, by the end of that call I know if I want to hire them. So I saved the last 10 minutes, by like tell me why you would decline my offer, if I were to make you an offer. On average, how long does it usually take you to do all four of those steps? If the candidate has availability, a week.

What I found, this is not normal. Two years ago, it would have taken longer, but a week is about how long you have with a candidate before they accept another job. Okay, so you hit on a few key points here. I think for most of- the way most organizations run their interview process I think four steps is too many, but you do two things.

One, you’re the first call which I think is key because I think that’s where most companies screw up because when you’re the first call and they’re talking to you and you’re the top person, you’re getting them excited and you’re buying leeway to have an extra step or two, you know what I mean?

I think when you don’t have your leader being the first call, it doesn’t matter who it is. If it’s not the person they’re going to be reporting to, you can have a great recruiter or you may be one of your kind of line managers or something like that, they’re not going to have the same level of excitement.

Period. The interview may be conducted well, but it just kind of, it’s just more impactful. I also think that- so I really like that. I like that you can get it done in a week potentially because that’s the biggest thing is it just takes too long. The number one reason why I think that companies are struggling to hire from what we’re seeing is that good candidates, especially the lower down they are, the more opportunities they have. These BDR levels, which is what everyone always complains

they can’t find people at. Yeah, they’re going to have an offer in a week if they’re good. And if it takes you longer than that to do it, you’re going to miss out. You almost lost me on the homework because usually when I see homework, it’s like an hour or two hour prep project. But if you’re asking them to a five or 10 minute thing I think it’s such a solid, so.

I’m going to recommend that to companies we work with when they these long lengthy things. Because I think I’ve been trying to talk them out of doing those, but maybe if I talk them into a five or 10 minutes, I’ll be able to have more success. Well, and for me the other thing is I’m looking, I know exactly why I’m having them do the homework, which I’ve been in interview processes where I’m like why am I- what am I showing you by doing this?

It took me five hours. What is it showing you other than I can build a great PowerPoint? For the example that I gave, I only do that when I worry that somebody is too far removed from prospecting. So I want to make sure they still have the prospecting chops or I’m interviewing for a sales operations right now.

Somebody who is very tactical, like a Salesforce administrator, maybe I am worried that they don’t have the strategy to help me build a system that will allow us to scale. So maybe the homework there is I give them a business challenge and I say, tell me three questions you’d ask if I asked you to work with me on this project. What are some things you’d need to know before you could start making recommendations?

And so it is very specific to something that I’m pressure testing, as opposed to just a blanket everybody give me your business pitch. The thing that I hate is when people, especially in sales, when the final step is come demo our product back to us.

All right. So another thing I want to dig into here is, one thing we hear most frequently on our end- it seems like BDRs, I think I mentioned a second ago, that’s one of the hardest things to hire for and there’s a few reasons for that. One of which is it’s a level that people don’t want to be in very long.

If you’re a BDR, you and be there for one years, two years tops, and you’re looking to get out. So then there’s companies that want to hire BDRs with experience. I was just going to say the experience thing drives me crazy. Yeah. But then there’s the- I don’t know if you see this, but obviously we see this, there’s also companies want to hire BDRs with experience in specifically SaaS experience.

So some other kinds of sales is completely inapplicable to our business and you couldn’t possibly figure it out, right? What’s your hot take? I mean my hot take is that’s the dumbest thing I’ve ever heard for two reasons. First, if you’re an experienced BDR, you’re not good at your job or there’s something going on because to your point, most companies, especially SaaS companies the time to promote a BDR is between nine and 18 months. And so if you’re looking for somebody with a year of BDR experience, a good BDR would never jump ship because they’re on the verge of a promotion. And so I would ask, why are you interviewing for a job if you have experience? The second thing is, it’s not rocket science.

The thing that makes a good BDR is not skill it’s will. And you should be screening for that and exclusively that because you can train the rest. And so I’d rather have somebody who’s fearless, who’s aggressive, who has an internal locus control, who has pride in what they do and responsibility towards just being accountable

and somebody who wants to win. I would rather have that person than somebody with five years of BDR experience. Yeah. I think on top of this too, the experience they look for, there’s certain, there’s a lack of diversity, right? There’s a lack of people being- when I say that, I mean on a couple levels, but people being open to backgrounds, there’s that mentality

we want the former, we want people from big 10 schools who are athletes or in fraternities and sororities, and we want type A personalities. But I think there’s a lot wrong with that in general, but there’s also wrong with the fact that this idea that sales, like the best salespeople are the people who are just like ultra competitive, in your face, type A.

That’s something we see too, is that everyone wants the exact same profile. Yet a lot of these companies do tout like we are looking for a diverse slate of candidates, except for when it comes to things like the actual experience or where they come from.

I completely agree. And I think people who did sports in college can be great BDRs, but so can theater majors. Two of the best sales professionals I have ever worked with who came up as BDRs, started their career in Nordstroms, as salespeople. To the point where I now take business cards

every time I go to Nordstrom’s and if there’s a great sales person, I hand it over and I say, if you ever want to get out of retail, give me a call because I’d love to hire you. It’s too narrow a view on what grit looks like. I mean, honestly, think of somebody who went to community college and like fought their way to get a degree or didn’t go to college or- there’s just so many other profiles of people who can demonstrate a commitment to succeeding and a grit to get there that go beyond big 10 athletes. And to your point about like ultra competitive personalities, one of my best sales reps right now, he’s not

really motivated by winning as an individual. He’s really motivated by winning as a team. And that doesn’t mean he doesn’t work hard. He’s my top dialer. He has the most meetings. He has the most opportunities, but what gets him out of bed is like the team winning. And so I just wouldn’t pigeonhole yourself, especially at the BDR level.

Yeah. I was think too, it’s as simple as- and this is maybe one of the overused catch words of last year but I mean it in a serious way, I still think that one of the most important aspects of being good at sales, it’s more listening. It’s more empathy than it is about being a hard closer.

And I think that – not to make my own stereotype about that classic athlete, fraternity, big 10 per- you don’t think of that persona as someone who’s a great listener, very empathetic, very touchy feely with people and trying to understand their needs and being able to pull it.

But I think that’s really what it takes to really connect with people is kind of maybe being more focused on the listening aspect which you know is important, but it’s not something I necessarily- I love your examples of retail because I actually think that’s a great- we’ve seen kind of success there too in finding people who would make that kind of transition because that is

an environment where you’re going to deal with a lot of bullshit on a daily basis. And if you can make it there, you’ve proven more success than- I guess it’s more applicable to kind of transferring something like more of a SaaS place.

Yeah, and so for BDR or full sales cycle reps, one of the most undervalued traits is the ability to bounce back from rejection. Think of jobs, where people are rejected over and over and over again, and they’re fine and they keep going. The hardest part about sales is not hard because it’s

mentally difficult or intellectually challenging. It’s emotionally challenging. And it’s emotionally challenging to pick up the phone, call someone you don’t know who’s trying to get off the phone with you and convince them to stay on the phone and book a meeting. Emotionally challenging. And you need somebody with like emotional grit.

So retail is great. On the fly, what are some other great work professions where you get rejected all the time? I mean, being fat in high school, I got rejected all the time.

All right. I got one more area that I wanted to cover- and I don’t know what to do with that. So the stigma of sales, right. Do you think that-there was a article I’m pretty sure… did we talk about this one? I know it came up in one of the Sales Assembly calls. Is Gen Z just not into sales because it’s seen as cold calling, dollar for dollar.

It’s not a high IQ profession or very high intelligence profession. Do you think that’s real? Do you think that’s any different than- do you think it’s going out of style and that’s why people are having a hard time getting people? Or do you think that’s just another kind of generational?

I feel like that you could say the same 20 years ago they would have said the same thing about the Millennials. Well I think there’s been a lot of press recently to try to rebrand sales and to the point where sometimes I’m like actually, no sales is what it’s saying it’s not. It is hard.

There are high highs, low lows. It is high paced. It is you wear your number on your back. And so it is, the risks are bigger. The rewards are bigger. I don’t think Gen Z doesn’t want to sell. I think what’s happened in the past couple of years is we have broken the mold that we all were being forced into.

And what I really respect about Gen Z and the younger generations is that I call my daughter a Honeybadger cause she doesn’t give a fuck. And that is Gen Z, that they wear their hair how they want to, and they get tattoos and they I don’t know, they dress the way they want to dress. And sexuality is a spectrum and it just, they don’t give a fuck.

They are who they are. And that has not been something that is okay in a sales culture. And so I think somebody that’s really true and authentic to themselves walks into to most sales floors and says no way, I don’t want to be a part of that. And I get why. I was lucky that I had pockets of people that I felt like I could be myself with, but the first 15 years of my career, it was all about hiding who I was to be successful.

And I think the burden is on the sales leader not to sell a dream and then deliver a nightmare, say that we really want a diverse culture, but you walk in and it’s all white males under the age of 30 on the sales floor. It’s our job to actively seek out diverse skillsets, diverse populations, somebody who is empathetic, somebody who’s charming, somebody who’s a good listener.

All of those people can be good at sales. It’s just sometimes hard to put all those people in a room together and have them get along. And we need to lead by example. We need to hire salespeople who are over 35. That’s another big pet peeve of mine is that diversity is skin color. It is gender, but it’s also age.

And we need to create cultures that are comfortable for everyone and that means, for me, it’s being my authentic self in all interview phases. And if somebody opts out because they don’t like that I swear like a sailor or I am so dorky it is painful, or that I get distracted or that I don’t hide when I’ve lost my train of thought and that I cry when I’m proud of people and like all of that, that’s who I am. And I will obviously adjust to my team where I can, but I show that because it’s going to attract a diverse population of people that are thinking, yeah, I could work for somebody like that. The jokes I can’t stand. but Not going to lie

that was kind of a pretty perfect place to I guess put an end to this podcast because I have no response. That was perfect as James Carville said in old school. I hope that everyone out there got a lot of value from this conversation. Is there anything else that you want to throw in at the end?

I guess I should give you one last, in case anything we forgot that you really need to get out on this topic. I’ll just do a pitch for sales in general. And that is that if you like money, if you like working with people, if you like connecting with people, and if you have a drive to succeed, sales can be an amazing career.

And if you’re walking into places and thinking it’s not find a new home, don’t find a new department. Sales has been really good to me. It has bought this house and this life, and I think more people who are not the mold should consider it. So that’s my pitch. Awesome. That’s great. So I hope you had a fun time with this one because I’d like to do another one.

Again, we talked on employee engagement and your synchronized swimming career, which I think people really want to hear about. Thanks again for tuning into the Talent Insights podcast. If you want to hear what we have to say, you can check out the talent insights site: where you can subscribe to our YouTube as well as the podcast on Apple, Google, Amazon, and Spotify.

Debra, thanks again for joining us. Everyone out there, we will see you soon!

More from Talent Insights

Episode 36
As a remote worker, it can be easy to find yourself overworking because it’s hard to just “close the laptop” or ignore the work...

Episode 35
This past season of The Bachelor was unlike anything we’ve seen before. One of the final contestants made the unprecedented decision to remove...

Episode 38
In this episode, Dan and Louie start by chatting through the new MLB Season kicking off with Dan’s Pirates going 5-0 out of...

Episode 34
 The struggles of being a newbie on the team are vast, especially in a remote work environment. Join Liz and Shania as they...

Episode 23
Creating a positive candidate experience is crucial in the hiring process. Regardless of whether a company ends up making an offer, candidates should...

Episode 22
In this episode of Cracking the Career Code, Matt and Kierra discuss the importance of having a clearly defined interview process. They stress...

Our Shows

Our Latest Blog

The Green Banner debate is over

And stop being so serious. The dumbest debate on LinkedIn (and there’s a lot of contenders) is if the “Open To Work” green banner is good or bad. That debate is over. If you’re not familiar with the controversy: Pro-Green Banner people like ...