EPISODE 677: Sales Development Success Strategies with Alleyoop Women in Sales Leaders Nicole Wasilnak and Holly Sauer

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Today’s show featured an interview with Alleyoop Women in Sales leaders Nicole Wasilnak and Holly Sauer.

IES Women in Sales Program Director Gina Stracuzzi conducted the interview.

Find Nicole on LinkedIn. Find Holly on LinkedIn.

NICOLE’S ADVICE:  “The SDR job is tough but keep doing it because the experience that you will get out of that role is something that you can’t learn in any other role in sales. All of my program directors started out as SDRs”

HOLLY’S ADVICE:  “My advice is for the people who SDRs call. Be curious about a value proposition that is presented in a way that made you lean in, because they might be calling with a solution to something that’s going to change your entire organization.”


Gina Stracuzzi: I have Holly Sauer, who is the Growth Director at Alleyoop, and Nicole Wasilnak. She is the Chief Operating Officer. Welcome to both of you. Nicole, why don’t you go first and tell everybody a little bit about yourself?

Nicole Wasilnak: Thank you so much for having us on the show. I’m really excited to be here today and share our experiences, what we do on a day-to-day basis, and how we can help. My name is Nicole Wasilnak, which is very hard to pronounce my last name. My maiden name is Graham, which was a lot easier, but I didn’t have a choice and made the switch. I am the COO here at Alleyoop. I actually started my sales career in medical sales, so door to door account executive, started that over close to eight years ago. Shortly after that, moved over to another company to sell software. That was the first place where I actually had a sales development rep that was dedicated to me booking meetings for me. Up until that point, I was always the one booking, finding my own prospects, and then going to close and sell them.

I learned how beneficial the SDR role really was. I remember saying to my boss I would never take another job without a dedicated SDR ever again, because of how helpful it was. My boss at the time originally was from Alleyoop, he came over, ran this software company, came back to Alleyoop. When he came back, about six months later, I connected back up with him and he tagged me over to Alleyoop, which is where I got to see that there were actually companies out here that just do that for a living. That’s my experience up until this point. Started at Alleyoop running the sales team here, and then moved over to operations as it was more in line with what I was doing on a day-to-day basis. But really excited to be here today, answer any questions that you may have and go from there.

Gina Stracuzzi: Holly?

Holly Sauer: A bit of a different path than Nicole. I’m a lot newer to traditional selling. I started off selling Kirby vacuums door to door, phone internet plans door to door. I was a travel agent in Australia. When I landed back in the US I got into beverage sales through a distributor. Ended up working for Red Bull for 10 years. I sold on-premise, which if you’re not familiar with that term, that’s to bars, restaurants, a lot of door-knocking still. About four years ago when COVID hit, obviously couldn’t sell door to door in bars and restaurants, and was lucky enough to get picked up by actually a competitor of Alleyoop. I spent three years there. I’m newer to Alleyoop. I’ve been here about eight months now, and it’s just been awesome so far.

When I first came to lead generation, I didn’t even know what an SDR was, so I came to the table like many of our customers. Our clients come in, some of them have never even heard of an SDR role, or what prospecting can really be. Here at Alleyoop, I have the pleasure of helping inform people about what we do and finding the right solution to help them with their growth through traditional outbound selling.

Gina Stracuzzi: I love that both of you started right in the nitty gritty of it. That you went door to door and you’ve done all those hard things because that really makes you appreciate what it means to get leads and to connect with people and be able to verify them. It is not for the weak of heart, for sure. It’s great when you come across people that have actually walked that walk versus people who haven’t and they’re like, “Just do it. It’s easy.” I’m sure that what you do as a service for companies is got to be really well received because it is hard work. With all of that said, let’s focus around some key questions, so that we can really pull apart how you all do this prospecting. Let’s talk about talent and the qualities that you look for in SDRs, and how do you know that when you see it?

Nicole Wasilnak: For us here at Alleyoop, we bring in a wide variety of reps. Some come from years of experience doing this role. Some are newer to the role, have maybe done it for six months or less. But two of the things and character traits that I always look for in reps that are coming to us is going to be, one, if they’re coachable, and two, if they’re consistent. Showing up to work, being consistent, hitting your daily KPIs. A lot of this work is a numbers game, so you have to know if you show up and you hit your numbers, eventually the numbers will fall. But being consistent in that. Being willing to, even though it is a tough job and you get a lot of nos before you get a yes, being willing to keep hopping on that phone and going after it, and then being coachable.

There has been reps who have come to us in the past who have never done this before and have looked to us to train them. We’ve taken a chance on, “This rep could be really good. We see the potential in them.” If they come in the door and they’re willing to go through our training process and they listen to feedback and they implement the coaching that’s being given, a few months in, they’re at the top of our leaderboard. It’s so exciting to see. I would say for me personally, when I am going through these interviews with these reps, it’s, are you coachable and are you consistent? If you can be those two things, I really think you could be successful.

Gina Stracuzzi: Holly, do you have something you’d like to add to that?

Holly Sauer: I’m not as involved with the actual hiring, interviewing process. We have some great recruiters here that do that, and they always have to pass the Gabe and Nicole gauntlet before they get hired. But I was hearing, I think it was just maybe two weeks ago about some of the more non-traditional talent that we’ve found success with. Wasn’t there a story, Nicole, about some theater people or actors and actresses that we were able to onboard to do some outreach for our company personally?

Nicole Wasilnak: Yeah, it’s interesting. It’s such a different background to come from, but when you’re learning a script and learning a program and taking that on and memorizing it and the repetition, we have hired a few reps who have been aspiring actors and actresses and have actually been really successful here. They do that on the sides. It’s pretty cool.

Holly Sauer: Then we have some talent that comes in with tons of sales experience, and they’ve got a great resume about how much they’ve built up sales in the past, and then they turn out to not want to put any effort because they’ve been spoiled and they’ve done it too much. Also, our great recruitment team really has an eye for those best of the best.

Gina Stracuzzi: Well, people get to a certain level and then they don’t want to be coached in the particular way you’re doing it. “I’ve been successful, I know what’s going on.” I can see how that could be. But let’s talk a little bit about data and where do you all find great contact data for people that you’d like to prospect?

Holly Sauer: We’ve got multiple data partners, and I think anytime someone’s looking to spin up an outbound program, that’s the number one problem you have to solve. Having great contact data, accurate phone numbers, accurate email addresses, that’s going to form the foundation of any campaign you put together. We use an omnichannel outreach program, that means we’re hitting people on multiple channels as we target a particular prospect. Finding that accurate contact data of the individuals that meet your decision maker profile within your ideal customer profile, some databases are going to be stronger than others.

We have multiple data partners here at Alleyoop. Some of our clients come to us with great data that we help enrich. Some people come to us and they have no contact data. The beauty of working with Alleyoop is you don’t have to go and sign up for your subscription to a data provider that can get to be really pricey. Rather than getting yourself into one of those contracts, if you’ve never done this before, your data can be packaged up with our program here. It saves you that step, and you don’t have to go through the painstaking process of wondering, “Is the data I’m purchasing going to be accurate or not?”

Gina Stracuzzi: Nicole, I’ll switch this over to you because it’s something that we hear a lot when we’re talking to sales leaders, and that is that their qualifiers and prospectors are really having a hard time getting people on the phone. How do you all work around that, and what do you come up with to address it?

Nicole Wasilnak: It’s definitely tougher than it was probably 10 years ago. There’s a lot more filters on it, spam blockers, there’s definitely different things you have to get around when you’re calling people on the phone. One thing that’s interesting, and what we’ve always done with our programs and really targeted more recently, is when we look at our data of who we’re going to be targeting is we first start with mobile and direct lines. Filtering out headquarter lines, filtering out main lines, that does traditionally help. Then of course, the volume behind it, which is now you may have to make a hundred more dials than you used to to get enough people on the phone to have enough at bats.

Internally, when I started here at Alleyoop three years ago, our reps were making 100 to 150 calls a day. Now our reps are making 250 to 350 calls a day. Our volume has doubled, if not tripled, on a lot of our programs because with the numbers and the way that they fall, you do have to make more. The other thing we always look at is spam blockers, changing our phone numbers, doing things to make sure that the integrity of our dialer stays intact. Right now, compared to industry standard, which is I think 2% to 3% connect rate, we’re seeing on average an 8% to 15% connect rate internally. But we have a whole team behind that constantly monitoring our technology to be able to support and have those types of rates.

Gina Stracuzzi: Let’s talk a little bit about technology. What are some of the other ways that you use technology to enable your teams, or would you suggest for people who are doing this on their own? What kind of technologies are in the market today?

Nicole Wasilnak: We use Orum as our parallel dialer internally that we have implemented. Like I said before, we were using a dialer that was just one at a time, which was working at the time, but now with the volume that we need to make, it hasn’t been important for us to do that internally. I’ve had a few leaders come to me that they’re not looking to outsource this, but they want to enhance their internal technology, so what’s working for us that they could implement. We use Orum as our dialer and we use Apollo to run our email cadences.

Gina Stracuzzi: Holly, did you have something you’d like to add to that?

Holly Sauer: Outside of just the sheer volume, somebody without utilizing technology at SDR might be able to make 40 calls, 40 emails a day. Nicole mentioned what we can do around 5Xing that amount. Without the activity, you can’t have as many conversations. Conversations is what leads those dials. But the other cool thing about utilizing great technology is it can really tell you about the intent of those prospects. For instance, if your email send tool tracks the amount of time someone has opened an email, you can make an assumption that somebody who opened an email multiple times is probably more ready to take a meeting with you than someone who never opened that email at all. We use technology in other ways to discover intent of those prospects outside of just being able to get a lot of volume of outreach into the market.

Gina Stracuzzi: You’re right. There are so many tools now to help us figure out what’s resonating, who’s opening things. All of that wasn’t even there 10 years ago, 5 years ago, really. It was just in its infancy.

Let’s talk about content and messaging and let’s make it a little more generic in terms of the kinds of messaging and content and the channels that people can use to get those open rates, to get people interested.

Holly Sauer: When you go to create messaging, you have to put yourself in your prospect’s shoes. The first question they’re going to ask themselves when they get an email or a phone call or a LinkedIn message is, “Why me? Why are you reaching out to me now and why do I care about this?”

First of all, making them feel like you are reaching out for a reason. That means reaching them on multiple channels and then reaching out to them where it hits a pain point that that prospect should be experiencing. What you want to do is create a short, punchy message that says, “You, Mr. Prospect, in your specific role, has this pain and I can solve it for you.” That’s going to make them want to lean in and take that first discovery call with you to learn about how you’re going to solve for something that worries them every single day in their role. Punchy outreach that touches your prospects on multiple channels is typically the way to get those meetings booked faster.

Nicole Wasilnak: It’s funny, we always joke internally, is the level of personalization that a rep puts onto something and how they personalize it is so important, because I think for a while there’s this emphasis around personalized emails, personalized emails, and then you talk internally, you’re like, “What is personalized to you?” Because I get an email from somebody that says, “I saw you went into Edinboro,” blah, blah, blah, and then all of a sudden it’s jumping right into the offering. It’s like, “Okay, so you looked at my LinkedIn and that’s your level of personalization,” which is fine, but I think you get so much further if the personalization is, “Hey, I see you’re doing this role currently and this is what Alleyoop is doing.” With that, I think we could help here. This is my supplement into it, of doing more of that level of digging in and personalizing, I think really does help because we see these messages come in all the time and sometimes they don’t even make sense. I don’t even know where they get the information that they got. We always send a screenshot into the team like please don’t do this ever.

Gina Stracuzzi: Here’s what not to do.

Nicole Wasilnak: Then it’s funny because you’ll see now this person, this person, and this person, five of us on the leadership team actually got that same note. But the first line was tweaked. I just think your level of personalization, and if you’re going to do that, really take the time to say, “Okay, this is their role, this is what they’re doing, this is what the company does, here’s how I can help.” If you can put that in a short email that’s to the point and direct, I think that’ll get you so much further than calling out maybe where the person went to school 30 years ago that isn’t getting as far.

Gina Stracuzzi: I always love it when I get messages to my email and it says, “Dear Fred. I have so much admiration with what you’ve done with the Women in Sales programs.” I’m like, “Okay, so are you actually writing to Fred or are you writing to me?”

Nicole Wasilnak: I know. Or you’ll see the field first name. They didn’t actually personalize over and you write back like, “Hey, I don’t think your personalizer is working.”

Gina Stracuzzi: You didn’t do your test emails, did you?

Nicole Wasilnak: Test again.

Gina Stracuzzi: Holly, would you like to add to that?

Holly Sauer: I think I would just top it off with, I’ve heard the word tossed around the industry a lot, personification rather than personalization. By that I mean try to hit someone in their persona and reach that pain point rather than where they went to school or something personal about them. That’d be the topper and the overarching theme of how to personify rather than personalize.

Gina Stracuzzi: Let’s get the conversation full circle and then I want to move over into women in sales specific topics. How do you do reporting on all of this? Because that is such a large piece and one of the joys of being a sales manager, is being able to have all these reports and being able to talk about what your team is doing. But that’s a lot of work. How do you know if your SDRs are performing and what do you do when they’re not?

Nicole Wasilnak: Internally, we’ve implemented all of our reps power up with their sales development manager in the morning and power down at the end of the day. In their power up, they’re talking about what is my goal for today? I’m this far in my percent to quota. My goal is to make this amount of calls. My goal is to make this amount of meetings to get me to where I need to be. I have a meeting that’s set to go off with my account executive this afternoon that I’m going to follow up with and I hope it completes. We’re holding them accountable in the beginning of their day of what is their true personalized goal for that specific day, and measuring it day over day because you look at the month span of where they need to be, but if they keep on track day over day, then it doesn’t get away from them.

Then at the end of the day, they send in a screenshot of where their KPIs ended and how they ended the day and anything they may need from the sales manager. That allows us to keep our reps on track daily to say, “Okay, this is their goal, this is what they held themselves to, and this is where they ended the day.” But from a sales agency, it’s a lot of dashboards and reporting. Internally we’re constantly monitoring our rankings of where the reps are, who’s hitting KPIs, where everybody’s at. But then we have to report that to the client. We do have weekly client syncs where you have a program director, a sales development manager, both hop on with every single client on a weekly basis going over, “Here is our metrics this week compared to last week. Here’s where we’re sitting this month compared to last month. Here’s industry standards, here’s where we want to be, here’s the strategy.” It’s really important for us to be tight with our reporting, not only for ourselves to keep our reps accountable, but then to be able to report that back to the client and say, “This is where we’re at. This is where you’re comparing in your industry. This is maybe the strategy or the pivot we want to make, or this is working really well,” so that we can monitor and keep track of it week over week before it gets too out of hand.

Gina Stracuzzi: Holly, do you deal with this directly yourself?

Holly Sauer: Yeah. I value it because I get to stay on with the clients. While I am in sales, I get to stay on with them for the first 60 days and make sure that they are seeing the success in the actual measured metrics before I offboard them to a program director. But what’s interesting about it is I think it’s one of the most challenging part about creating an outbound program. You can go and hire an SDR that seems friendly and cool on the phones. You can spin up the right technology that industry tells you to buy. But when it comes down to it, if you’re a VP of sales and you’re managing three sales executives and then you bring on one FDR, the amount of time that you’re going to spend training that individual, getting them to log their activity, but then figuring out how to run all those reports around how many dials were made and how long were your talk tracks, and what was working and not working, you’re going to spend half your day on just that SDR when you have a whole other sales team to pay attention to. When I talk to potential clients who have done this in-house, this is one of the things they just don’t want to deal with. They love Alleyoop because someone else is going to do all that management and reporting for them.

Gina Stracuzzi: None of this is an easy task and for small to medium sized businesses, the whole process can be quite overwhelming. Let’s now switch the conversation a little bit and let’s talk about women in sales. Let’s start with this particular role and if you see a difference in the success rate of male versus female in the SDR roles?

Nicole Wasilnak: Here at Alleyoop, our sales floor is 60% women. Now, a lot of the time that has been whoever’s the best talent that comes to us, that’s who we want to bring on, and whoever continuously hits their KPIs and hits their metrics gets to stay here. We’re definitely focused on talent. But of course, having women on our sales floor is important. But then when you see how the numbers shake out themselves, and we come to every single month, it’s over 60% is women, I think a lot of times because of the personas that we call on, women tend to have further success and you’ll see that they stay on the phones longer, conversation rates are higher. That is something that I, being here a woman in sales, it’s definitely important for me to have my sales team be consistent of at least 50% and equal to that. But it always somehow shakes out since I’ve been here that it’s actually we’re about 60% female.

Holly Sauer: Again, I’m not as hands-on with the SDRs as Nicole, but I do have to wonder if it’s something about women taking instruction a little bit better too. We want multiple people and women do tend to, and I don’t have the statistics behind it, but I would think that women tend to be a little bit more agreeable and coachable than men sometimes.

Gina Stracuzzi: I always found when I was talking in my early days of selling and I was talking to prospects, I would actually have the guys lined up outside my office because I was always hitting my numbers and going on band. They’re like, “Can you just do this for me?” I’m like, “No.” They’re like, “Well, what is it you say to them?” There was just more listening and more confirmation of their concerns versus bulldozing onto the next thing. I think either it comes to you naturally or it doesn’t. You can be coached if you are open to it, but then people get stubborn too. It’s a prideful thing I think sometimes.

Nicole Wasilnak: It’s always funny too because I see in our chats at Alleyoop of, “Hey, I just spoke to this prospect. I didn’t get very far. They shut me down pretty quickly. But I feel like the way that you go into your sales calls would be a better approach for this prospect. Can I pass you this lead and can you call them in a few days?” They’ll pass leads back and forth and they tag team and it ends up always evening itself out. But there’s definitely reps with different approaches on ways that they take on calls that they’ll work with their teammates on it, which is great to see from a leadership perspective of that they’re willing to work together, they’re willing to pass a lead to someone else, but they know eventually it will come back around and there will be somebody who’s a better fit for them to go after. But it is interesting because they think there’s definitely different approaches and people take different cold callers very differently depending on whom they’ve approached.

Gina Stracuzzi: It is sometimes just the luck of the draw too. You get somebody on a really good day or you get somebody on a really bad day.

Nicole Wasilnak: Yeah, you never know.

Gina Stracuzzi: That is true. If somebody is considering getting in sales and knowing that for the most part, if you don’t have experience, this is how you’re going to cut your teeth, what advice might you have for them?

Holly Sauer: It’s interesting, our CEO just had a post on this on LinkedIn today just discussing how the SDR role is almost not even an entry level role these days. He recommended trying out some customer service roles perhaps, just getting your feet wet in those customer interaction scenarios and in transitioning into it, just to dip your toe in the water and make sure it feels like the kind of thing that you’d want to transition into. A lot of customer service roles do have a transition to account management where you do a little bit of upselling maybe alongside customer service. If you can prove yourself out there, then the transition to SDR is pretty smooth. Then lots of SDRs do go on to be SEs. I think gone are the days where you just step in and you’re an enterprise sales rep.

Gina Stracuzzi: One of the things that Fred and I often hear when we’re talking to employers is because so much is virtual now, even brand-new reps they might come into the office if they’re in the area for initial training, but then they go to their own corner, so to speak, to actually do the work. We hear time and time again that it’s hard to keep them engaged. They have monitoring tools to track things and they can see that there’s downtime and yet it’s not like you can just walk over and put your hand on your shoulder and say, “How’s it going? Are you having trouble today or is this a tough one?” What do you all do in those kind of situations?

Nicole Wasilnak: We actually run sales floors internally. Even though we’re fully remote, we have pods inside of Alleyoop that consist of anywhere from 5 to 10 SDRs up to one sales development manager. The team actually logs onto a live sales floor where they can see each other. In it, you can actually spotlight a rep live on a call and listen in and then give each other feedback. That has really helped with our culture. At first there was a handful of reps that I don’t want to call on a floor like that. I would rather do it on my own. But then it quickly turned to now they’re all rooting for each other and one of the teams, the manager ordered them all cowbells. When someone would get a set, they’d all ring it loud in their office and then they shout it out. We have a scoreboard where they check in, I got a meeting and they tag it over to their teams so the teams compete internally for prizes. But that has really helped because it can be when you’re getting no, no, no, and you’re in an office by yourself and you feel down about it, so that was one thing.

Then the second thing is we actually run a sprint schedule. We call for 45 minutes and then we take a 15-minute break, and we do that together. You all dial together, work hard for 45 minutes, get it out. Now you’re getting actually more break time than you would in a traditional role, but as soon as that 45-minute hits, everybody stops, puts the phone down, and they walk away. That gives them time to go walk your dog, get a snack, get a drink, motivate yourself to come back and get after it. I would say those two things have really helped our culture internally to keep people motivated and involved. You’re working alongside people who are working hard, and as soon as someone gets one, now you want to be the next. But then you have a team behind you supporting you. I think those are two big things that any team could implement that really do help.

Gina Stracuzzi: That’s amazing because it is, and I say this often, if I was coming into sales now and I was trying to do it from my kitchen table, I’d be done. Because the only thing that kept me going was the comradery and the competition and that learning that happens over the divider, in this case, maybe just on screen or whatever the case is. That is great to hear that you built this environment that simulates an actual sales floor. Holly, did you have something you want to add to that?

Holly Sauer: I think Nicole covered that one.

Gina Stracuzzi: I could visualize the whole thing while you were talking about it, and I’m hoping that anybody that’s listening, or I’m sure anybody that’s listening that has the capacity to bring that kind of technology to their office should think about it because it could be a game changer. I could see that for sure.

We like to ask all of our guests to leave us with one piece of advice or something that people can put into action today to take their careers or their selling to the next level. Something that’s easily implemental. Nicole or Holly, who would like to go first?

Nicole Wasilnak: One bit of advice that I would give sales development reps that are doing this job today, it is tough and we all know that. I think it’s one of those jobs that you take for granted, and especially sometimes AEs even. It’s like, “Yeah, they’re setting meetings for me,” but it’s not as appreciated as it should be. It is definitely tough. You have to get a hundred nos before you get that yes. But know that the work that you put in is, one, going to be huge in your career later on.

I look at my program directors today who act as many VPs of sales for these clients. Every single one of them was an SDR at one point. That’s something that I require out of every leader that comes into here, is did you ever do the SDR role? Because if you didn’t, you won’t understand the value and how hard these people are actually working to appreciate it. As much as it seems day to day, it’s very repetitive and it could be tough, it is so important for your career and you will look back at it five years from now when you are an account executive one day and you know, “I can do that job, I can prospect anybody, I can go after anybody.” You also are building a pipeline for somebody else that is in turn really turning into revenue for your company. I would just say like, your job is tough, but keep doing it because the experience that you will get out of that role is something that you can’t learn in any other role in sales.

Holly Sauer: I’ll give some advice on the other side for the people who receive the calls from the SDRs. We know that it’s interrupting your day, we know your inbox is cluttered with emails, but be kind to these people who are working hard. If you do happen to pick up the phone and someone’s polite and just managing objections, maybe give them a little hurrah. It’s also a benefit to you. While maybe 85%, 90% of those emails are not relevant and a lot of those cold calls are annoying, be curious about a value proposition that is presented in a way that made you lean in, because they might be calling with a solution to something that’s going to change your entire organization. Lean into them sometimes. Some of the people don’t deserve respect, I suppose, but many of them do.

Gina Stracuzzi: That is great and very kind advice. I appreciate you saying that because yeah, be nice. Just be nice. Well, Nicole, Holly, thank you so very much for joining us. It’s been a great conversation. I’m sure we’ll be hearing more things from you guys again very soon. Thank you everyone for listening, and we will hear you and see you next time.

Transcribed by Mariana Badillo

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