Podcast Pit Stop: Gabrielle Blackwell on Winning Strategies for Sales Development Managers

Winning Strategies for Sales Development Managers

In episode 84 of Pit Stops to Podium, we sit down with Gabrielle "GB" Blackwell, the brilliant mind behind The One on One at Workweek. With an impressive background as the former SDR Manager at Airtable and Gong, Gabrielle brings a wealth of experience in sales development to the table.

Gabrielle will be sharing her winning strategies for Sales Development Managers. From emphasizing the human element of selling to nurturing successful sales teams, she'll delve into the intricacies of implementing effective sales development processes and methodologies. Tune in as Gabrielle unveils her SDR Manager's Survival Guide, tackles remote work challenges, and offers valuable tips on maximizing productivity through technology-driven remote team management.

If you’re ready to learn from one of the best, then buckle up and hold on!

Pitstop Highlights

Onboarding SDRs in a Remote Work Environment

Keys to success:

• Recognize that technology plays a huge role in supporting a remote or hybrid team. 
• Managers to be very intentional with their communication.  (e.g. how frequent are meetings and what are their purposes)
• Have solid 1:1s (use frequent communication)

The Power of Follow-Up and Multi-Channel Approach

The importance of following up can't be understated.  A good follow up can negate a bad first communication.    

Personalization is great, but without follow ups it's a dud.

To increase the likelihood of engagement, you need to get people in to sequence and have enough touches to have a chance.  If they don't respond to the first sequence, pause for a few months and then have another sequence.  (should 3 sequences per year, per prospect before revisiting strategy)

It's also important to meet your prospects where they prefer to be by using a multi channel approach.

SDR Success through Follow-Up and Nurturing

Many sales reps do not reach out past the second attempt.  Therefore, if you're reaching out for the sixth or seventh time, you're not competing against many others.

If an email is well-personalized, it stands a chance at causing someone to respond later when the timing wasn't right during the initial touch.  It's important to remember that the vast majority of people are not going to be in market for your particular solution at the exact time you reach out to them.

When someone is not in market, you need to be educating and nurturing them, so that when they are in market, they come to you.

Connect with GB

LinkedIn:  https://www.linkedin.com/in/gabrielleblackwell/

Website:  https://workweek.com/brand/the-one-on-one/

Full Transcript

Brendan:  Hey everyone, welcome to Pit Stops to Podium, the RevPartners podcast where we talk to execs who have competed and won in taking their companies from high growth to high scale. My name is Brendan Tolleson and I serve as the co-founder and CEO of RevPartners and I'm delighted to have with me today, Gabrielle Blackwell for this episode of Pit Stops to Podium. And I should say welcome, GB.

GB:  Yes, thank you. Thank you for having me.

Brendan:  Well, we're excited to have you. And for our audience who may not know who GB is, she's a creator of the one-on-one at Workweek. And GB, what we'd like to do for our audience who may not know who Workweek is, just give you the opportunity to share a little bit about the organization and ultimately how this idea came about. So, floor is yours.

GB:  Yes, I'm gonna do my absolute best to give a quick Workweek recap, but I think at a really high level, like Workweek is a media company and they're supporting creators in providing their audiences with really great content. And when I think about maybe what Workweek is doing a little bit differently is putting creators at the forefront versus creators just supporting the brand of Workweek. And then secondly, at least what I'm finding is they're very much like, hey, G.B., you have a point of view and we want to support you in sharing that point of view. We want to help you operationalize that point of view. And we always want to encourage you to take up that much more space. So I think it's really nice to be able to share out a strong perspective through the one-on-one, which is focused on sales management or frontline management and to be encouraged to like say the things that might be scary to say, but that other people are going to benefit from hearing.

Brendan:  I love that we had a, and we'll probably get into that a little bit when we get into the meat of this podcast of this creator, the Who Economy kind of concept of content. And we were just talking to a podcast with Andrew, the founder, CEO of acquire.com and just talking about brand affinity and a lot of what you're describing gets into that. So I'm excited to hear that you've created a safe place and an opportunity for those creators to collaborate

GB:  Yes. Yeah. I get to benefit from the work that the folks at Workweek do. So yeah, I had created a plan of things I wanted to do. Someone asked me, hey, what are your plans? I showed them. Like, let me introduce you to some folks that I know. And so it was the folks over at Workweek and the rest has been history.

Brendan:  That's great. Well, GB, before we get into the big idea, we do have a tradition here at Pit Stops to Podium and that's to get to know our guests outside of work. And so just to learn a little bit more about you, maybe the passions, hobbies, interests that you have.

GB:  So I really like doing hot yoga, power vinyasa most of the time, just like sweat my butt off and also feel like I got to meditate along the way. I have two long haired mini dachshunds named Luna and Missy who y'all might hear bark at some point in time during this recording. And I think thirdly, I played basketball and volleyball in college for a couple years each time. So, you know, people want to get beat up on the court.

Brendan:  And you may hear my four-year-old who has a friend over. So this could be a very interactive and engaging conversation.  Well, GB, I really appreciate you sharing a little bit about who you are and the passions that you do have. And it's always fun to hear that we've got an athlete on our hands. And if anyone wants to take you up on your offer, I'm sure they will.  Well, let's get the big idea. You know, one of the things that we do not get into too deeply in your introduction is your background before work week in terms of the role that you played and your experience. And you know, one of the topics that I'd love to talk to you about is winning strategies for sales development managers. And you know, Maybe we'll start there. Let's give your audience a little bit of background on your experience as an SDR, SDR manager that allows you to kind of speak into this big idea before you get into some of the tactics on how they can be successful.

GB:  Yeah, definitely. So I started off working in software sales in 2015. I started off as this, I guess, a enterprise or strategic SDR at a, what did we call ourselves? A translation management company or platform. There it is, what it was. It ended up doing really well there and had this invitation from the manager that I had at the time. And he'd said, you know, you're doing really well as an individual contributor and what's going to help you. access more opportunities later on is being able to operationalize your own success. So the better able I was to explain why what was working for me was working, the better off I would be. And so I took that invitation, I took that challenge on, and that led me to being able to have an opportunity to become an SDR manager. companies after that. So I'd only been working in software sales for about a year and some months before someone said, hey, like you should be a manager at like 26 years old. So I've managed at companies that have, that have gone from like 50 to 100 people. I've managed at companies that have been about 150 people. I've been at companies like Gong and Airtable. So coming in as an SDR leader around the 400 or 500. 500 person mark and getting up to a thousand plus within a year kind of thing. And so now an SDR manager at Culture Amp.

Brendan:  I appreciate you sharing your background and what's fun too is you've experienced it. So this is not just theoretical. These are actual insights based off of application, which is really powerful. And I think, you know, and probably there, I have so many questions for you. And I'm sure the SDR role, or at least how you even think about it has changed with COVID. I mean, kind of where I wanna start, which is maybe, jumping ahead, but I'm trying to think through, when you just think, hey, this is the, typically it's a first job for most people getting into sales. You mentioned, hey, I was a manager at 26, and that's what my first job was really more in the SDR seat. As you think about like SDRs that are coming in, who have never been in a physical workspace because they're dealing with, you know, COVID world where people just work at home. Like, how do you integrate these new SDRs into an organization who have no experience and are expected to immediately start to contribute, whether it's dialing, outreach, et cetera. I mean, it's a different dynamic than maybe what you experienced and certainly what I experienced when I was first starting.

GB:  So I've been managing teams for about five years now. And if we think about how long we've been in COVID, majority of my management experience has been in a pandemic like world. So I think the, I personally have found a way to make it work very well. And I also do have a preference for flexibility and being at home. That being said, where I see most leaders or teams struggle is not recognizing the value that technology plays in supporting a remote or hybrid team. And secondly, where I believe managers and leaders have opportunities to support a flexible work arrangement and make sure their team is knows exactly what they need to do, how they need to do it, and what the level of quality is, is to make sure that managers are being very, very intentional about their communication. So everything from written communication to support different learning styles. So if it's videos, if it's listicles, if it's things that are recorded in Gong, whatever it might be. I think a second part of this too, and the communication is thinking about your team communication and how frequently you want that communication to be. And then what the purpose of those team meetings, like what's in service too. I think thirdly as well as making sure you're really solid on your one-on-ones. So I like to tell the folks on my team who are coming on board is I'm not a micromanager. I'm not a hands-off manager, but I am very involved, meaning that I wanna make sure that my reps are feeling confident and comfortable before I start to give them a little bit more autonomy, a little bit more on their own. And I usually find that people actually like that. Like they want people, they want a manager who'll check in on them in the morning. They want a manager who will let them know like, hey, by the way, I'm looking at your numbers, you're pacing behind for the week, what's in the way. So this is the kind of intentionality that I mean in the communication, which is you have to, in the office, it might be really easy to take for granted how important your presence, just pure presence in the office is. Doesn't mean that people need to talk to you all the time. It just means that if you're there, they feel like they can come up to you. And so when we're now in our homes, people might feel like, oh, I don't want to bother her when instead I need to be the one kind of bothering my reps a little bit, but then also reminding them like part of my role or my whole role basically is to make sure that you are performing, right? And that you're given the opportunity to be promoted when the time comes for you. And the most critical piece of this is that we're in frequent communication so that I don't see your world. I don't always know what's going on. I could always do my best, but I need you to help me fill in the gaps here. So if you're really like establishing this world of leveraging the technology to communicate effectively and get a better gauge on work, while also too, cultivating an environment where communication is really solid for both sides, you'll meet up. you'll be in a really great position to set, even if it's SDRs, but also like just anybody who's never been in a remote first environment, like you'll be able to support your team much better.

Brendan:  Yeah, I really appreciate that perspective. And to your point, it's not even that they, it may be their first experience in remote first, it may just be their first experience period in professional life. And so like, they don't have the benefit of being physical, to your point, physically with, you know, whether it's the manager or even their peers candidly to understand, hey, what'd you just do that was so effective or listening to the phone calls or just real kind of like the water cooler aspect. And so... I think your point of being intentional, proactive communications and expectation setting, and then leveraging tools to facilitate that allows for you to kind of experience the best of both worlds doesn't mean it's the same, but it's mindful. It's being cognizant of the realities and addressing it.

GB:  Yeah. Yeah. I have a lot of very strong opinions about like the perceived importance of an office. And I think that to me signals that that company is behind. And that's just my opinion, given what's capable with technology. So I think about call recording software, for example, if you're using a sales engagement platform, like I have almost every piece of data that I could ever need. And I can also see my people's work. Does it mean again, that I'm micromanaging? It's just more so. I need to trust that my people are going to do the work. I also need to trust in my ability to coach effectively. And part of that is I actually need to get into the weeds of their work. But even if you don't have that kind of technology, like you always have the opportunity to shadow people from a different location. So there's all again, there's just, I think if managers or leaders are really curious about what is the most important piece of being in the office. Like what are the things that actually happen? If it's the... camaraderie building, okay, you can simulate that in a remote environment or on a Zoom. If it's a, okay, I wanna be able to sit side by side with somebody, okay, you sit screen to screen with somebody. Or if it's a, I really wanna be able to whiteboard with somebody, for example, open up a Word doc and do it. So if we really think about what are we actually trying to accomplish here that we were able to do very well in an office, it's not gonna look the same. here, so let me adjust. And so I don't think that's an SDR specific thing. I think that's just like the ways of working. And if we are not, I think there's a camp of revenue leaders who are like, well, I learned in the office by osmosis, so therefore learning by osmosis in the office is the best way to go. And I've said this to CROs that I've worked for, like, yeah, you are 20 years behind. Like, how about, how about like, let's rethink what this looks like.

Brendan:  Yeah, I like it. And so let's, I want to get into kind of the, you mentioned tools a little bit. I think there's some benefits we can talk through in terms of practical, hey, here's some tools and process that I've seen be helpful. Before we get into, to me, that's all like a supporting function before you even get into that app element, there's, hey, what's the approach that SDR, like in terms of messaging and point of view and style, from a tactical perspective, like what are some of the trends that you're seeing in terms of how, what are the modern approach to prospecting or? Maybe not even prospecting because it can be inbound too, but what are you seeing being effective and what's resonating in the market these days?

GB:  Yeah, so first time I was in SDR was 2015. So in terms of prospecting experience, it's been a long time. And the one thing that I've seen to be true and hold true at every company and every year is the importance of following up. Like it's really not rocket science, like there are no silver bullets. Like I don't have anything that's like, oh, here's this trend of the year. I think you'd have the worst first touch email and still book a meeting because you were able to iterate along the way, you have something more relevant to follow up with later on. And typically what we see happen is if we're outbounding, what is it? There's some stat that says only about 5% to 10% of your target market is in market for your solution at any given point in time. And so that's the first piece. The next piece of this is then the likelihood that you're actually going to be able to engage with them. in this situation, what I tell my SDRs is like the first part of this is we need to get people into sequence. Like we need to make sure of course that our messaging is tailored to them and their jobs to be done, potentially their interest, potentially to what's going on with the accounts. Yeah, sure. But the most important piece is that we've started to engage with them. We have sequences from an outbound perspective that have enough touches on them for the, to have a chance to like respond to what's received, what's interesting. But then just because someone doesn't respond to the first pause for 60 days and then have another sequence going. So you really should be reaching out to your top targets or top accounts, top prospects, whoever it is. There should be like probably three sequences per year for a prospect before we're like, okay, let's revisit our strategy. And is this the right prospect to go after? But again, time and time again, that is what I see the best performing reps do is they're following up with their prospects. and they have a really great system for tracking that follow-up. So I feel like that's like the one thing that doesn't get talked about enough. Like you can personalize and tailor all your emails and do all these things. But if you're not following up, it's a dud. And I think secondly is making sure that you're meeting your prospects wherever they prefer to be. So using some kind of multi-channel approach. So if that's like, and then using each channel to maximize. results or success on other channels. So for example, if you're going to make calls, leave a voicemail. If you leave a voicemail, refer to your email that you're going to send. If you send an email, also connect with them on LinkedIn, right? So that all of a sudden you've now kind of got this, I guess there's like the combo prospecting effect, but I think it's just like this nice like bouncing around until someone goes, all right, this person's really trying to grab my attention.

Brendan:  Yeah, well the first part is not sexy in terms of the follow-up or being timely in the follow-up.  But to your point, it is. It seems so basic yet it's very often neglected, which is crazy.

GB:  Yeah. There's like, there's some graph that I saw was an image that I saw when I started. And it, um, it said something on the lines of like, uh, only let's say, um, only 50% of sales reps, uh, reach out twice to a prospect before giving up. So if you're a sales rep who's reaching out a six, seventh, eighth, ninth, 10th time, you're by yourself. Like you're not competing. You're not really competing for or competing against other sales reps for attention, you're starting to stand out. So with my reps anyways, what I tell them in a little bit of this is to help them realize like you don't have to have success on the first touch because that can be very anxiety driving. Like let's have enough of a tailored message for someone to go, okay, this is for me. It's something I care about. the timing might not be right, but a lot of people will, if they see an email, they think it's interesting, they'll put it in a folder and then they'll reach back out. So we see that happen a lot. We reach out a first time and actually somebody comes back in inbound from a company, like sometimes a month or two after the initial outbound outreach, but then also it can happen is we reach out that second time. So we've done a 30 day sequence, we wait 60 days, and then we've reached back out at the 90 day mark, right? And they say, Hey, listen, we've actually been researching this because I don't know, maybe we planted some seeds. And like, yeah, so we've been researching this, it seems really interesting and we wanna learn more. So I was working with this one company and I had a top performing rep who would hit like 200% of her number every month. And I would just say like about 60% of her number or of what she got was coming from follow ups.  So like if we're talking about like pure pipeline generation, recognizing that again, majority of folks are not going to be in market for your solution at that very specific time. Secondly, it can be really hard to get people in general. So part of that means that you have to take people who are not in market and educate them and get them nurtured up. And then by the time they're in market, right? Like now, now it's time, especially for SDRs, like now it's time, it makes sense to pass them over to sales. because they've had that like three, four months to consider what is the use case for your technology.

Brendan:  Yeah, I think it's a really good data point. I think you said 5% in market are actively looking. So therefore don't be discouraged if you're not seeing the conversions that you would hope to see because over a longer period of time, there will be, to your point, when they are ready, then you're gonna probably see that higher conversion. Does that, with that data in mind, and switching topics just a bit, not like, there's a... I don't know how familiar with the near bound kind of concept of with social selling and kind of the human element of how you think through prospecting. But do you see a change in approach as it relates to messaging and how to connect with that audience in light of that five percent kind of concept or or what should the takeaway be for our audience on how they should think through that initial message to get people to at least potentially express interest.

GB:  Yeah, so I'm just going to go with like, I've got the brain of a Neanderthal. So I'm not really trying to overthink anything until the time comes where I'm talking to somebody live. So I just want to preface it by that because again, what I observe is there is a lot of analysis paralysis that happens in crafting an email. And I'm like, just write something that is relevant to them. Like even today I was having a coaching call with one of my reps and I'm like, all right, you're going to reach out to someone if it's on the phone, if it's over email or even over social and they're probably going to be asking a few questions, right? Which is who is this? Why are they reaching out to me? Why should I care? And what do they want? And those are the questions that you need to answer, whether it's a phone call or if it's an email.  And so like, I've flipped it into like a framework or an opener, which is like, again, like, who is this? That's your intro? Like, hey, hey, Brandon, it's Gabrielle, right? Then secondly, relevance. Like I was, I saw this, like your company's experiencing this, like, here's what your CEO shared. Like, there's something that I'm seeing. And I'm reaching out to you about it. Because here's what I saw in your profile. So like, why should you care that I'm calling you? I want to share something like what's in it for you potentially. So I always like to say something easy peasy lemon squeezy, such as like, hey, your company is trying to do something over here. We have a solution that helps people do it way easier and faster. I keep it really simple. And then afterwards it just asks the question. It could either, the question could be the call to action of like, hey, would you be open to chatting about it? Like, if not, no worries, right? Or if it's like, oh, hey, you know, is this of interest? Like whatever the call to interest or call to action is, whatever. Keep it simple. Um, so I think that the, again, the only thing that's blocking somebody from having a conversation with someone is like the amount of overthinking that happens and trying to craft the message. Right. So the sooner that you can help yourself or your teams get into like taking action, the better that framework can really help the coarser things that you can plug and chug that are going to influence what that looks like the actual messaging, um, but again, recognizing that people might not bite on the first touch. that still gives you room to find meteor information later on that might be more timely when you reach out. So I just don't think that you need to over complicate or over engineer sending another person a message that they may or may not read.

Brendan:  Yeah, I can't tell you how many emails I get on a daily basis that I just move on to the next one. And I can't imagine how long they probably spent trying to craft the perfect message for what I just did.

GB:  Like keep it, yeah. I say like, you know, spell the person's name right. Make sure the company information is correct. Like, yeah, make sure you're actually reaching out to the right person. And then again, if the first messaging doesn't work, like reflects and go, okay, well, what messaging is working with who is that? With whom is that messaging work? And then that to me starts to influence, okay, how do you want to segment out your book of business or prospects? And then maybe use that message on that segment. It's like, okay, cool. If that works, wonderful. If the messaging over here with this segment isn't working, I'll just iterate and test and see what does. But again, I think the biggest thing is a lot of people, unfortunately, what can end up happening for outbound SDRs is you plug them in. It's like, why don't we have all this pipeline right away? It's probably going to take us six months to actually deliver a really great pipeline. But they're also like, I'll see sales leaders also be like, well, the messaging was wrong and that's why they didn't respond. I'm like... people respond to messaging for the silliest reasons and it really is a little bit of a guessing game. So you just wanna create a system for helping yourself guess better and provide your reps a framework so that they're not going into analysis paralysis during that guessing period.

Brendan:  Well, I think it also speaks to what you mentioned. I think it's what, 50% of reps give up after one. And so like, as a result of that, that first email, it's like a novel and they're trying to sell me on the first email.  And it's like, you don't need to write a five paragraph email.  The percentage success rate is probably less than, you know, 0.0001%.

GB:  Yeah, no, I can recall like one, I can count on one hand in the entirety of my career where I sent an outbound email to someone and it was more than six lines long. And it was because there was just too like, like saw press release, saw quotes, saw business strategy, the person was right in the middle, I was in their LinkedIn profile. And I probably put at the end, like, I'm about to tell you a story, but you need to know, right? So it was a really like very, very precise. email and got back to me right away. So I'm like, okay, awesome, wonderful. But again, that's like one person in eight years.

Brendan:  Yeah. Yes. And it's even just simple things. And most people look at their phone for emails. So if you're running me, it should fit on my phone screen, the whole email, where I like that idea. OK, as we wrap up, GB, I would love to know, kind of final lab question. Favorite piece of software for prospecting these days?

GB:  Favorite piece of software for Prospect. So can I, all right, I want to answer your question, but like not very well. So, yeah, so I think, I mean, there's like the, hey, like I don't think that it's, they're all, I don't know. I really like SalesNav. I really, really do. I think it's just, you have to have it for B2B outbound. However, like what I'm really, really curious about is the application of generative AI within prospecting to automate or augment the processes for SDRs and also the application of generative AI to stimulate creative outreach without breaking the SDR's brains. So it's a real thing. It's a real thing. Like, okay, be creative. And there's some people who are like, oh, like it comes to them naturally. And then you, but for the vast majority of folks, they're like, I have no idea. I don't know. Like I know how to talk about business value and whatever. So, so that people aren't having to grow a different brain, they can outsource that to generative AI and get something back. So I'm very, very curious about like what creativity looks like as we move forward. And I think that's also gonna stimulate more of that human to human, person to person interaction too.

Brendan:  Yeah, I agree. Well, I think everyone's kind of interested to see what AI is going to do. I mean, gosh, it's only been, what, like three months? And it's pretty crazy what's already been happening. And we're big fans of it. We use HubSpot a ton, and we're big partners of theirs. And even just ChatSpot and what they're trying to do with AI embedded inside of CRM is pretty powerful. Well, GB, as we conclude, if our audience wants to learn more about Workweek or just to get to know you, what's the next step they can take?

GB:  Yes, I would definitely say follow me on LinkedIn. And then under my tagline, I have a link to subscribe to the one-on-one. So that's my newsletter. It goes out every Thursday, I think at 1130 Central, and 11 AM, 1130 AM Central. And that is where I pour all of my heart and soul and sweat and tears into sharing tactics and approaches, sales managers, just frontline can use anytime. 

Brendan:  Well, GB, thank you for stopping by. I really appreciate the perspective on the SDR motion and tactics and ways in which people can be successful. I know our audience really appreciate it. So have a great day and thanks so much.

GB:  Thank you, you too.