In short
Podcast Summary: The Thoughtful Entrepreneur - Episode 2222
Episode Overview Title: The Sales Strategy That Won't Leave You Out in the Cold with Alleyoop's Gabe Lullo Duration: 15-25 minutes Host: Josh Elledge Guest: Gabe Lullo, CEO of Alleyoop
This episode features Gabe Lullo, who shares his insights on modern B2B sales strategies, emphasizing the crucial role of founders in leading sales initiatives. The discussion spans topics such as effective lead generation techniques, the importance of personal branding, and the integration of marketing and sales efforts.
Key Concepts
- Role of Founders in Sales
- Founders should actively lead early sales efforts.
- They possess unparalleled knowledge about their products and can connect authentically with initial customers.
- It is recommended to hold off hiring a VP of Sales until a repeatable and scalable sales process is established.
- Shifting Sales Strategies
- Traditional cold emailing is becoming less effective.
- Gabe advocates for a return to the basics:
- Cold Calling: Engages prospects in real-time conversations.
- Content Creation: Especially on platforms like LinkedIn, to establish thought leadership and build trust.
- Building Authentic Engagement
- Authentic storytelling is vital for long-term customer engagement.
- Consistent and strategic content sharing on social media helps founders position themselves and their businesses effectively.
- Alleyoop's Role
- Alleyoop specializes in bridging the gap between marketing and sales for B2B companies.
- Services include appointment setting, lead qualification, and optimizing sales processes.
- They work with a range of clients from startups to large enterprises like Adobe and ZoomInfo.
About the Guest Gabe Lullo
- An experienced entrepreneur and executive with a strong background in sales, marketing, and management.
- Previously owned a sales training and marketing firm and has extensive experience in executive recruiting.
- Currently focuses on building scalable sales systems and maintaining a positive company culture at Alleyoop.
Key Takeaways
- Founders should engage in the sales process to gather insights and iterate on their approach.
- Effective sales strategies in today鈥檚 environment require a mix of personal branding, authentic communication, and leveraging both cold calls and engaging content.
- Building a good relationship between sales and marketing teams is essential for scalable growth.
Episode Highlights
- Founders leading sales efforts allows for deeper product knowledge and authentic connection with early clients.
- Cold calling and content creation are returning as effective lead generation strategies.
- Authenticity in storytelling fosters long-term engagement and trust with prospects.
- Alleyoop helps companies streamline their sales development processes for better outcomes.
Conclusion Gabe Lullo offers a roadmap to develop a successful sales strategy that emphasizes authenticity, founder-led initiatives, and the importance of connecting marketing efforts with sales development. The episode is a valuable resource for startup founders and sales leaders looking to enhance their outbound strategies.
Links Mentioned
- [Alleyoop Website](https://alleyoop.io/)
- [Gabe Lullo on LinkedIn](https://www.linkedin.com/in/lullo/)
Final Thoughts This episode provides actionable insights for entrepreneurs seeking to refine their sales strategies and emphasizes the necessity of founder involvement in early-stage sales processes. For those interested in furthering their understanding of B2B sales, tuning into the "Do Hard Things" podcast hosted by Gabe Lullo is recommended.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:05Hey there, thoughtful listener. Are you looking for introductions to partners, investors, influencers, influencers, influencers, and clients? Well, I've had private conversations with over 2 ,000 leaders asking them where their best business comes from. I've got a free video you can watch with no opt-in required where I'll share the exact steps necessary to be 100 % inbound in your industry over the next six to eight months with no spam, no ads, and no sales. What I teach has worked for me for over 15 years and has helped me create eight figures in revenue for my own companies. Just head to upmyinfluence.com and watch my free class on how to create endless high-ticket sales appointments.
0:51Also, don't forget, the thoughtful entrepreneur is always looking for great guests. Go to upmyinfluence.com and click on podcast. I'd love to have you.
1:05With us right now is Gabe Lulo. Gabe, you're the CEO of Alleyoop. You're found on the web at Alleyoop.io. Gabe, it's great to have you. Thank you, Josh. Welcome. Thank you for having me, man. It's going to be super fun. I'm a big fan of yours, so I'm excited about this. Thank you. I appreciate it. I should also point out that you are the host of the Do Hard Things podcast. That's at DoHardThings.io. We'll get into your superpowers, but before we do, Do you mind maybe sharing just a little bit about like when you're not at work? What have you been geeking out on like that? I don't know if you're watching anything, just into anything hobby-wise or otherwise.
1:42Well, we're big F1 fans, Formula 1. So we're big racers. You know, I got helmets back here. We like motorcycles and cars. And so we've always been into Formula 1, which is really kind of creeping into the United States right now. It's becoming more and more popular. Netflix had a great show on it. And so right now we're in the middle of the Grand Prix. So we watched it on Sundays and my wife and my daughter were always, you know, putting putting bets on who's going to be the driver of the day and those things. So it's been fun. You didn't get to Vegas, did you? For that first one? I didn't, but we watched it, you know, Miami just happened recently.
2:17So we, yeah, we're going to probably go, we're in upstate New York. So we're probably going to go to the Canada one when, when they're on the circuit. So a lot of fun. Yeah. We were there when they were setting up in Vegas for the first F1 race and, you know, Pretty remarkable to take over the entire strip, but I think that's one of the joys of F1 is just, again, you're just setting up in some pretty amazing locations. Yeah, exactly. Well, very cool. Well, Gabe, let's talk a little bit about Alleyoop. What is Alleyoop? What do you do? Yeah, we work with B2B companies. We work with their founders or their chief revenue officers, and we build out really customized white-labeled sales development engines for them.
3:00So essentially what we're doing is we're staffing, managing, and running appointment setting, qualification, lead generation, really the top of the funnel for their sales and go-to-market teams. And so we have attracted huge enterprises like Peloton, ZoomInfo, Adobe. And then we have worked with thousands of startups, founder-led sales companies really going to market, and we helped build that team for them. Yeah. Well, let's do a quick 101 for that earlier stage startup owner. what are the what is the infrastructure of a great founder led sales system today in B2B? Yeah, it's funny because a lot of founders come to me like, hey, I just hired my VP of sales and and I'm ready to go.
3:43I'm like, I think you did that wrong. My recommendation is not to hire a VP of sales day one to be a founders really to be be the salesperson as a founder, right? As a founder, you know your story more than anything, your passion, you're authentic, you believe in your product and offering. And so whether you're a software developer, and let's say not a sales person, it's still we want to hear your story. So generating appointments and putting demos on your calendar first, is really where we should start. And then we can build process around that understand product market fit, understand, you know, what features or pricing or competition is out there that makes sense to really morph your product or offering into a marketable product.
4:28And then we go to market from there. So that would be my initial advice to the founders out there. Yeah. Well, I think one of the concerns that I hear most frequently when it comes to B2B sales development is a lot of old systems for lead gen may just not be performing like they used to. So it's not the fault of, you know, it's not their fault. It's just, I think a lot of, a lot of waters have been overfished. I'll just say it that way. So your sales navigator, your cold email is, I know for me, I mean, it's just such a non-starter for me. So, you know, someone looking to build a relationship with me, it's pretty challenging.
5:11Like if they're looking to market or sell to me, what is like, if you're giving us a state of the union for that part of, you know, kind of the wholesale system, what would you say is working well right now? What's no longer working well? Yeah, I think, you know, email right now is either dying on the vine or almost extinct. You know, rules and regulations have come in with both Microsoft and Google as preventing, you know, spam and just mass emailing to just be a thing of the past. So us for right now, what we're focusing and doubling down on is cold calls and content, right? So calls and content is really how it's working, right?
5:52Doing shows like this, you know, being a thought leader, building your own brand, you know, speaking, especially in the B2B world, right? We live in this TikTok, Instagram generation, but, you know, bringing that in B2B is really important right now. So LinkedIn has been a massive place for this. And then following that up with really human, authentic conversations over the phone. It's like almost like the old is new again, right? We all used to remember cold calling years and years ago was the way to do it. It's definitely bouncing back in a big, big way. And it's the way to really stand out and cut through the noise.
6:29And if you can figure that out and do it well, you're definitely going to get some conversations that are worthy. Yeah. So what sort of activity, like if someone says, listen, I'm going to spend a few hours or a couple hours a week and I'll use LinkedIn any way you tell me to use LinkedIn. How should they be using LinkedIn? Right. Well, I post every single day. So if you go to my LinkedIn, there's 750 videos of me talking about my industry. Right. And so just creating valuable content is step number one. Of course, following and connecting and networking and engaging with the right people, specifically in your ideal client profile, we call your ICP, is step number two.
7:13And then proactively doing outbound to them, not in a spam automated way where you're just pitch slapping people every single time you connect with them, but genuinely figuring out what their problem may be and then how can you solve their problem with whatever it is you're offering them. And that's how you have those genuine conversations. That's where LinkedIn lives for sure. And Alleyoop, so where does Alleyoop kind of step in the journey? And by the way, congratulations, because you've been with Alleyoop for quite some time, and you've been promoted, promoted, promoted, and now you're the CEO.
7:52Yeah, it's funny. It's kind of like, thank you. It's like one of those mailroom to CEO stories, right? I was in the mailroom, right? But I was actually on the sales floor making calls when I started here and worked my way up to take over as co-owner and CEO. But yeah, it's been quite the journey. But at the end of the day, what I focus on is building in between marketing and sales. So prospecting and sales development, think about it. We want full cycle sales reps to be spending time booking appointments and generating leads. But what we found is that many of them are spending 80 % of their day doing that.
8:29And you don't want a salesperson spending 80 % of their day prospecting. And of course, you want marketing to create demand and interest. So that sales development where we sit is right in between those two departments. We work with marketing to determine what the right person is, who the right person is. And then we work with sales to qualify those leads for them and give them alley-oops, all pun intended, by the way, an alley-oop to throw that ball up perfectly for them so they can take that lead and slam dunk and enclose business. So that's how we approach the market. What sort of content do you see performing well on LinkedIn right now?
9:05Yeah, it's interesting. Of course, you want it to be within your audience, right? I wouldn't say just be you and be authentic. But right now, what I'm seeing is resonating is HR, culture, working from home, different types of how to lead, how to coach, how to mentor. Those are things that are just resonating in big, big ways. But figure out what your specialty is and then just double down on it. And then your audience will come follow you versus having you go find them with your just trying to play with different content ideas. So I like that. So just basically pick a lane, stay in your lane and be the trusted source for all things in that topic.
9:46Yeah. You know, to the point where you might feel like you're getting typecast a little bit, but I actually see where that's valuable, right? I know if I follow Gabe, Gabe is always sharing really high value content around X. Therefore, I always think of Gabe as my friend who does X is kind of where my brain is going with this. Yeah. Yeah, listen, you don't want to be a jack of all trades here when it comes to content, right? Almost like I was saying with your offering your product, you want to be very strategic and specific, right? So pick your lane, find out what you're good at, find out what your focus is.
10:20And hopefully that generates you money, what you do. But at the end of the day, it's having people come to you because they know you as that. And yeah, it is almost like typecasting, but it's a, you know, instead of jack of all trades, you know, master of none. It's you want to be a master at whatever it is you're good at. Now, how do you create content around that is also a little different. Do I post pictures of my family and me traveling and doing things on PTO? Yeah, absolutely. It gives people a human connection of who Gabe is. And do I want to work with this guy? Is he someone that I can trust?
10:54Is there someone that resonates with me? That's important. So, of course, I'm going to do those things so people know I'm a human and not just this banner and billboard all day long about what I do. But they also know that they can come to me if they need to know exactly how to do a cold call or if they exactly how to manage a team or lead an organization. Those are things that I talk about. So that's why I think you should do. Yeah. Tell me a little bit about your podcast, Do Hard Things. Yeah, it's funny because sales is hard. You know, I grew up in a blue collar town in Buffalo where everyone had to physically lift heavy things or, or build homes or work in construction or smell like fish at the end of the day at the restaurant.
11:33And that to me was always hard. And that's what I looked at. And I was really the first person who actually figured out I can talk and make money in my family. Then sales kind of found me as opposed to the other way around. But then I realized is sales is just as hard, right? We get punched in the face. There's a lot of rejection. There's a lot of negativity. There's a lot of things to do differently and to get good at this trade. So I said, you know what, let's start a podcast about finding people who didn't go to school to Harvard to be a salesperson and how they started in humble beginnings and they pushed through that difficulty to become ultra successful.
12:12And those are the guests that we have on the show. Yeah. And so for our friends listening, just very simple, just in your podcast app, just search for the words, do hard things, and you should be able to find that pretty easily. Hit subscribe and start listening. Gabe, to our friends that are listening right now, how might someone know that they would be ready to have a conversation with you versus, you know, what might they want to make sure that they've got locked down before they initiate that conversation? Yeah, I mean, they obviously need to have either funding or some sort of revenue coming in.
12:50What we do is not an inexpensive offering, right? We're building full cycle sales teams and appointment setting departments. So it is costly, but we do bring it to a price point that it is absolutely acceptable for founders or, you know, solo entrepreneurs. We do work with people on that. But at the end of the day is, do you have a offering that you know the market will accept and get excited about? And if it's a game changer, that's what we can work with. I'll give you an example. Adobe Sign, right, the signature platform was looking to go against a DocuSign back in the day. And we built that entire sales team for them.
13:29Zoom Info, the number one data provider in B2B in the world, they came to us when they were zero with no sales reps at all. And we built their sales development function for them. And now both of those brands are billion-dollar brands. So those are the types of things. Yes, they're great now. But when they started, they were looking to be the next big thing. And that's what we help companies do. Very, very cool. And then, Gabe, what does kind of the initial engagement look like? and like what do you build to? Like how long are you typically working together? I would imagine there's some stages involved.
14:06Yeah, so we can go down to what we call a fractional resource. So instead of having to hire an entire team and take that on financially, you can actually have an SDR sales development rep with us part-time. So they're spending 20 hours a week on your campaign and 20 hours a week on someone else's campaign. But at the end of the day, you're getting it at a great price point. We're talking about about$4 ,500 a month. Now, that comes with data, that comes with a manager, that comes with dialers, that comes with email, it comes with all the tools to enable that person, not just the person. And that's really the hard part to figure out and also the most expensive part.
14:42So you can do engagement with us for as low as six months to do a pilot, to build that pipeline, and then we grow from there. Yeah. By the way, you'd mentioned your LinkedIn. You're a great follower there. We mentioned the podcast. Someone goes to alleyoop.io. If they're listening to this and they're like, okay, they're interested. I know you've got both resources and maybe next steps for someone that might want a demo or something like that. What are those next steps? Yeah, for sure. If you go to the website, it'll tell you a lot of information about what I just mentioned and a few other campaigns and types of programs we work with.
15:18Great case studies, these videos, testimonials of past clients, some of which I just mentioned, Adobe and ZoomInfo. And then if you say, hey, I want to meet or I want to start talking, literally our calendar is right on our website. You can book a call with one of my sales directors and they will walk you through our entire process, answer your questions and go from there. Awesome. Gabe Lulo, CEO of Alleyoop, found on the web at alleyoop.io. The podcast, Do Hard Things. Also, you could just search for that in your podcast app. Gabe, it's been a great conversation. Thank you for joining us. Thanks, Josh.
16:18Every day. Together, we are empowering one another as thoughtful leaders. And as I mentioned at the beginning of this program, if you're looking for introductions to partners, investors, influencers, and clients, I have had private conversations with over 2000 leaders asking them where their best business comes from. I've got a free video that you can watch right now with no opt-in or email required where I'm going to share the exact steps necessary to be 100 % inbound in your industry over the next six to eight months with no spam, no ads, and no sales. What I teach has worked for me for more than 15 years and has helped me create eight figures in revenue for my own companies.
17:03Just head to upmyinfluence.com and watch my free class on how to create endless high ticket sales appointments. Make sure to hit subscribe so that tomorrow morning, that's right, seven days a week, you are going to be inspired and motivated to succeed. I promise to bring positivity and inspiration to you for around 15 minutes every single day. Thanks for listening and thank you for being a part of the Thoughtful Entrepreneur Movement.
From the publisher
On this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Gabe Lullo, CEO of Alleyoop, a leading B2B sales development company. Gabe dives into the critical strategies that modern founders and sales teams need to adopt鈥攃overing everything from founder-led sales and shifting lead generation tactics to building authentic engagement through personal branding. This episode is a goldmine for startup founders, sales leaders, and anyone aiming to scale their outbound strategy with more precision and impact.
Building a Modern B2B Sales Engine
Gabe emphasizes that founders must be on the front lines of sales early in their journey. Founders bring unmatched product knowledge and passion that resonates with early customers and helps shape go-to-market messaging. These firsthand sales experiences offer valuable insight into what prospects actually care about, allowing for real-time iteration and refinement. Gabe cautions against hiring a VP of Sales too early鈥攆ounders need to establish a repeatable, scalable process before expanding the team.
In today鈥檚 sales environment, traditional cold emailing is losing its edge due to regulation and deliverability challenges. Gabe recommends a return to high-impact basics: cold calling and content creation. Phone calls allow for real-time, human interaction, while content鈥攅specially on LinkedIn鈥攂uilds trust and positions founders as thought leaders. Gabe practices what he preaches with his consistent posting strategy and his podcast, Do Hard Things, which highlights authentic stories of grit and resilience.
Gabe also explains how Alleyoop helps B2B companies bridge the gap between marketing and sales. Their done-for-you systems manage appointment setting, lead qualification, and process optimization for clients ranging from startups to giants like Adobe and Zoom Info. For founders ready to scale their outreach, Gabe recommends focusing on authenticity, strategic connection building, and consistent engagement to generate high-quality pipeline.
About Gabe Lullo
Gabe Lullo is a seasoned entrepreneur and executive with deep expertise in sales, marketing, recruiting, and management. After graduating from the Barney School of Business at the University of Hartford, he launched his own sales, training, and marketing firm, which he successfully ran for over a decade. Gabe has also had a notable career in executive recruiting, expanding placements across IT, software development, sales, customer success, and executive leadership. As CEO of Alleyoop, he focuses on company culture, customer success, and scalable sales systems.
About Alleyoop
Alleyoop builds high-performing sales development systems for B2B clients. Their services include lead qualification, appointment setting, and outbound process design tailored for scalable growth.
Links Mentioned in this Episode
Episode Highlights
- Founders must lead sales to learn and iterate early
- Cold calling and content outperform traditional cold email
- LinkedIn content builds brand and trust
- Alleyoop connects marketing to sales with proven systems
- Authentic storytelling drives long-term engagement
Conclusion
Gabe Lullo delivers a compelling roadmap for building and scaling a sales engine rooted in authenticity, process, and founder-led momentum.

