March 11, 2026

Why your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet)

Why your cold emails suck (and what to send instead) | Kyle Weiss (Parakeet)
Spotify podcast player iconApple Podcasts podcast player iconYouTube podcast player icon
Spotify podcast player iconApple Podcasts podcast player iconYouTube podcast player icon

In this episode, I sit down with Kyle Weiss, Head of Sales and Customer Success at Outbound Sales Pro and Parakeet, to break down what third-party outbound actually is, why some companies outsource it instead of building SDR teams in-house, and what’s still working in outbound right now when everyone’s inbox is flooded with the same tired sales messages. Kyle explains the three main types of companies that hire outside outbound teams, from founder-led startups trying to minimize risk to larger venture-backed companies looking to scale pipeline fast without adding a ton of internal headcount.

We also get into Kyle’s current thinking on cold email, including why the classic “pain + value + CTA” structure has gotten easier and easier to ignore, how subject lines should create just enough curiosity or doubt to earn an open, and why his team now often starts with a simple “heartbeat check” email before trying to pitch anything. Kyle shares why phone calls still outperform everything else, how he thinks about call backs after the “send me more info” objection, and the cold call structure his team uses to get prospects talking instead of shutting down.

TOPICS WE COVER

  • What third-party outbound is and why companies outsource SDR work instead of building everything in-house
  • The three main client buckets Kyle sees, from founder-led startups to large companies with internal SDR teams
  • Why consistency in outbound matters and why full-cycle reps often struggle to prospect consistently
  • Why the old cold email formula stopped working even for highly valuable products
  • Kyle’s philosophy on subject lines and how to create curiosity without being overly deceptive
  • The “heartbeat check” email approach and why a simple question can outperform a polished pitch
  • What patterns instantly make a cold email feel like obvious spam
  • Why phone calls still drive the majority of meetings, even in modern outbound
  • How to handle “send me more info” without relying on the prospect to reply
  • Kyle’s cold call framework, including the permission-based opener, quick value statement, and question-driven approach

ABOUT THE GUEST

Kyle Weiss is the Head of Sales and Customer Success at Outbound Sales Pro and Parakeet. He helps companies build outbound pipeline through a mix of outsourced sales development, cold email, LinkedIn outreach, and phone-based prospecting. Over the past several years, he has worked with a wide range of clients, from founder-led startups testing go-to-market motion for the first time to larger companies looking to scale outbound faster.

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Parakeet: https://www.parakeet.io/
Learn more about Outbound Sales Pro: http://outboundsalespro.com

Carter (00:01.111)
Hey Kyle, introduce yourself, tell the people who you are, what do you do now?

Kyle Weiss (00:05.934)
Hey everybody, my name is Kyle Weiss.

I am currently the head of sales and customer success at Outbound Sales Pro and Parakeet. Outbound Sales Pro is kind of the agency model we started about five years ago and then ultimately built a software called Parakeet. they're kind of, know, Outbound Sales Pro powered by Parakeet is probably the best way to say it.

Carter (00:36.911)
Yeah, and explain third party outbound to me. This is not something I really knew what it was. Everywhere I've worked just has outbound in-house as W2 employees. Why would someone pay an outside company to do it instead? Like who are you guys targeting?

Kyle Weiss (00:47.075)
Yeah.

Kyle Weiss (00:52.214)
Yeah, there's a few reasons why companies would look outside. I put our clients into three buckets.

One, that first bucket is founder led sales startup. The founder has this great idea. A lot of times they're a technical founder, so they built an amazing product. And they look around and they're like, okay, I've sold to all of my network, my friends, family, they're all using my software. I need to take this thing to market for real.

And what happens is like, OK, do I hire a SDR? OK, if I hire an SDR, I'm going to pay him all in employer costs, W-2, 80 grand a year. Right. I'm to have to get him or her data, software, training. You know, am I going to run all those meetings? Like, how is that going to take place?

I have to hire someone, find the right person, so it takes time managing them. And then oftentimes, you you can't just hire an SDR as just the founder led sales, the whole company's technical. You don't want to just hire an SDR. So what happens a lot of times is the founder in this first bucket is like, okay, there seems to be some traction. have some product market fit with my network. I want to minimize risk and go to market

get as many at-bats on the calendar as I can, I'm gonna run those meetings and, you know, kind of prove the concept before I take on a lot of risk. And so with our, in that first bucket, with our cost for like a fully baked out outbound engine and kind of like, you know, we put multiple people on the account, you know, we have all the software, we have all the data, we have all the targets, we have the model, the training.

Kyle Weiss (02:51.472)
everything. If we understand their value that they're delivering and the pain that they're solving for their clients, we can be pretty dangerous really quickly. And we can be putting meetings on their calendar in three weeks. that ability to minimize risk is really valuable to founders who are just starting to go to market.

And the last piece is they don't risk turnover. You hire an SDR. The SDR lifespan in a role is not very long. It's a tough job. It's demanding. It's degrading at times. You're getting shut down all the time. And with us, you'll have a constant, as long as you want meetings on your calendar, it'll happen. So that's that first bucket. And then the second bucket is probably what I

Carter (03:36.195)
Yeah.

Kyle Weiss (03:47.731)
say the

It's the best bucket and like where we're most successful is where we work with a company that is a little farther along, maybe Series A they just raised. You know, they got 20 to 40 people in the organization and they have someone other than the founder who is responsible for the sales. know, there's a head of sales or there's someone who is like in charge carrying the sales bag. And a lot of times they have full

Carter (04:17.592)
Yeah.

Kyle Weiss (04:19.872)
cycle reps. So the reps are farming their own land, taking some inbounds, start to finish, cold to closed. Their sales reps are doing it all.

Sales reps at times, they can be like water. They're gonna take the path of least resistance. What'll happen is like, you'll see this roller coaster of sales rep has a ton of meetings on their calendar for the week, so they're not prospecting that week. They're focused on, I wanna close deals, right? So then the following week, I don't have any meetings, or the following whatever, I don't have any meetings, now I prospect a bunch, right? And it's just this up and down cycle and it's not consistent.

Carter (04:56.792)
Yeah, okay.

Kyle Weiss (05:02.796)
relying on inbound and it's like okay if we're gonna scale this thing we need outbound and again it comes back to all right do we want to hire SDRs do we want to put the time and effort into training them motivating them you know software data all that good stuff

And a lot of times in that situation, they're like, okay, we're growing. I need my sales reps focused on closing. don't want them closing or running 10 meetings a month. I want them running 30 meetings a month each. How can I get them 30 meetings a month like tomorrow?

relatively speaking and you know, oftentimes they look at us and go okay for you know, less risk lower cost all in of hiring an in-house SDR and a lot of companies they'll we'll put multiple SDR resources, you know, we'll build a whole a whole outbound team for them and So they'll they'll look to us and obviously that we don't win them all, know Some some are like and I want to keep this in-house. I want to have control more control over it. But in that bucket

Carter (05:59.479)
Right.

Kyle Weiss (06:05.902)
that second bucket, it's a really, a really good relationship because there's ownership and outbound meetings are a lot different than inbound or referral meetings. And having a team that understands that, you know, the work together goes really well. And then that last bucket, we have multiple clients. They have, you know, 200 person company. They've got full like, you know,

verticalized like senior executive, account executive, know, like mid-level account executive, SMB account executive. They have an SDR team and they're looking to just like, they have a lot of, you know.

They have lot of opportunity and growth. They've raised Series C, Series D, and they're flying. And they need to double their revenue this year. And they look at it, how are we going to do it? We need double the opportunities. need whatever that may be. And they look internally like, okay, we've got an SDR team that's working. You know, how can we scale this fast without investing in hiring, you know, 10 more SDRs, another SDR manager. And then they use us to build out

Carter (07:13.943)
Yeah.

Kyle Weiss (07:16.648)
their SDR team, they already have the proven model. So they can kind of communicate that to us pretty quickly. And some of our clients we've had for years, they have their own internal SDR teams. And they may send them, you know, focusing in on one market or one type of persona. And they might tell us, okay, you guys are focused on this type of persona. And we work in tandem. So those are the three buckets.

Carter (07:45.345)
And let's talk about cold emails. What is your highest converting cold email look like? Walk me through it. Like what are you, I know you, you test a lot of variations, but subject line, body, call to action, all of it. Yeah. What is the best?

Kyle Weiss (07:47.724)
Yeah.

Kyle Weiss (07:59.255)
Yeah, what is the best? So I think the best way to describe...

like what is working or release what we've what we've kind of we've got a crack in the matrix a little bit that we've discovered just by sending so many outbound emails for various clients. I'll start back like two, three years ago, two, three years ago. We you know, I'll use a client that sells an unbelievable tool. It's a AI platform that scans millions and millions of public documents.

Carter (08:14.51)
Yeah.

Kyle Weiss (08:33.233)
daily, like board meeting minutes of local towns, know, like tax filings, everything that's public, local governments and municipalities. And if I was a general contractor and I build firehouses, police stations, I can literally use their tool and go, you know, who's talking about budgeting, you know, upcoming projects for a new firehouse, you know, in the state of California. And it'll pull all those relevant

in documents and tell me, hey, Sacramento is looking to build two new firehouses in 2027. They're talking about budgeting, you know, eight million for that. That's kind of in doubt, you know, debate right now. But I would find that out.

12 months before it goes to RFP. And as a general contractor who knows this RFP process and competes for these all the time, like that is so valuable. Like, my gosh, I can get in there 12 months before anyone else, build a relationship. When it goes to RFP, it's a foregone conclusion. They're working with my company, right? And so like super valuable product. Two, three years ago, we used to send it, we used to send the classic sales email. Like, hey, you know, first name, we know, you know, we know how challenging.

it is to tackle the RFP process. It's a race to the bottom, the lowest number, you know, who can do it for the cheapest, best quality, whatever. And we know that on average, you know, companies will win 20 to 25 percent of the RFPs they go after. You know, and we understand how big of a headache that is. And then the next part is like, that's why we built this tool to help companies, you know, learn about local government initiatives, projects, you know, up to 12 months before

they go publicly to RFP. What kind of business impact would that have for X company? And we used to get handfuls of replies like, my gosh, this sounds too good to be true. I'd love to see it. I'd love to check it out. It was unbelievable. was like selling hotcakes. Here we go. We never had to make a cold call. We could just send more emails and book more meetings. It was amazing.

Carter (10:41.954)
That's excellent. That's beautiful. Wait, what was the subject line though on this?

Kyle Weiss (10:46.243)
The subject line on that was, know, we could talk about subject lines, but the subject line and what my philosophy is there, but because that's a whole nother conversation. subject line might be like.

You know, we use, we use smart fields about the territories that these companies focused in. So we could take, we could take 10,000 companies, you know, have a column that had like the county they're in or the state they're in. And, you know, the subject line could be like upcoming, upcoming RFPs for Monroe County. Right. And it's like, and if you want, I can dive into the subject line theory that we've sort of built. can do that. All right. So.

Carter (11:28.344)
Yeah, well let's hear this. Anything with cold email I'm curious about.

Kyle Weiss (11:32.673)
Yeah, so this is kind of my theory and this is still working today. And, you know, if millions of people listen to this, like I'm probably ruining my theory now. They're all going to, they're going to catch on. But, you know, executives and leaders are getting

50 cold emails a day, who knows, maybe more, right? Everyone's trying to sell to the same people. And it goes back to what our new philosophy on email, why we had to change from that standard sales, like, here's the pain we know you have, here's the value, why we built it to solve your pain, what kind of business impact could that have? Like, let's talk. That's your typical five years ago sales email. And today, even today, 50 of those are hit and inbox.

same structure over and over and over. Our brains are so good. We're so fast at seeing an email and knowing it's a sales email and it's deleted. And the reason I, my theory why even if it's like, so to go back to that story of this amazing product that everybody wanted.

we all of a sudden that email stopped getting replies. we would change variations of it so we weren't like burning the copy. Because there's an element of that. But.

we just stopped getting replies. And it kind of boiled down to we weren't getting their attention. They weren't paying attention to it. It was getting lost in the noise, right? Even though we could predict most people would be interested in that product if they're the right, you know, the right ICP. But it just stopped getting replies. And...

Kyle Weiss (13:15.095)
It was because like their brain, you get in the, open your email in the morning and you're like, my gosh. And you're like, the first thing you're doing is like, what does it matter? Or what does matter? Or what does matter? And it's kind of like, if you think about it, it's like, what do I have to open? It's almost like this seed of doubt, this little bit of fear personally. Like, you know, if I don't respond to that email, like it's going to affect me in some way. Like, you know,

Thank

it's going to come back like, my boss knows that or like my boss told that person to reach out to me. I better respond and take care of what that person wants because it came from my boss or, you know, that's a deal I'm working or whatever it may be. Like what is going to affect me? And so when I think about subject lines, like without being too deceptive, there has to be a seed of doubt in that subject line that if they don't open that email, they may miss

something that could come back to hurt them personally. Like, you know, the president of the company has a nephew that like, you know, you he said, hey, reach out to this hiring, this hiring manager, like they'll get you squared away. Right. Like, imagine I look through my emails, I just delete that. I'm like, screw that. Right. Like, all of a sudden, it's going to be painful to me. I'm going to hear from my president like, hey, did

Carter (14:42.284)
You're saying that's what you would put in the subject line, something of that. Okay.

Kyle Weiss (14:44.651)
Not necessarily, not necessarily. What I would put in the subject line, let me get an example. You know, like new, new project for Monroe County, right? Like if I don't check that out, they could come back to me in my position that like, hey, did we go after that RFP I saw that came out for Monroe County? It's exactly what we want. And it's like, I'm like,

I don't know. I didn't know about that or I didn't, you know, it's like, yeah, we got an email about it, right? Like there's a seed of doubt that if I don't open that to check it out, there, it could come back to hurt me. I don't know if I'm describing it the best. Yeah, it's almost like.

Carter (15:28.27)
Well, that makes sense. That makes sense. Yeah.

Kyle Weiss (15:33.775)
I don't know if this is good of me as a person, but people operate off of fear a lot more than they do off of the value. Those subject lines, increase your sales by 50 % with this tool. That thing's getting deleted 99 times out of 100, right? But like,

You know, if we flip it and go off of the fear element, and when I say fear, it's like, it's the seed of doubt. Like if I don't open this just to make sure that it's not something that I have to, you know, that's going to come back to affect me. That's that little doubt that I like to have in subject lines. You know, we all see the ones like, new product to make this more efficient, or like,

make your sales team 10 times more efficient, blah, blah. It's like, yeah, that's a sales email. And like, if I'm a busy executive, that's the first, like, that's the last thing I'm gonna look at, right? If I'm not busy, sure, those will still get replies. But there's like a certain person those get replies from, and that person's replying to all the sales emails, right? They like to check things out. They're tire kickers. They're tire kickers. And so,

Carter (16:32.076)
Right, that's so obvious, yeah.

Carter (16:49.963)
Yeah. Right.

Kyle Weiss (16:53.623)
Now moving forward to like what is working now.

Carter (16:56.866)
Right, right.

Kyle Weiss (16:57.007)
So going back to that example, unbelievable product can give you the insights of business initiatives in local municipalities and cities across the US and Canada 12 months before they go to RFP. I get a 12 month head start to all the other competitors that are trying to get that same RFP. Give me that head start. Let's go. We know they want it, but this email stopped working. So now our philosophies take a step back from solving

their problems or delivering them the value. Take one step back. We have to go even higher in the funnel. Like they're not even, you know, we almost need to check their heartbeat first, right? To make it super simple. Like do you have a heartbeat? Right? So now what we do for that specific client is, you know,

Upcoming, you know, like upcoming RFP Monroe County subject line. I'm just making that up. So there's a little seeded out there. I better check that out. And the email, our first email will only say, Hey, Carter, does like Briggs construction still target local, local municipality RFPs or local government jobs? Thanks. No, I'm just making it up. I'm just making it

Carter (18:14.902)
And they're, Brit, who is Briggs? They're Briggs? No, no, I know, I know, but like the people that you're emailing is Briggs. Yeah, yeah, okay.

Kyle Weiss (18:19.287)
Yeah. Yeah. So like, hey, do you at your company, do you still take on local government contracts? Right. Are you guys still taking on local government contracts? Question mark. Thanks, Kyle. Right. That's all I say. All of a sudden, we turn that on all of sudden.

replies. Yes, of course. Why do you ask? Yeah, absolutely. Like, of course we do. We work with like 10 different counties on their local projects. Like the replies all of a sudden, boom, boom, boom, boom, boom, boom, boom, in. And it's like, okay, now they're paying attention. Now I reply to them with, great, the reason I ask is because we know how difficult it is.

to win RFPs. The success rate is 20, 25%. I'm sure you understand that better than I do. That's why we developed this tool, to scan millions of public documents in your territory constantly and give you the exact business initiatives that are being talked about in all these different places 12 months before they even put it to RFP. What kind of business impact would that have for Briggs Construction?

They're paying attention now. Like, now when I deliver that, it's not a cold email.

Carter (19:36.022)
Right, at least click on it, yeah.

Kyle Weiss (19:37.539)
they're gonna click on it because they're like, wait, why do you ask? Yeah, of course we go. It's like, do you have a new job that you wanna tell me about? Are you referring me something? Are you telling me something? What do you have? They're curious now. And so by taking a step back and kind of checking their heartbeat, getting them to peak their ears a little bit, poke their head up.

Now we can deliver them that value email that if we had sent that first, we'd probably get nothing from. And then there's some other things about emails that are just things that I see today that are just driving me crazy. Because I get cold emails all the time. I think I may have posted about it. I try to post on LinkedIn. I get busy. It's hard. I'm in prep.

Carter (20:23.212)
Yeah, let's hear this. Let's hear this.

Carter (20:33.11)
Yeah, you were saying something about this, yeah, you get 50 emails a day, you delete all of them though, that's what, I did see that.

Kyle Weiss (20:38.071)
Yeah, yeah, like it's and it's it's almost unconscious and the reason why I now I pay attention is I just make a folder. I have a folder now

And I'm just dropping them in there because like I have a huge I have a huge team And I'm just like guys I want you to see like I want you to see what my inbox looks like right like know that this is happening to Most people that we're targeting for our clients like we have to be more strategic than this I see an email that starts with most the word most like see you later See you later most sales leaders most executives like most blah blah blah like it is

Carter (21:04.664)
Yeah.

Kyle Weiss (21:18.105)
Amazing. It's amazing. know, when I see emails, let me go to that folder real quick. There's some gems. Hey Kyle, reaching out to high value customers can be a challenge. Like, right then and there, that is a sales email. Don't tell me...

Like don't tell me what I already know, right? Like, it's just so obvious in my brain. We help, we help. Like so many emails start with we help, we help, we help, right? Like I'm getting 10 of those. So like now I know like none of those are important.

Carter (21:48.014)
Okay, yeah.

Kyle Weiss (22:03.757)
I have 10 emails that start with the same phrase. Like none of those are important. Nothing's going to affect me by deleting those emails. Like, and I'm busy and a lot of the, a lot of people, they're very busy, you know? And so like, if it's not something important, like I know it's not, and I could see three or four of them that start the same way, see you later. It's not like my time is better spent on the things I need to get done that are priority.

Carter (22:29.12)
And so some level of differentiation is good too, you're saying. Cause a lot of people use the same type of format and.

Kyle Weiss (22:32.527)
Absolutely. Yeah, absolutely. You know, most SaaS websites, like WeHelp, buyers engaging with your competitors, like, my gosh, like, like, it's like, you're trying to, you know, it's hard to, it's funny. It's like you get this after you see so many. After you see so many, you're just like,

Because in the email you see the preview. So you got that subject. You got that subject in that first line to get me. if I was a if I was a government like if I was a general contractor going after government contracts, you know, and it just said, you know, maybe don't even say, hey, Kyle, just say like, does Briggs Construction still target local government contracts? Like I would see that in the preview and be like, hmm, like, what do they got for me?

Carter (23:01.548)
Right, so yeah.

Kyle Weiss (23:27.983)
Like, you know, that would get me perked up. Like, don't try to sell me before I'm paying attention. You know? That's the...

Carter (23:37.495)
Yeah.

Kyle Weiss (23:39.627)
And like, there's a lot of other philosophies. Sometimes there's good ones. Sometimes the offering is so freaking good that like, like, and it's right in the beginning. Like I had one cold email. was like, Kyle, we can get parakeet on, on the side of a NASCAR car. You want to talk? Like you want to talk? I responded because I was like, that sounds amazing. We probably don't have the money for that, but like that got me. That got me good. Like that's a great, that's awesome. and so.

Carter (23:55.241)
okay. Yeah.

Carter (24:03.575)
Yeah.

Kyle Weiss (24:08.907)
It's one of those things where, you know, and I'm not saying like use our style, it's going to work. Like, you know, we're still pumped if we get, you know, a 1 % reply rate. Like that's, that's pretty good these days. if we're sending a huge volume. Now, if we have a strategic list of 150, we want to get a lot more and we're putting a lot of tender love and care into that. But, you know, it's the email world is hard. We, you know,

we're always ready to iterate and change because as...

I like to tell our team, like, if you read something from like a sales guru on LinkedIn about this email is so good, so great, love the format, love the style, like, your emails should look like this. Well, you and thousands of other people are now sending that same email, like you're too late. You're too late. It's almost like you got to give kudos to whoever sent that email. Like, nice work. Like you, you got creative. You created a good, a good email. I'd be, I'd be mad at that sales guru for

Carter (24:59.104)
Right, everyone is gonna start. Yeah.

Kyle Weiss (25:13.231)
telling everybody about it, you know?

Carter (25:15.348)
Yeah, I didn't. mean that makes that makes a lot of sense. So, you know, let's say let's say someone's listening is an AE doing their own prospecting. They've got no agency. They've got a very limited budget for tools. What's the one thing you'd tell them to change about their outbound this week?

Kyle Weiss (25:18.723)
Yeah.

Kyle Weiss (25:34.703)
I would tell them, if you did one thing this week, just make phone calls. If you got a cell phone and you got a list of numbers, just make phone calls. Like, your email and your LinkedIn outreach, that stuff's gonna work, but that's a lagging return, right? Like, it's a lag to the time you get any kind of market feedback from your market. I would say...

I would say like 80 % of the meetings that we book

come from the phone call. Now we get a lot of those prospects like bubbled up from our email and our LinkedIn where they're engaging with email and LinkedIn. But like if we got someone responding to LinkedIn with like questions and curiosity about whatever we're, you know, whatever client we're working for, our first thing is to call them. Like I'm not relying on like this written back and forth that could take a few days. Like we're calling them right away. And

Carter (26:32.96)
Right.

Kyle Weiss (26:39.009)
And even before that, like when we start off with a new client, and this is what I tell that AE, like it's almost like, yeah, like if you're, you've limited everything and you just need production. It's the same way we onboard a new client. Before we do any emails or any LinkedIn, we're making hundreds of phone calls before we send anything out. And we're having conversations with the ideal customer profile.

of our client, like we're trying to have as many conversations as we possibly can, as quickly as we can. Some of them will turn into meetings, a lot of them will not, but the learnings from that, they don't really care about this value, like that didn't mean anything to that director of IT. But it did mean something to that head of HR. It's like, okay, so now, like that early, those early conversations you have,

One, you can have them immediately when you're using the phone. Get on the phone and talk to people. The feedback's immediate, the learnings are immediate, everything's immediate, and that information will drive how you build out this cool, extensive outreach model that has multi-channels. But until you have the feedback and learnings, you're kind of just guessing what they care about. Now, that AE might be at a company that's been operating for a long time, and they know exactly

who and what, but the fastest time to value for that AE is a phone call. Like that phone call is gonna do everything. And I would say half of the meetings we book from Cold Call, we don't book them on the first time we talk to the person.

you catch them off guard, you you call them cold. They don't pay attention to the first 30 seconds. They didn't even hear the company name you said you were calling for, whatever. But as you kind of get through, they give you a couple, you know, they give you a minute, you know, towards the end, they're like, Whoa, you can give me some insights before it goes to RFP. That sounds interesting. But they don't remember the name of the company. They don't really know who I am. They don't remember much. So they're like, Hey, they give you the classic. Can you send me more? Send me more info. Like send me an email. Right. Classic objection. You know, we

Carter (28:47.278)
Right.

Carter (28:53.991)
Yeah, yeah. Right, email him and you'll never hear back from him. That was always my thing.

Kyle Weiss (28:56.475)
got strategy. Yeah, email him, email him and you never hear back from. I don't need to hear back from him. That's the thing. Like, we know we're not going to hear back from an email. Now, sometimes we do and it's, whoo, it's icing on the cake. It's great. But like, it's not about hearing back from them. It's not their job to get a meeting, like for you to get the meeting. It's your job to get the meeting, right? So they say, yeah, send me an email. It's like, absolutely no problem. Now I have their email.

in the data right in front of me.

But I'm not gonna just say, sounds good. Hang up the phone. I'm gonna say, hey, what's the best email to send that over to? Right? Because a lot of times, maybe the data's wrong that I have, maybe they have a better email address that they actually use, right? And it'll at least give me options to evaluate. A lot of times, if they tell me something different, I'm gonna send it to the one I have and the one they gave me. And so they'll tell me the email and then I'll say, I'll be like, great, and I'm taking it slow. Like, sounds good, awesome. Yeah.

I'm being honest, like, if your inbox is anything like mine, I'm probably just adding to the problem with this email. Would you mind if I give you a call back in a couple days around the same time? Is this a good time to call you back Friday? You know, just to make sure you got the email, answer any questions. And they're usually like, they usually are like, yeah, if they say no, like, it's not a real, that's not a real lead. But like, if there is curiosity, like, yeah, Friday actually.

Carter (30:21.623)
Yeah.

Kyle Weiss (30:25.849)
You know, tomorrow morning I'm in the office. I'll just be hanging out. don't have any meetings. Call me back tomorrow morning. Like, absolutely. Sounds good. You know, have a great day. Right. Hang up. Tomorrow morning at the like at that time that we agreed on, I am calling them back. And sometimes you don't get them. It's all right. I'm going to keep calling them back. When you get them back on the phone, they remember.

They're like 99 times out of 100. They're like, yeah, I didn't see that email. I didn't really see that email. whatever. Like, they don't see that email. But it's fine. You don't need them to see it. Right? And they're like, yeah, tell me a little bit more about what you got going on. I was a little interested. You know, I got to be honest, I wasn't really listening. But like, you kind of piqued my interest about getting in early with RFPs. And then, boom, you've got them paying attention. It's the second time you've talked to them. They already, in their brain, think they're interested. Like, now you just got to

Carter (30:53.003)
Yeah, yeah.

Kyle Weiss (31:18.115)
lead them to the book and a meeting. You know, it's like, hey, I know I've caught you off guard. I've interrupted you a couple of times now. You can give them a little bit more value in exactly what you do and how you help companies, you know, get early insights to RFPs. But it's like, hey, I'd love to get you on a call, you know, when we're, you know, it's more planned and structured to talk a little bit more about what you're doing internally right now as with your RFP process and things like that to see if this even makes sense for you. I've got some time tomorrow at either like 11.

in AM Eastern or, you know, I could probably meet at 2 30 Eastern as well. Like I go slow. Like I go slow and I make it sound scarce. I make it sound like I'm looking for availability, trying to fit them in. Right. And there's that element of like, all right, this guy's, this guy's busy. Like he's, he's on top of his game. He's not like eager to get me in. Like I can meet any time tomorrow. I can meet any time. Right. You know, and, that's a lot of our meetings come from.

Carter (32:09.55)
Yeah.

Kyle Weiss (32:15.817)
One, the cold calls, and usually it's like the second call. Like you don't always get them on that first call.

Carter (32:20.384)
You know, and I wanted to go back, I know you've been on here for a minute, but you did mention on LinkedIn, you talk a lot about cold calls. said you've got to win the first five seconds. Do you have any great cold call openers? What should somebody be saying on the phone? Yeah, openers that are good.

Kyle Weiss (32:24.942)
Yeah.

Kyle Weiss (32:35.439)
Openers? Yeah, so our team has like a few that they love to use. I still jump in there every once in a while and I'll make some cold calls. Like you can't stray too far away from what what built this and what got you here. I love making cold calls. I think the number one, like we like like the permission opener, like.

I'm not trying to like hold you down. It's like, hey, this is Kyle from Outbound Sales Pro. Do you have a moment for a quick call? Right. That's my opener. But I am. It is it is probably majority.

not about what you say, right? This is very cliche, but like how you say it, your tone, your tone, your demeanor. Like when you get on the call, like I'm talking to these people like, hey, like one, I really respect you, your time. Like if you tell me you don't have a moment for a quick call, like...

Carter (33:15.808)
Yeah.

Kyle Weiss (33:31.277)
There's one thing I'll do, but like, I'm not going to be like this bulldog necessarily. Right. Cause in my mind, I'm like, yeah, yeah. In my mind, there's a million fish in the sea. Like, dude, like your loss, like your loss, man. sometimes I'll say, Hey man, this could have been the one call that just changes your 2026. Like I'll, I'll, I'll hit them with that. And they're like, okay, what are you calling about? Right. Like, and they'll be like, all right, tell me. Like, what are you calling about? you know, oftentimes, you know, it's just like, Hey, this is Kyle from.

Carter (33:36.396)
Right, like hard closing them right off the bat.

Kyle Weiss (34:01.183)
outbound sales pro df 30 seconds for a quick call. And most of the time they're like, yeah, one lady yesterday, I was calling yesterday. One lady is like, I got 20 seconds. I was like, a challenge. love it. Okay. And I was like, you know, and I just made it fun. you know, and humanizing it a lot, a lot of cold calls and I'll pick up cold calls. A lot of them are very robotic and like, you know, it's like, it's cringy. And what the number one thing that bugs me when I get cold called is that

like the prospect will often ask a question like, hey, are you calling me because I'm the VP of sales? Like, are you calling me because I work in manufacturing? Like, is that why you're calling me? Cause I work for this company, right? Like a lot of SDRs that are calling, they're not listening to the prospect, right? They're so, they're so driven on getting their message across that like,

Carter (34:51.532)
Rather just like rushing through you're saying.

Kyle Weiss (34:57.197)
We preach every day. Once they start talking and they're saying things, like...

there are nuggets, valuable nuggets in the things they're saying. Why are they asking? Why are they saying that? Like, what are they concerned about? Like, that's what's gonna, you know, tell you which direction to go on the call, right? That's gonna tell you what might be more valuable to them than what you thought was gonna be valuable to them, right? And so like, once our style asks for permission, they say something like, yeah, what's this about? You got about...

15 seconds right there. Two line high value. Like we help XYZ solve this problem. Right. Two lines. Once you say that the worst thing you can do is just stop and let them respond to that. Like we help we help companies you know drive their drive their close rate on RFPs. We work with companies like Briggs and Stratton blah blah blah. Right.

And then they go, oh, we already have an RFP tool. Like, we're all set there, thanks. Right? So if I just stopped after I pitch, they're going to have an objection and everyone's going to have an objection. Right? But our model is, you know, permission, like, hey, do have 30 seconds? Yeah. What is this about?

give them like, hey, we help companies like you solve this problem by doing X, Y, Z. And then ask a question. Don't stop. Ask a question like, curious, how are you currently managing your RFP process today? Right?

Kyle Weiss (36:34.635)
Now I broke them a little bit because I gave them the value what we do. They probably had an objection ready to go. And then I asked them a question that like most people are like, we use this, this, we do this. Like they answer that question. Right. Now I got the conversation rolling. I can take it where I want to go. Like, OK, yeah, a lot of companies I talk to use bid prime. We actually are a strategic partner with bid prime.

What's great about us is once you get to the bid prime stage, you're in the same boat as every other contractor competing for that contract, right? Where we come in is we'll get you involved with that upcoming contract 12 months before anybody else knows about it. Curious, what's your close rate right now on RFPs? Ah, it's about 18 % every RFP. You know, what kind of business impact would it have if that was a 35 % close rate?

Like now all of a sudden, I'm like we're so far away from the pitch. Like we're so far away from the pitch. The pitch for me is just to get the ball going. Right. I want to start learning about you. And that's that's our kind of strategy and model around cold calling.

Carter (37:47.082)
Okay, that's very good. I think we got some, this is very helpful. I think we got some good stuff here. I'll end it here.

Kyle Weiss (37:50.895)
Right on, right on.