Cold Email Outreach With Jeremy & Jack

About this episode (#406): In this episode, Jack and Jeremy revisit the question: should AI be trusted to write and send first-line personalization in cold outreach? It’s late Q2 2025, and AI tools are smarter than ever. But are they smart enough to handle something as nuanced (and reputation-sensitive) as email intros without human review? The guys go deep on how far the tech has come, what’s still risky, and where it might actually make sense in your workflow. Key topics discussed in this episode: Why letting AI send unchecked intro lines is still a risky move How the quality of personalization has improved and where it still breaks Why buyer awareness of AI is making personalization harder, not easier The evolving role of the first line (and why the PS line might be safer) What makes a smart AI prompt and how to reduce hallucination risk Testing AI-generated personalization vs. handcrafted lines When AI might make sense for high-volume outbound vs. niche campaigns This episode is a no-fluff look at what

About this episode (#405): In this episode, Jack and Jeremy run a two-part teardown of real cold outreach messages. They start by analyzing a LinkedIn message that pitches AI agents for lead generation, then break down a clever follow-up email from a SaaS tool the recipient had signed up for months earlier. You’ll hear what worked, what didn’t, and how to write outreach that actually gets replies, whether your audience is ice cold or just cooling off. Key topics discussed in this episode: Why vague or generic subject lines instantly signal cold outreach - The dangers of pitching without credibility, proof, or a clear ask How to use curiosity properly in cold messages (and when it backfires) Why offering value or reciprocity makes outreach more effective A teardown of a SaaS follow-up email that used a “you never used your free credits” angle The difference between cold, warm, and “lukewarm” outreach (and why lukewarm might be your best audience) How small, specific asks can increase reply rates This episode

In this episode, Jeremy from QuickMail and Jack from SalesBread tackle a tough question from a head of growth at a small B2B SaaS company: How do you succeed in cold outreach when your product lacks a clear edge in a crowded market? The two dive into real-world tactics and mindset shifts that can help founders and marketers compete against bigger players even without a flashy differentiator. Key Topics Discussed: The importance of market education and timing when entering a saturated niche Competing on price: the most basic but often effective strategy for early traction Why strong marketing can outperform a superior product Alternative ways to position your offer—such as "trial as a gift" Why commoditized tools (like email verification) need creative outreach angles Using consulting or audits as a Trojan Horse to sell your core software The game-changing idea of targeting consultants and incentivizing them with affiliate deals Whether you're selling "salt" or software, you don’t need to reinvent the wheel

In this rapid-fire episode, Jack and Jeremy tackle six cold email and outreach questions submitted by listener Trey. From proper greetings and cultural nuances to incentives and defining success, the hosts share actionable insights based on real-world experience. Whether you're new to outreach or refining your strategy, this episode has something for every B2B emailer. Key topics discussed: - Why using “Hello” in cold email greetings can sound too formal or robotic - The importance of matching your tone to your recipient’s culture or geographic location - Using industry-specific language to better connect with your prospects (e.g., “What are y’all building?”) - Clarifying the definition of a “qualified lead” versus a “prospect” - Measuring the success of cold email campaigns based on conversations started, not just closed sales - Offering gift cards or incentives in exchange for sales calls — when it works and when it doesn’t - The psychology of value perception when offering monetary incentives This episode

In this episode, Jack and Jeremy break down a simple, no-fluff cold email strategy to help you land your first sales meetings—even if you’re starting from scratch. No marketing budget, no followers, no fancy tools—just a clear step-by-step process to get conversations started with your ideal customers. Key Notes:  How to define your Ideal Customer Profile (ICP) without overthinking it Why starting with just 20–30 hand-picked prospects is more effective than buying a list The exact cold email script you can send to “dead leads” to re-engage them Tips for writing personalized, human emails without using any automation How to craft a value-driven follow-up that surprises and engages your prospect Why simple yes/no call-to-actions outperform vague “let me know” language When and how to scale up your outreach once the manual process starts working If you’ve been hesitant to start cold outreach, this episode will show you that it's not only doable—it can be fun and effective. Tune in to learn the baby steps that

In this episode, Jack and Jeremy dive into the brutal reality of the one-second test that every cold email must pass. They explore the psychological and structural cues that influence whether a prospect replies—or hits delete almost instantly. Key Notes:  Why you only have 100 milliseconds to make a first impression The importance of email layout, subject line, and paragraph length How visual and sender identity cues (like avatar and display name) can make or break your outreach The red flags of impersonal or poorly set-up automations (e.g., email addresses instead of names) Why the first sentence must immediately answer "Is this for me?" The value of smart, skimmable call-to-actions and how placement affects response rates Why unsubscribe links, oversized signatures, and fake flattery can kill trust—and how to fix them Whether you're running outbound campaigns or fine-tuning your cold outreach game, this episode offers practical, nuanced tips to help your emails survive the one-second test and stand out in

In this episode, Jeremy & Jack reveals a powerful yet under-the-radar LinkedIn feature that transforms how sales professionals can target their outreach. They explore the possibilities and practical applications of this new discovery, comparing it to the psychographic targeting capabilities of early Facebook Ads. Key Notes:  The discovery of LinkedIn's “followers of creator” filter and how it mirrors Facebook-style psychographics How to find U.S.-based CEOs who follow specific influencers like Alex Hormozi Exporting search results to build targeted outreach lists The potential of combining creator-following filters to identify shared beliefs or preferences in prospects Real-world applications, including event marketing and webinar promotions Comparison between Sales Navigator and basic LinkedIn search features The broader implications for the future of LinkedIn’s ad and outreach capabilities This episode is a must-listen for sales pros and marketers eager to build smarter, more relevant outreach campaig

In This Episode: Jack and Jeremy return from a break with a fresh teardown of a LinkedIn InMail pitch. They dive into whether the message hits the mark, who it’s really for, and how to make outreach campaigns more effective. It’s a fun, punchy critique packed with real-world advice for sales pros and copywriters alike.   Key Notes: The importance of clear value propositions in outreach messages Why lazy list-building kills good campaigns How to rewrite messages to include relevant personalization and social proof The role of silent objections and when to handle them in cold emails Whether certain low-ticket offers really warrant a call-to-action for meetings Tips for list targeting: looking for buyer signals like team size and premium usage The case for directing recipients to a high-trust landing page vs. asking for a call This teardown highlights how even simple offers require thoughtful positioning. Jack and Jeremy show that with the right tweaks, even a lukewarm pitch can be reworked into a compelling o

In this episode, we dive into a unique direct mail marketing piece targeting vehicle owners. We analyze its effectiveness, discuss how similar approaches could work in other industries like business brokerage, and break down the nuances of personalization, format, and copywriting. If you're interested in cold outreach or direct response marketing, this one's for you! Key Notes: A breakdown of a direct mail piece designed to buy used cars The impact of handwritten-style marketing and personalization How this approach could translate to business brokerage and other industries Strengths and weaknesses of the copy, including the use of urgency and credibility The role of objection handling in direct mail vs. email outreach The effectiveness of PS statements and how they can be improved The key takeaway: Less is often more when it comes to direct response copywriting This teardown revealed some important lessons in cold outreach and direct mail effectiveness. Removing unnecessary elements and focusing on clarity

In this episode, Jeremy & Jack break down and analyze two cold email campaigns, offering insights and feedback on what works and what falls short in email outreach. They dive into the importance of personalization, the power of a strong call to action, and common pitfalls in email marketing strategies. Key Notes:  - The importance of a compelling subject line and the impact of personalization. - How using "fishing for no" tactics in your call to action can be an effective strategy. - The role of a concrete case study or specific examples in increasing credibility. - Why emails that sound too generic or automated often fail to engage recipients. - The challenges of offering free services (like a 40-hour trial) and how to make such offers more appealing. - The negative impact of using a generic "from" email address in outreach campaigns. - How tailoring your email to the specific recipient and their business can make a huge difference in outreach success. The hosts wrap up by stressing the importance of au

In this episode, we dive into a rapid-fire Q&A on cold outreach strategies, covering everything from leveraging AI for personalization to optimizing LinkedIn profiles for better response rates. The discussion explores how sales professionals can balance automation and human connection while improving deliverability, personalization, and follow-up strategies.   Key Notes: How AI can enhance outreach efforts without losing the human touch Key differences between cold emailing and LinkedIn outreach in 2025 Optimizing LinkedIn profiles to support sales efforts and increase engagement Social selling techniques to warm up prospects before reaching out Strategies to avoid spam filters and improve email deliverability Personalizing cold emails effectively without crossing privacy boundaries The importance of balancing value and promotion in cold outreach With practical insights and actionable strategies, this episode provides a roadmap for sales teams looking to refine their cold outreach approach. Tune in to l

In this episode, we dive into effective sales outreach strategies, particularly when working with a limited number of new prospects. The discussion focuses on prioritizing leads, leveraging high-touch channels, and using engagement signals to maximize impact.   Key Notes: Why "response lists" are more effective than demographic-based lists for prospecting The power of high-touch outreach methods like phone calls, personalized videos, and in-person visits How to identify engaged prospects based on email opens and LinkedIn profile views The importance of making outreach feel personal and avoiding overly scripted messaging Creative approaches to stand out in a crowded sales landscape The evolving trends in cold outreach and why traditional mass-email tactics are losing effectiveness Best practices for balancing personalization and scalability in sales strategies By focusing on genuine engagement and strategic targeting, sales professionals can improve their outreach efforts and build stronger connections with

In this episode, we conduct a deep dive into an SEO-focused cold email sequence, breaking down its structure, effectiveness, and areas for improvement. From subject lines to follow-ups, we analyze what works, what falls flat, and how strategic personalization could make all the difference. If you're looking to refine your outreach strategy, this teardown is packed with valuable insights. Key Notes Initial impressions of the subject line and its ability to spark curiosity. The effectiveness of using organic traffic signals as a lead-in. The value of visual elements like Ahrefs or SEMrush screenshots in email outreach. How messaging can shift to focus on the recipient rather than the sender. Analyzing the follow-up sequence and why it ultimately failed to build trust. The importance of specificity when discussing SEO opportunities. Alternative approaches that could have improved engagement and conversions. Cold email success relies on more than just persistence; it requires value-packed insights and genuine

In this episode, Jeremy and Jack discuss the evolving landscape of email deliverability and why it's no longer a major concern for most sales teams. They explore how a shift in focus is needed toward refining your list and message rather than obsessing over deliverability, as the technology has already solved many of those issues. Key Notes Why deliverability is no longer a major issue in 2025 due to advancements in AI and automated inbox switching. The importance of having a quality message and a laser-focused list over relying on volume. Real-life examples comparing high-volume campaigns to low-volume, high-targeted campaigns, demonstrating the effectiveness of focused outreach. The shift from optimizing deliverability to improving your outreach strategy, emphasizing smaller, well-targeted lists. The role of AI in list cleaning, ensuring the right companies and people are being contacted. Message optimization strategies, including using social proof and adjusting the ask to increase engagement. Personaliz

In this episode, Jeremy and Jack explore how traditional sales methods can be adapted to today’s business world. They dive into strategies that can enhance your outreach, from in-person interactions to innovative downsells and refining your pitch. Key Notes How Lunch and Learn sessions can be a fresh take on traditional sales tactics. Using alternative outreach methods like sending thoughtful gifts or offering value upfront when cold emailing falls short. The power of in-person connection—visiting potential clients or attending events to build relationships before pitching. Networking with competitors by becoming a customer of theirs or engaging in their communities to learn more about their audience. The benefits of downselling as a way to maintain engagement and create opportunities for future business. The need to adapt your pitch when the current approach isn’t working, with a focus on creativity and relevance. Why investing more in your outreach efforts can lead to better long-term returns, even if it

In this episode, Jeremy and Jack dive into the evolving world of sales outreach, discussing how the traditional approach of cold emailing and templates may be shifting toward more organic, conversational strategies. They explore the concept of using a two-part campaign to warm up prospects and how starting with a casual conversation can lead to meaningful business interactions.   Key Points: The concept of a two-part sales campaign A real-life example of a company using a "messenger" to start casual conversations before transitioning to sales. The importance of warming up prospects before pitching, as opposed to direct sales messaging. How AI and tools may influence outreach strategies in 2025, focusing on more natural, less templated interactions. The future of outreach: Moving away from volume-driven strategies and toward more personalized, slower-paced campaigns. The psychology of outreach and the idea of “pivoting” from a casual to a business conversation on different channels. The potential death of tra

In this episode, Jeremy and Jack dive into the details of a multichannel lead generation campaign they've been working on for 2025. They walk through the campaign's strategy, including LinkedIn and email outreach, while sharing valuable insights on optimizing connection requests and cold outreach.   Key Points: Combining LinkedIn and email strategies to reach lead gen agency owners.  Tips on writing connection requests and balancing transparency with personalization.  Crafting messages with a value proposition and focusing on superior deliverability. The power of embedding images to showcase analytics and improve engagement. Transitioning from simple questions to more impactful, value-driven CTAs. The benefits of changing communication platforms, like from email to LinkedIn, for better engagement. The importance of adding more personalized touches when leads show interest. Jeremy and Jack wrap up by reflecting on the effectiveness of their strategies and how the use of visuals and personalization can elevat

In this episode, Jack and Jeremy dive into the art of prospecting for outbound sales - exploring strategies that prioritize efficiency and results. The hosts break down a unique visualization of the prospecting process to help sales professionals refine their approach.   Key Points Understanding prospect proximity to your offer Introducing a unique visualization to represent prospect engagement Trust, decision-making power, and belief in your solution as key factors Leveraging past customers and referrals Marketing tactics to boost engagement while reducing barriers to entry This episode provides actionable insights into visualizing and optimizing your prospecting strategy. Whether you're a seasoned pro or new to outbound sales, you'll find tips to help you close more deals and engage more effectively with your prospects.   About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails

This episode discusses strategies for conducting cold outreach during the holiday season, such as the best days to send emails, whether to pause campaigns during holidays, and opportunities to connect with prospects in a more personal way. Key topics discussed: Data on email performance based on send days The pros and cons of maintaining cold outreach campaigns during holidays like Thanksgiving and Christmas Differences in email performance over the holidays based on industry Ideas for more personal outreach during the holidays Jack and Jeremy encourage listeners to think creatively about how they can reconnect with customers and prospects during the end-of-year holiday period, whether through email, phone, physical mail, or other personalized outreach. They wish all of their listeners successful outreach and a happy holiday season.   About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and c