Cold Email Outreach with Jeremy & Jack - podcast cover

Cold Email Outreach with Jeremy & Jack

Jeremy Chatelaine and Jack Reamerquickmail.io
Jeremy Chatelaine, founder of QuickMail.io and Jack Reamer, founder of SalesBread.com talk about the strategies and tactics around cold email outreach. Straightforward, to the point, no fluff for actionable insights to help you succeed with your cold email outreach.
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Episodes

#418 - 10 LinkedIn A/B Tests Worth Trying Today

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#418): In this episode, Jeremy and Jack brainstorm high-impact LinkedIn A B tests you can run immediately to boost reply rates. What starts as a casual speedboarding session turns into a rapid-fire list of practical experiments, from voice notes to list tweaks to creative CTAs. If you are sending LinkedIn messages and want better results, this episode gives you at least 10 ideas ...

Mar 18, 202620 minEp. 418

#417 - How to Spot Cold Email Lies, And What To Do Instead

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#417): In this teardown, Jack and Jeremy dissect a cold email from a video clips agency that promises "viral" shorts on a pay-by-results basis. They pick apart the subject line, the fake-sounding flattery, the weak proof, and then live-rewrite the message into something that a busy podcast host might actually reply to. Key topics discussed in this episode: Why subject lines like ...

Mar 04, 202619 minEp. 417

#416 - 12 Ways to Reveal Your Buyers "Hidden" Purchase Intent

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#416): In this episode, Jack convinces Jeremy to go deep on one of the hardest problems in cold outreach: building a list when your buyers are essentially invisible. They unpack how to find prospects who use internal processes like Scrum or cold calling, even when there is no public signal that gives them away. The conversation introduces creative ways to spot indirect clues and ...

Feb 18, 202614 minEp. 416

#415 - Cold Outreach Hot Seat: What Founders Are Asking in 2026

📫 Don't miss the best cold outreach tips, join the newsletter. https://quickmail.com/newsletter About this episode (#415) Jeremy and Jack answer 10 straight up questions about cold outreach across LinkedIn, email, and phone. They cut through common myths and share practical advice on what actually works when you are launching or scaling outbound today. Key topics discussed: How to set up your LinkedIn profile and outreach safely when you are just getting started Best practices for building Link...

Feb 04, 202612 minEp. 415

#414 How the Pros 2X Their Sales Meetings (No Extra Prospecting)

📫 Don't miss the best cold outreach tips and cold email tactics, join the newsletter - https://quickmail.com/newsletter About this episode (414): In this episode, Jack and Jeremy share practical ways to boost booking rates when handling warm leads from outbound campaigns. They walk through simple habits and tactics that help you reply faster, cut friction, keep momentum high, and ultimately get more prospects to show up to the calls they requested. The conversation focuses on what really moves ...

Jan 21, 202614 minEp. 414

#413 - Fix any campaign with 2 simple changes

📫 Don't miss the best cold outreach tips and cold email tactics, join the newsletter - https://quickmail.com/newsletter In this episode, Jack and Jeremy tackle a simple but powerful question. If you could only pull two levers to improve a cold outreach campaign, which ones would produce the biggest lift in both reply rate and ROI? What starts as a theoretical exercise turns into a deep breakdown of strategy, list quality, offer strength, and how to diagnose a campaign that is getting crickets. ...

Jan 07, 202614 minEp. 413

#412 - Takeaways from the 5 "Can't Miss" Episodes of 2025

📫 Don't miss the best cold outreach tips and cold email tactics, join the newsletter - https://quickmail.com/newsletter About this episode (#412): Jack and Jeremy do a laid back end of year "water cooler" recap of the episodes that hit hardest in 2025. They revisit the moments they still think about, from sales psychology and empathy to offer creation and a new way to visualize prospecting, plus a quick trip down memory lane with the outreach email that helped kick things off back in 2017. Key ...

Dec 25, 202530 minEp. 412

#411 - Gun to Head" Offer Workshop

📫 Don't miss the best cold outreach tips, join the newsletter. https://quickmail.com/newsletter About this episode: Jack walks Jeremy through his "gun to the head" exercise for building irresistible offers in cold outreach. They explore why most campaigns suffer from weak, boring offers and how to move from ridiculous fantasy promises to bold, realistic offers that actually get replies. Along the way, they break down concrete examples and the psychology behind what gets someone to respond to a ...

Dec 10, 202516 minEp. 411

#410 - Stop obsessing about your subject lines. Here's why.

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#410): In this episode, Jack and Jeremy tear down a cold email that opens with the line "No one likes a cold email." They explore why this approach fails to stand out and how small details in your inbox preview can make or break your open rates. The conversation turns into a masterclass on subject lines, preview text, and how the overall "look" of your message shapes trust before...

Nov 26, 202515 minEp. 410

#409 - LinkedIn DM Autopsy: Watch us Fix These Common Mistakes

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#410): Jeremy and Jack are back in the studio breaking down a pair of cold outreach messages, including one that went viral on LinkedIn. They explore what worked, what didn't, and how small tweaks in tone and structure can make a big difference in response rates. The episode dives into writing conversational, curiosity-driven messages that actually open doors on LinkedIn. Key Top...

Nov 12, 202516 minEp. 409

#408 - Josh Braun Shares Sales Techniques That Work

About this episode (#409): In this episode, Jack and Jeremy sit down with sales legend Josh Braun to explore how to start smarter, more effective cold outreach conversations. They break down Josh's "poke the bear" method, a way to uncover hidden pain points without triggering resistance, and share practical tips for making prospects pause, think, and actually want to talk to you. Key topics discussed: Why cold outreach fails when it starts with pitching or convincing How to "poke the bear" by as...

Oct 29, 202530 minEp. 408

#407 - Selling in a LinkedIn connection request? (2025 Example)

About this episode (#407): In this episode, Jack and Jeremy break down a bold connection request on LinkedIn that skips the usual small talk and goes straight for the pitch. They debate whether this "go for the kill" approach ever works in cold outreach, and if so, under what conditions. Along the way, they define a framework for when pitching in a connection request might actually make sense and when it's still a terrible idea. Key topics discussed in this episode: Why most people shouldn't pit...

Oct 15, 202515 minEp. 407

#406 - Don't Let AI Cripple Your Reply Rate

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 epis...

Oct 01, 202515 minEp. 406

#405 - "Came across your profile" and other sales mistakes to avoid

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 va...

Sep 17, 202517 minEp. 405

#404 - Transforming Silent Rejections into Profits

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#404): In this episode, Jeremy and Jack dive into a smarter way to structure follow-up emails in cold outreach. Instead of repeating the same call-to-action (CTA) or simply lowering commitment levels, they introduce a sales-letter-inspired approach using upsells and downsells to increase engagement and conversions over time. Key Topics Discussed: Why sending the same CTA in follo...

Sep 03, 202518 minEp. 404

#403 - How to Win at Outreach When Your Competitors Are Better Than You

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 Compe...

Aug 20, 202511 minEp. 403

#402 - Sales Questions from a CEO

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 y...

Aug 06, 202518 minEp. 402

#401 - AI Overkill: Watch AI Destroy Their Reply Rate

In this episode, Jack and Jeremy break down an especially long and highly personalized cold email that made its way through the noise—though not without some controversy. They explore what worked, what went too far, and how AI-driven outreach can either charm or alarm your prospects. Key topics discussed: - The use of deeply personal references in cold emails—and where it crosses the line. - Why referencing hobbies, spouses, and old clients might not earn you points. - The difference between rel...

Jul 23, 202518 minEp. 401

#400 - How to Get Your First 10 Sales Meetings — Without Ads or a Huge Audience

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 scri...

Jul 09, 202511 minEp. 400

#399 - The 1-Second Test: What Gets Your Cold Email Read (or Deleted)?

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 ...

Jun 25, 202512 minEp. 399

#398 - Use This New LinkedIn Filter For Your Next Campaign

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 lik...

Jun 11, 202513 minEp. 398

#397 - Fixing This CEO's LinkedIn Outreach

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 ...

May 28, 202516 minEp. 397

#396 - Need leads? Steal this Direct Mail Approach

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 personalizat...

May 14, 202513 minEp. 396

#395 - Cold Email Surgery: 3 Real Examples Dissected & Rewritten (Live)

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...

Apr 30, 202525 minEp. 395

#394 - 13 Sales Questions You Should Be Asking in 2025

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 outrea...

Apr 16, 202514 minEp. 394

#393 - The secret to finding (and winning over) your dream clients

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 ...

Apr 02, 202517 minEp. 393

#392 - SEO Cold Email: Full, 4-Step Campaign Review

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 us...

Mar 19, 202514 minEp. 392

#391 - The Brutal Truth: Why Your Reply Rate Is Under 5%

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...

Mar 05, 202515 minEp. 391

#390 - Leveraging Old-School Sales Techniques in 2025

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—visiti...

Feb 19, 202530 minEp. 390

#389 - The Future of Sales is "Organic" Outreach

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 casu...

Feb 12, 202516 minEp. 389
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