Emphasizing relationships over product features can lead to better sales outcomes.

I think that's so underrated, Jeremy. Thinking about what most B2B selling is it's relationship first and, you know, deep understanding of their needs second, followed by a damn good product. Like if you do it in that order, you typically do well.

Takeaway:

• Jack believes prioritizing relationships is key in B2B sales.
• Understanding customer needs comes before presenting product features.
• Focus on building connections to improve sales performance.

Incorporating phone calls into holiday outreach can deepen connections with high-value prospects.

I phone rarely, but when I do, it's always with people that are very much in the bull's eye or the black hole of my sales solar system. So people that have matched my ICP and engaged with a bunch of my emails or videos or content somewhere on LinkedIn, I might pick up the phone.

Takeaway:

• Jack uses phone calls selectively for engaged, high-priority leads.
• Direct calls can enhance relationships during holidays.
• Reserve calls for prospects showing strong engagement.

Personalizing holiday greetings can strengthen customer relationships but may require significant time investment.

One thing I did do one time, I did do a video to thank all my customers at one Christmas. Didn't get anywhere really. It took me a lot of time, to be honest. Like each one got a video.

Takeaway:

• Jeremy attempted personalized video messages during holidays.
• Such efforts may not yield significant returns for the time invested.
• Consider resource allocation when planning personalized outreach.

Exploring the effectiveness of direct mail during holidays can enhance outreach strategies.

What do you think of actually sending like physical, you know, mail for Thanksgiving or Christmas?

Takeaway:

• Jeremy considers using physical mail as a holiday outreach method.
• Physical mail may stand out during the digital rush.
• Assess whether direct mail aligns with your audience and resources.

Leveraging holiday times can help in re-engaging with prospects and clients.

You can circle back, you'd say, you know, like end of the year, I love it because I just say like, hey, you know, what's your goal for next year or like start of the year, like I really like those sort of time because it just resets and gives you an opportunity to just reconnect.

Takeaway:

• Jeremy recommends using the year's end to inquire about prospects' goals.
• Holidays offer a natural moment to reconnect and reset conversations.
• Use seasonality to re-engage with dormant leads.

Holidays present an opportunity to focus on relationship-building in email campaigns.

But we're probably not discussing the important thing about the holiday season, and this is the opportunity to send a very different kind of message to the people you want to do business with.

Takeaway:

• Jack suggests using holidays to send personalized, relationship-focused messages.
• Shift from sales pitches to genuine connections during holidays.
• Leverage holidays to warm up prospects for future engagement.

Understanding the risks of increasing email volume during peak times is crucial for deliverability.

It's crazy how I see people during Black Friday messing up their domain because they're trying to crank up all the volume, just cram as much as they can in as little time as possible, and it always backfires.

Takeaway:

• Jeremy warns that sudden increase in email volume can harm domain reputation.
• Overloading recipients during peak times may backfire.
• Maintain consistent sending practices to protect deliverability.

Recognizing industry-specific behaviors during holidays can improve campaign effectiveness.

And let's talk about industries, because if you're in finance, they're not there... I'm talking about Christmas to New Year's, they're gone. Probably want to pause the finance, banking, credit union style campaigns. And yet if you're reaching out to SaaS startups, they're working.

Takeaway:

• Jack highlights that some industries shut down during holidays.
• Adjust campaigns based on industry activity levels.
• Continue outreach to industries that remain active during holidays.

Understanding how holidays impact open and reply rates can help optimize email campaigns.

But of course you're gonna get less open rates and you're gonna get less reply rates because, you know, the time between when you're sending an email and the reply, you know, the longer it takes the less chance you have of getting a reply. But it does happen.

Takeaway:

• Jeremy notes that open and reply rates may decrease during holidays.
• Longer response times reduce the chance of replies.
• Adjust expectations and strategies during holiday periods.

Continuing email outreach during holidays may yield surprising results.

I keep my campaigns on Thanksgiving... I keep them rolling, man. I really do. It's crazy to me how many people reply and how very few people will say things like take a break... why would we turn them off?

Takeaway:

• Jack maintains that holiday email campaigns can still generate replies.
• Few recipients are bothered by emails during holidays.
• Consider keeping campaigns active during holidays for better results.