Using cold emails to invite prospects to webinars?

Don't make these mistakes

👇

A rep sent me this webinar invite the other day.

⛔️ Here's where they missed the mark:

→ Subject line is too "markety" sounding, doesn't feel 1-to-1
→ Email is too long to skim (148 words total)
→ Way too much information
→ Formatted like a marketing email
→ No clear call out for why I'd be interested
→ Too many options (3 hyperlinks)

✅ What they could have done instead:

I like this simple framework for webinar invites:

- [Short, boring subject line]
- [Personalized call out]
- [Social proof + takeaways from webinar]
- [ONE CTA]

💡 The rewrite:

▶︎ Email #1 (variation A) ◀︎

Subject line: Quick invite to Outbound 2.0

Hi Jason,

Your work with Rippling and Gong might make this interesting to check out.

Scott Martinis (8 years of experience growing SDR teams) is hosting a webinar with us on Outbound 2.0.

He's showcasing how sales teams like x, y, z are using AI to land higher-quality meetings (without wasting hours researching and writing email copy).

Mind if I shoot over an invite for the event on 3/8?

Katie

P.S. Don't have time to attend? Let me know, I'm happy to send a short recap

▶︎ Email #1 (variation B) ◀︎

Hi Jason—Scott Martinis is showcasing how sales teams like x, y, z are using AI to land higher-quality meetings (without wasting hours researching and writing email copy).

Mind if I send the invite your way for 3/8?

Katie

P.S. Might be some cool strategies you could show your clients like Rippling & Gong

▶︎ Email #2 (bump) ◀︎

Here's the link to check it out. 👈 (hyperlinked)

Katie

▶︎ Email #3 (bump) ◀︎

If it's quicker—I could sign you up and send over a 3-5 bullet recap.

Sound good?

Katie

______________________

Use this framework for webinar invites, and you'll see a massive increase in replies and sign-ups.

What feedback do you have for this cold email?

"Should we outsource SDRs?"

No, with rare exceptions.

There's a reason why customer churn is high at most of the outsourced SDR shops.

Outbound isn't as easy as paying $3-5k / month for a part-time SDR. And then expecting to see high-quality opportunities in 30-60 days.

I've NEVER worked with a client that was happy with their SDR agency.

- Poor show rates to meetings
- Terrible expectation setting with handoff
- Low-quality meetings with non-decision makers
- Few, if any, closed/won deals

But to be fair—it isn't always the SDR agency's fault.

Many of their clients expect them to be miracle workers.

An outbound-led sales motion is very different from an inbound-led sales motion.

If your AEs are used to meeting with inbound leads, they must be taught how to close outbound leads.

Prospects will likely not be problem-aware, there isn't a budget in place, and they probably won't have brand awareness.

Do not hire an SDR agency if:

⛔️ You've never done outbound before as an org.
⛔️ You sell enterprise
⛔️ You're breaking into new industries
⛔️ You haven't figured out your messaging or value drivers
⛔️ Your AEs aren't self-sourcing and doing their own outbound

No outsider will ever understand your customers as well as you do.

And it's only a bandaid to build a sales culture that doesn't understand how to excel at outbound.

It might make sense to work with an agency if:

✅ You know outbound works, but need help scaling it
✅ You've mastered messaging and value drivers
✅ Your AEs know how to close outbound deals

~~~

Agree or disagree?

“My young reps don’t believe in using the phone.”

👆

From a recent convo I had with a sales leader. I had to challenge his thinking.

Me: "Can I give you a different take? I don't believe this is a Gen Z thing. 'Young reps' aren't phone-averse because they grew up on texts and DMs. They’re a generation that values authenticity."

Sales Leader: "Okay..."

Me: "Follow me here...you know what might feel inauthentic? Making cold calls using techniques that feel scripted or inauthentic. Gen Z questions authority more than their older counterparts—like every previous generation. And they’re less willing to blindly follow advice and direction that doesn’t make sense to them. I'm curious—who are your top reps?"

Sales Leader: "Uh...David and Ashley."

Me: "How closely do they follow the talk track you provided them?"

Sales Leader: "They sort of do their own thing."

Me: "If you incorporated their feedback to update the talk tracks—how do you think that might affect the buy-in from the rest of the team?"

~~~

To my surprise, this sales leader took my feedback like a total champ 😂

Then I shared a few ideas on how to get their reps to pick up the phones:

✅ Rub shoulders and make calls with them (that’s right, get in the pit!)

✅ Don’t teach scripts, teach principles so they can make it their own

✅ Invite your reps to contribute to the talk tracks and messaging

✅ Move to 10% product training, 90% your prospect’s problems training

✅ Capture tons of examples and recordings of what good sounds like

✅ Run group virtual call sessions (using a tool like Orum)

✅ Invest time and budget in training your front-line managers

Lead by example—show your reps that the phone works.

And involve them in the creation of talk tracks & messaging. The buy-in will be much higher.

Agree or disagree?

 

#sales

The worst VP of Sales I've worked with:

- Managers were scared of him

- Could never get honest feedback from reps

- Only lasted 10 months

The best VP of Sales I've worked with:

- Managers loved him

- Always got honest feedback from reps

- Been there for 3+ years and counting

The difference between the two?

The better VP of Sales avoided these two mistakes:

⛔️ Making questions personal

It’s hard to give a person feedback. It’s way easier to give feedback to a process.

“What feedback do you have for me?”

vs.

“If you came up with this process yourself, what would you do differently?”

⛔️ Responding poorly to feedback (especially in group settings)

I've seen this over and over again.

A rep or manager shares feedback in a group setting. The senior leader gets heated and shuts them down. Now the entire team is afraid to share feedback.

When you get feedback, thank the rep or manager (regardless of their delivery). Restate back what you heard in your own words. And then share how you’ll use the feedback.

Here’s an example:

Rep: “I’m finding this new territory plan difficult. And I wish we could go back to the old system. I’m confused about exactly who owns the upsell/cross-sell because the BDR/AE/AM relationship isn’t totally clear with existing business.”

Leader: “Thanks for sharing. So, you’re finding the new territory plan difficult. I’m guessing that you might be worried about the time it takes to implement this, and how it might affect your performance. And you want to avoid overstepping your bounds with your teammates?”

Rep: “Yep.”

Leader: “Got it. Totally legitimate concern there. Candidly, we’re still working out the kinks as a sales org. This is new for us. And it’ll likely take another quarter or two for everyone to feel comfortable. But what I’m hearing from you is that if we laid out a better process for exactly when and how you’ll interact with the BDR and AM assigned to your accounts, that’ll help you do your job. I’ll take this back to the rest of our team and come to the next all-hands with a clear plan. Sound good to everyone?”

=============

If you want more trust and feedback from your team:

1) Encourage it

2) Respond well to it

3) Implement it

Agree or disagree?

 

#sales #leadership

Want to prevent an exec from multi-tasking on your sales call?

Deliver "non-obvious insights" that challenge their status quo.

Why?

Because execs who learn something will:

→ Make time to attend future sales calls with you
→ Invite more of their peers into future conversations
→ Go to bat for you (especially with their boss)

Insights build credibility and confidence. When delivered correctly, you'll get access to power faster. And you'll win more deals.

Want to know if you have a great insight? Here's the question you must answer for the buyer:

"What did I learn today that I can take back to my team?"

The best time to leverage insights is throughout the initial intro call, when you meet an exec for the first time, and throughout demos.

Here's how to get started :

✅ 1) Current Narrative

You must master the buyer's current state. Know it inside and out. If you've met with enough prospects, you know how they tackle problems your solution helps with. Start with their current state.

Example:

- You sell a solution to help contact centers reduce the cost to serve
- Common mistake: To reduce incoming call volume, companies will implement chatbots, FAQ pages, and/or surveys
- Why this is a problem: Customers can't get the help they need, end up calling into the contact center anyway, and now they're angrier. You don't know the root cause behind WHY they can't self-serve.

✅ 2) Insight

Now, it's time to deliver an insight that challenges how the prospect views this problem. Ideally, this is backed by data and proof points.

Example:

- Most companies are reactive instead of proactive
- Only 7% of customers complete surveys (the vocal minority)
- The best data exists in the chats, texts, and phone calls with all of your customers
- Ask the prospect: "How are you capturing data today from chats, texts, and phone calls? And using that data to identify the root-cause behind why customers are calling in so you can prevent it?"

✅ 3) Customer Story

Let's wrap a bow on the insight by sharing a real example of a customer getting positive results.

Example:

"ABC Electric Co. was dealing with a similar problem. Increasing inbound calls, with no end in sight. By extracting data from texts, chat, and phone—instead of relying only on surveys—they could identify specific reasons why customers kept calling in. These insights reduced incoming call volume by 23% while increasing NPS by 36 points."

~~~

This is how you make executives pay attention. Challenge their status quo and way of thinking with real proof points and a relevant customer story.

Sales leaders, you must provide your reps with insights like these.

#sales