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Cracking The Code of Cold Outbound: Exclusive Insights with Gong's Sales Maestro, Caspian Lewke


Unlock the insights from Caspian Lewke, an expert intertwining technology and sales prowess at, as we explore the multifaceted realm of cold outbound strategies.

Caspian, with his robust experience in Sales Development Representative (SDR) activities, imparts not just knowledgeable, but also deeply practical advice on cold outreach.

Gong, renowned for enhancing sales team performance through analytics and various services, enables Caspian to offer a distinctive viewpoint that is must-read.

1. Core Components and Strategies in Cold Outreach

Q : What are the pivotal elements and successful strategies in cold outreach from your experience?

A : The essence of successful cold outreach lies in mastering basics like cold calling and emailing, while evolving with technology to embrace valuable methods like social selling on platforms like LinkedIn. Video prospecting and strategic gifting are also potent methods. In a nutshell, prioritize cold calling and emailing, with a close second being social selling.

2. Integrating Best Practices into an Effective Playbook

Q: Can you delve into best practices for each component and discuss how they integrate into an effective playbook?

A: Beginning with cold email, the primary objective is ensuring your email gets opened. While many reps heavily focus on email content, a compelling subject line is paramount. Effective subject lines are typically two to four words long and provide a glimpse into the email content.

I use the "Triple Curious Approach" when crafting subject lines, selecting one keyword from each unique part of the email to ensure it's both captivating and honest.

Here's an example:

Suppose we're crafting an email that discusses:

- A new feature of CRM software

- How it saves time in managing contacts

- A special discount for early adopters

We might choose the following keywords:

- New Feature

- Save Time

- Special Discount

A subject line using the "Triple Curious Approach" might look like:

"New Feature, Exclusive Savings"

It's worth noting that you may need to rewrite the title to ensure smoothness, as the keywords might not directly relate when placed in a sentence.

This subject line is concise, gives a sneak peek into what the email is about (new feature, timesaving, and a discount), and it's honest and straightforward.

In terms of the email body, keep it concise. Often, sellers make the mistake of focusing on their product rather than solving the prospect's problem.

A good email should consist of four main elements:

  1. An attention-grabbing hook: Mention something recent about them, like a social media post or event.

  2. Reason for contact: Explain why you're reaching out and identify a problem you think they're experiencing.

  3. Value proposition: Clarify how your product or service solves their identified problem.

  4. Call to action: Clearly state the next steps, such as scheduling a meeting.

By connecting these dots concisely, you can create compelling cold outreach that resonates with your prospect.

"The key is to see things from the prospect's perspective and answer the question: why should they care?"

3. Suggested Sequences for Cold Outbound

Q: What sequences do you recommend for cold outbound, especially considering responses or lack thereof?

A: I advise initiating with an email, followed by a call, and then a LinkedIn connection request, all within the first day. The rationale is to maximize the chances of reaching the prospect, as individuals allocate their time across various platforms.

Starting with email is beneficial due to its tracking features, which can inform subsequent communication, such as phone calls. The ultimate goal is to capture your attention in the first few seconds by showing that I've researched you.

As for LinkedIn, I've found that connection requests without personalized notes have higher acceptance rates. Once the connection is established, it opens avenues for deeper, more personalized interactions.

There are mainly three approaches for LinkedIn outreach: the relationship-based approach, video prospecting, and the stepping-stone approach. In the relationship-based approach, the initial goal is purely to add value and optimize for a response, not to sell. Once that initial interaction has occurred, you can start identifying problems the prospect might be facing.

4. Elaborating on Social Selling

Q: Can you elaborate more on your points about social selling?

A: Absolutely. The relationship-based approach on LinkedIn, while a slower process, can forge meaningful connections. Conversely, video prospecting allows for a more direct and immediate connection, enabling you to express your personality and make a strong impression, especially when you need to book a meeting swiftly.

Voice notes are another option, although not my personal preference. I believe video messages can be more impactful. Lastly, there's the stepping-stone approach, where you build off other successful outreach methods. If someone is repeatedly opening your emails, consider sending a follow-up email acknowledging this.

5. Video Prospecting: Content and Length

Q: Regarding video prospects, what should the video primarily contain, and what should be its duration?

A: A prospecting video should ideally be under a minute. If you have valuable information, extending it to a minute and a half is acceptable. Aim for around 46 seconds to encourage prospects to watch it. The content should be structured similarly to a phone call or email, including a hook, relevance explanation, and a proposal for a follow-up conversation.

6. The Future of Outbound and Utilizing Current Practices

Q: How do you envision the future of outbound? How can SDRs or founder-led growth teams at startups best utilize current practices?

A: Creativity is becoming increasingly vital in outbound marketing. Companies are beginning to leverage AI for personalized outreach, but even this is reaching a saturation point. The expected level of personalization is escalating, and what might have been a compelling email three years ago will not yield the same impact today.

The importance of omni-channel outreach is growing. Creative methods like strategic gifting and social selling are likely to become more significant. In summary, as the bar for effective outreach rises, creativity and multi-channel strategies are going to be more essential for standing out and engaging prospects.

Final Thoughts

Adaptability and creativity are paramount in today's ever-evolving outbound landscape. From mastering email subject lines to leveraging video prospecting, Caspian provides actionable tips that are invaluable for anyone in sales or growth-focused roles.

His perspectives on the future of outbound underscore the necessity for a multi-channel strategy and escalating creativity to effectively engage prospects. In essence, to thrive in outbound sales, concentrate on understanding your prospect, being adaptable, and adopting innovative strategies.

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