Why is it so hard to break into enterprise?  

Enterprise sales is more competitive than ever — prospects tend to resist outbound sales pitches, and managing large buying committees remains complex. We’re here to help you cut through the noise and prospect more effectively and with intention.

On this episode of B2B Power Hour, we talk to two enterprise sales experts: Anthony Natoli, co-founder of The Revenue Lab, and Melissa Gaglione, an AE at Deel.

They break down everything from where your best opportunities lie to the best way to fill your time at work. Anthony even covers his amazing 5x5 strategy to help you hit more goals and land more deals!

When building your prospecting list, make sure you know exactly why you’re contacting someone. If you don't have a reason to reach out to them, don't.

The best opportunities are people who have a problem you’ve already solved. Confirming that they’re experiencing the right pain point takes the pressure off and lets you confidently lead with the results you’ve gotten for similar companies.

Stay on top of your prospecting (and professional) goals by creating a “North Star” to guide you. For example, you should always have a why behind your actions. Leverage the research and support of other AEs to learn who their top 15 accounts are and why. Then, use that info as your guiding light for why you should reach out.

Make sure your first contact with prospects is relevant. Instead of meaningless personalizations, like a common interest in playing golf or a comment about their dog, tailor your outreach to be hyper-focused on their pain points.

Want to supercharge your enterprise prospecting strategies?

Listen in for some of the best ways to build personas and stay productive in the world of enterprise prospecting.

B2B Power Plays

Top takeaways from this week’s conversation

⭐ Relevancy > Personalization.

A lot of sales tactics go heavy on personalizing your outreach. But many SDRs take this to mean that they can customize the first sentence of a cold email and leave the rest generic.

What’s more important than personalization is relevancy. Understand how your solution is relevant to your prospect’s problem, and only reach out if you know you have the solution to their problem.

The relevancy approach makes it easier for the prospect to connect the dots of who you are, why you’re reaching out, and what you’re potentially going to help them with.

Plus, it takes the pressure off you. All you need to figure out is whether the prospect has the problem you may be able to solve.

5️⃣ Follow the 5x5 Rule.

Anthony created what he calls his “five by five” rule.

The approach is simple: Choose five accounts per week to target for outbound, and pick five prospects within each of those accounts.

With this strategy, you’ll be reaching out to 25 new people per week!

🎥 Using videos to ignite a stale prospect.

While videos don’t fit in everywhere in the sales cycle, they can help push your prospect closer to making a deal when used strategically.

These tips can help you use videos successfully throughout your cycle:

  • Use them in the middle of your sales cycle
  • Send raw clips on LinkedIn
  • Use Twitter and LinkedIn DMs to send videos
  • End the video on a high note, such as the results your solution has gotten for other clients

What he does: Anthony is an SDR turned AE. Most recently, he was an enterprise account executive at Lattice, where he closed deals that help people leaders make work more meaningful for their people. Now he's the Co-Founder at The Revenue Lab.

Key quote: “That’s the point of prospecting — find as many people as possible that have a problem that you can potentially solve.”

Where to find him: LinkedIn

What she does: Melissa is an account executive for Deel, where she focuses on SaaS sales and video prospecting strategies.

Key quote: “Maybe you’re not going to book a meeting right away — maybe it’s going to take a nurture campaign and a couple of months. But you have to be consistent and understand the full picture and know that you’re playing the long game.”

Where to find her: LinkedIn

Episode Highlights

Inflection points from the show

[3:14] Why enterprise sales are difficult: As prospects increasingly ignore outbound sales messaging, enterprise sales have become more difficult than ever. We offer our take on this shift.

[8:45] Prioritizing your list: Be confident about what you’re saying and who you’re targeting when reaching out to anyone on your list.

[10:16] Relevancy > personalization: Think about the problems your previous customers solved using your solution and how those problems relate to your prospect’s persona.

[13:51] Understanding personal motives: Melissa explains how understanding your prospect’s personal motives can help make a stronger case for your solution.

[15:53] Prioritizing your time: Give yourself the best opportunity for success by using white space on your calendar to focus on revenue-generating activities.

[26:53] TGIF: Melissa and Anthony break down how to approach the work week so you feel accomplished by Friday.

[33:37] Create your North Star: Use data from your AEs to create a guiding light — or your “North Star goal” — and create an outreach plan from there.

[36:37] 5x5 rule: Choose five accounts per week to target for outbound. Then, pick five prospects with each account. Now, you’re reaching out to 25 new people weekly!

[40:36] When to give up: Don’t. Instead of giving up, you can nurture and educate the prospect to continue building a relationship if you foresee value with them down the line.

[49:00] Video strategy: While video doesn’t fit in everywhere, Melissa has seen success working it into the middle of her outreach cycle. Utilize raw clips in Twitter DMs and LinkedIn messages.

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