Outbound Sales is *Not* Blasting Emails

July 24, 2020

Go-to-market , Sales & Marketing


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Effective Outbound Sales

Pouyan Salehi, Co-Founder & CEO at Scratchpad hosted a talk discussing effective outbound sales on May 26 as part of the Pear’s speaker series This is a recap! Watch the full talk at pear.vc/speakers.

What’s the best source for leads? How can I automate emails? What tools should I use?

If you’re putting together an outbound sales strategy and asking these questions off the bat, you’ve started off with the wrong questions, and you’re probably in the mindset of blasting emails.

Here’s what Pouyan Salehi, Co-founder and CEO at Scratchpad, has to say about that:

If you want to feel good about the number of people you’ve reached out to and say, ‘Hey, we’ve done activity top of funnel,’ then spray and pray is a great method.’ If you want good results, it’s not.

Why you shouldn’t just “spray and pray”

Why you shouldn’t just “spray and pray”

(1) Spray and pray creates operational debt.

In the early days of being a “zero” founder, the most crucial thing is learning what works and what doesn’t work. Once you know if something works, you can step on the gas and keep throwing more resources on it, you can do a lot more and automate more.

If you’re spraying and paying off the bat, you may get some responses, but because you haven’t put in the work to personalize and make the messaging relevant, you haven’t actually learned anything from the response. You still face the learning challenge, and you still need to do all the segmentation work.

(2) The results are usually just worse.

Just look at your own inbox. We’re all getting flooded with emails now, as more and more companies use automated systems.

(3) You can actually run into technical issues blasting emails.

So, let’s rewind and start with the three key components of great sales: strategy, data, and execution, in the correct order of operations.


The most important tool: your story. Start here. Often, this comes too late or as afterthought, but slowing down and spending some time getting your story right will pay dividends down the road.

Think of this story not just as an “outbound story,” but as your foundational company story, which can help you with fundraising and recruiting later. It captures the benefits and core problems you are solving and for who, what it is you’re actually selling, and how you are different.

The key components of a story are your headline and your messaging framework (pain, priorities, and motivations).

Your Headline

This may seem counterintuitive, but your headline is not what you sell. In fact, what you sell should come in last.

Your headline should instead be the benefit of what you sell, or the customer issues you solve. This is a subtle distinction from describing what your product can do or the features it has.

For example: Scratchpad is the fastest experience for account executives to update Salesforce, take notes and manage your tasks.

This is different from something like: Scratchpad is a Chrome extension that you can access and it’s a freemium model. This comes later.

Your Messaging Framework: Pain, Priorities, Motivation (PPM)

Now is the time to think about the people you are serving and break them out into personas. For each persona, you must deeply understand that they care about.

“Usually you can think about that through: what pains are they facing? What are their priorities or what are they motivated by?” says Pouyan.

Example: if your end user is a salesperson or account executive, it could be their top priority is hitting their quota. They’re also motivated by that because if they hit their quota, their job may be on the line. Another pain they have may be logging activity. They don’t need to do it to hit their quota, but their manager needs it so that they can understand what’s going on, which is annoying.

Don’t overthink this too much. When you’re starting out, just take your best stab and write something down.

Your messaging comes from your work here.

Note: this is not the time to be asking for email templates. Write your own! It depends on who you’re contacting and what it is they care about, or there could be multiple things they care about — which you should have discovered in your thinking above.

What to do if you’re a “zero” founder and don’t know what the story is yet:

This is common in the zero stage and it’s okay — still take 30 minutes to write down your best assumptions. You can come back and modify them as you learn.

This step is absolutely critical, as Pouyan points out:

If we can’t even get them to care about the problem through words, I wonder: why would we spend all this time building the product?

At Scratchpad, Pouyan created a one pager for this, just a “nugget” of a story that he eventually built around.

“In the early days we did a lot of outbound, but we did it solely to see ‘Can we get people to even care about this problem? Does this problem resonate?’ If it does, then it’s our job to solve that problem through a product,” says Pouyan.

This can be done even before you have product!

“You’ll learn a lot about what type of users might be more interesting to solve for first, who has the problem. Or maybe there was a secondary problem you never even thought of. It gets conversations going.”

Things to keep in mind:

  • Nobody cares about how awesome your product is, or who your investors are, or that you went through this awesome accelerator, or made this killer hire, or released a new version.
  • Make your story about them — your prospects and core customers. They need to understand what they are getting out of this and why they should care.
  • The more time you spend empathizing with users, understanding their problems and crafting messaging and, ultimately, solutions for them, the better your results.


You may be asking: Okay, *now* what’s the best data source? Where can I scrape leads? Where can I buy leads?

This section is short because the reality is: there is no one single best data source. It depends on who you’re going after and what industry they’re in — so use multiple sources. Then, clean the data and validate your emails.


Now is the time to combine your strategy and data to execute personalized and relevant communication at scale.

Relevance and personalization are different.

Personalization: “Oh, wow, I saw you went to this school. And we both grew up in this state and now let me talk to you about my product.”

Relevance: “Hey, I noticed your app is really popular in this country, but you haven’t localized it for this country yet.”

Personalization might involve mentioning things like first name, company name, and title in your email. Relevance is mentioning company competitors.

Relevance, in Pouyan’s view, is much more important than personalization, because it shows you’ve done your research and knows what your prospect cares about.

Keep it simple: your goal is simply to start a conversation.

At this point, you may be tempted to pack everything into one outbound email. Do not do this. Remember: you are not trying to get to all the way to close in one email. That’s way too much.

You might not even be trying to schedule that conversation on the calendar yet. Start small and figure out what works.

“The ask could simply be, ‘Hey, does this sound interesting to you?’ And all you’re hoping to get is an email response of ‘Maybe’ — just that there’s some signal on the other side that you can then use to strengthen the conversation,” says Pouyan.

Don’t ignore the neutral responses.

It almost never happens that a cold email is going to elicit something like “Oh, this sounds amazing. Please send me a calendar invite and I’m going to invite my whole team so we can talk about purchasing.”

More often than not, you will receive replies like: “No, thanks. Not ready right now.” “We’re busy. Can you please get back to me next quarter?”

Anything but a hard complete no, Pouyan considers a neutral response. These responses are signals that your messaging just didn’t land in the right area. Maybe it was close, but it didn’t quite hit the pain point.

Here, you need to be ready with objection handling. You need to have a response ready for “Hey, not right now, or we’ve already invested in a different solution,” and similar objections. Pouyan created a series of templates for these.

Unfortunately, we can’t give you the magic words that will get the results you want. That comes from hard work, and at ground zero, this work should be founder-led.

“You learn so much in terms of crafting that narrative, sending it out there, seeing what resonates. And you take that learning, not just for sales, but also in how you position your company. And how you position the product. And what you work on. So the effort has got to be there,” says Pouyan.

It’s like going to the gym. You just gotta show up, and then you’ve got a system for how you work out. You get into that flow.