How to Hire an SDR to Handle Cold Emailing at Your Company?

Sandra Wilk - Senior Content Creator at Woodpecker

When you’re about to hire an outbound specialist but know zip about cold mailing yourself, you might find yourself stabbing in the dark. Should you hire one specialist or split the job into two positions? Where do you look for candidates? What questions should you ask them to assess if they’ll do a good job prospecting and reaching out to prospective clients?

I believe this blog post will help you maneuver through the hiring process and find a good Sales Development Representative to handle cold mailing at your company.

Let’s start the hiring process, shall we?

Step #1 Decide how many people you want on board

If we were to strip the process of cold email outreach to its bare minimum, we might say that it consists of three main elements: an interesting email copy that is relevant to the prospect, the sending strategy and a quality list of prospects.

With this in mind, take a look at the possible scenarios of an SDR hire:

  1. You hire a full-stack outbound specialist to handle prospecting, come up with a sending strategy, create the email copies and run campaigns.
  2. You divide the job into two positions: an SDR Strategist and SDR Researcher.
  3. You hire an SDR Strategist to take care of creating the email copy, strategizing and sending, and freelancers to assemble a list of prospects.

I wouldn’t choose the last option, though. You can never be sure if the list you got hasn’t made its way to many other companies besides yours as well. It would be even worse if you decide to buy a list. Email addresses on those lists are often outdated (which harms your deliverability) and they’ve already been sold to many other people as well. Not to mention that basically you’d just be sending emails to random people who may not fall within your ICP at all.

If you have the resources to do so, I’d recommend you go with the second option. Why? Both jobs require a different skillset and a different disposition.

Step #2 Create ‘candidate personas’

Coming up with the ideal candidate may mean more work upfront, but will ultimately pay off, streamlining the whole hiring process. If you know exactly who you’re seeking, finding them will be much easier.

Here’s what to look for in an SDR Strategist and an SDR Researcher.

SDR Strategist

Hard skills

A cold outreach strategist has to not only strategize (choose what they’re going to write in the emails, when, how many and how often will they send them). They also have to be a skillful copywriter (to come up with a captivating subject line to catch your prospects’ attention and compose a valuable and relevant email copy to engage them in a conversation).

How to test if they really know what’s what in cold emailing when you yourself know little or nothing about it? I’ll give you some example questions in step #3. But for now, let’s move on to the next thing at hand – the candidate’s disposition.

Soft skills

This type of work requires creativity and a certain amount of empathy (to create a persuasive message you need to be able to get in your prospects’ shoes). Such a specialist should keep their finger on the pulse of the company: is the CEO attending a conference next month? Maybe it would be a good idea to send some networking emails beforehand?

SDR Researcher

Hard skills

When it comes to hard skills, a researcher has to know their way around certain tools, such as Excel. I’ll come back to this in step #3, where you’ll also find out what questions to ask them.

Soft skills

First and foremost, they need to have an analytical mind. They’re going to be handling data on a daily basis, so they need to be diligent, patient and curious. I’d say people who possess the ability to stay calm and are in general more on the quiet side would be a good fit for the position.

Both of these positions need to share one quality, though: a genuine interest in their work.

How to determine if they are interested? Ask them not only about their experience, education, courses, and certifications, but also about the blogs, podcasts, or companies they follow. You’ll be able to assess if they’re taking any activities to improve in the field of outreach marketing.

But they need to be passionate about more than just marketing – your company’s mission matters as well. You need to make sure they’re in line with your company’s core values, so they’ll stay with you for the long run and bring value to the table.

Now, since you know exactly who you’re looking for, it’s time to start the search.

Step #3 Search for the best candidates

You might choose to go old school and just post a job opening online. Even though it’s the easiest and often the most convenient solution and you might find a promising talent this way, it’s worth to single out other options I encourage you to try out.

  1. Word of mouth referral – what better way to find a good specialist than by getting a recommendation from someone you know? Ask around in your network to see if your colleagues and acquaintances have heard of a good-fit candidate for the opening.
  2. Active sourcing – look for your next talent in online places that draw the kind of professionals you want to hire, e.g. Quora or marketing groups on Facebook and LinkedIn. Seek passive candidates and try to get in contact with them. The best specialists are often being found instead of looking for an open position.
  3. Social media ads – this might be a not-so-popular route to take, but it might prove effective.

Great – now that we’ve got the issue of how to find the candidates handled, let’s move on to the next step: the interview.

Step #4 Prepare questions to ask at the interview

Now let me show you what questions you could ask during the interview to check the candidates’ cold emailing knowledge.

I’ve split the questions according to the two positions.

SDR Researcher

1. What tools, if any, do you use for prospecting?

Check this list of prospecting tools for reference. If they know their stuff, they’ll most probably mention one or more of them.

2. What do you think about ready-made lists?

Spoiler: they’re a big no-no. Might ruin your deliverability and result in angering the prospects. More on this here.

3. Where on the web are our clients?

This depends on your niche, so you yourself are the best person to answer this.

4. What positions would you target?

This boils down to one thing: when it comes to buying your product, who decides to make the purchase? That’s who they should be targeting.

SDR Strategist

1. What best campaign results did you get?

That’s an easy warm-up question you can begin with. Here are some benchmarks for reference.

2. What tools do you use?

They should mention an email automation tool. Make sure, though, that they’re not referencing an email marketing tool. There’s a huge difference between the two (we covered it here) and email marketing tools should not be used for cold outreach.

3. What 3 prospect groups would you target (for our product/company)?

This, again, depends on your particular niche, so you need to answer it yourself.

4. If you were to launch campaigns to different countries, how would they be different?

There might be many variations of this question, for example: If you were to launch a campaign to start-ups and finance companies, how would they differ? The general idea is to check if the candidate is able to create campaigns tailored to different prospect groups instead of one general message.

5. How will we acquire leads? (i.e. What kind of campaigns can we conduct, other than cold mailing?)

Some possible answers include: campaigns to reactivate old leads, to convert trial users to paid customers or LinkedIn campaigns.

6. What do you think about ready-made lists?

Check the answer to question #2 in the researcher section.

7. How would you know our emails are getting into spam?

The open rate is low – this might be a sign either of bad targeting (i.e. a poor quality prospect list), a weak subject line, or that your emails are being diverted into the spam folder (this may be a result of using too many spam-triggering words).

8. What would you do if the open rate was low?

This question aims at assessing if the candidate’s down with the technical basics.

You can find the answer here.

9. When would you say is the right time to iterate the campaign?

An example answer might be a week after the last follow-up has been sent and our campaign results are unsatisfactory. It depends, though, on the country and the industry you’re in.

10. Who would you offer X to?

X being a bit more unusual product. They may not be able to find the best answer, but the point here is to see if they’re creative enough to come up with an answer at all.

Bonus: if you’d like to test the candidates’ knowledge, here are two tasks you may ask them to do:

  • Ask the researcher to find and remove duplicates in an Excel file
  • Ask the strategist to write an email copy

A good email copy is short, personalized, brings value to the prospect and ends with a clear CTA.

Your turn to share

I hope you’ll find the hiring process as easy as pie now. If you’ve decided to hire a full-stack outbound specialist, try to combine the two sets of questions and positions described above as best as possible.

Feel free to share your experience in the comments.


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