Startup Recruiting Part 4: Outbound Messaging

July 27, 2020

In our Startup Company Growth blog series, we’ve talked about the Job Description and the Sourcing of Candidates.  Posting a job where active candidates are searching for a position, or leveraging social media or referrals for sourcing, will, in essence, take care of itself.  However, you have also sourced a list of potential passive candidates, so you need to start “marketing” the job opportunity to those prospects – reaching out with an initial message in order to get their attention and start a dialog.

As in all aspects of hiring, each step is important.  Your recruitment messaging needs to embrace the best practices of outbound marketing, including subject line, content, timing and other aspects. In this blog post, we’ll look at each of these components of messaging.

Recruiting Messages

Having identified a list of possible candidates, you need to get your job opportunity message in front of them.  This is your initial touchpoint.  First, you might ask yourself, is it worth reaching out to already employed, passive candidates. They aren’t looking for a job, are they? Interestingly, Gallup reports that 51% of US employees are actively looking for a new job or watching for new job openings.1  And there are twice as many “actively disengaged” workers in the world as there are “engaged” workers who love their jobs.2  Employed workers are definitely a great source of potential candidates.

Whether using email or LinkedIn InMail, the most common messaging techniques, there are some important guidelines to follow. According to Monster’s 2018 State of Recruiting Survey, 67% of recruiters “said they felt that they needed to understand marketing to be successful”.3  And they are right. You need to embrace email marketing best practices.

Subject Lines

Let’s start with the critical subject line. Needless to say, there is lots of clutter in today’s inbox, so trying to get your message opened is the crucial first step, and the subject line is the key.  Here are some thoughts and best practices to keep in mind:

  • Subject line length is important. The best subject line length is one that uses as few words as possible to provide the information or incentive that gets the reader to open it (simple, but needs to be your mantra).  Best performers are between 30-50 characters, including spaces.
  • Be specific. Make it relevant.  Why should the recipient open this email?  A good subject line tells what is inside, and drives the call-to-action.  Show the value and make sure it ties to the content.  No bait and switch.
  • Use keywords that are relevant. Titles and industry specific terms can help. First two words in a subject line are key. Move keywords up front.
  • Make it personal. According to multiple sources, the candidate's name in the subject line can increase an open rate by up to 26%. Referencing other personal data can help even more. As an example, according to Beamery, this is one that they have found effective:
  • Subject lines framed as a question, can perform well. “Interested in a dream Sales Job at [Company]?”, as a general example. And adding a sense of urgency is a good way to inspire action. “Ruby-on-Rails developer job opening - expires in one week.”
  • Not going to get deep into SPAM filtering but avoid using promotional phrases or words and punctuation that make it sound spammy, i.e. urgent, $, make money, etc.  Plenty of online resources to help there. Here is a quick guide from Hubspot, and below are the ones tied to Employment (although not all relevant to this discussion, you get the idea):
Terms to Avoid

Message Content

Now, the actual message.  The content of your email needs to be carefully crafted. The essentials:

  • Include where you heard about them — e.g. “I saw your contribution on GitHub”, “Reviewed your LinkedIn profile and saw you worked at X, which is very complimentary to our company.”  You might want to put this first to demonstrate your message isn’t a generic email blast.
  • According to Glen Cathey, noted expert on recruiting, “My secret weapon was to be incredibly detailed and specific about exactly why I was reaching out to them, which wasn't [about] the job I was recruiting for, but rather their skills and experience, to show them I understood them.”(5)
  • You want to offer a brief introduction (who you are, role) and let your candidates know about your current opening.  Include only what’s absolutely necessary, but the more personal, the better: define what your company is working on and what the job is, how that relates to what the candidate is currently doing, and why what you’re doing would matter to them.  Highlight the major challenges in the job rather than listing skills and “must haves.”  Tell a story.

Key: your purpose is to elicit a response, not share a long story. Keep the message focused on “why they should care”, and “how they take action”.  

Some other content thoughts:

  • Consider including a link to the job description, and since you are a startup and there is a chance the candidate hasn’t heard of your company, you might want to include some company information (or even better, a link to the “About” page on your website).  
  • Definitely include a specific call-to-action, like asking when they would like to schedule a call to discuss the job opportunity, which could either require a simply reply or a “Let’s Chat” button, or you could provide a link to an open calendar where they can schedule their own call time (using something like Calendly).  Or suggest a specific day and time. And a soft sell is usually more suitable: “I’d like to get to know you better and introduce our company to you.”  Versus “Please let me know when you can do a phone interview”.
  • Depending on the role and if you want to do some screening first, you could also provide a link to the actual online job application. Situations vary, so think through your process and match in your email communications.
  • People scan emails. Use bullets, bolding, headlines, underlines to make for easier consumption.
  • Re. overall length, the shorter the better. Again, your goal is to elicit a response.

And for closing your communication, use what is most appropriate and what you are most comfortable with. Some basics:

  • Sincerely, Regards, Yours truly - These are the simplest and most useful closings to use in a formal business communication
  • Best regards, Cordially, and Yours respectfully - These closings are slightly more personal.


Who the email is “from” is something good to test. The company recruiter, the hiring manager? See what works best. Note that reach-outs from founders aren’t intrinsically more valuable, unless they’re personal and targeted.


There are no definitive rules on best time of day to send.  Top Echelon says right around mid-morning or mid-afternoon, specifically between 10 and 11 a.m. and 2 and 3 p.m. Those timeframes are generally considered to be ideal for recruiters to send out their emails.(6)   They also suggest to not send at night, before 7 a.m. and after 4 p.m.  On the other hand, Yesware data suggests early morning (6 a.m. or 7 a.m.) or evening (8 p.m.) time slots work best.(7)  Re. InMails, LinkedIn says there is no magical time of day. Response rates all the same.(8) Argh! What to do? You must test to see what works best for you and your target audience.

What day to send?  Same here – nothing definitive. During the week, Tuesdays and Thursdays are traditionally the best days for marketing emails, with Tuesday number one.  What about weekends?  Conflicting data on this.  The Yesware study says the best reply rates are on the weekends.(7), and Beamery says they have found Sunday evening works best.  Others, like Top Echelon, say don’t send on the weekends.(6) LinkedIn says day of week has no impact on InMail response rate.(8)  Dizzying. Again, testing is highly recommended here.  See what works best.


Quick mention of mobile devices. A good percentage of your candidates will probably view your message on their phone. (Most?)  Make sure it’s mobile friendly.  Should be responsively designed, and as noted above, as short and scannable as possible.


While reaching out to passive candidates is best served via direct email/messaging, texting is another way to communicate with candidates. Jobvite’s 2018 Recruiter Nation Study had some interesting stats re. texting. According to the study, 43% of recruiters have used texting to reach out to candidates or current applicants, and 88% report positive feedback from the job seeker. They also note that it works better for younger candidates.9  Texting as a communication channel does have its risks, depending on the audience and the type of message (e.g. one can assume a reminder for a scheduled interview might be better received than an initial cold outreach message).  Use your best judgement as to when and how for texting.

Metrics and Measurement

Most email platforms have tracking capabilities, and it’s extremely valuable to get campaign metrics – open rates, click through rates, and even conversion rates if you send them to a job application form, for example. Metrics allow you to see the effectiveness of your subject lines (driving open rate) and your message content and design (driving click throughs).  More on the value of metrics below in the Testing section.

It’s best to use an email marketing platform to do your sending, since analytics are a standard feature.  Or look at a solution like Upsider which has candidate engagement tools and the corresponding email metrics built in.  Even if you send from your personal Gmail account though, Google Analytics can be used for tracking email opens (add the Google Analytics tracking code to your Gmail messages).  Get as much data as you can so you can measure effectiveness.

Regarding conversion rates, the system you use for your communications will determine what you can track. As noted, it’s possible to look at the job application form submission tied to sends and click throughs to get true conversion rates, but you need an analytics system that allows that type of tagging and reporting.  Keep in mind you can also measure success in a manual way, counting interviews, offers tendered, and job offers accepted, and tie that back to campaigns and messages sent. You can even look at conversion between each step, from contact to interview to close.  Even if it’s manually done, measurement and metrics give you the information you need to optimize your recruiting process. Get the data and use it!


And that brings us to the last part of this discussion, using that data – i.e. leveraging metrics in testing to optimize performance.  In A/B testing, a single element competes against the original (control) version.  You use metrics generated through A/B testing to identify the optimal approach (the winner!).  For example, basic subject line testing uses two (or more) subject lines to see which gives you the best open rate.  Or in an email, a new version of a headline might compete against the original headline to see where you get the best click through. Testing is an ongoing effort, and the current champion (the winner) can continue to be challenged until a new winner is found, driving even higher performance.  It’s classic “test, learn, and optimize”.

Typically, for larger lists, a subset of recipients is pulled out, broken into two or more “cells”, the message is sent to all cells with only one test element changed for each, and the results show the winner, which is then sent to the remaining recipients on the list. In the case of working with smaller lists, you might just send half the list one message, half the other, and see which performs best. That will inform your next message send, and you can challenge that winner again. Slowly build your best practices and ratchet up results.

Each element of your communications can be tested. Besides the subject line, you can test copy length, messaging, HTML vs. text, the close, who it’s “from”, call-to-action, day/time sent, and many other elements. Of course, you must balance the time it takes for testing with the ROI, but at the least, start testing the basics like subject line and length of copy. Test and learn and optimize!

Bottom Line

Messaging to passive candidates is an essential component of the talent acquisition process driving your company’s growth.  It’s crucial that your communications are effective and follow the latest in digital marketing best practices. Focus on each piece. You can send a message to an extremely qualified candidate that talks about the best job offer on the planet, but if the subject line is horrible, that person may never see it. Spend the time crafting great communications. Follow the guidelines above on how to structure your subject line and your message. Track what is happening and test and optimize. Embrace the proven methods of email marketing to be a great communicator and fill the positions with amazing candidates as fast as possible.


Upsider will continue to provide information in our upcoming posts that focus on this critical aspect of a startup’s life - hiring.  If you’d like to automatically receive new blog posts and insights as they become available, please click here and have the latest delivered straight to your inbox.

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1. Note: From “State of the American Workplace”, published by Gallup | 2018

2. Note: From “Unhappy Employees Outnumber Happy Ones by Two to One Worldwide”, posted by Forbes | October, 2013

3. Note: From “Facing Challenges Attracting Quality Candidates, Recruiters Are Embracing a Multi-Solution Approach to Sourcing”, posted by Monster | August, 2018

4. Note: From “How to Write Email Subject Lines that Make Candidates Stop, Click, and Read”, posted by Beamery | 2018

5. Note: From “7 Ways to “Hack” Your Interactions with Candidates, Glen Cathey Style”, posted by LinkedIn | April 19, 2017

6. Note: From “What Time of Day Should Recruiters Send Out Their Emails?”, posted by Top Echelon | June 14, 2016

7. Note: From “The Best Times To Send Email For Replies (Backed By Data)”, posted by Yesware | June 14, 2014

8. Note: From “Data Reveals the Best Time to Send InMails (and the Answer Will Surprise You)”, posted by LinkedIn | September 12, 2016

9. Note: From “2018 Recruiter Nation Study”, published by Jobvite | 2018

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