Warming up your cold outreach: Tips from Drift’s recruitment director

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Whether you’re on the sending or receiving end, cold outreach can be intimidating. It doesn’t have to be. If there’s anyone who has it down, it’s Keith Pescosolido, head recruiter at Drift who helped build their robust tech team from the ground up. After talking to Keith, we got a pretty good idea of what makes a good cold outreach email, so we did the hard part for you and made some templates for every occasion.

 

1. THE SIMPLE REACH OUT


Subject: Catching up

Hey [Person],

It’s been forever! How’s it going at [their company]? [Drop a quick one liner on what has changed at your company since last connecting].


This cold email works for people you’ve reached out to before, but haven’t talked to in a while. It accomplishes two things: It re-establishes a friendly connection, and it subtly gets to the candidate’s feelings about their current position or if they’re seeking a career change.

 

2. THE ATTENTION CATCHER


Subject: Coffee with [founder/manager’s name]

Hey [Person],

Hope everything’s going well! Just wanted to reach out because [your company] is growing really fast, and we just added a couple [their college] students/alum to our team! Our [position & name of HM] would love to buy you a coffee or beer after work, or just hop on a hangout to chat.

Let me know!

[Your name]


This email keeps it friendly and fun, but by letting the candidate know that you’re growing fast, students from their college are working there, and that your HM is specifically interested, you’re showing that also shows the candidate that your company is offering a valuable opportunity that should be taken seriously. 

 

3. THE CRED-BUILDER


Hey [Name],

Happy [Friday/holiday etc]! I know I’ve reached out a few times already, but it’s my job to stay in touch with promising candidates.
I just wanted to get in touch so that [your company] stays on your radar. Any chance you’d be up for grabbing coffee or jumping on a google hangout with our [founder/manager]?  Super informal, just to hear more about what we’re building here.
You can check out a little more about what we’re up to here [link]. [Or add quick Cliff notes section — “Cliff Note: Founded by HubSpot Engineering execs, 15 million in funding, 40 employees (70 EOY), and over 30k Orgs using the product within a year of launch].

Please let me know! 🙏

Thanks,
[your name]

PS –  Our current team is made up of [alum from relevant & notable companies]


This email keeps it friendly and human-sounding, but also emphasizes your company’s value. The link in the email should be whatever current story about your space is most compelling — even if it’s a competitor getting funding, because that shows market growth. Adding third-party articles and material about your company or the industry you’re in proves you’re the real deal. Then, to close it, throw in some of your team’s past experience to hammer the credibility home.

“I sometimes send a P.S. email right after the original email so they know I’ve spent time on the outreach and it’s not automated. The “Cliff Note” section is always good because the prospect gets a quick snapshot of the company” – says Keith.

 

4. THE REMINDER


Hey [Name],

I know I’ve reached out several times in the past, but wanted to try again because I’d still love to connect you with [founder/manager]. If you’re interested, the two of you could grab a coffee or drink this week, super informal, just to talk about what we’re doing.

At the very least, it could be good to network 😁

Please let me know.

Thanks,
[Your name]


When you’ve repeatedly sent emails to a promising candidate, it’s important to keep the same energy and openness you had when reaching out the first time. Sometimes, it just takes a change in circumstance on the candidate’s end for them to start considering your company. Acknowledging the fact you’ve reached out several times in a light-hearted manner keeps it casual and inviting. Then, re-emphasize you’re just so interested you can’t give up. It’s flattering, and also shows your belief in the candidate’s value.

 

THE BOTTOM LINE

Whoever you’re reaching out to, here are your basic rules to live by:

  • Know who you’re talking to
  • Build credibility
  • Be friendly
  • Be authentic
  • Persistence is key

Use names. Invite them out for coffee or a drink. An email that reads more like a text message will keep the ‘cold’ out of cold outreach. And a couple emojis never hurt 👍

 

You can read more recruiting tips from Keith himself here.

 

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