Practical, automated outbound (via LinkedIn)

A play you can run next week

Hi all —

I’ve been messing around with LinkedIn automations with a few companies, and figured it might be useful to share a couple of practical things I’ve observed that seem to work pretty well.

The promise of LinkedIn is that you have really interesting data in Sales Navigator that can help you prospect quickly & effectively… PLUS, you can use automated prospecting tools that don’t require a huge team.

The downside of LinkedIn? It’s insufferable. Everyone sounds the same in your messaging inbox… which means all your prospects are *wildly* skeptical of any connection requests and messages that come inbound.

Here’s 4-step LinkedIn approach that breaks through the noise and doesn’t take a ton of time. It works for founders and GTM teams.

Step 1: Fix your profile

If your profile says “sales” or “business development” → change it. You want people to accept your connection request… not to immediately ignore it.

See below (hi Nikita) for a good example of a profile I’d actually connect with:

Nikita’s title doesn’t say, “hey I’m a salesperson so get ready for 40 automated and increasingly passive-aggressive emails.” It says something pretty interesting.

Then, treat your LinkedIn profile like a landing page:

I know, mine’s not great, and I look like a goddamn goober in that picture. Sigh. Will fix it eventually. Anyway, few principles:

1. Have a CTA link (the highlighted thing) in your profile that’s tactical. What do they get by clicking the link? Link to a Calendly, landing page, etc.

2. Have a background image that’s similarly tactical. Who are you and why do they care?

Step 2: Figure out how to automate LinkedIn adds and messages

I use a tool called Dripify for this. It automatically adds your perfect-fit customers, and can message them too. There are a ton of different tools you can use though, and they range from $50-$100 per month.

Start by searching for your target customer profile in LinkedIn - upgrade to Sales Navigator for better search criteria, it’s worth it. For example, want to know all the Harvard Business School graduates who currently work as CXOs in utilities? No? Too bad:

You take the LinkedIn URL and paste that into Dripify, so Dripify knows who to connect.

Now, the secret. Usually I see founders make two mistakes:

1. They create way too broad a LinkedIn search (e.g., including any leaders in their target industry)

2. They send an annoying sequence of messages

Do this, and you’ll wind up with a <1% response rate. I’ve seen others with a 20%+ response rate on more targeted messages.

Here’s the experimentation approach I recommend:

Step 3: Experiment by setting up multiple searches & sequences every week

You *can* have a broad search and message running targeting your perfect-fit customer that’s “set and forget.” However, I recommend starting with a portfolio of narrow approaches to figure out what “angle” works.

Here’s a bunch of ways you can slice a broad market into narrow niches:

• Fellow university alums at target companies

• One specific title at a target company (e.g., Marketing Ops at a SaaS company with 11-50 employees)

• 2nd connections of happy customers who fit your ICP

• Companies hiring for a particular role

• New hires for a particular role

• Companies that just raised money

• People who’ve opened an outbound sequence

• Companies that just announced a product release

When you focus more narrowly, you can start a conversation that’s NOT: “Hey let me tell you about our game-changing software.” Instead you can say something like, “Hey I saw you’re connected with Jim at XYZ Corp - we’re working with him on QA automation. Jim’s great!”

My approach to testing these signals:

• Test 2-3 ideas every week manually. Each test takes 30 mins - 1 hour to set up, and should send to a *max* of 100 people. This way you can test each approach with a finite number of contacts to see what really works.

• Check the results regularly, and for particularly effective ones (10%+ response rate, leads to meetings) - double down on that approach!

• Certain approaches require a lot of manual effort (e.g., looking at who’s hiring for particular roles). Do it yourself first, and if it actually drives results, then you can write up a process doc and outsource it to a virtual assistant or hand off to an SDR.

Some tips on sending non-cringey messages:

• Don’t include a message in your connection requests

• Think of your initial messages as “making deposits” rather than “making withdrawals.” (Shoutout to Jay Green for this formulation.) Start conversations, don’t pitch. Examples:

  • Nice to meet you - we work with Jim over at XYZ Corp. Jim’s great!

  • Hey, saw you’re hiring for a QA analyst. LMK if I can help you think that through - have done that a lot.

  • I post about unconventional approaches to B2B sales for startups - would love any tips or tricks you have!

  • Saw you just hired for a QA Eng - congrats! Happy to be a resource as you think through your QA automation timeline & approach.

And then when people respond - have a conversation like a human!

Step 4: Actually post on LinkedIn

Now that you’re adding a bunch of potential customers, why not post interesting content regularly? This might not immediately lead to them buying your product - but do this over 6-12 months regularly and you’ll find you have:

1. A decent-sized following of your ideal customers who want to hear what you have to say

2. Random referrals & speaking opportunities

3. A lot of content that allows you to start conversations in other sales channels

4. Inbound leads on your website that first heard of you via LinkedIn

Do this from your personal profile, not your company’s - nobody’s looking at your company profile on LinkedIn. Posting something 3x per week is the gold standard.

Instead of just randomly posting things that come to mind, you’ll win if you find an interesting angle to post about. An example:

Ross Geiger at Ciro sells to companies that sell to dentists. He’s got interesting data on dental practice websites. So he and his team post cool data about dental practices:

Cool, right? Other things you can do, based on what “angle” works in your automated outreach:

• Companies who are hiring for a particular role

• Certain kind of tips & tricks for a certain kind of person (e.g., customer onboarding tips for CS teams)

• Post website teardowns

Yes, you feel like a total dingo when you start posting on LinkedIn. Do what I did: Commit to doing it for 6+ months and be clear about what you’re NOT going to do (for me, that’s “selfies” and “lowest-common-denominator content”).

Need help? Want to riff? Reach out.