What's the Best LinkedIn Outreach Strategy for Early-Stage Startups?

5 min read By Vishesh

What's the Best LinkedIn Outreach Strategy for Early-Stage Startups?

Let’s be honest—when you're an early-stage startup, you don’t have:

  • A sales team
  • A budget for ads
  • A CRM full of warm leads

But what you do have is your founder story, a point of view, and access to LinkedIn—where your buyers already hang out.

So, what’s the most effective, founder-led outreach strategy that doesn’t feel spammy, doesn’t break LinkedIn’s rules, and actually works in 2025?

Let’s break it down.


🔁 The LinkedIn Outreach Flywheel for Startups

Outreach works best when it’s not cold. The most reliable strategy is to build a trust-driven loop:

  1. Post relevant content that your ICP cares about
  2. Get seen by your target audience
  3. Send targeted connection requests to those who engage or fit your ICP
  4. Get higher acceptance rates thanks to the visibility and relevance
  5. Start conversations with warm DMs
  6. Close the loop by sharing those conversations as learnings in future posts

The more you do it, the better your engagement, targeting, and reply rates get.


🧠 Principle: Content Drives Conversion

Founders who write 2–3 times per week:

  • Stay top of mind
  • Build familiarity before outreach
  • 2–3x their connection request acceptance rate

It’s not about going viral. It’s about becoming recognizable and relevant before you DM.


🚀 The 6-Step Outreach Playbook

✅ Step 1: Post Content Regularly

  • Talk about what you’re building
  • Share lessons from conversations
  • React to trends in your ICP’s world

This sets the foundation. You become known before you reach out.


✅ Step 2: Send Thoughtful Connection Requests Daily

  • Prioritize people who engaged with your posts
  • Send 10–15 personalized or semi-personalized requests per day

Optional message:

"Hey Rohan—noticed we’re both in the async work space. Would love to connect and learn from what you’re seeing."


✅ Step 3: Track Who's Engaging

People who like, comment, or view your profile are warm.

Use tools like Jerry to surface these signals without manual tracking.


✅ Step 4: Engage Before Messaging

  • Like or comment on their latest post
  • Acknowledge their perspective
  • Look for shared language or worldview

This makes your DM natural—not random.


✅ Step 5: Send a Contextual DM

Example:

“Hey Priya—loved your post on async onboarding. We're building something similar at Relay—always curious how others are thinking about this.”

Short. Specific. Soft CTA.


✅ Step 6: Revisit and Follow Up

Not everyone replies on Day 1. That’s okay.

  • Track who accepted
  • Follow up after 2–3 weeks with a new post, feature, or insight

🧠 Pro tip: Use your follow-up to share value—not to chase.


❌ What to Avoid

  • Mass connects + immediate pitch
  • Long DM essays
  • Cold emails disguised as DMs
  • Waiting for the “perfect message”—you’ll never send it

TL;DR — Founder-Led LinkedIn Outreach That Works

  1. Post content relevant to your ICP
  2. Send 10–15 connection requests/day to engaged or qualified leads
  3. Warm them up through likes and comments
  4. Send personalized DMs after you’ve shown up
  5. Follow up with value

When you do this consistently, outreach becomes trust-driven—not transactional.


P.S.

We built Jerry to help you run this exact play—daily.

It tells you:

  • Who engaged with your content
  • Who to connect with next
  • What to say
  • And when to follow up

All without breaking LinkedIn’s rules or your voice.

Try Jerry →

Booked 5 demos in 7 days—without cold DMs

Jerry helps founders turn LinkedIn attention into revenue using content + AI—not spam.

  • AI drafts your posts in your voice. Hook → Outline → Boom.
  • Only reach out to leads who actually engage. No more guessing.
  • Inbox-safe. 100% compliant with LinkedIn's Terms of Service.

Loved by founder-operators. No automations. Just results.