Ways to prospect different company sizes

Aaron Reeves, a top-performing SDR, booked 131% of quota for 11 months straight.

The key? Doing outreach based on company size. Here’s how to approach each segment:

1. SMB (small & midsize businesses)

Relevancy at scale is the main priority.

⇢ SMB has a large total addressable market (TAM), so personalization for each prospect isn’t realistic.
⇢ The goal is high-volume outreach while maintaining relevance.

↳ Structure sequences using: Trigger + Persona + ICP

Example: Recently hired sales leaders in 100-200 employee SaaS companies.

2. MM (mid-market)

Prioritize top accounts with more personalization.

• Fewer total accounts means account tiering is critical.

• Split accounts into:
⇢ P1 (5%): High-value, similar to current customers, strong intent (e.g., downloaded resources).
⇢ P2 (15%): Medium-priority accounts.
⇢ P3 (80%): General outreach using the SMB structure.

↳ Personalization should connect to business pain, not just random personal details.

Good sources for research:

• Blogs written by prospects.

• Company fiscal reports.

• Recent product launches.

3. ENT (enterprise)

Balance relevancy with deep personalization.

⇢ Enterprise buyers get bombarded with outreach, so generic triggers won’t work.
⇢ Find publicly mentioned information that ties to their challenges.

↳ Cold outreach alone isn’t enough. Talk to below-the-line (BTL) contacts to understand the company before reaching out to decision-makers.

Prospecting thoughts

SMB is about volume, mid-market requires tiering, and enterprise needs patience and research. Adapt your approach to book more meetings across all segments.

Cold outreach with zero friction

Connor Murray breaks down how to run efficient outbound without wasting time on research.

Build segmented lists, write reusable scripts, and remove friction between calls. You’ll sound personalized—without wasting hours researching every lead.

The result? 70–100 dials per day, less mental fatigue, more booked meetings.

Build segmented lists by role and industry

Pick one ICP segment and go all-in.

Don’t jump between personas or verticals.

• VP of Marketing in Retail

• VP of IT in Healthcare

• Director of HR in Manufacturing

↳ Create a separate list and template for each.

Use the same script for everyone on the list

Cold calls get easier when you don’t switch context.

• Say who you are

• Call out their key priorities

• Explain how you solve them

• Offer to help or meet

↳ Reuse the script for all 100 contacts in the same list.

Email templates should feel targeted, but scale

Structure stays the same—only swap out parts.

• Change outcomes, challenges, or priorities per vertical

• Example: Foot traffic for Retail, campaign efficiency for SaaS

• Keep the tone simple and confident

↳ Write once, send 300+ times.

Use ChatGPT to jumpstart your drafts

Don’t write from scratch. Use AI to get ideas.

• Ask for top outcomes and challenges per title

• Feed in your existing script and ask it to rewrite for a new vertical

• Use it to reword, never to blindly write

↳ It saves hours. Just don’t let it sound robotic.

Avoid unnecessary research

No need to read company websites, blog posts, or LinkedIn bios.

• The ICP + industry combo already tells you 80% of what you need

• Focus on relevance, not personalization theater

↳ More calls. Less stress. Higher output.

Make your opener count by winning fast

Jason Bay shows how top-performing reps get better results during cold calls. It’s not about luck or longer calls—it’s about how you open in the first 30 seconds.

1. Avoid weak openers

Stop using intros that waste time.

⇢ Don’t ask how their day is going.
⇢ Don’t confirm their name—they already know it.
⇢ Don’t start with what your company does.

↳ These make you sound like every other salesperson.

2. Add social proof to your intro

Mention well-known companies you work with.

⇢ Example: “We work with Google, Zoom, and Shopify.”
⇢ Name 2-3 companies your prospect respects.
⇢ If you’re a certified partner (like AWS), say that too.

↳ This builds instant credibility.

3. Schedule regular skill-building activities

Meet bi-weekly for 30 minutes to work on a specific sales skill.

⇢ Choose a skill, like asking good questions or handling objections.
⇢ Role-playing helps you improve and receive feedback.

4. Make it relevant to them

Use something specific about their company or industry.

⇢ Example: “Saw your recent acquisition of _____.”
⇢ Mention something about their role, company news, or market trend.
⇢ Only use facts they care about, so don’t be vague.

↳ This shows you did your homework.

5. Combine social proof with relevance

Use both for a stronger impact.

⇢ Example: “Heard about your new plant in Detroit. We work with other manufacturers like ________.”
⇢ Blend name-drops with tailored research.
⇢ Then ask for 30 seconds to explain why you called.

↳ This sounds confident and direct—not pushy.

6. Keep your ask short and specific

Don’t ask for a full call right away.

• Just ask for 30 seconds.
• Keep your tone casual but focused.
• Make sure the opener earns their attention.

↳ The right start changes everything.

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