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I developed the Weekly Invoice as a platform to give back and continue to experiment/learn what works together with you on your business. The only payable is time invested with me in thought experiments of growth.

In ‘26 I am trying (2) new things:
>moving to bi-weekly content, but likely longer (with the exception of when a topic really motivates me)
>alternating between delivering value and adding context

Over the course of the year I will try to color in my learnings, with my story. Especially when it comes to building out modern growth teams.

I realize that one of my unique selling points is my varied background; by continually betting on myself I’ve developed a broad canvas of examples that showcase how growth is common and stealing from alternative industries can set your teams ahead.

Over the past few weeks I’ve been developing this playbook to share with you; based on the Rising Tides and my direct client experiences in ‘25.

State of Outbound 2026: The Definitive Playbook for Modern B2B Pipeline Growth

The era of spray-and-pray cold outbound is officially over.

In 2026, outbound success is built on three non-negotiable pillars:
>pre-qualified prospecting with precise segmentation
>enterprise grade infrastructure
>quick response to intent signals

This playbook synthesizes learnings from fractional CMO engagements, pipeline-building metrics and build predictable, high-quality pipeline.

The Three Pillars of Outbound in 2026

Individualized Prospecting with Strategic Segmentation

Traditional cold outbound treated all prospects the same: build a list, send a message, hope for the best. The results were predictably terrible.

• Cold email reply rates in 2026: 1–5%, with only 0.2–2% converting to sales[1]

• Generic LinkedIn messages: Ignored or deleted within seconds

• Purchased lists: Outdated, misaligned with your ICP, and often unqualified

The friction isn't the channel—it's the lack of relevance.

Intent-Based Outbound vs. Cold Outbound

When I shifted my approach as a fractional CMO, the data became undeniable:

• Cold emails to purchased lists: 0.5% response rate

• Cold direct messages on LinkedIn: 1.2% response rate

• Outreach to prospects showing buying intent signals: 40%+ response rate[2]

That's an 80x difference, driven entirely by timing and context.

When someone posts on Reddit asking, "Looking for a B2B sales tool," they're:

• Actively researching right now

• Open to hearing from vendors

• In the decision phase (likely within 24-48 hours)

• Comparing alternatives

When you send a cold email, the recipient is:

• Not thinking about your category

• Preoccupied with other work

• Skeptical of unsolicited messages

• Likely to delete without reading

Strategic Segmentation: The Foundation of Personalization

To make personalized outbound work at scale, you need to segment ruthlessly. Not everyone is a fit. The best outbound programs create unique ICPs and sub-segments within those ICPs that align with your core offers and industries of best fit.

Here's how to structure it:

Level 1: Primary ICP Definition

• Company size (ARR, employee count)

• Industry vertical

• Geographies where you win

• Typical buyer titles and departments

• Budget indicators

Example: "Mid-market SaaS companies ($2–50M ARR) in vertical software, US-based, with 50–500 employees, where the VP of Sales or Director of Pipeline feels pain from manual CRM workflows."

Level 2: Sub-Segments Within ICP
Once you've defined your primary ICP, create sub-segments based on:

By Use Case/Pain Point:

• Segment A: RevOps-focused (pain = manual processes, bad data)

• Segment B: Growth-focused (pain = inefficient pipeline, low conversion)

• Segment C: Retention-focused (pain = churn, expansion risk)

By Industry Best Fit:

• Segment A1: Vertical SaaS (higher ACV, longer sales cycles)

• Segment A2: Horizontal SaaS (larger TAM, competitive)

• Segment A3: Enterprise software (complex buying, longer deal cycles)

By Buying Stage (Critical for Message Fit):

• Early Stage: No solution in place yet; need educational content

• Active Research: Comparing vendors; need differentiation

• Final Stage: Ready to buy; need pricing, terms, proof
  

Real Case Study: Fractional CMO Pipeline Build

I worked with a series-A SaaS company that was burning through $15K/month on cold email with a 0.8% reply rate. Their mistake: they were sending the same message to everyone—CTOs, CFOs, VPs of Sales, all in companies from $1M to $500M ARR.

What we changed:

1. Defined tight ICP: Mid-market SaaS ($5–50M ARR), US, founders or operators who had previously raised capital

2. Created three sub-segments:

   • Segment A: "Pipeline-focused"—companies showing hiring in sales/marketing roles

   • Segment B: "Scale-focused"—companies that recently raised funding (Series A/B)

   • Segment C: "Retention-focused"—companies with public churn problems

3. Built targeted messaging: Each segment got a completely different email angle, timeline, and CTA

Results:

• Overall reply rate: 3.2% (baseline = 0.8%)

• Qualified meetings: 18% of replies (vs. 4% before)

• Sales-accepted leads: 62% of qualified meetings (vs. 38% before)

• Pipeline generated in 90 days: $1.2M (vs. estimated $280K at old rates)

The math: Better segmentation → Relevant messaging → Higher engagement → Cleaner pipeline.

World-Class Infrastructure 

Why Infrastructure Matters More Than You Think

Most teams buy an email automation platform (like Instantly, Lemlist, or Smartlead) and assume that's "infrastructure." It's not. A platform is where you execute your strategy (sequences, templates, scheduling). Infrastructure is what protects your ability to execute at scale.

The infrastructure reality:

• Teams WITHOUT proper infrastructure see deliverability collapse from 95% to under 50% within 3–6 months of scaling

• Teams WITH infrastructure-first setups maintain 90%+ inbox placement rates month after month[3]

Here's what actually constitutes cold email infrastructure:

1. Domain Management and Rotation

• Separate sending domains (not your main corporate domain)

• Rotation across 5–10+ domains for volume distribution

• Dedicated domain reputation monitoring

• DNS records properly configured (SPF, DKIM, DMARC)

Why: Email providers track domain reputation. If you send 50 emails a day from [email protected], you burn that domain's reputation. With rotation, you distribute volume and reputation hits across multiple assets, keeping each one healthy.

2. Inbox Management and Warmup

• 20–50+ email inboxes across multiple providers (Gmail, Outlook, custom domains)

• Automated warmup process: gradually increase volume from new inboxes before full-scale sending

• Per-inbox volume limits (e.g., 40–50 emails/day per inbox max)

• Inbox health monitoring and cleanup

Why: A new inbox has zero reputation. If you send 500 emails from it on day 1, email providers flag it as spam. Warmup gradually builds reputation so it reaches inbox by week 3–4. This is not optional for scaling above 100 emails/day.

3. Deliverability Monitoring and Diagnostics

• Real-time seed account testing (send test emails to known email addresses and check if they land in inbox vs. spam)

• Bounce analysis and automatic suppression

• Spam trap detection

• Provider reputation tracking (Spamhaus scores, blocklist status)

Why: You can't fix what you don't measure. If 40% of your emails are going to spam, you need to know why—and fast. Monitoring catches issues before they destroy domain reputation.

4. Volume Management and Throttling

• Set daily/hourly volume limits per inbox

• Smart spacing between emails (avoid sending 50 emails in 2 minutes)

• Automatic scaling up (add inboxes as volume grows)

• Provider distribution (don't send 100% from Gmail—mix in Outlook, custom domains)

Why: ISPs flag anomalies. Sudden spikes in volume from a previously quiet inbox look suspicious. Throttling keeps your sending pattern consistent and natural.

Case Study: Infrastructure Saves the Campaign

A B2B sales team I worked with was doing everything "right"—great list, solid messaging, tight ICP. But their reply rate was 1.2%, and bounces were climbing. After audit, here's what they found:

• Sending from: 1 domain, 3 inboxes

• Volume: 300 emails/day across 3 inboxes (~100 each)

• Warmup: None—they went live immediately

• Monitoring: None—they had no idea 35% of emails were hitting spam

What we built:

• 8 sending domains (rotating)

• 20 inboxes across Gmail/Outlook

• Proper warmup for 2 weeks before full-scale sending

• Seed account testing 2x per week

• Per-inbox daily limits (40 emails/day max)

Results after 30 days:

• Inbox placement: 89% (up from estimated 60%)

• Reply rate: 3.1% (up from 1.2%)

• Bounce rate: 2.1% (down from 8.3%)

• Same list, same messaging, same team—just better infrastructure

Intent Signals Trigger Your Pipeline

The New Outbound Formula: Intent In → Outbound Out

Here's the insight that changes everything: outbound isn't about the message you send. It's about when you send it and to whom.

The most sophisticated B2B GTM teams in 2026 are using a simple formula:

External Intent Signal → Sequence Trigger → Multi-Channel Campaign → CRM Signal → Follow-Up

Let me break this down:

External Intent Signals: The Three-Platform Strategy

Intent signals live on three platforms where your prospects are already congregating:

1. LinkedIn (Company and Personal Updates)

Monitor for:

• Funding announcements (Series A/B = 2–5x growth in hiring/spend)

• Hiring announcements, especially in Sales, Marketing, or Ops roles

• Product launches or pivots

• Rebranding efforts

• Executive changes (new VP of Sales or CMO)

• Company milestone posts (X customers, X growth, etc.)

Action: When you see a LinkedIn intent signal, you have 24–48 hours before the market floods them with inbound. Respond with a tailored message that shows you know about the change and how your offer fits the new reality.

Example: "Saw you raised Series B. Typically, teams at your stage optimize sales infrastructure. Curious if you're working on that now or planning post-integration?" (Follow with case study of post-Series B pipeline optimizations)

2. Reddit Communities (Problem Discovery and Solution Seeking)

Monitor subreddits relevant to your ICP:

• r/startups (founders talking growth problems)

• r/cto (engineering leaders discussing tooling)

• r/saas (SaaS operators discussing metrics, challenges, solutions)

• r/sales (sales leaders asking for tools, advice, benchmarks)

• r/growth (growth marketers crowdsourcing tactics)

• Industry-specific communities

Monitor for:

• Direct problem statements: "We're struggling with [X]"

• Requests for recommendations: "Looking for a tool that does [X]"

• Complaints about competitors or current solutions

• Benchmarking questions: "What's a good conversion rate for [X]?"

Action: Respond helpfully (not salesy) with a recommendation, framework, or insight. If the conversation is relevant to your offer, mention it naturally. Include a link to a resource, not a sales page.

Data on Reddit intent: When someone posts, "Looking for a B2B sales tool," they're actively comparing and likely to make a purchase decision within 48 hours. Response rates on these posts: 40%+ (vs. 0.5% on cold email)[2].

3. Facebook Groups (Community Problem Solving)

Monitor Facebook groups where your ICP congregates:

• Industry-specific founder groups

• Operator peer groups

• Function-specific groups (CMO roundtables, CFO forums, etc.)

These are higher-quality intent signals because members are paying to be there and are actively engaging.

Monitor for:

• Direct questions or problems in the group discussion

• Introductions or onboarding posts

• Weekly/monthly discussion threads where members share challenges

Action: Participate authentically in the group. When someone posts a challenge you can help with, respond helpfully. Build your credibility in the group over time. Once you're established, your recommendations carry more weight.

Building the Intent-Triggered Flywheel

Once you've identified external intent signals, the next step is to orchestrate a multi-channel campaign that follows the prospect as they move through the buying journey.

The Sequence (30–45 days):

Day 0–2: Awareness Email (Warm Up to Offer)

• Subject: References the intent signal directly

• Body: Acknowledges what you saw, relates to their situation, provides value upfront

• CTA: Soft (not a meeting—maybe a relevant resource, article, or framework)

• Goal: Get them to open and engage

Example:

Subject: Great news on the funding—quick thought on pipeline timing

Hi [Name],

Saw you closed Series B. Congrats. That's a big milestone.

Here's what I've noticed: 7 out of 10 teams at your stage underestimate how much their sales infrastructure needs to change post-Series B. Growth accelerates faster than your tooling can handle.

I put together a playbook on what to prioritize in the first 90 days—happy to share if useful.

[Link to Resource]

Talk soon

Days 3–5: LinkedIn Soft Engagement

• Connect on LinkedIn (if not already connected)

• Like/comment on 2–3 recent posts

• Don't ask for anything yet

• Goal: Establish presence and familiarity

Days 6–10: Second Email (Social Proof, Specificity)

• Subject: Uses a stat or insight, not another "Re:" line

• Body: Includes a specific data point or case study from similar company, shows you understand their situation better now

• CTA: Slightly warmer—maybe a 15-min intro call

• Goal: Move conversation toward a commitment

Example:

Subject: 3 changes post-Series B (for teams like yours)

Hi [Name],

Quick follow on my last email. I worked with [Company X] (Series B in [Month], similar vertical) through their first 90 post-funding.

They made these changes to their sales process:

All three compounded to 2.5x pipeline growth in their first 12 weeks.

Curious if any of those resonate. Happy to walk through what worked for them.

[Meeting link to 15-min intro]

Days 11–20: Secondary Channel (LinkedIn Messaging)

• Send a message on LinkedIn (not email)

• Personalized to their recent activity

• Maybe reference a post they made

• Keep it human and brief

• Goal: Break through email fatigue with a different channel

Days 21–30: Email + Resource (Value, Not Pitch)

• Case study or specific checklist relevant to their situation

• Position as helpful, not salesy

• Final soft CTA

• Goal: Give them an easy way to engage without feeling sold

Days 31–45: Final Push (Make It Easy to Say Yes)

• Email with a clear, narrow CTA: "Are you open to a quick 20-minute sync?"

• If they haven't engaged, this might be a breakup email

• Or: Invite them to a relevant webinar, event, or content offer

Closing Thoughts on Intent Signals

Intent signals compress the sales cycle by meeting prospects where they are ready to buy, not where you want to sell. The data supports this: Response rates to intent-based outreach are 40x higher than cold outreach when timing is right.

Common Pitfalls and How to Avoid Them

1. Segmentation Theater (Not Real Segmentation)

Mistake: Creating 10 segments but sending the same message to all.

Fix: Each segment gets:

• Different subject lines

• Different email body (tailored pain point)

• Different resources/case studies

• Different CTA (early-stage vs. late-stage prospects need different asks)
  

2. Infrastructure Neglect (The Silent Killer)

Mistake: Setting up campaigns, ignoring domain reputation, then wondering why deliverability collapses.

Fix:

• Monitor seed account testing weekly

• Review bounce rates monthly

• Check domain reputation scores (Spamhaus, etc.) bi-weekly

• Rotate inboxes proactively (don't wait for deliverability to die)
  

3. Intent Signal Waste (Seeing Signals, Not Acting)

Mistake: Finding great intent signals (Series B funding, hiring in sales, Reddit problem posts) but sending generic follow-ups.

Fix:

• Respond within 24 hours of intent signal

• Personalize to the specific signal (mention the funding round, the hire, the problem they posted)

• Use a different angle than competitors (most teams send generic outreach; you send signal-specific outreach)
  

4. Platform Over Infrastructure

Mistake: Buying an expensive platform (Lemlist, Instantly) but running it on weak infrastructure (1 domain, 3 inboxes, no warmup).

Fix:

• Infrastructure first, platform second

• Proper infrastructure is the foundation; platform is the tool

• Budget 70% infrastructure, 30% platform
  

5. Timing Alignment

Mistake: Finding a warm prospect, waiting 2 weeks to follow up.

Fix:

• Intent signals have a half-life: respond within 24–48 hours

• This especially applies to Reddit posts, LinkedIn announcements, and hiring news

• Build processes that alert you immediately when new signals appear

Example Iteration Cycle:

Starting point: Open rate 20%, click rate 4%, reply rate 1.8%

Issue: Subject lines are too generic. Testing shows personalized subject lines (mentioning company name or recent news) perform 40% better.

Change: Implement dynamic subject lines that pull company name or intent signal.

Result after 2 weeks: Open rate 28% (+40%), click rate 6.2% (+55%), reply rate 2.8% (+56%)

Compound effect over 3 months: 2.3x more pipeline from same outreach volume.

The Future of Outbound is Intent-Driven

The old playbook—build a list, send a message, hope for replies—is dead. The future of B2B outbound is:

1. Precise segmentation (know who you're talking to)

2. Enterprise infrastructure (reliable, consistent inbox placement)

3. Intent-first approach (reach people when they're ready to buy)

4. Multi-channel coordination (email + LinkedIn + content + timing)

5. Relentless measurement (iterate, don't spray)

Teams that master this framework will build 2–3x more qualified pipeline with the same budget. Teams that don't will keep getting killed by low response rates and high CAC.

The good news: This isn't rocket science. It's systematized execution, good infrastructure, and respect for your prospect's time.

Start with segmentation. Layer on infrastructure. Add intent signals. Then watch your pipeline grow.

What’s next?

I’m currently building follow up content (for both Linkedin and the Weekly Invoice) on intent signals. 

We’ve been running tests on our offers (and several clients) using Google, Meta and Linkedin intent signaling (think keywording, topics and engagement harvesting) using other people’s content to help identify buyer stage interest within qualified prospects and those falling within our ICP.

I’ll be reporting and following up on that further so make sure you give me a follow ) and check back here for detailed solutions.

I hope you find this information helpful and as always, I’m here to chat if you’d like to discuss your specific growth challenges.

Happy growth,

Grady

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