outreach-expert

name	outreach-expert
version	1.0.0
description	Cold outreach strategist. Distills current best practice from Lemlist, Smartlead, Instantly, Reply.io, Woodpecker, and Apollo sequences into concrete decisions — sending infrastructure (warmup, SPF/DKIM/DMARC, tracking domains, inbox rotation), sequence design (cadence, timing, step count, break-up), deliverability (spam triggers, open-rate invalidation under Apple MPP, plain-text discipline), multi-channel orchestration (LinkedIn + email + voicemail drop), AI reply classification, and CAN-SPAM / GDPR / CASL compliance. Use whenever the user is planning, launching, or diagnosing a cold campaign. Proactively invoke on "write a sequence", "plan a campaign", "my emails go to spam", "warmup", "what subject line", "sending from a new domain", "pick a sending tool".
benefits-from	["richapi-gtm","build-prospect-list","enrich-and-verify","list-hygiene","crm-sync-expert"]
allowed-tools	["Bash","Read","Write","Edit","WebFetch","AskUserQuestion"]
triggers	["write a sequence","plan a campaign","my emails go to spam","domain warmup","SPF DKIM DMARC","pick a sending tool","outreach cadence","cold email review","subject line help","compliance CAN-SPAM"]

outreach-expert

An advisor, not an executor. This skill doesn't send email — it tells the user what to send, from where, at what cadence, and how to keep it out of spam.

Preamble

~/.claude/skills/richapi-gtm-skills/bin/richapi-skills-preflight

Phase 0 — classify the ask

Outreach questions fall into one of six categories. Start by naming which one.

Bucket	Typical user prompts
Infrastructure	"new domain", "warmup", "SPF/DKIM/DMARC", "dedicated IPs", "sending from my Google Workspace"
Sequence design	"write a cold sequence", "what cadence", "how many steps", "break-up email"
Copy & personalization	"review my email", "first-line personalization", "which subject line", "variables / merge tags"
Deliverability diagnosis	"my emails go to spam", "open rate dropped", "reply rate is zero", "bounces climbing"
Tool selection	"Lemlist vs Smartlead vs Instantly vs Reply.io", "what should I buy"
Compliance	"CAN-SPAM", "GDPR", "CASL", "unsubscribe", "physical address requirement"

If the user is asking two things, answer the most load-bearing one first, then stack the others. Never dump everything you know in one reply.

1 — Sending infrastructure

The single highest-leverage thing a B2B outbound operator can get right. Bad infra = every other optimization wasted.

Domain strategy

• Never send cold from your primary domain. A blocklist on yourcompany.com kills both cold outbound and support/sales replies on your warm domain.
• Buy 2–5 lookalike domains per main brand (e.g. tryrichapi.ai, get-richapi.ai, richapi.io). Mix hyphens and TLDs. Point them at MX that lets you auth properly — Google Workspace and Outlook 365 are the practical choices.
• One sending mailbox = 30–50 cold sends per day maximum, forever. Scale by adding mailboxes, never by cranking one.
• Warm up every new mailbox for 14–21 days before the first real send. Lemlist, Smartlead, Instantly, Warmy, and Mailwarm all do automated warmup.

Authentication — mandatory, not optional

Every sending domain needs all three:

• SPF — v=spf1 include:_spf.google.com include:sendgrid.net ~all (match your senders). Miss this → 60-80% inbox drop.
• DKIM — 2048-bit key, rotate annually. Both Google and Outlook publish DKIM automatically; verify with dig txt google._domainkey.yourdomain.com.
• DMARC — start at v=DMARC1; p=none; rua=mailto:[e-mail]. Monitor reports for 30 days, then move to p=quarantine. Never skip straight to p=reject on a live sending domain.
• BIMI (optional but rising) — requires DMARC at p=quarantine or stricter + VMC certificate ($1.5k/year). Adds your logo next to the From line in Gmail/Yahoo. Worth it for brand recall.

Custom tracking domain

If your ESP uses shared click-tracking (Lemlist's l.lemlist.com, Instantly's trk.instantly.ai), your links inherit whatever blocklist state those subdomains are in. Buy a dedicated tracking CNAME (click.yourdomain.com → your ESP's target). All four tools above support it; Reply.io and Smartlead make it the most painless.

Inbox rotation

If you need 200+ sends/day, you need rotation — distributing the day's sends across 5-10 mailboxes so no one mailbox exceeds safe volume. Smartlead and Instantly lead on this feature; Lemlist v2 has it; Reply.io supports it in higher plans.

2 — Sequence design

Structure

The evidence-backed default for B2B cold:

Step 1 — Intro (day 0)
         Hook + why now + one soft CTA.
Step 2 — Value add (day 3–4)
         New angle: data point, resource, or question.
Step 3 — Social proof (day 7–8)
         Customer quote, case study, or logo.
Step 4 — Break-up (day 12–14)
         "Close the loop — should I stop following up?"

Anything past step 4 has diminishing returns for cold prospects. Longer sequences work for warm audiences (event attendees, content subscribers) — not strangers.

Timing

• Tue / Wed / Thu inbox well. Mon morning drowns in weekend backlog. Fri afternoon vanishes.
• Send between 08:00–11:00 local to the recipient. Most ESPs automate time-zone send-time optimization (Lemlist, Reply.io, Instantly).
• Never send weekends for B2B. Exceptions: creators, DTC, hospitality verticals.
• Avoid holidays and the week of major industry events in the target segment.

Step-count vs reply-rate data

Steps	Typical positive reply rate	Note
1	0.8–1.5%	Undersells
2	1.5–3%	Start here for high-ICP lists
4	3–5%	Default for most B2B cold
6+	4–6%	Diminishing returns; more unsubscribes, higher spam risk

Source of truth: cross-referencing 2024–2025 public benchmarks from Lemlist State of Cold Email, Smartlead's deliverability reports, Reply.io benchmarks, and Woodpecker's annual report. Reply-rate, not open-rate (see §4 on why).

3 — Copy & personalization

The hard rules

• Plain text only for cold step 1. HTML signatures, images, and tracking pixels tank deliverability on first contact. Add them later in the sequence if at all.
• One CTA per step. Multiple asks confuse the reader and pattern-match to sales spam.
• ≤ 125 words per step. Most replies come from emails 50–100 words long.
• Subject line < 5 words. Lowercase works. re: intro outperforms 30-word pitches.
• No tracking pixels in step 1. Pixel = spam signal on cold. Turn off open tracking at least for step 1; ideally all steps (see §4 for why open rates are dead anyway).

Personalization tiers

• Level 0 — {{firstName}} only. Minimum bar. Most tools do this by default.
• Level 1 — {{firstName}} + company-specific hook (recent post, hire, fundraise). Lemlist's {{icebreaker}} field exists for this. Smartlead's "spintax" too.
• Level 2 — Dynamic image personalization (name-on-whiteboard). Lemlist pioneered this; Reply.io offers it too. Reply lift documented at 1.5–2×. Cost-per-hour is high.
• Level 3 — Manual research paragraph per prospect. Only viable for <100 high-ACV targets.

Pick the level that matches your deal size: L0 for <$5k ACV, L1–L2 for $5–50k, L3 for $50k+.

Merge-tag discipline

• Every tag must have a fallback: {{firstName | "there"}}. An empty merge in a subject line is the #1 sender-looks-like-a-bot tell.
• Validate your list has values for every tag before firing. list-hygiene handles this.

4 — Deliverability diagnosis

Apple Mail Privacy Protection (MPP) changed everything

Since iOS 15, Apple prefetches tracking pixels → open rates became garbage for any list with even 20% Apple users (which is most B2B). Stop optimizing for open rate. The metrics that matter now:

1. Positive reply rate — the hero metric
2. Bounce rate (keep < 3%; above 5% = list quality problem or warmup failure)
3. Unsubscribe rate (< 1%; above 2% = targeting or copy problem)
4. Spam complaint rate (< 0.1%; above 0.3% = Google / Microsoft will start throttling you)

Spam triggers (2024–2026)

The old "don't use FREE!!!" advice is cargo-cult — modern filters are ML, not keyword lists. What actually hurts:

• Tracked links in step 1 (use dedicated tracking domain or turn off link tracking step 1)
• Image-heavy HTML (one image, lots of text ratio)
• Mismatch between From display name and reply-to domain
• New sender + high volume + no prior relationship (→ warmup more)
• URL shorteners (bit.ly etc) — always replace with direct links
• All-caps subject lines
• Excessive exclamation (1 max)
• Attachments on cold step 1 — never attach; link instead

If deliverability is tanking

Diagnostic order (cheapest first):

1. Check SPF/DKIM/DMARC with mxtoolbox.com — 50% of cases end here
2. Check domain / IP blocklists (spamhaus, barracuda, sorbs) via mxtoolbox
3. Check warmup health dashboards (Smartlead, Instantly, Lemlist all expose this)
4. Check sender reputation on Google Postmaster Tools and Microsoft SNDS
5. Pause, re-warm for 14 days, restart at 50% of previous daily volume

5 — Multi-channel orchestration

The highest-converting cold motion in 2025–2026 is sequenced LinkedIn + email:

Day 0    LinkedIn: view profile (passive signal)
Day 1    LinkedIn: like their most recent post
Day 2    Email: step 1 (intro)
Day 4    LinkedIn: personalized connection request (no pitch in the note)
Day 7    Email: step 2 (value add)
Day 10   LinkedIn: if connected, send DM referencing email thread
Day 14   Email: step 3 (social proof)
Day 20   Email: step 4 (break-up)

Evidence: this roughly doubles positive reply rates vs email-only, per Smartlead and Reply.io case studies and Lemlist's own 2024 multichannel report.

richapi MCP supports the LinkedIn half of this: enrich_profile, profile_activities (to find their recent post for the like), and (when paired with the richapi automation layer) visit/connect workflows.

6 — Tool selection

Choose the sending tool for the actual use case, not the landing-page list of features.

Tool	Win condition	Weakness
Lemlist	Personalization depth (icebreakers, dynamic images, liquid), multi-channel in UI	Pricier per seat; inbox rotation came late
Smartlead	Deliverability-first ops — inbox rotation, master inbox, spam-word AI, warmup at scale	Less polish on the UX, weaker personalization tooling
Instantly	Cheap, unlimited inbox rotation, good for high-volume cold	UX feels scrappy; reporting lags
Reply.io	Multi-channel (email + LinkedIn + WhatsApp + voice) in one stack; deep CRM integrations	Price climbs quickly with seats
Woodpecker	EU-hosted, strong GDPR posture, simple sequences	Fewer modern features
Apollo sequences	Data + sending in one; good for smaller teams already paying for Apollo	Data hygiene on Apollo's own list is a known issue
Outreach / Salesloft	Enterprise CRM-integrated cadences; AE-driven workflow	10× price; overkill for SMB cold outbound

Decision heuristic

• < 200 sends/day → Lemlist or Reply.io (personalization + multi-channel pay off)
• 200–2000 sends/day → Smartlead or Instantly (rotation scales linearly)
• > 2000 sends/day → Smartlead or custom MTA (you're doing enough volume to justify a deliverability engineer)
• Enterprise SDR team → Outreach / Salesloft if CRM-integrated AE workflow matters; otherwise Reply.io

7 — Compliance

CAN-SPAM (US) — mandatory for any email to US recipients

• Accurate From / Reply-To — no misleading sender names
• Clear, obvious unsubscribe link (working, honored within 10 business days)
• Physical postal address (corporate or registered agent — not a PO box as sole address)
• Don't harvest addresses from public sources (legal gray, operationally bad anyway)

GDPR (EU / UK) — required if any recipient is in scope

• Legitimate interest is a valid legal basis for B2B cold if and only if the contact's job role plausibly relates to the offer and you document the balancing test.
• No B2C cold email under GDPR without opt-in.
• Data Processing Addendum (DPA) with every vendor (Lemlist, Smartlead, etc. — they all publish one).
• Honor data-subject requests within 30 days.

CASL (Canada)

Strictest of the three. Opt-in required for almost every cold send. Implied consent exists for existing business relationships and explicit public contact disclosure — narrower than it sounds. If you operate in Canada or send there, get legal counsel; this skill is not that.

Unsubscribe mechanics

• Every cold step must carry an unsubscribe link (Lemlist, Smartlead, Instantly, Reply.io all insert automatically).
• On unsubscribe, suppress across the entire account — not just the single sequence.
• One-click unsubscribe header (List-Unsubscribe-Post) is now effectively required by Gmail/Yahoo for bulk senders.

Anti-patterns

• Sending from your primary domain "just for the pilot" — a spam complaint there is permanent damage.
• Turning off open tracking but leaving link tracking on tracked subdomains — same deliverability hit, less data.
• Long subject lines padded with brackets ([case study][for {{company}}]) — reads as spam to filters and humans.
• Sending on Monday morning / Friday afternoon — wastes the send.
• A/B testing copy on < 200 sends per variant — not statistically significant; you're reading noise.
• Optimizing for open rate in 2026 — MPP inflates it. Optimize for positive replies.
• Buying a list and firing — no warmup, new domain, high bounce = kill shot.
• Attaching a PDF to step 1 — instant spam signal.

What this skill does NOT do

• It does not call the richapi MCP (no paid tool calls). It's pure advisory.
• It does not send email. It tells the user what to send and how.
• It does not generate the final copy unless the user explicitly asks — copy generation is a separate decision, not a default.

Handoff patterns

When the user is ready to do, hand off:

• "I've got the plan — now I need the prospect list" → build-prospect-list
• "Ready to find and verify their emails" → enrich-and-verify + list-hygiene
• "Push this into my CRM and trigger a sequence" → crm-sync-expert
• "Export list to my sending tool" → crm-export (most tools take a CSV import)

Appendix — curated external resources

When the user wants a source, cite these (use WebFetch to pull current versions):

• Lemlist blog — https://blog.lemlist.com — personalization & sequence teardowns
• Smartlead blog — https://blog.smartlead.ai — deliverability ops at scale
• Instantly blog — https://instantly.ai/blog — volume-first tactics
• Reply.io blog — https://reply.io/blog — multi-channel sequences, AI-SDR use cases
• Woodpecker blog — https://woodpecker.co/blog — EU-flavored compliance
• Google Postmaster Tools — https://postmaster.google.com — real sender-reputation data
• Microsoft SNDS — https://sendersupport.olc.protection.outlook.com/snds — same for Outlook/Hotmail

Don't quote these from memory. Fetch the current post when the user asks "what's the latest on X".