GTM Automation — ShiftOS / Holly

Clay → HeyReach → Smartlead, end to end

The automation stack only. No layers, no events, no partner channels — just the machine that takes a list of pharmacy ops leaders and turns them into booked demos on Samantha's calendar.

The stack

Tool	Job	Cost
Clay	List building, enrichment, AI personalization	~$349/mo
HeyReach	LinkedIn outbound	~$79–200/mo per seat
Smartlead	Email outbound + warmup + reply routing	~$94/mo
Google Workspace	Sending mailboxes on lookalike domains	$6/mailbox/mo

All-in: ~$650/mo. One Holly deal pays for it for the year.

HeyReach and Smartlead both fire native webhooks straight to Slack incoming webhook URLs — no middleware needed.

Step 1 — Sender infrastructure (do this first, takes calendar time)

Cold email cannot go from @shiftos.com or @shiftrx.io. You'll burn the primary domain's reputation and break transactional/customer email. Use lookalike domains.

Buy 5 lookalikes

getshiftos.com
tryshiftos.com
shiftos.team
meetholly.ai
holly-shiftos.com

Set up Google Workspace on each

$6/user/mo. One mailbox per domain to start, two if you want more volume later. Use real human names: samantha@, noah@. Never info@, sales@, hello@ — those get filtered before they're read.

Set a forwarding rule on each mailbox → all replies forward to a shared replies@shiftos.com inbox so nothing gets lost.

Authenticate every domain (SPF / DKIM / DMARC)

For each lookalike, in DNS:

SPF — TXT at root:

Host: @
Value: v=spf1 include:_spf.google.com ~all
One SPF per domain only. If one exists, edit it instead of duplicating.

DKIM — generate inside Google first:

admin.google.com → Apps → Google Workspace → Gmail → Authenticate email
Select the domain → Generate new record → 2048-bit
Copy the host (google._domainkey) and the long v=DKIM1; k=rsa; p=... value
Add as a TXT record in DNS, wait an hour
Go back to that Google page and click Start authentication. Until you click that button, DKIM is configured but not active. This is the step everyone forgets.

DMARC — TXT record:

Host: _dmarc
Value: v=DMARC1; p=none; rua=mailto:postmaster@shiftos.com
Start at p=none (monitor mode). After 3 weeks of clean sending, tighten to p=quarantine.

Verify each domain by sending to a personal Gmail → Show original → SPF, DKIM, DMARC all PASS. Then run through mail-tester.com — don't launch any domain that scores below 9/10.

Warm every mailbox in Smartlead

Connect all mailboxes to Smartlead. Turn on warmup the moment the mailbox exists. Settings:

Ramp from 5 to 40 emails/day over 14 days
30% reply rate
Weekday-only sending
Minimum 14 days of warmup before any real cold email goes out

Keep warmup running at lower volume even after launch — it props up reputation indefinitely.

Steady-state sending capacity once warmed: ~30 emails/day per mailbox × 5 mailboxes = ~150 cold sends/day = ~750/week.

Step 2 — Clay (list + enrichment)

ICP filters

Industry:    Retail Pharmacy, LTC Pharmacy, Specialty Pharmacy,
             Compounding, Surgery Centers, Urgent Care, DSOs
Locations:   3–50 (under 3 = no budget, over 50 = procurement hell)
Headcount:   50–1,000
Geography:   US only; prioritize CA, NY, IL, WA, MA (strict labor law = sharper pain)
Tech signal: currently on When I Work, Deputy, Homebase, paper, or Excel

Title filters

Pharmacy Director / Director of Pharmacy / Pharmacy Operations Manager
Director of Operations / COO / VP Operations
DON / Chief Nursing Officer
Scheduling Manager / Workforce Manager
Owner / Principal (independents)

Skip HR generalists, recruiters, IT directors. They are not the buyer.

Target list size: 3,000 verified contacts. That's ~6 weeks of sending capacity.

Enrichment columns (the difference between 1% and 12% reply rate)

In every Clay table, add these columns before exporting:

Verified email — Clay waterfall: Findymail → Datagma → ZeroBounce. Drop anything not Valid.
LinkedIn URL — required for HeyReach.
Number of locations — pulled from Google Maps API or website scrape.
Recent news — funding, expansion, new locations (Clay's Google News integration).
Current scheduling tool (if detectable) — turns into a "ripping out X" angle.
One-sentence company description — Clay's Claude integration generates from the website.
Glassdoor pain signal — Clay AI prompt scans recent Glassdoor reviews for "scheduling," "shifts," "called off," "short staffed." If hits, flag the lead as Tier 1.
Personalized opener — Clay AI prompt that takes columns 3–7 and writes one sentence specific to that company. This is what gets injected into the message as {{personalized_opener}}.

Example computed openers Clay should produce:

"Saw Mercy Pharmacy just opened your fourth location in Sacramento — congrats."
"Three of your techs mentioned short-staffing on Glassdoor in the last quarter — that's exactly what Holly was built for."
"You've been on When I Work for ~3 years from what I can tell — most pharmacy ops leaders we talk to outgrow it around the 4-location mark."

The rule: if the first sentence could be sent to anyone else on the list, rewrite it.

Export

Push to HeyReach via Clay's native integration. Push to Smartlead via CSV (or via Clay's webhook → Smartlead API). Same lead in both, same week.

Step 3 — HeyReach (LinkedIn)

Sender setup

2 LinkedIn profiles minimum. Both need to look like operators, not marketers:

Headline: "Helping pharmacy operators automate scheduling with Holly | ShiftOS"
Pin one Holly demo video and one customer logo wall to Featured
Recent activity in feed (Holly auto-poster — 2x/week, customer wins or short demo clips)

Connect both profiles via the HeyReach Chrome extension (sticky session, fewer flags).

Sending limits — DO NOT exceed

Week 1: 15 connection requests/day per profile
Week 2: 25/day
Week 3+: 50/day, hard cap 100/day

A flagged profile is dead for 30+ days. Don't push past the limits to "test."

The sequence

Day 0  → Connection request + note (<300 chars)
         "Hi {first} — saw {personalized_trigger}. Building an AI 
         scheduler for pharmacy ops, would love to connect."

Day 2  → If accepted: warm intro
         "Thanks for connecting. Quick context — Holly handles 
         call-offs, PTO, swaps, and license tracking for multi-site 
         pharmacy ops. Open to a 15-min look?"

Day 6  → If no reply: value drop
         "Easier to show than tell — 90 sec of Holly handling a 
         shift swap: {video_link}"

Day 11 → If no reply: peer proof
         "We just helped {peer_company} cut 18 hrs/week of scheduling 
         work. Same setup as yours. Worth a quick look?"

Day 17 → If no reply: breakup
         "Last note from me — should I close the loop, or is there 
         a better time to circle back?"

Day 30 → If no reply: warm touch (no message)
         Profile view + post like

Config that matters

Sending hours: 9am–5pm in recipient timezone, weekdays only
Random delays between actions: ON
Skip on out-of-office detection: ON
Stop on reply: ON
Webhook on reply: native HeyReach webhook → Slack #linkedin-replies channel

Step 4 — Smartlead (Email)

Email runs in parallel against the same list, with a deliberate timing offset.

The orchestration rule

LinkedIn connection request fires Day 0. First email fires Day 2. By the time the email lands, the recipient has already seen the LinkedIn notification — open rate jumps 15–25%.

The sequence

Day 2  → Email #1 — short, personalized, single CTA
         Subject: "{first}, quick Q on {company}'s scheduling"
         Body: 4 sentences. {personalized_opener} → problem → 
         one-line Holly pitch → ask for 15 min.

Day 5  → Email #2 — peer proof
         Subject: "how {peer_company} cut scheduling time 60%"
         Body: 5 sentences. Case study + same CTA.

Day 9  → Email #3 — concrete offer
         Subject: "free schedule audit?"
         Body: offer to run a free audit on their current workflow 
         and show where Holly saves time. Low-friction ask.

Day 14 → Email #4 — breakup
         Subject: "should I close the loop?"
         Body: 2 sentences.

Reply branch: pause sequence, route to Slack

Config that matters

Volume: 30/day per mailbox, 5 mailboxes = 150/day
Sending hours: 8am–5pm in recipient timezone (Smartlead supports this — turn it on)
Stop on reply: ON, across all sequences for that lead
Stop on auto-reply (OOO): ON, resume after 7 days
Lead categories: ON (Smartlead auto-classifies into Interested / Not Interested / OOO / Wrong Person / DNC)
Webhooks: EMAIL_REPLY and LEAD_CATEGORY_UPDATED → native Smartlead webhook → Slack #email-replies

Subject line rules

Lowercase first letter (looks human, not blast)
Questions beat statements
Under 50 characters
Use the company name when possible
Never: "free," "guaranteed," "limited time," "act now," exclamation marks. Healthcare spam filters hammer these.

Step 5 — Cross-channel orchestration

Two channels, one list, same person. They have to coordinate or you look like a bot army.

Stop rule

A reply on either channel pauses both. The AE who responds in Slack also pauses the sibling sequence by hand as part of their reply SLA — open the other tool, find the lead, click pause. At 150/day volume this is ~30 seconds per reply and not worth automating yet. Build that automation when reply volume crosses ~20/day.

Dedupe rule

Match leads across channels on LinkedIn URL first, email second. Same person should never get sequenced twice — handle this in Clay before exporting (one master table, two export views).

Reply routing flow

Reply hits HeyReach or Smartlead
Native webhook fires → Slack incoming webhook URL
Slack #replies channel shows: name, company, channel,
   full reply text, link to the lead in HeyReach/Smartlead
AE responds within 30 minutes during business hours
AE manually pauses the sibling sequence in the other tool

Speed-to-reply is the single biggest conversion lever. Going from 4-hour to 30-minute response roughly doubles meetings booked. This is the one SLA the team must hold.

The CTA

One Calendly link, 15-minute slots, M–F 9–4 in Samantha's timezone, 10-min buffers, Zoom auto-attached. SMS reminder 1 hour before. No phone — every intro is video.

Step 6 — Metrics (what "working" looks like)

Per 8-week cycle on a 3,000-account list:

Metric	Bad	Target	Good
LinkedIn accept rate	<25%	35–45%	>50%
LinkedIn reply rate (of accepts)	<8%	12–18%	>20%
Email open rate	<40%	55–65%	>70%
Email reply rate	<4%	6–10%	>12%
Combined positive replies	<1%	2–3%	>4%
Demos booked / positive replies	<40%	60%	>75%
Demo show rate	<60%	75%	>85%

Funnel math at target: 3,000 leads → ~75 positive replies → ~45 demos booked → ~35 demos completed → ~12 pilots → ~6 closed deals per cycle.

Reading the numbers

Accept rate low → LinkedIn profile or connection note is broken. Profile first.
Opens fine, replies low → message body is generic. Sharper personalization in Clay.
Opens low → deliverability. Run mxtoolbox + mail-tester, check warmup status.
Demos no-showing → calendar friction. Cut to 15 min, add SMS reminders, send "looking forward" 1 hr before.

Weekly cadence

Monday — 30 min

Pull last week's metrics from HeyReach + Smartlead
Triage every reply still sitting in Slack
Note the bottleneck stage, pick one fix to test this week

Wednesday — 30 min

A/B review: kill worst variant, double best
Spot-check Clay enrichment quality on the new batch
Confirm warmup is still running on every mailbox

Friday — 15 min

mail-tester.com on each sending domain
Confirm no mailboxes throttled or blacklisted
Push next week's lead batch from Clay → HeyReach + Smartlead

Total operator time once running: ~75 min/week.

Two-week launch plan

Week 1 — Infrastructure

Mon: Buy 5 lookalike domains, start Google Workspace setup
Tue: SPF/DKIM/DMARC on every domain, click "Start authentication" in Google Admin
Wed: Connect all mailboxes to Smartlead, start warmup (14-day clock starts now)
Thu: Clay account, build ICP filter, start enrichment on first 500 leads
Fri: HeyReach account, connect 2 LinkedIn profiles, profile cleanup

Week 2 — Build

Mon: Clay enrichment columns finalized, first 500 leads cleaned and verified
Tue: HeyReach sequence skeleton built, first 100 leads imported
Wed: Smartlead sequences built, same 100 leads imported
Thu: Copy session — write all sequence copy with someone who knows the buyer
Fri: Slack incoming webhook URLs created, plugged into HeyReach + Smartlead native webhook configs, internal test sends to team Gmail accounts, confirm replies surface in #replies correctly

Week 3 — Soft launch

Mon: First 50 leads enter LinkedIn sequence
Wed: First 50 leads enter email sequence
Fri: Review reply quality, deliverability, message tone. Adjust before scaling.

Week 4+ — Scale

100/day LinkedIn, 150/day email
Weekly cadence kicks in
First demos: end of Week 4. First closed deals: ~Week 10–12.