BEN HOLLEY · GTM ENGINEER

GTM, engineered.

I build the systems that run go-to-market: signal automations, cold email infrastructure, attribution, and AI workflows. Shipped and used daily by real sales teams. Started on a sales floor, not in a CS program.

What I'm looking for
A GTM-engineering-adjacent role
Remote from Charlotte, NC · Would relocate to SF or Austin for the right offer

[email protected]  ·  727-637-2778  ·  LinkedIn

$1.7M
pipeline influenced in Q2 at AirOps
$700K
pipeline from one lead magnet, in weeks
$1.6M
pipeline in one quarter as an SDR
10+
systems in production
gtm-systems, live pipeline

> ~

1. Job-change signal received...

Title match: VP of Content. Former champion.

2. Finding and verifying their new work email...

Verified. New company: 240 employees.

3. Running the checks...

Not a customer. No open deals. Rep assigned.

4. Enrolled in outreach. Slack card posted to the team.

[ Builds with ]

HubSpot Salesforce EmailBison Lemlist Apollo LeadMagic Claude / Anthropic Slack Vercel Neon Postgres Supabase Trigger.dev Clay Gong Common Room Exa Metabase Python TypeScript Next.js
[ The Work ]

Three pillars.

Everything I built falls into three buckets. Each has its own page with the systems, the diagrams, and what they actually did for people.

Pillar 1

Working with SDRs

The campaigns and automations that fed the SDR team: job-change and job-posting signals, Lemlist lead routing by CRM ownership, reply handling from Slack, and warm intro discovery.

the SDR systems →
Pillar 2

Cold Email

The full "email BTW" program: an AI-operated campaign pipeline with do-not-email rules it can't skip, plus granular deliverability monitoring on EmailBison and EmailGuard.

the cold email program →
Pillar 3

Evergreen Infrastructure

The things that keep producing on their own: a lead magnet that generated $700K in pipeline in weeks, an attribution portal leadership trusts, and the Claude Code operating system underneath it all.

the infrastructure →
[ How It Fits Together ]

One map, every box shipped.

This is the actual mental map of the systems I built at AirOps: every signal, every workflow, every place the work lands, on one chart. Picture your own company's GTM stack laid out the same way, then imagine it a little more connected and a little less manual — this is roughly how I'd go about closing that gap.

flowchart TB
  subgraph Signals["Buying signals come in"]
    CR[Contact
changed jobs] JOBS[Target company
is hiring] REPLY[Prospect replied
or email bounced] LI[Team LinkedIn
networks] end subgraph Systems["Systems I built"] JC[Job-change
auto-enroll] JP[Job posting
bot] PEL[Pelican
reply hub] BISON[Email
health ops] ROUTE[Lemlist
ownership routing] NM[Network
Mine] EMAIL[Campaign
factory] OS[OutboundSync] PORTAL[Attribution
portal] AEO[AEO Scorecard
connector] S360[Strategy360
engine] end subgraph Destinations["Where the work lands"] SEQ[Outreach
sequences] CRM[(CRM: the
shared record)] SLACK[Slack, where
the team works] SCORE[Public scorecard
product] end CR --> JC JOBS --> JP REPLY --> PEL REPLY --> BISON LI --> NM JC --> SEQ JC --> SLACK JP --> SLACK JP --> SEQ PEL --> SLACK PEL --> SEQ BISON --> SEQ BISON --> SLACK NM --> SLACK EMAIL --> SEQ SEQ --> OS BISON --> OS OS -->|writes activity| CRM BISON -->|writes bounce status| CRM SEQ --> PORTAL PORTAL -->|writes attribution| CRM CRM -->|nightly sync| ROUTE ROUTE -->|writes new owner| CRM ROUTE --> SEQ CRM --> NM CRM --> JC AEO --> S360 S360 --> AEO AEO --> SCORE style Signals stroke:#8b5cf6 style Destinations stroke:#10b981 style CRM stroke:#10b981,stroke-width:3px

swipe sideways to explore the full map →

[ The Systems ]

A sampling of what I've shipped.

Not everything, just a representative slice. One line each, and every diagram and detail lives on the pillar pages.

AI Search Readiness Scorecard Public lead magnet scoring companies across ~30 data points. $700K in pipeline in a few weeks. details → Lemlist Ownership Routing Nightly HubSpot-to-Lemlist ownership sync, plus a scoring pipeline that round-robins brand-new accounts. Reps never build campaigns. details → Job-Change Auto-Enroll Past champions get outreach within minutes of starting a new job, with do-not-contact checks built in. details → Job Posting Bot Watches target companies for relevant openings; reps approve AI-drafted outreach in Slack. details → Pelican Reply Hub Interested replies become Slack alerts; reps answer in one click. Nothing dropped, nothing doubled. details → Email Campaign Factory Describe a campaign in a sentence; AI builds the list, writes unique copy per person, validates, uploads. details → Outreach Philosophy Evergreen templates for trigger-based sends, and the fully AI-personalized, modular-line email I never finished building — but think is where cold outreach is headed. details → Deliverability Command Center Per-domain health, provider-level analytics, placement tests, and automated bounce suppression. details → Attribution Portal Human-reviewed campaign-to-deal matching, built before the company had multi-touch infrastructure. Evolved into company-wide linear multi-touch through HubSpot. details → Network Mine Team LinkedIn networks matched against open deals to surface warm introduction paths. Unfinished: never got to the multi-hop version. details → EmailBison vs. SmartLead Why the program runs on EmailBison instead: missed replies, broken webhooks, and per-lead pricing that punishes a real CRM. details → GTM Data Scaffolding Validation statuses, enrichment timestamps, rollback files. The CRM gets better every week. details → Claude Code Operating System The referential context and memory system behind all my work in Claude Code, not just email. details →
[ Career ]

Carried a bag before I built the systems.

Everything I automate, I've done by hand first. That's why the systems work.

FEB 2026 – PRESENT

GTM Engineer

AirOps · Charlotte, NC (remote)

Built the systems on this site: signal automations, cold email infrastructure, attribution, deliverability ops, and AI research products.

  • Influenced over $1.7M in pipeline in Q2
  • Lead magnet I productized generated $700K in pipeline in a few weeks
OCT 2024 – FEB 2026

Head of Growth

Cyft · voice AI for MSPs, backed by Base10

Employee #2 and first sales hire. Helped the team raise $5M from Base10. Built the outbound and channel partner program from the ground up: recruiting, RevOps, brand, trade shows, the sales playbook, strategic partnerships, and a six-figure budget.

AUG 2024 – PRESENT

Unpaid Shill and President of Propaganda

Clay Cafe

Closed, application-only community for GTM engineers, lead gen agency owners, and growth hackers. DM me for the link :)

FEB 2024 – JUN 2025

Content Creator (Freelance)

Clay

Produced social content as a partner for Clay.

JAN 2024 – AUG 2024

Growth

Lightyear · enterprise telecom ML platform

True enterprise outbound, built from the ground up: targeting, messaging, process, and tooling.

  • Booked meetings with 1% of the Fortune 500
  • #1 in outbound sales accepted meetings, H1 2024
NOV 2022 – DEC 2023

Midmarket SDR → Strategic Enterprise SDR

PandaDoc
  • #1 in pipeline generated, Q1 2023 on a 10-person SDR team ($1.6M)
  • #1 in pipeline for May 2023 across the entire 50+ person sales org ($570K)
  • #1 SDR in opportunities created in four separate months
  • Promoted to help pioneer a new enterprise outbound motion
JAN 2022 – NOV 2022

Sales

iMotorsports · #1 Indian Motorcycle dealership in Tampa Bay
  • 116% average quota attainment, over $1.5M sold
  • #1 earner for 40% of tenure
2010 – 2021

A Bunch of Random Jobs

Music education startup · my own recording studio · restaurants · warehouses

I am not afraid of getting my hands dirty, literally. Working these jobs is what makes me great at what I do now. I know how lucky I am to work from home and get paid a good wage. I'm not some trust fund kid who has only ever worked at big SaaS companies and never bussed a table or handled a mop.

Sound like your kind of hire?

Schedule a meeting Contact Me 727-637-2778