Howard Woodham, Jr.·Sales operator and AI systems builder·Brooklyn, New York·Twelve months as the only salesperson at Looking Glass Factory·Lead sales engineer across 27 enterprise deals·Available May 28, 2026·Howard Woodham, Jr.·Sales operator and AI systems builder·Brooklyn, New York·Twelve months as the only salesperson at Looking Glass Factory·Lead sales engineer across 27 enterprise deals·Available May 28, 2026·
Howard Woodham, Jr. · 2026
Download résumé (PDF)

Howard Woodham, Jr.

I sell things people don’t understand yet.

Four roles. One pattern. Own the number, then build the system that makes the number easier to hit.

Sales is my training. AI agents are my edge. I’ve spent the last year as the only salesperson at Looking Glass Factory, owning the day-to-day sales motion across enterprise, defense, retail, healthcare, and AI infrastructure.

The U.S. operation is winding down. I’m using the transition the way I use everything else — as a forcing function.

Now I’m looking for the next thing: a senior in-house role where I can sell and build, or advisory work helping small businesses deploy AI agents that actually drive growth.

Brooklyn, New York Senior in-house roles Agency advisory

At a glance

Months at quota12 / 12
Enterprise deals27 closed
Markets sold into6 verticals
Sales team headcount1 (me)
Agent pipeline19,000 prospects
Prior product140K users
Output Twelve consecutive months
01

12 / 12

months at quota

Twelve months on quota.

I'm the only salesperson at Looking Glass Factory. Twelve straight months on quota and counting.

02

27

enterprise deals

Lead sales engineer on every one.

I worked alongside the VP of Business Development as the lead sales engineer — positioning Looking Glass hardware into larger customer solutions and running the technical and creative reviews that aligned engineering goals with non-technical business stakeholders.

03

19,000

prospects

Pipeline run by an agent I built.

I built an outbound automation system for prospecting, qualification, and meeting booking across seven industries, replacing most of the manual pipeline work.

Show, don't tell

The system behind the number.

A snapshot of the agentic outbound system I built and the revenue line it helped carry.

Pipeline Operations · Night Watch
● representative

Active queue

0

Prospects remaining

Hourly throughput

0

Forms / hour · 91% ok

This week

0

Meetings booked

Lifetime

0

Booked → calendar

Conversion funnel · trailing 90 days

Submitted

0

Replies

0

11.4% reply

Qualified

0

16.9% of replies

Booked

0

23.4% of qualified

Industry coverage

19,000 prospects · 7 verticals

  • AI Infrastructure
    4,200 38%
  • Defense
    2,100 42%
  • Healthcare
    2,600 24%
  • Animation
    1,400 51%
  • Developer Tools
    3,800 16%
  • Luxury Retail
    1,800 19%
  • Experiential
    3,100 28%
Industry Coverage Count Reply

Live activity

streaming

  • 09:14:02 [REDACTED] / contact OK
  • 09:13:51 [REDACTED] / sales OK
  • 09:13:38 [REDACTED] / .gov WAIT
  • 09:13:24 [REDACTED] / contact RPLY
  • 09:13:11 [REDACTED] / pipeline-form OK
  • 09:12:58 [REDACTED] / contact BOOK
  • 09:12:42 [REDACTED] / partnerships OK
  • 09:12:31 [REDACTED] / sales OK
night-watch · pipeline ops github ↗

Personal monthly contribution

Twelve months on quota.

● representative
$72K
May
$89K
Jun
$76K
Jul
$102K
Aug
$86K
Sep
$88K
Oct
$125K
Nov
$113K
Dec
$64K
Jan
$84K
Feb
$98K
Mar
$108K
Apr
Quota: $60K Twelve of twelve · 100% at quota

$92K

Average month

$125K

Peak month

12 / 12

Months at quota

Form Blaster is a Playwright outbound engine I built. The dashboard reflects pipeline I personally drove. Case studies under NDA.

Where I have operated

Where I have operated.

Six years. Each role closer to the work I’m doing now.

Looking Glass Factory

Sales Operator · AI Systems Builder

Holographic light-field displays · 86″ HLD · Looking Glass Go

I own the day-to-day sales motion from first touch through close, working directly with the VP of Business Development as the only salesperson on the team.

  • → Lead sales engineer alongside the VP of Business Development on 27 enterprise deals — including multiple thirty-thousand-dollar days across enterprise and mid-market accounts.
  • → Positioned Looking Glass hardware into larger customer solutions across six verticals: defense, retail, healthcare, AI infrastructure, experiential, and developer tools.
  • → Ran the technical and creative reviews that aligned engineering goals with the business goals of non-technical stakeholders in marketing, procurement, and security.

Artificial intelligence and automation.

19,000 prospects · seven industries

  • → I built and deployed an AI agent system that automates prospecting, inbound triage, qualification, and meeting booking — replacing most manual pipeline generation.
  • → I designed the data workflows for market mapping, lead scoring, and segmentation typically outsourced to external consultancies.

Defense and intelligence.

I built early business-development pipeline across the defense and intelligence ecosystem, including stakeholders at the Pentagon and major prime contractors, and sourced pursuits of Small Business Innovation Research awards positioning the team for follow-on work.

Feel Good AI

Co-founder. Product and go-to-market.

  • → I co-founded a B2B-to-consumer AI wellness platform and scaled it to 140,000 users — capital-efficient, single-digit-team, distribution through coaches and trainers.
  • → I built and launched the product end-to-end across a regulated vertical, solving cold-start data and distribution challenges.
  • → I owned product, go-to-market, and early hiring while validating a multi-stakeholder distribution model across coaches, trainers, and organizations.

TEKsystems

Account Manager. Enterprise artificial intelligence and machine learning.

  • → I worked enterprise artificial-intelligence and machine-learning accounts at RTX (Raytheon) across engineering and digital-transformation programs.
  • → I helped surface and develop pipeline for multimillion-dollar managed-service opportunities within defense accounts.
  • → I was promoted from Technical Recruiter to Account Manager within seven months.

Dunne Goodwin

Creative Director and New Business.

  • →I led the New York market expansion and built the new-business pipeline from prospect to signed retainer.
  • →I managed creative and strategy across brand, content, and partnerships for mid-market and enterprise clients.
  • →I owned revenue outcomes for the New York office during a multi-quarter growth phase.

The roster

Brands I have worked with.

Enterprise accounts I’ve worked sales engineering on.

Deal sizes range from $5,000 developer pilots to $100,000-plus enterprise licenses. Specific case studies and references available on request.

NVIDIA
● AI infrastructure
Pixar
● Animation studio
Accenture
● Enterprise consulting
U.S. Space Force
● Defense
Schrödinger
● Drug discovery
Loro Piana
● Luxury retail
Louis Vuitton × Nike
● Luxury × sport
Esri
● Geospatial
Adobe
● Creative software
Unity
● Game engine
Unreal Engine
● Visual effects

How I work

The toolkit, end-to-end.

Three lanes I work in: closing the number, building the system that makes the number bigger, and shipping with the tools at hand.

A · Sell the thing

Sell the thing.

Carry the number. Translate complexity. Close revenue.

  • Full-cycle enterprise sales
  • Outbound, inbound, and partner-led pipeline
  • Technical demos and multi-stakeholder sales cycles
  • CRM administration across Salesforce, HubSpot, and Pipedrive
  • Conversation intelligence with Gong
  • Account and contact data with Apollo and Clay
B · Build the system

Build the system.

Automate the repetitive work. Keep the human judgment.

  • AI agents and multi-step workflow orchestration
  • Python, LangChain, LangGraph, and Playwright
  • RAG systems, vector databases, and API integrations
  • Browser automation at scale (19,000 prospects shipped)
  • Lead scoring, segmentation, and market mapping
C · Ship with what works

Ship with what works.

Use the tool that gets the job done. Move.

  • Commerce: Shopify and Stripe
  • Data: Airtable, Google Sheets, BigQuery
  • Operations: Slack, Notion, Linear
  • Creative: Figma and Adobe Premiere
  • AI development: Claude Code, Codex, Cursor

Background

Education.

Roberts Wesleyan College — Bachelor of Science, Organizational Management 2014 — 2018

Proof of work.

NVIDIA Inception Program admit — Looking Glass Factory 2025
AI sales agent system — 19,000 prospects across seven industries 2026
night-watch — Playwright outbound automation engine (open-source) 2026
howardwoodham.com — this site, hand-built in Astro 2026

Get in touch

Bring me in when the thing is hard to explain but worth selling.

I’m open to two kinds of work: a senior in-house role where I sell and build, or hands-on advisory for small businesses shipping AI agents that drive growth. New York preferred. Remote considered.

Senior in-house roles Agency advisory for small businesses
Open a conversation
Email me
howie@howardwoodham.com
Or take it offline
Download résumé
PDF · one page
Email
howie@howardwoodham.com
Phone
+1 347 853 3691
LinkedIn
/in/howardwoodham
Available May 28, 2026·Lead sales engineer across 27 enterprise deals·Twelve months as the only salesperson at Looking Glass Factory·Brooklyn, New York·Sales operator and AI systems builder·Howard Woodham, Jr.·Available May 28, 2026·Lead sales engineer across 27 enterprise deals·Twelve months as the only salesperson at Looking Glass Factory·Brooklyn, New York·Sales operator and AI systems builder·Howard Woodham, Jr.·