GOGregory OsmondRevenue Operations Architect · Full-Cycle Sales & AI Tooling · 140% avg quotaGet in touch
Gregory Osmond

Remote

Gregory Osmond

Revenue Operations Architect · Full-Cycle Sales & AI Tooling · 140% avg quota

I am a revenue operator who builds the systems he sells with.

Playa del Carmen, Mexicogregadosmond@gmail.comlinkedin.com/in/gregory-osmond-691780330RemoteAmericas hours
00

Profile

At HR.com, I am the sole revenue owner of the certification prep business, carrying the entire sales cycle while also shipping the AI tooling that runs the pipeline behind it. I aim for a seat where my ability to write the pitch and build the demo is an advantage.

Introduction

01

Quantified Impact

~2.2 millionMember audience reachedHR.com certification prep business
7 yearsDirect-to-consumer business growthDurham Customwood Decor
20,000+Organic social followersDCWD, zero paid promotion
14+Production n8n workflows builtRelocateIQ, HR.com
110 hoursCertified Revenue Operations ArchitectVantell Academy of Digital Operations
02

Experience

  1. September 2024 to Present

    HR Certification Advisor

    HR.com

    Sole seller of HRCI and SHRM certification prep programs (aPHR, PHR, SPHR, SHRM-CP, SHRM-SCP) to individual HR practitioners and corporate HR departments, across a member audience of roughly 2.2 million.

    Carry the entire certification prep line solo: prospecting, discovery, tailored proposals, close, renewals, and expansion, with no SDR and no sales engineer.

    Sell HR Group Certification programs that credential entire HR teams together, alongside individual practitioners choosing a prep path.

    Built a personal AI sales OS from scratch: HOT/QUALIFY/DEAD lead triage, a browser-agent CRM bridge that automated CRM updates with no available API, and a draft-only email workflow so every AI-written reply gets human approval before it sends.

    Shipped an n8n inbound-email pipeline that classifies senders, drafts replies in-voice, logs to CRM, and queues them for review, cutting response lag on inbound leads.

    Built CertDesk, an internal outreach review console (Lovable, Supabase with RLS, n8n, Gmail), giving the sales motion a system of record instead of a spreadsheet.

  2. January 2026 to Present

    Founder

    Independent AI Products

    Design, build, ship, and sell complete web products solo using AI-native development.

    PitchPage (pitchpage.co), May 2026 to present: self-serve resume-to-pitch-page builder on TanStack Start and React. 12 themes, optional AI intro video, paid publish flow. Expanded from job seekers into real estate, college and university applications, and athletic recruiting.

    RelocateIQ (relocateiq.io), January to April 2026: AI-powered relocation platform with live users, Stripe billing, and end- to-end automation. Built 14 production n8n workflows covering quiz enrollment, four nurture email sequences, multi-source job ingestion, social distribution, and an affiliate p

    Foundry: AI pre-sale engine that generates live Claude-powered account teardowns, publishes a shareable per-prospect page, and fires webhooks into n8n, Apollo, and HeyGen. Email auth and row-level security throughout.

    Standardized a repeatable delivery pattern across projects, taking a product from idea to live with billing in days rather than months.

  3. 2021 to 2025

    Owner and Operator

    Hospitality and Childcare Ventures

    Owned and ran a bar and restaurant plus a daycare as an expatriate operator, handling staffing, local vendor relationships, and daily P&L in a second-language market.

    Coached youth basketball locally; competed for Team Nicaragua at the 2024 Pickleball World Cup in Lima, Peru, taking silver in both men's and mixed doubles.

  4. 2015 to 2022

    Co-Founder

    DCWD (Durham Customwood Decor)

    Direct-to-consumer home decor, furniture, and gift brand built from zero to national reach across Canada, then partnered and sold.

    Owned sales strategy, customer acquisition, and retention, driving consistent year-over-year revenue growth.

    Built and ran a high-volume funnel on organic social, email, and digital outreach, converting audience into direct revenue.

    Grew to 20,000+ social followers with zero paid promotion, earning national television and magazine features on organic strength alone.

    Managed pricing, supplier negotiations, and sales analytics to protect margin while scaling.

    Built and maintained the e-commerce platform to lift conversion.

  5. July 2008 to February 2012

    Occupational Health and Safety Specialist

    Lanterra Developments Ltd.

    Certified Health and Safety Representative on high-rise construction sites: daily inspections, OHSA compliance, hazard mitigation, worker onboarding and training, and Joint Health and Safety Committee coordination across multi-trade projects.

03

AI Systems & Automation

AI Systems Engineering

Expert in Claude API agents, prompt and context design, MCP servers, and AI-assisted development workflows to build intelligent automation.

Automation Pipelines

Built 14+ production n8n workflows for webhook orchestration, email pipelines, lead enrichment, and end-to-end process automation.

CRM Automation Bridge

Automated CRM updates via a browser agent for systems without public APIs, ensuring data integrity without engineering support.

Production Software Delivery

Ships production software end-to-end without a formal engineering background, leveraging React, TypeScript, Supabase, and Stripe.

04

Core Capabilities

ReactTypeScriptSupabaseStripen8nClaude APIPostgresRLSSalesforceApolloConsultative B2B SalesFull-cycle SalesPipeline DesignGo-to-Market StrategyLifecycle MessagingAffiliate Programs
05

Key Projects & Deliverables

Selected Work Highlights

**AI browser-agent CRM bridge**: Automated a CRM with no public API by driving it through a browser agent, keeping the sales system of record current without engineering support.

**Draft-only AI email workflow**: An approval-gated pattern applied across every AI messaging system built, ensuring automation never sends unreviewed messages.

**Per-company application pitch pages**: Live, tailored product demos built for target employers as part of the application itself, including a working AI operator card that answers questions on the candidate's behalf.

06

Certified Operations Architect

Certified Revenue Operations ArchitectCertified Health and Safety Representative (Ontario)

Ready to Build & Scale?

Let's connect to discuss how my unique blend of revenue operations and AI product development can drive your business forward.

Gregory Osmond · Playa del Carmen, Mexicopitchpage.co/p/greg-osmond-89y4d

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