Gregory Osmond

Revenue operator building AI-powered sales systems and shipping production software end-to-end.

I am a revenue operator skilled in full-cycle sales and GTM strategy, who also designs and builds the underlying AI tooling.

Gregory Osmond

Profile

With no engineering background, I ship production software using modern stacks, bridging the gap between sales and technology. My work spans from leading certification prep businesses to launching complete web products solo.

Introduction

About Me

How I work

I operate as a sole revenue owner, managing the entire sales cycle while simultaneously designing and deploying the AI tooling that powers the pipeline. Comfortable on both sides of an AI sale, I can write the pitch and build the demo.

I ship production software end to end, leveraging React, TypeScript, Supabase with RLS, n8n automation, and Claude API agents, even without a formal engineering background. My focus is on creating systems that drive revenue and efficiency.

Experience

  1. HR Certification Advisor

    September 2024 — Present

    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, serving a member audience of roughly 2.2 million.

    Managed the entire certification prep line solo: prospecting, discovery, tailored proposals, close, renewals, and expansion, without SDR or sales engineer support.

    Built a personal AI sales OS from scratch for lead triage (HOT/QUALIFY/DEAD), a browser-agent CRM bridge for automated CRM updates without an API, and a draft-only email workflow ensuring human approval for every AI-written reply.

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

    Developed CertDesk, an internal outreach review console (Lovable, Supabase with RLS, n8n, Gmail), establishing a system of record for sales motion instead of relying on spreadsheets.

    Produced a gamified interactive lead magnet for marketing and social, and scoped a six-phase API and MCP roadmap as requested by the founder.

  2. Founder

    January 2026 — Present

    Independent AI Products

    Designed, built, shipped, and sold complete web products solo using AI-native development.

    Launched PitchPage (pitchpage.co) in May 2026: a self-serve resume-to-pitch-page builder on TanStack Start and React, featuring 16 themes, optional AI intro video, and a paid publish flow. Expanded its application from job seekers into real estate, college/university applications, and athletic recru

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

    Created Foundry: an AI pre-sale engine generating live Claude-powered account teardowns, publishing shareable per-prospect pages, and firing webhooks into n8n, Apollo, and HeyGen, complete with email auth and row-level security.

    Standardized a repeatable delivery pattern across projects, enabling product launches from idea to live with billing in days.

  3. Owner and Operator

    2021 — 2025

    Hospitality and Childcare Ventures

    Owned and operated a bar and restaurant, and a daycare as an expatriate in San Juan del Sur, Nicaragua, managing staffing, local vendor relationships, and daily P&L in a second-language market.

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

  4. Co-Founder

    2015 — 2022

    DCWD (Durham Customwood Decor)

    Co-founded a direct-to-consumer home decor, furniture, and gift brand, scaling it from inception to national reach across Canada before partnering and selling.

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

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

    Achieved 20,000+ social followers with zero paid promotion, leading to national television and magazine features based on organic strength.

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

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

  5. Occupational Health and Safety Specialist

    July 2008 — February 2012

    Lanterra Developments Ltd.

    Served as a Certified Health and Safety Representative on high-rise construction sites.

    Conducted daily inspections, ensured OHSA compliance, managed hazard mitigation, performed worker onboarding and training, and coordinated Joint Health and Safety Committees across multi-trade projects.

Skills

Claude API agents Prompt design Context design MCP servers Claude Code AI-assisted development workflows HeyGen ElevenLabs n8n Cloud (14+ production workflows) Webhook orchestration Email pipelines Lead enrichment Apollo React TypeScript TanStack Start

By the Numbers

~2.2 millionMember audience (HR.com)HR Certification Advisor
14+Production n8n workflowsIndependent AI Products
20,000+Social followers (organic)DCWD

What People Say

Greg jumped in, learned quickly, and has already begun offering thoughtful, creative, and agile ideas that challenge us to think differently. Thank you for jumping in with both feet and already making such a positive difference. We're lucky to have you on the team.
Peer nomination, Embrace and Drive Change Award · HR.com, July 2026

Let's talk

Interested? Get in touch — I reply quickly.

Gregory Osmondpitchpage.co/p/greggy-i99tn

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