GTM & Operations

DrewGilliam.

Founder and growth operator scaling AI and developer-tooling startups from zero to revenue. 10 + years building GTM engines at the intersection of AI, cloud infrastructure, and engineering productivity.

Current roleStartups GTM — Vercel
Raised$6M+ from top VCs
FocusAI · Cloud · GTM Systems
01

Experience

2025 — Present

Startups GTM

Vercel
2022 — Present

Startup Advisor

RepoScout
2020 — 2025

Co-Founder, Revenue & Product Operations

AutoCloud
2018 — 2020

Head of Growth — AI/ML & Strategic Partnerships

Reply.ai (Acq'd by Meta)
2014 — 2018

Principal Product Manager, iOS & Android

Pangea Money Transfer (Acq'd by ENVA)
2009 — 2013

Sr. Consultant, Product Lead — Emerging Technology Lab

PwC
02

Areas of Expertise

GTM & Growth

GTM Systems

Zero-to-one go-to-market engine design: ICP definition, outbound automation, lead nurturing, and full-funnel revenue motion — from first contact to closed revenue.

GTM & Growth

Growth Engineering

Intent signal-oriented lead-scoring and outbound workflows built on Clay, Apollo, Vector, Intently, Trigify, and Ocean. Engineering rigor applied to pipeline generation.

GTM & Growth

Revenue Operations

Full-stack RevOps across Salesforce, HubSpot, and modern growth tooling — CRM data integrity, pipeline reporting, MQL→SQL process design, and forecasting models.

Cloud & AI

Cloud Infrastructure

Multi-cloud architecture guidance across AWS, Azure, and GCP — OSS commercialization, B2B SaaS security posture, infrastructure visualization, and investment thesis support for operators and VCs alike.

Cloud & AI

AI Adoption

Translating GenAI and NLP capabilities into measurable business outcomes — workflow design, intent customization, and usage telemetry to drive adoption at B2B and D2C teams.

Product

Product Strategy

v1/v2 roadmap definition grounded in market sizing, TAM analysis, and competitive positioning — linking product direction to GTM motion and investor narrative.

Product

Product-Led Growth

Designing PLG motions where the product drives acquisition, activation, and expansion — from onboarding flows and usage-based triggers to converting self-serve users into enterprise contracts.

Product

Product Management

End-to-end ownership of B2C mobile applications — KYC, checkout, Stripe and SWIFT payment rails, growth experiments, and cross-functional execution on iOS and Android.

Operations

Founder Advisory

Coaching early-stage founders on zero-to-one GTM, product pivots, early hiring decisions, and building the revenue motions that outlast the initial burst of traction.

Operations

Fractional Leadership

Fractional COO and GTM strategy for startups and multiple agencies 0 → $1MM Annual (design and engineering) — cross-functional growth operations, production scaling, and leadership when you need an operator without the full-time overhead.

Operations

Tech Due Diligence

M&A technical assessment covering code review, cloud migration analysis, and acquisition risk — built on PE diligence experience across Prairie Capital, Frontenac, and Nautic.

Operations

VC Fundraising & Financial Modeling

Structuring seed and Series A narratives, building FP&A models, P&L forecasting, and board-level reporting. Hands-on experience raising $6.2M and managing ongoing investor relations at AutoCloud.

03

Projects & Ventures

2020–2025 · Co-Founded

AutoCloud

VC-backed ($6.2M Seed) B2B SaaS platform for multi-cloud infrastructure visualization and cybersecurity. Scaled GTM from zero to 7-figure ARR.

Cloud SecuritySaaSAWS · Azure · GCP
2022–Present · Active

RepoScout

Elite engineering talent marketplace. Advising on product strategy, go-to-market systems, and early revenue motion as the platform scales.

MarketplaceEngineering TalentGTM
Advisory Practice

Lambda Consulting

Fractional advisory focused on cloud infrastructure and AI strategy — helping startups and scale-ups navigate technical decisions and GTM investments.

Cloud/AIFractionalStrategy
Founded · Early Stage

HaveMyShift

Early work-shift marketplace connecting service industry workers with flexible shift opportunities — an early exploration of gig economy marketplace dynamics.

MarketplaceGig Economy
04

Writing