Matt Cavallaro

mcav09@gmail.com · 0401441949

Summary

Enterprise Account Executive with 5+ years of consistent quota attainment selling SaaS platforms into complex, multi-stakeholder enterprise accounts, and current experience building go-to-market from zero inside an early-stage AI startup. Owns the full sales cycle, prospecting through negotiating and closing complex, C-level enterprise agreements, and has personally stood up a new market from scratch, growing it to $700K ACV, $3M pipeline, and $2M TCV. Genuinely energised by AI as a category: works hands-on in the CLI to build and demo prototypes that bring technical and executive stakeholders to a shared vision, and is looking to bring that founder-level ownership to building out a region.

Current role

GTM Lead, Education & Social Enterprises

Apr 2026 - present

monō ai

Operate as a founding go-to-market contributor at an early-stage AI startup, engineering and executing territory strategy from zero in a high-ambiguity, fast-moving environment.
Pioneer AI-native selling methods: building and deploying custom, clickable prototypes directly in the CLI to accelerate technical and executive buyer alignment, well ahead of typical seller technical fluency.
Partner cross-functionally with engineering and product to shape roadmap around customer needs.
Forge strategic channel and industry partnerships to scale pipeline; on pace to generate $2M ARR within 12 months.

Previous experience

Account Executive, Enterprise

Feb 2024 - Apr 2026

Salesforce

Owned full-cycle enterprise sales, prospecting through negotiation and close, across large, complex accounts spanning the entire east coast of Australia.
Structured and closed complex, multi-stakeholder enterprise agreements with senior executives; delivered 94% quota attainment in a newly built territory, 200%+ multi-year attainment, and 140% new-logo attainment.

Account Executive, Mid-Market

Jun 2021 - 2024

Salesforce

Managed end-to-end strategic growth across a large enterprise account base on Australia's East Coast; maintained 100% median quota achievement over 5 years (vs. <50% team average), exceeding multi-year targets 3x with consecutive years above 200%.
Built an entirely new market from the ground up, $700K ACV, $3M pipeline, $2M TCV, including closing the first three cloud platform customers live in the region.
Recruited and developed a network of systems-integrator partners to support the new market, and worked cross-functionally with marketing and product on regional go-to-market strategy.

Lead AU Account Executive

Aug 2020 - Mar 2021

Crimson Education

Advised and sold directly to individual decision-makers in a fast-paced, target-driven advisory role.

Earlier career

Director of Student Development & Wellbeing

2020 - 2021

Knox Grammar School

Head of Positive Education

2016 - 2019

Knox Grammar School

Head of Year, Geography & English Teacher

2006 - 2016

Knox Grammar School

Nearly 20 years in senior leadership roles managing complex stakeholder relationships, leading teams, and driving organisational change inside large institutions: the foundation for the executive presence and stakeholder management this role demands.

Core competencies

Full-Cycle Enterprise Sales

Prospecting through negotiation and close, MEDDPICC, value-based selling, executive alignment, multi-threaded deal execution.

AI-Native Selling

Hands-on CLI/terminal prototyping, AI/ML workflows, autonomous AI agents, RAG architectures, building live demos that move technical and executive stakeholders together.

Cross-Functional Deal Leadership

Leading teams through major deal processes, systems-integrator and channel partnerships, close collaboration with Product, Marketing, and Customer Success.

Education

Deakin University

MEd Leadership and Administration

Boston University

MA Secondary English

Graduate Assistant Coaching Scholarship

Northeastern University

BA Psychology & English Literature

Cum Laude, Baseball Scholarship. AmeriCorps, Athletes in Service to America (2021-2024)