Matt Cavallaro
Enterprise AE selling cloud and AI platforms into Australian education, preceded by fifteen years as an education leader.
mcav09@gmail.com · 0401441949
Executive summary
Enterprise AE selling cloud and AI platforms into Australian education, preceded by fifteen years as an education leader. Five years' field closing experience across mid-market and enterprise, with 100% median quota attainment against a team median below 50% and 140% new logo attainment. Builds pipeline independently: created an entire ANZ K-12 market for Salesforce from a standing start, convening the buying community, shaping the tenders that followed, and generating $3M+ in pipeline where no territory previously existed. Works the hybrid-to-cloud transition directly. Extensive experience working with a range of SI partners and consultants. Hands-on technical fluency across cloud architecture, APIs and AI workflows.
Current role
GTM Lead, Education & Social Enterprises
April 2026 - present
monō ai
- Pipeline from zero: Built and executed a national territory plan across ANZ higher education and public-benefit accounts with no existing installed base, closing early enterprise deals on a path to $1M USD ARR within twelve months.
- Executive access: Reached the president of Western Governors University (300,000+ students) directly, progressing to CIO and CTO on a student retention deployment now in negotiation.
- Partner-led coverage: Working with a partner to solve use cases at UTS shared across the sector and with an external architecture consultant shaping UNSW's future state.
- Technical value proof: Engineered CLI-based, clickable prototypes in place of static architecture slides, demonstrating live application behaviour, API orchestration and workflow visibility to technical decision-makers.
Previous experience
Account Executive, Enterprise Education
Feb 2024 - April 2026
Salesforce
- Higher education portfolio: UNSW, UTS and University of New England alongside TAFE NSW, the largest ANZ Catholic diocese and state-wide K-12 systems across the east coast.
- New logo performance: 94% attainment in a newly expanded territory, 200%+ against multi-year targets, 140% new logo attainment.
- Winning against an incumbent: Won an early tender at University of New England for their AI lab against an entrenched Microsoft footprint; built and sustained the Vice-Chancellor relationship, the only AE on the ANZ team to do so.
- Hybrid-to-cloud pursuit: Partnered with the AWS field team on TAFE NSW's exit from on-premise infrastructure at Villawood, aligning platform value to the migration business case under NSW Government cloud-first direction.
- National coverage under pressure: Covered the entire Australian education territory when the team turned over, identifying and closing a $200K expansion at QUT inside a compressed window by trading capability the customer needed against seats and licences we wanted.
- Market building: Established a Salesforce partnership with the HEDx higher education platform, described internally as the strongest education partnership the team had held; selected to represent the ANZ education team at Salesforce's Education Summit in Chicago.
Account Executive, Mid-Market Education
June 2021 - February 2024
Salesforce
- Built a market with no installed base: K-12 buying in ANZ was organised around student information systems, which Salesforce did not offer. Convened independent and Catholic school groups with the Association of Independent Schools NSW into a recurring forum, brought in a partner who built the missing layer, and the resulting tenders were written around that architecture, generating $3M+ pipeline, $700K ACV and $2M TCV, with deals still closing four and five years on.
- Deal range: Transactional through transformational deals, including land use cases from $50k to above $250K ACV and $750K-$1mil TCV.
- Reference customer: Closed Christian Education Ministries, which expanded across Education Cloud, Slack, Data Cloud, Agentforce and Marketing Cloud over 17 schools to become Salesforce's leading K-12 education reference customer, and a direct influence on subsequent Catholic and Anglican school system tenders.
- Sustained attainment: 100% median quota attainment across five years against a team median below 50%, exceeding multi-year targets three times with consecutive years above 200%, in a territory where no AE had previously cleared 50%.
Earlier leadership & institutional experience
Lead Australia Account Executive (Academic Advisor)
Aug 2020 - Mar 2021
Crimson Education
Director of Student Development & Wellbeing
Jan 2020 - Jan 2021
Knox Grammar School, Wahroonga Preparatory Campus
Head of Positive Education
Jan 2016 - Dec 2019
Knox Grammar School
Head of Year, Geography & English Teacher
Jan 2006 - Dec 2016
Knox Grammar School
Core competencies & technical fluency
Higher education
National coverage experience across universities, TAFE and K-12 systems.
Self-generated pipeline
Repeatable methodology for opening markets with no installed base: relationship mapping, convening buying communities, pre-tender requirement shaping, partner-led coverage.
Hybrid-to-cloud transition
On-premise legacy estates and migration drivers in the sector; joint pursuit with hyperscaler field teams; security, sovereignty and IRAP accreditation as evaluation criteria.
Enterprise deal craft
Multi-threaded engagement across Vice-Chancellors, CIOs, Chief Digital Officers and procurement; negotiating pricing and commercial terms on value and ROI; forecast accuracy across long, multi-stage cycles.
University procurement
RFP and RFT response and pre-tender influence, probity, panel arrangements, ICT and Master ICT Agreements, security and privacy assessment.
Technical fluency
Cloud architecture, API orchestration, CLI prototyping, AI workflow governance; translating technical architecture into business value for technical and executive audiences.
Education
Deakin University
MEd, Leadership and Administration
2016
Boston University
MA, Secondary English
2003
Northeastern University
BA, Psychology & English Literature, cum laude
2002 — Baseball scholarship; Athletes in Service to America (AmeriCorps).