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Matt Cavallaro, built for Datadog's ANZ higher-ed book.
Enterprise AEs now need to be AI-native to keep up with their customers. This site shows how I work: my track record, my territory, and the tools I use to run it.
01 · Proof
Numbers pulled straight from the CV.
What people say
Matt is the example of the tech salesperson for today that I tell everyone about. He is knowledgeable and consultative. He feels like an extension of our team. While we know his goal is for us to buy from him, he is always working with us to help us achieve our goals. He opens doors for us and has enabled us to be successful even when it isn't directly tied to him selling. This has built a deep trust in our organisation.
Chief AI Officer, University of New England
Matt opens doors most sellers can't, especially in education. He got us in front of the president of the largest university in the US, and he builds his own prototypes to prove value instead of waiting on anyone else. He's a true enterprise seller who brings an energy and enthusiasm to his work that made him a joy to have on the team.
Former manager, monō ai
Matt is the person the rest of us went to when we needed to understand a new product. He learns faster than anyone I've worked with, and he builds markets other reps wouldn't touch.
Peer, Salesforce
Matt didn't sell us software, he helped us rethink how 17 schools could run as one. He built the roadmap with us, stayed with it long after the contract was signed, and he's still someone I call.
Co-CEO, Christian Education Ministries
02 · The Fit
Mapped directly to the JD's “About You” bullets.
Enterprise closing & quota discipline
Consecutive years above 200% on multi-year targets at Salesforce, 140% new logo attainment, and 107% in my best full year, with deal sizes from $50K to above $250K ACV and $750K-$1M TCV.
For Datadog
Trained in Sandler and running deals in MEDDPICC, so the forecasting discipline is already there. The muscle transfers to whatever qualification framework Datadog runs.
Market creation & pipeline build
Opened the independent and Catholic K-12 segment for Salesforce, not by prospecting harder into an existing list: hosted regular community events to convene schools, then built out a solution with an SI partner that was the missing link in the Salesforce product stack. That work opened up an estimated $25M+ market across independent and Catholic schools on the Australian East Coast, plus 140% New Logo Attainment in a newly expanded Tier-1 university and TAFE territory.
For Datadog
This is the exact bar the JD sets for breaking into a newly formalised higher-ed segment: not filling a quota against an existing patch, but building the go-to-market motion, events, and partner capability for a market that doesn't exist yet.
State, local, and education new-logo wins
Not an adjacent vertical translated in: this is the vertical. The last two years at Salesforce were spent moving that education foundation up into Tier-1 Universities, large TAFE systems, and K-12 school systems, landing the first 3 Education Cloud enterprise implementations live across ANZ.
For Datadog
A Strategic AE for Higher Education who already has the relationship map, the procurement rhythm, and the stakeholder language for this exact buyer set across NSW, VIC, and QLD.
Technical fluency, built not borrowed
Builds AI prototypes that replace static architecture slides for technical decision-makers, and hand-builds real infrastructure discipline into his own tools: rate limiting, monitoring, and a custom retrieval layer, not just the sales narrative around them.
For Datadog
Not observability-specific expertise, that's honestly still new ground, but proof of the same builder instinct and speed of ramp he'd bring to closing that gap fast: comfortable with real infrastructure, not just repeating a deck.
03 · Technical Fluency
Ask me something. Really.
This is a real, streamed chat, not a scripted demo, grounded on a small retrieval layer over this résumé and this plan. I'm not pitching myself as an observability engineer: I'm showing you I understand why observability matters, because I hand-built the same discipline into this site's own infrastructure. Rate limiting to protect it from abuse, a “last verified” check that actually runs on a schedule instead of a date I forgot to update, and a retrieval layer that answers honestly when it doesn't have grounding, the same way I would in a deal review.
Pick a question below, or ask your own.
04 · Partners
Partners are how one AE becomes a sales team.
I learned early at Salesforce that one AE can only cover so much ground. Build a partner network and you've built your own sales team: more reach, more credibility, and more ways into an account.
- 01
Opened a new segment with partners
Opened the independent and Catholic K-12 market at Salesforce by recruiting hungry SI partners, convening schools into a recurring forum, and building out a solution with a partner that was the missing link. Result: $3M+ pipeline and $700K ACV.
- 02
Used partners to open doors
Leveraged a strong AWS field relationship to build my own relationships at TAFE NSW during its move off on-premise infrastructure, worked alongside GSIs on enterprise accounts, and established Salesforce's partnership with the HEDx higher-ed community.
- 03
Matched partners with each other
Paired a small partner's innovative product with a larger SI's account access to open a conversation with one of the largest Catholic dioceses in ANZ. Neither could have got there alone.
- 04
Trusted enough to be brought inside
Those relationships went deep enough that a Salesforce partner now has me helping grow its ANZ footprint. I've seen partnering from both sides of the table.
Featured partner
HEDx: a trusted adviser to the sector's leading community
- Built the HEDx relationship at Salesforce, establishing the partnership, then brought it with me to monō ai.
- Got us to the HEDx conference both times. It generated millions in pipeline for both companies.
- Used the conference to open a deal with Western Governors University, the US's leading digital-native university, by researching its president and showing up to every session he spoke at.
- Now a trusted adviser to the HEDx leadership team.
HEDx podcast
EP 198. Why trust is our social capital for change
Co-hosted with Kivanch Oner, CIO of the University of Nevada, Las Vegas
For Datadog
For Datadog higher ed, it's the same play: co-sell with AWS on the Sydney region, work the HEDx community and the ed-tech integrators already inside universities, and bring in the GSIs running modernisation work across the sector.
05 · Territory & Relationship Map
Nine ANZ higher-ed relationships, built the way this role actually asks you to build a territory.
Not cold research: these are existing relationships from Matt's Tier-1 University and TAFE work at Salesforce and his higher-ed work at monō ai. One is already a Datadog customer to expand and reference; the rest are whitespace. Several are hybrid institutions actively transitioning workloads to the cloud, exactly where this role is built to unlock territory.
Monash University
VICGroup of Eight, multi-campus research-intensive
- Relationship
- Covered Monash at Salesforce, its largest higher-ed account in Australia by annual order value, working with procurement, the CIO and the development team on new licences and contracts.
- Datadog entry angle
- Observability across a genuinely distributed research-computing and student-systems estate: the kind of multi-campus complexity that makes a single pane of glass a real unlock, not a nice-to-have.
The University of Sydney
NSWGroup of Eight
- Relationship
- Met with the Chief Information and Digital Officer while at monō ai, and worked alongside the Deloitte team consulting extensively across the university's executive team.
- Datadog entry angle
- A CIO/CDO-level modernisation story: aligning observability investment with an institution-wide cloud migration the same way Matt aligned Education Cloud adoption to it.
UNSW Sydney
NSWDatadog customer · anchor account
Group of Eight
- Relationship
- Account Matt managed directly at Salesforce, including UNSW's procurement and IT governance process, then at monō ai held discussions on UNSW's digital transformation with a key adviser and member of the university's governing council, alongside the architecture consultant shaping its future state.
- Datadog entry angle
- Already a Datadog customer and a public one: UNSW's platform team has presented at Datadog Summit and Datadog Live Sydney on making reliability a shared priority for engineering and leadership. The play is expansion and reference: grow the footprint across a hybrid cloud and on-prem estate, and let UNSW's story open the rest of the sector.
University of Technology Sydney (UTS)
NSWInnovative Research Universities, tech-forward
- Relationship
- Relationship built through NSW higher-ed territory coverage; UTS's own reputation as a technology-forward institution made it a natural fit for modern platform conversations.
- Datadog entry angle
- UTS actively invests in its own engineering and DX culture, which makes a developer-experience-led observability pitch land faster here than at a more traditional institution.
University of New England (UNE)
NSWRegional, largest distance-education cohort in Australia
- Relationship
- Relationship built covering NSW's regional and distance-education institutions, where digital delivery isn't a side channel, it's the core operating model.
- Datadog entry angle
- Reliability of the distance-education platform itself is existential for UNE's operating model: an outage isn't an inconvenience, it's thousands of remote students locked out, which makes uptime observability a direct business-continuity conversation.
TAFE NSW
NSWLargest VET provider in Australia, state-wide multi-campus network
- Relationship
- Direct relationship from Matt's state-wide public-sector and TAFE territory work at Salesforce, covering TAFE NSW's cloud and digital-delivery footprint across dozens of campuses.
- Datadog entry angle
- A state-wide, multi-campus network is exactly the fragmented-footprint problem Matt has already solved once for a flagship account spanning dozens of sites, just at public-VET scale: land on one platform team's footprint, expand campus by campus.
Western Sydney University
NSWGrowth university, multi-campus across Sydney's western growth corridor
- Relationship
- Relationship built through NSW territory coverage of Western Sydney's rapidly growing student population and multi-campus expansion.
- Datadog entry angle
- A growth institution expanding physical and digital footprint simultaneously needs observability that scales with it, a timing-driven entry point tied to its own expansion roadmap.
James Cook University (JCU)
QLDRegional, multi-campus (Townsville, Cairns, Singapore)
- Relationship
- Facilitated discussions directly with JCU's Vice-Chancellor at HEDx, alongside Salesforce's Head of Education Cloud.
- Datadog entry angle
- A genuinely distributed, cross-border campus footprint (regional Queensland plus an international Singapore campus) makes centralised visibility a concrete technical need, not an abstract pitch.
Queensland University of Technology (QUT)
QLDAustralian Technology Network, applied/industry-focused
- Relationship
- Covered QUT at Salesforce while working the entire national education territory alongside the education leader during a period of vacant seats; QUT's applied, industry-partnership-driven culture makes it a natural fit for enterprise platform conversations.
- Datadog entry angle
- QUT's industry-partnership model and applied-research computing footprint make a platform-engineering-led pitch (reliability, developer velocity) resonate more than a pure IT-operations angle.
This territory map is built from Matt's own relationships across ANZ higher-ed, carried over from his Tier-1 University and TAFE coverage at Salesforce and his higher-ed work at monō ai, not cold research. It's also backed by real partner and hyperscaler relationships built the same way: AWS solutions architects, the HEDx higher-ed community, and the ed-tech integrators and GSIs already running modernisation work inside these institutions. UNSW is the anchor: an existing, public Datadog customer and the natural reference for the rest of the sector.
The other 8, last checked against Datadog's public customer page: 2 Nov 2026 · none listed there (automated weekly check; public pages don't show every customer)
06 · 30-60-90
What I'd actually do with the first quarter.
Days 1-30
Map the territory
- Formalise the relationship map from this site into active account plans: an expansion and reference plan for UNSW, and new-logo plans for Monash, Sydney Uni, UTS, UNE, TAFE NSW, Western Sydney Uni, JCU, and QUT.
- Map Datadog's partner surface in ANZ higher-ed: AWS/Azure/GCP Marketplace relationships, GSIs, and ed-tech integrators already inside these institutions.
- Build the first account plans using the same relationship/segment/entry structure as this site's Territory Map section.
- Shadow SE-led technical conversations to calibrate where I can run point vs. where I still need one.
- Start Datadog's CAUDIT registration and shape a sector-wide offer, so universities can buy through a recognised, pre-vetted path instead of a fresh tender each time.
- Lock in HEDx sponsorship for 2027, using my relationship with the HEDx leadership to secure time with the CIOs, CDOs and Vice-Chancellors who attend.
Days 31-60
Build pipeline
- Convert the top relationships into active outreach: multi-threaded, targeting both a technical buyer (Platform Engineering, SRE) and an economic buyer (CIO, CDO) per institution.
- Stand up the first co-sell motions with identified hyperscaler and GSI partners on 2-3 accounts.
- Get the first qualified opportunities into MEDDPICC-disciplined pipeline with real close dates.
- Universities Australia Solutions Summit (23-24 February 2027, Canberra): pre-book meetings with VCs and senior leaders from target accounts, and follow up within the week.
Days 61-90
Prove the model
- First deals in late-stage evaluation with named economic buyers and validated technical champions.
- Refine the account-planning template based on what actually worked in the first 60 days.
- Lock in Datadog's presence at THETA 2027 (23-26 May, Melbourne Convention and Exhibition Centre), the sector's main higher-ed technology conference: submit an abstract with UNSW on reliability and AI governance, and plan exhibitor meetings with target accounts.
- Ramp toward full quota carrying, validated pipeline coverage in place for the next two quarters.
Let's talk about the ANZ higher-ed book.