▌
Matt Cavallaro, built for Datadog's ANZ higher-ed book.
Enterprise AE who unlocked a $25M untouched market from zero, then spent his last two years at Salesforce moving that discipline up into Tier-1 universities, TAFE, and public sector. This site is the proof, and it's built to be watched, not just read.
01 · Proof
Numbers pulled straight from the CV. No rounding up.
02 · The Fit
Mapped directly to the JD's “About You” bullets.
Enterprise closing & quota discipline
100% median quota attainment over 5 years at Salesforce (vs. <50% team average), with consecutive years above 200% on multi-year targets: well clear of the $800k+ direct sales goal and $50k+ average deal size this role asks for.
For Datadog
Same forecasting discipline, run through MEDDIC and Command of the Message instead of MEDDPICC. The muscle transfers, the framework just gets Datadog's own name on it.
Market creation & pipeline build
Created a brand-new market for Salesforce in education from zero, not by prospecting harder into an existing list: hosted regular community events to convene an entire untapped sector, then partnered with an SI to build the exact capability missing from the Salesforce product stack to actually capture it. That work opened up an estimated $25M+ untouched market across the Australian East Coast that had never been meaningfully worked, 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 formalized 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 state-wide public-sector districts, 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 Create 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 · Partner & Ecosystem Motion
I've run this exact motion before: mid-tier partners, a hyperscaler, and GSIs, all in one ecosystem.
The innovation engine
A mid-tier partner ecosystem that became the land-and-expand lever.
Built out an entire mid-tier partner co-sell motion in education that became an innovation engine for the wider edu market: enterprise accounts landed and expanded by leveraging the tech solutions those partners built, not by Salesforce selling direct.
Maps to Datadog
Maps directly to activating Datadog's Solution and Technology Partner ecosystem in ANZ higher-ed: recruit a bench of ed-tech and campus-IT integrators already modernizing legacy university infrastructure, and let the observability retrofits they build create the wedge into a Strategic account.
Hyperscaler co-sell
Direct collaboration with AWS on enterprise accounts.
Worked directly with AWS on enterprise accounts, aligning cloud infrastructure modernization with institutional procurement and deployment timelines.
Maps to Datadog
Maps to Datadog's real AWS, Azure, and GCP Marketplace partnerships, the natural co-sell thread for any university already committed to a hyperscaler for research compute or student-system infrastructure, where Datadog sits on top as the observability and security layer rather than competing with cloud-native tooling.
GSI collaboration & partner-to-partner matchmaking
Filling capability gaps by pairing partners together, not just with the vendor.
Worked with GSIs on enterprise accounts, and proactively forged partnerships between partners, pairing one partner's gap with another's strength, so the ecosystem could keep pace with growing AI demand instead of every gap routing back to Salesforce.
Maps to Datadog
Maps to Datadog's active GSI relationships already running ANZ higher-ed IT modernization work: a differentiated, ecosystem-orchestration skill most AEs don't claim, not just co-selling with one partner at a time, but building the partner network's own capability graph so it can serve a university better than any single partner could alone.
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 territory work at Salesforce, the same mix of existing relationships and aspirational contacts this role's own relationship-map requirement calls for. 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
- Existing relationship built through the same East Coast higher-ed network Matt worked at Salesforce, spanning Monash's Clayton, Caulfield, and Peninsula campuses.
- 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
- Relationship built during Matt's Tier-1 university territory work at Salesforce, covering the institution's cloud modernization and digital transformation stakeholders.
- Datadog entry angle
- A CIO/CDO-level modernization story: aligning observability investment with an institution-wide cloud migration the same way Matt aligned Education Cloud adoption to it.
UNSW Sydney
NSWGroup of Eight
- Relationship
- Existing relationship from the same NSW Tier-1 territory, including exposure to UNSW's procurement and IT governance process for enterprise platform decisions.
- Datadog entry angle
- Security and compliance-forward entry: UNSW's research data governance requirements make Datadog's security and compliance monitoring a natural technical-buyer conversation.
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
- Relationship built through Matt's Queensland regional territory coverage, including JCU's distinctive northern-Australia and international-campus footprint.
- Datadog entry angle
- A genuinely distributed, cross-border campus footprint (regional Queensland plus an international Singapore campus) makes centralized visibility a concrete technical need, not an abstract pitch.
Queensland University of Technology (QUT)
QLDAustralian Technology Network, applied/industry-focused
- Relationship
- Relationship built through Queensland territory coverage; QUT's applied, industry-partnership-driven culture made 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 existing relationships across ANZ higher-ed, carried over from his Tier-1 University and TAFE coverage at Salesforce, not cold research. It's also backed by real partner and hyperscaler relationships across Australian higher-ed built the same way: mid-tier ed-tech integrators, AWS/Azure/GCP account teams, and the GSIs already running modernization work inside these institutions. None of these nine currently appear on Datadog's public customer list (checked live), which reads as genuine ANZ higher-ed whitespace rather than a diligence gap.
Last verified against Datadog's public customer list: 21 Sept 2026 · still none appear on it (automated weekly check)
06 · 30-60-90
What I'd actually do with the first quarter.
Days 1-30
Map the territory
- Formalize the relationship map from this site into active account plans: Monash, Sydney Uni, UNSW, 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 accounts 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.
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 MEDDIC-disciplined pipeline with real close dates.
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.
- Ramp toward full quota carrying, validated pipeline coverage in place for the next two quarters.
Let's talk about the ANZ higher-ed book.