Gonzalo (Glo) Maldonado
Founder | CTO | AI Infrastructure Engineering | C-Suite Mentor
At $2M-10M valuation, infrastructure decisions compound for 18-24 months. I've made every mistake—so you don't have to.
- • Yammer: 1B+ events/sec (acquired $1.2B)
- • Nextdoor: IPO-scale infrastructure
- • 5 exits across 20+ years
15-30 minutes, no obligation
INFRASTRUCTURE DECISIONS AT SEED→SERIES A COMPOUND FOR 18-24 MONTHS
Technical Debt Spiral
You chose fast-to-market over scalable. Now you're rewriting core systems during fundraising.
AI Strategy Paralysis
Everyone says 'add AI.' No one explains which problems AI actually solves at your scale.
Leadership Transition
You're still writing code. Your team needs strategy. Investors want a leader.
Hiring Under Pressure
Series A closes. You need 10 engineers. You've never hired at scale before.
20+ YEARS SCALING INFRASTRUCTURE
Companies
- • Yammer (acquired $1.2B by Microsoft)
- • Nextdoor (IPO 2021)
- • 5 total exits
Scale
- • 1B+ events/sec (Yammer)
- • 100M+ users (Nextdoor)
- • Series A → IPO twice
Expertise
- • Infrastructure architecture
- • AI/ML strategy & implementation
- • Technical leadership transitions
- • Vibe-engineering (culture design)
"At Yammer, we hit 1 billion events per second before most CTOs had heard of event streaming. We made every infrastructure mistake—Kafka before it was stable, microservices before containers, distributed systems before observability tools existed.
I don't sell solutions. I teach you the frameworks for making infrastructure decisions that compound for 18-24 months—the window where you can't afford to rewrite core systems."
—Gonzalo Maldonado
TRACK RECORD
Former CTO & Co-Founder, Mocksi
Backed by a16z Speedrun, Character Labs, Deftly, Upside Partnership
5 Exits
Yammer → Microsoft $1.2B, Nextdoor IPO. Do.com → Amazon, Gixo → OpenFit, Must Win → Lyric
Scaled Nextdoor 200% in 2 months
Global infrastructure during COVID surge as SRE
Re-architected Yammer push notifications
1B+ events/sec, 10s → 80ms delivery
Created first Terraform provider for OCI
Oracle Cloud Infrastructure
Built Kubernetes/Mesos hybrid at Cisco
100% OSS Heroku-like platform, ahead of its time
Available for full-time roles, advisory & strategic partnerships
Deep experience in large-scale distributed systems, AI infrastructure, SRE, and engineering leadership.
WHO I WORK WITH
Startup CTOs
CTOs at $2M-10M companies
- • Infrastructure scaling
- • AI strategy implementation
- • Technical leadership
- • Team building
Typical engagement: 3-6 months
Fortune 500 Leaders
VPs/Directors at enterprises
- • Vibe-engineering practices
- • Cross-team alignment
- • Culture transformation
- • Velocity at scale
Typical engagement: 6-12 months
VC Portfolio Support
Partners supporting portfolio
- • Technical diligence
- • CTO coaching
- • AI/infrastructure strategy
- • Leadership transitions
Typical engagement: Ongoing
Minority Mentorship
Underrepresented engineers
- • Career navigation
- • Technical growth
- • Leadership pathways
- • Community support
Subsidized or sponsored
RECENT ENGAGEMENTS
DiagnoVet
Problem
Founder building veterinary AI diagnostic platform. Exploring B2C approaches. Needed business model refinement and YC application strategy.
Solution
Advised on premium subscription structure, ambassador program for feedback, and market positioning. Recommended Latin America as testing ground (less regulation).
Outcome
Established clear YC application path. Connected to UC Davis veterinary student market. Delivered MVP development timeline framework.
Nevara AI
Problem
$200k ARR traction but needed deck positioning for fundraising in competitive AI sales space. VCs liked founders but wanted more differentiation proof.
Solution
Repositioned from "AI assistant that works" to "AI copilot for salespeople." Restructured competition narrative around coaching vs monitoring. Recommended $500k-1M bridge round.
Outcome
Delivered deck review and memo format examples. Connected to VC network for warm intros after memo refinement.
Polis
Problem
Strong founders, $100K ACV verbal LOIs. Needed pitch refinement for A16Z Speedrun (20,000 applications → 60 selected). Lacked structured presentation.
Solution
Applied Sanscourier evaluation criteria (talent/traction/trends/transgression). Coached on 3-2-1 framework. Multiple pitch practice sessions with detailed deck review.
Outcome
Prepared team for A16Z Speedrun video interview. Established ongoing coaching through application process. All three founders participated.
HOW IT WORKS
Discovery (15-30 min)
Free discovery call. We discuss your current state, pain points, and whether advisory makes sense.
No obligation. No sales pitch.
Engagement Design (Week 1)
If we're a fit, we co-design the engagement:
- • What problems are most urgent?
- • What outcomes define success?
- • What's the timeline and budget?
Typical engagements: 3-6 months, $15k-30k/month
Execution (Ongoing)
Weekly check-ins, async Slack support, frameworks delivered, code reviews as needed.
You get clarity, velocity, and infrastructure decisions that compound for 18-24 months.
SCHEDULE YOUR DISCOVERY CALL
15-30 minutes, no obligation. We'll discuss your current infrastructure challenges and whether advisory makes sense for your company.
business@sanscourier.ai
Based in San Francisco Bay Area
Available for remote & in-person engagements