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Leadership · Operations · Applied AI

Grounded in leadership.
Focused on AI.

I’m Massimo Gaifa, Principal, AI Operations at Sinch. I help shape how we identify, engage and support companies building products and services around AI—from targeting and ways of working to testing and launch.

Alongside that work, I build AI applications and explore the technology’s implications for business and society.

Explore the projects

01 / Ideas put into practice

Selected projects

Built to be used.
Designed to make something clearer.

02 / The experience behind the work

Built on years of operating.

Customer success, revenue operations, and operational experience across five major acquisitions. Explore the career behind the projects.

Read my CV (PDF, opens in a new tab)

An AI conversation about my career, leadership, and projects.

03 / Thinking, and everything around it

A little more of my world.

← Selected projects

PlateScore / Behind the build

Make the record easier to read.
Keep the evidence in view.

Choosing somewhere to eat is a simple question. Reading a food-inspection history is less simple: visits happen on different dates, violations have different severity, and a missing county grade does not mean a missing inspection.

The decision that shaped the product

PlateScore brings public records into searchable histories and maps. The important design choice is to keep three things separate: the latest inspection grade, a score that reflects inspection history, and the original county evidence. Each answers a different question.

A small degree symbol matters here. A° is a computed equivalent, not a grade awarded by the county. The distinction stays visible beside the result, with an explanation of the method and a route back to the official records. A cleaner interface should help people understand the evidence without making it look more authoritative than it is.

My role, and where AI helped

I direct the product: the questions it should answer, the distinctions the interface needs to preserve, and the experience of moving from an overview to the underlying record. I use AI coding tools to help turn that direction into working software and refine it through iteration. The inspection evidence comes from county records; it is not an AI assessment of a restaurant.

What this example shows

The work is as much about restraint as simplification. Freshness is visible, the score has an explanation, and inspection history remains available beneath the summary. The next test is whether people can explain the difference between a county grade, a computed equivalent, and a history-based score after using the page.

Explore PlateScore ↗ (opens in a new tab)Read the methodology ↗ (opens in a new tab)
← Selected projects

Arcade Nostalgia / Behind the build

A place for the machines.
And the life around them.

Retro hardware carries memories, but choosing a machine is only half the question. Where does it live? What changes when it is time to play? Can a room feel considered without putting the things you enjoy out of sight?

The decision that shaped the product

Arcade Nostalgia pairs a hardware field guide with room stories. The organizing idea is how people live with the objects: quietly integrated, proudly displayed, or brought out for play. Specifications still matter, but they sit alongside placement, storage, controls, and the transition from everyday room to gaming space.

This mid-century living room concept makes that idea tangible. “At rest” and “In play” show the same setup: the console stays beside the TV, while the wireless controller moves between storage and the coffee table. HDMI and power remain connected behind the TV unit; no controller cable crosses the room.

AI-generated mid-century living room with a Japanese Super Famicom Mini beside the switched-off TV and its wireless controller stored away.
At rest · AI-generated interior concept
AI-generated view of the same room in play: Super Famicom Mini remains beside the TV, with Nintendo’s wireless Super Famicom controller on the coffee table.
In play · AI-generated interior concept
Original design, wireless play. The Japanese Super Famicom Mini uses an 8BitDo Retro Receiver for Classic Edition consoles (opens in a new tab) to connect Nintendo’s official wireless Super Famicom controller for Nintendo Switch Online. The receiver plugs into the console’s controller port, with the front cover open. HDMI and power remain connected behind the TV unit.
AI-generated interior concept, including the TV image. Hardware details are illustrative; this combination has not yet been tested first-hand.

My role, and where AI helped

I set the editorial direction and guide the selection, visual language, and interaction design. AI coding tools help build and refine the site; image generation helps explore device studies and imagined interiors using visual references. The work is in selecting, questioning, and revising those outputs until the experience feels coherent.

The evidence boundary is part of the design. Generated images are labelled; manufacturer-sourced hardware details remain separate. A convincing room image is not a measured installation, a hands-on test, or proof of cable reach. The guide explains those limits and links its sources.

What this example shows

This is a personal-interest project with the same product discipline as the more analytical tools: a clear organizing idea, useful interaction, and care about what the interface implies. The next useful test is whether readers can move from liking a room to identifying what they would need to check in their own space.

Explore the room story ↗ (opens in a new tab)Sources & image notes ↗ (opens in a new tab)

How I think about operations, AI, and what comes next.

Notes from nearly two decades of building post-sale organizations, alongside smaller experiments in applied AI.

Customer Success

Why Customer Success Should Own Its Data

Most CS teams operate on data models they didn't define. That makes it harder to act proactively, and harder to be treated as a commercial function.

Further experiments

Smaller tools and demonstrations behind the same curiosity.

Project

Analytics Dashboards from Normalized Data

A live demonstration on anonymized, randomized data — a dashboard built from messy inputs (Tableau exports, Excel trackers, CSV files) normalized into a single model with AI.

Customer Cohort Dashboard →
Customer Success

Why Customer Success Should Own Its Data

Most Customer Success organizations operate on borrowed data. Health scores built on product telemetry they didn't define. Usage metrics aggregated by engineering teams solving for different questions. CRM fields designed around pipeline progression, not customer outcomes. The result is a function that's accountable for retention, expansion, and increasingly for gross profit contribution, yet has no authority over the inputs that drive those results.

This isn't an access problem. Most CS teams can get to the data they need eventually: after a request to BI, a compromise on definitions, and a lag that makes the insight stale by the time it arrives. The problem is structural. When CS inherits its data model from Product, Sales, or a centralized data team, it inherits their priorities, their assumptions, and their blind spots.

The consequence is predictable: CS operates reactively. It responds to signals someone else decided were important, on a timeline someone else set, using definitions that may not reflect what actually drives outcomes in a specific book of business. A health score that weights login frequency is meaningless when your product is an API. An adoption metric that counts active users tells you nothing about whether the economic buyer, the person who signs the renewal, has seen value.

None of this is controversial in isolation. Most CS leaders would agree with every sentence above. Where it gets harder is the implication: that the fix isn't better dashboards or faster data access, but a fundamental shift in who owns the data model that CS runs on. That shift requires investment, cross-functional negotiation, and a willingness to challenge how the organization has always worked.

Before any of that, though, it requires a more basic decision. One that most companies skip.

What do you actually want from CS?

The question sounds obvious, but the answer rarely is. In practice, CS organizations tend to fall into one of two models. In the first, CS is an education and enablement function: it drives adoption, handles renewals, and serves as a trusted resource for the customer. Expansion and commercial negotiation belong to Sales or Account Management. In the second, CS is a full commercial function that owns net revenue retention, drives upsell and cross-sell, and is accountable for a number.

Both models are valid. But they have very different data requirements, and most organizations never make the choice explicitly. They end up somewhere in the middle, asking CS to surface expansion opportunities without giving it the commercial authority or the data infrastructure to act on them.

In the commercial model, the case for data ownership is direct. If CS is accountable for revenue retention and expansion, it cannot run on data definitions it didn't set. You can't commit to a retention target when someone else decides what "at risk" means at the data layer. You can't forecast expansion when the signals that indicate a customer is ready to grow — consumption patterns, multi-product adoption, stakeholder engagement — are aggregated in ways that serve Product's roadmap, not your pipeline. And in the current environment, where boards and investors have shifted from rewarding top-line growth at any cost to demanding profitable growth, the stakes are higher. CS is increasingly expected to protect and grow not just revenue but gross margin: retain the right customers, expand in ways that don't erode unit economics, and flag accounts where cost-to-serve is outpacing value. That requires visibility into gross profit at the account level, which in most organizations lives in Finance's systems, not CS's.

In the education and renewal model, the argument is less about accountability and more about operational autonomy. CS needs to know which customers are actually adopting in ways that correlate with renewal, not just which ones are generating activity metrics. And even in this lighter model, the problem doesn't disappear; it migrates. Whatever team does own expansion inherits the same data gaps, often with even less context to fill them.

The model a company chooses should shape everything downstream: team structure, comp design, tooling, and above all, who has authority over the data that powers customer decisions.

Where the data actually breaks

Three points of failure show up consistently across SaaS and CPaaS organizations.

The handoff from Sales. When a deal closes, CS typically receives an opportunity record: ARR, contract dates, perhaps expected margin profile if it's lucky, and some unstructured notes. What CS actually needs is different: what was promised in the sales cycle, what use case the customer bought for, who the internal champion is, what their technical environment looks like. That information either doesn't exist in structured form or lives in places CS can't operationalize. In CPaaS, this is compounded by the technical dimension: is the customer integrating via API or a low-code interface? Are they replacing an incumbent, and if so, what's the migration complexity? These details determine the entire engagement model, and they're almost never captured in the CRM in a way CS can use. The result is that CS spends the first weeks of every new engagement doing discovery that should have been completed before the deal closed.

The gap between product telemetry and customer intelligence. Product teams instrument for product decisions: feature adoption, funnel conversion, roadmap prioritization. CS needs customer-level intelligence: is this account's consumption growing or plateauing? Are they broadening across the platform or stuck on a single use case? Did a usage spike come from a seasonal campaign or a new workflow integration? And critically, is this account's gross margin healthy, or is consumption growth masking a cost-to-serve problem? In CPaaS, where COGS can vary significantly by channel and by carrier route, an account that looks like a growth story on revenue alone may be margin-negative on its fastest-growing product line. The raw data may be the same, but the aggregation logic, the time horizons, and the entity model are different. Product thinks in features and endpoints. Finance thinks in consolidated P&L lines. CS needs to think in accounts, use cases, and commercial trajectories, with revenue and margin together.

The consultant playbook problem. Organizations that bring in external advisors to design their CS operating model often receive frameworks built on generalized SaaS best practices. These frameworks assume seat-based licensing, predictable usage patterns, and a customer engagement model that maps to QBR cadences and adoption milestones. In consumption-based or usage-based businesses like CPaaS, these assumptions break down. The metrics that matter, the signals that indicate risk or expansion readiness, and the cadence of engagement all look different. A one-size-fits-all data model applied to a business with fundamentally different economics leads to CS teams optimizing around the wrong signals.

What ownership actually looks like

CS doesn't need to build a data warehouse or hire a data engineering team. What it needs is defined authority over a specific layer: the customer data model that sits between raw telemetry and operational tooling.

In practice, this means CS has authority over how health scores are computed and what signals feed them. CS defines the thresholds and logic for risk and expansion flags, not a BI team interpreting requirements at a distance. CS participates in the instrumentation roadmap so that product telemetry includes the events CS needs, not just the ones Product prioritizes. And the handoff schema from Sales to CS is co-designed, with structured fields that capture what CS needs to operate, not just what Sales needs to close.

This is partnership, but it's structured partnership. Defined data contracts, not standing requests in someone else's backlog. The investment isn't in new infrastructure. It's in governance: clear ownership of who defines customer-facing data models, a process for resolving conflicts when CS's definitions diverge from Sales's or Product's, and executive sponsorship that treats this as an operational priority rather than a tooling request.

The barrier to doing this is also lower than it was even two years ago. Frontier large language models have made it possible for operations-minded CS teams to take fragmented data exports from across the business — CRM extracts, billing files, usage logs, margin reports — and normalize them into structured, actionable reporting without a dedicated engineering sprint. What used to require a BI team and a quarter on the roadmap can now be prototyped in days. The bottleneck is no longer technical capability. It's whether CS has permission to access the raw data in the first place, and the organizational standing to define what it means.

The objection will be that this creates duplication and competing definitions. The reality is that competing definitions already exist — they're just implicit. CS already maintains its own spreadsheets, its own health score overrides, its own shadow tracking of which accounts are actually at risk versus what the system says. The choice isn't between one clean data model and a fragmented one. It's between fragmentation that's invisible and ungoverned, and fragmentation that's visible, intentional, and managed.

The cost of not deciding

Companies that leave CS's relationship to its data undefined pay for it in ways that don't show up on a dashboard. They pay in longer onboarding cycles because CS is rebuilding context that should have transferred at close. They pay in missed expansion signals because the data model doesn't surface them until it's too late. They pay in retention strategies that protect revenue without regard to margin, because CS never had visibility into gross profit at the account level. They pay in analyst and ops time spent stitching together workarounds that shouldn't need to exist. And they pay in the slow erosion of CS's credibility as a commercial function, because a team that can't point to its own data with confidence will always be at the mercy of whoever can.

The starting point isn't a technology decision. It's an organizational one: decide what you want CS to be, then give it the data authority that model requires.

Taste

Retro games, real constraints

I grew up on arcade cabinets and 16-bit consoles, and never stopped. The design economy of early games — doing a lot with very little — translates directly to how I approach operational problems.

What draws me to retro games isn't nostalgia. It's the discipline they demanded. A development team working with 64KB of RAM couldn't hide behind feature bloat. Every sprite, every sound effect, every mechanic had to earn its place. The result was software that was tight, purposeful, and instantly readable. You understood what a game was doing within seconds of playing it.

That same principle shows up in how I think about systems and organizations. The best operating models aren't the ones with the most dashboards or the most process documentation. They're the ones where every element serves a clear purpose, where the signal-to-noise ratio is high, and where the people inside the system can understand how it works without a training manual.

A few things I keep coming back to:

Arcade design. The golden age of arcade games (1978–1985) produced some of the most elegant interaction design ever made. Games like Pac-Man, Galaga, and Donkey Kong had to teach themselves in real time — no tutorials, no onboarding flows. The constraints forced clarity. I think about this when designing onboarding processes and customer-facing workflows.

16-bit consoles. The Super Nintendo and Mega Drive era represented a sweet spot: enough capability to build rich experiences, but not so much that teams lost discipline. Games like Super Metroid and Streets of Rage 2 are masterclasses in pacing, progression, and doing more with less.

The collector's perspective. I maintain a curated collection of original hardware and software. There's something about holding a physical cartridge or sitting in front of a CRT that grounds you in what the designers actually intended. Emulation is convenient, but it strips away context.

Interests & recommendations

Books, ideas, operating principles

Books that connect my interests in leadership, AI and the ways technology changes how we work and imagine the future.

Build book cover

Leadership & building

Build

Tony Fadell

The reality behind making things.

The best book on what it actually feels like to build products and lead teams inside a company that's scaling. Fadell doesn't romanticize it. He talks about the politics, the compromises, and the decisions that look obvious in retrospect but felt impossible at the time. Required reading for anyone who builds things for a living.

About the book: Build (opens in a new tab)
The Thinking Machine book cover

Conviction & long-term bets

The Thinking Machine

Stephen Witt

Belief before the payoff is clear.

What fascinated me was the conviction behind the long-term bets: Nvidia building capabilities before their eventual uses were clear, and researchers persisting with neural networks while waiting for computing power to catch up. It made me reflect on how deeply held beliefs, sustained over years, can shape the world. The portrait of Huang also raises an uncomfortable question about leadership: how do we distinguish the intensity that drives progress from the abrasiveness that accompanies it?

About the book: The Thinking Machine (opens in a new tab)
AI Native book cover

AI & organisational change

AI Native

Kai-Fu Lee

AI changes the operating model.

A useful lens on what changes when AI becomes part of a company’s operating model. Its focus on workflows, organisational design and leadership connects closely to my current work in AI Operations: defining ways of working and helping teams move from opportunity to testing and launch.

About the book: AI Native (opens in a new tab)
Neuromancer book cover

Imagination & language

Neuromancer

William Gibson

A future made vivid through language.

Its vision of interconnected digital life and virtual reality feels remarkably prescient. What stands out just as much is Gibson’s language: it makes that world vivid and tangible, with an aesthetic that still resonates today. I recommend it for its technological imagination, its writing and its enduring influence on how we picture the future.

About the book: Neuromancer (opens in a new tab)

From reading to a project

Diverging AI Futures

What happens when leading thinkers disagree about AI?

Seeing AI’s progress up close led me to compare its immense potential with its profound risks. I built this application to bring competing perspectives into a coherent map, making their assumptions, common ground, and disagreements easier to explore.

Explore the public comparison (opens in a new tab)

No account needed for the preview.
Deeper access by approval.

Currently called AI Theory Map.

Also listening

Making Sense with Sam Harris

Long-form conversations about consciousness, ethics, technology, and how to think clearly about difficult problems. The episodes on AI and decision-making under uncertainty are particularly relevant to the work I do.

A design instinct

Products with a clear vision.

Products I admire for their distinctive design and thoughtful execution. Each has a clear idea at its heart—and the care to make it tangible.

Klydoclock with blue textured artwork and a wood case
Klydoclock · Blue artwork

Timekeeping & living art

Klydoclock

An everyday object, made delightful.

Klydoclock brings animated artwork into a familiar form. Its appeal goes beyond telling the time: the physical design and changing art give an everyday object a sense of discovery.

Explore Klydoclock (opens in a new tab)
C64 Ultimate Starlight Edition with a translucent illuminated case

Heritage & modern engineering

C64 Ultimate

Keep the character. Improve the experience.

A recreation of the Commodore 64 hardware using modern FPGA technology, with practical additions such as HDMI and USB. The attraction is the balance: respect for the original experience, with thoughtful improvements for using it today.

Explore C64 Ultimate (opens in a new tab)

What connects them

Clear intent, careful execution, and character worth keeping. Those qualities are what make these products interesting to me—and useful references when I think about what to build or improve.