A CTO’s Playbook: How to ‘Cherrypick’ High-Impact Engineering Wins That Shape Strategy, Roadmaps, and Team Culture

As a CTO, I don’t just manage technology—I hunt for it. My real job? Finding the quiet, undervalued wins that others miss. These aren’t just fixes; they’re strategic moves that shape our roadmap, budget, and team culture. Here’s how I turn engineering into a treasure hunt.

What ‘Cherrypicking’ Really Means in Engineering Leadership

In coin collecting, “cherrypicking” means spotting what others ignore. A 1913 Type 1 3.5-legged Buffalo Nickel isn’t magic—it’s just different. And that difference? Pure value. The same applies in tech. My team and I constantly hunt for hidden engineering treasures: overlooked code, forgotten tools, and skills buried in plain sight. We don’t see problems—we see opportunities.

While others rush to adopt the next shiny tool, we ask: *What’s already working, but no one’s noticed?* Technical debt? Legacy code? Nah. We see misclassified assets—code with untapped potential, tools collecting dust, and people with skills you can’t hire for. It’s not about rewriting everything; it’s about finding what’s already gold.

The CTO’s “Cherrypicking” Mindset

Cherrypicking in tech is all about spotting what others miss and acting fast. We look for:

• Unattributed value: That one script with zero bugs but zero fans? It might be a core platform piece.
• Mispriced labor: The engineer who knows a dying language? That skill could save you six months of work.

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• Legacy modernization with low risk: Some systems aren’t broken—just misunderstood. Fix them, don’t replace them.
• Hidden dependencies: That open-source project with 100 stars but 10,000 users? It’s your next secret weapon.

Take our monolithic Go service. The old team called it “legacy.” We called it “gold.” After a quick audit, we found it was one of our most reliable, well-tested services—just missing docs and metrics. Instead of tearing it down, we cherrypicked it. Added observability, broke it into gRPC modules, and turned it into a shared platform. Saved six months of work and built a strategic advantage.

Strategic Planning: Building a Tech Roadmap Around Hidden Gems

Too many CTOs chase trends. AI, blockchain, serverless—sure, they’re exciting. But the real wins? They’re in what we already have. The code, the tools, the people. That’s where the low-hanging fruit grows.

1. Audit Your Stack Like a Numismatist

Coin collectors don’t guess. They use loupes, UV lights, and years of experience. As CTOs, we need the same precision. Our audits look at:

• Code ownership: Who’s actually fixing bugs, and who’s just “maintaining”?
• Performance: Which service has the best uptime? That’s not luck—it’s potential.
• Library usage: That old Python script used in seven places? It’s a platform, not a prototype.
• Security: Is that third-party tool a time bomb? Find out before it explodes.

We found a Python library marked “experimental.” Written by a contractor, used by seven teams, zero bugs. We cherrypicked it: gave it ownership, added types, and turned it into an SDK. Now it powers our data pipelines.

2. Prioritize Low-Cost, High-Impact Upgrades

Rare coins aren’t always expensive. Some cost pennies. Same in tech. Our best wins come from small, smart changes:

• Add OpenTelemetry to one critical endpoint, not the whole app.
• Swap a slow SDK for a lightweight open-source option (like RedisJSON for caching).
• Pull a stable module from the monolith—make it a microservice.

3. Leverage “Unattributed” Third-Party Tech

We don’t need the most popular tool. We need the right tool. Like coin collectors who find misgraded rarities, we hunt for under-the-radar tech that just works:

• An eBPF-based observability tool that cut our debug time by 70%.
• A niche Wasm runtime for edge functions.
• A PostgreSQL extension that replaced a $10K/month service.

We adopted Vector.dev for logging. Small tool, big impact. Reduced costs by 40%, eliminated three roles. Sometimes, the best “upgrade” is just picking the right tool.

Budget Allocation: Where to Invest (And Where to “Cherrypick”)

Money doesn’t grow on trees. You can’t rewrite everything. But you can find the multipliers—where $1,000 of effort buys $10,000 of value.

1. Target “Junk Box” Projects

Coin dealers have “junk” boxes—coins sold cheap, just change. We have “junk” projects: old tools, abandoned prototypes, “nice-to-have” features. But some? They’re gold in disguise.

Our “junk” CLI tool, written in 2019, had no docs, no tests. But three senior engineers used it daily. We spent $5K to clean it up, added autocomplete, and published it. Now? 70+ engineers use it, saving 200 hours a week. That’s how you turn trash into treasure.

2. Cherrypick Talent, Not Just Skills

Hiring’s expensive. But promoting from within? That’s free. We look for people with hidden skills:

• The backend engineer who built a React dashboard on the side.
• The QA engineer who reverse-engineered a legacy API and documented it.
• The DevOps engineer who automated deployments with Terraform modules.

We cherrypick these people. Give them stretch assignments, pair them with architects, promote them. It costs nothing, builds loyalty, and grows our bench.

3. Outsource the “Common” Tasks

Collectors don’t spend time on common coins. They focus on rarities. Same for CTOs. Outsource the boring stuff:

• Use managed Kubernetes (GKE, EKS)—don’t build your own.
• Adopt third-party CI/CD (GitHub Actions, CircleCI) for standard pipelines.
• Buy security tools for compliance (Wiz, Lacework).

This frees up budget to invest in what matters: AI, custom observability, domain-specific tools.

Managing Engineering Teams: Cultivating the “Cherrypickers”

The best CTOs don’t just find gems—we build teams that find gems.

1. Reward “Scouting” Behavior

Collectors study. They don’t just buy. We reward engineers who:

• Write RFCs for overlooked improvements.
• Reverse-engineer third-party APIs.
• Document legacy systems.
• Find security flaws in dependencies.

Our “Cherrypick Awards”? $1K bonuses for the best finds. Last quarter, someone found a 50% performance boost in a core service. That’s the kind of insight that moves the needle.

2. Build Cross-Functional “Variety Teams”

Coin collectors have VAM communities. We have “variety teams”—small squads focused on high-leverage areas:

• Observability Variants: Better tracing, metrics, alerts.
• Legacy Modernization: Refactor, don’t rewrite.
• Edge Computing: Optimize for low latency.

These teams have autonomy, budgets, and direct access to me. They’re our scouts. They find what others miss.

3. Document Everything (Like a Grading Service)

Grading services (PCGS, NGC) create standards. We do the same for tech wins:

• Internal ADRs for major upgrades.
• Tool adoption playbooks (e.g., “How we cherrypicked RedisJSON”).
• Performance benchmarks for shared libraries.

This turns “lucky finds” into repeatable strategies.

Conclusion: The CTO as a Strategic “Cherrypicker”

My job isn’t to chase trends. It’s to find the undervalued, the overlooked, the misclassified. A forgotten tool, a niche library, an engineer with hidden skills—these are our real leverage.

As one coin collector said:

“Most dealers don’t care or check for varieties, even most of the major ones. It’s worked out for me as well.”

The same goes for tech. While others buy the same tools, hire the same profiles, and solve the same problems, we’re looking for the 1951-S/S repunched mintmark. We’re auditing our stack with a loupe. Rewarding engineers who find the 55/54 overdate in legacy code.

That’s how we build a strategic advantage. Not with big budgets or flashy rewrites, but with consistent, disciplined cherrypicking. The gems are out there. You just have to know where to look, and how to grade them.

Now go find your next big score.

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