Why the First Month Matters
Hiring a CTO—especially a fractional one—is a strategic move. But what they do in the first 30 days can make or break your roadmap.
At HoundDogDev, our Fractional CTOs are trained to diagnose, prioritize, and drive outcomes from day one.
Here’s what the first 30 days should actually look like if you’ve brought on the right tech leader.
🗓️ Week 1: Technical Discovery + Audit
Before anything is built or changed, your CTO needs to understand what exists—and what’s broken.
🔍 What they’ll do:
- Review your codebase and infrastructure
- Assess dev workflow and tooling
- Analyze deployment pipeline, hosting, and environments
- Interview the dev team and product stakeholders
- Identify immediate red flags (security, bugs, blockers)
🎯 Outcome: A clear map of your current technical landscape
🧭 Week 2: Strategic Alignment + Stack Planning
Next, a great CTO aligns your tech with your business goals.
🔍 What they’ll do:
- Clarify product vision and go-to-market timeline
- Recommend optimal stack and architecture choices
- Define MVP (or v2) scope
- Identify quick wins vs. long-term refactors
- Set dev priorities aligned to business OKRs
🎯 Outcome: A technical strategy that supports your roadmap—not slows it down
⚙️ Week 3: Systems, Team, and Workflow Optimization
Now it’s about setting the foundation to move faster, safely.
🔍 What they’ll do:
- Fix broken Git flows, deployments, or staging
- Assign or refine team roles/responsibilities
- Implement agile/sprint structure if needed
- Set up backlog grooming, sprint planning, and retros
- Optimize dev tooling (e.g., Jira, Linear, GitHub, Slack workflows)
🎯 Outcome: A dev team that can actually ship—on time and with fewer bugs
🚀 Week 4: Execution + First Wins
With a strategy in place, the final week is about momentum.
🔍 What they’ll do:
- Launch a key sprint or release
- Track bugs, push staging updates, or prepare investor tech deck
- Train founders on reporting/metrics dashboards
- Lay out a 60-day technical roadmap
- Evaluate hiring needs (internal vs. fractional devs)
🎯 Outcome: Tangible progress + a plan to scale with confidence
✅ What Founders Get From This 30-Day Process
💡 Clarity on technical direction
🧱 A clean foundation to build on
📊 Real visibility into team + progress
⚡ Faster time to market
🧠 Less stress about “is our tech right?”
“We were weeks behind until our CTO from HoundDogDev stepped in. Now we’re shipping every Friday and I actually understand the roadmap.”
— Marketplace Founder
Let’s Make Your First 30 Days Count
Whether you’re building v1, replatforming, or scaling fast—we’ll drop in the technical leadership you need to go from stuck to scaling.
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