Executive Transition Series

THE TECH VP’S FIRST 90 DAYS

A Strategic Blueprint for New Executives

David Froshiesar

Former VP Engineering & CIO | 30+ Years Technology Leadership

How to Use This Workbook

This is not a book to be read. It is a tool to be used. To get the ROI this document promises, follow these three rules:

1. PRINT IT OUT.

Digital reading is for skimming. Physical writing is for thinking. Print this document single-sided. Use a pen. The value of this workbook is not in the text I wrote, but in the ink you add to the margins.

2. BLOCK THE TIME.

You cannot do strategic thinking in 10-minute gaps between Zoom calls. Block 90 minutes on your calendar every Friday morning for the next 12 weeks. Label it “Strategy & Review.” Treat it as non-negotiable.

3. BE RUTHLESSLY HONEST.

No one else needs to see your answers. If you are struggling, write it down. If you don’t know who holds power, admit it. You cannot fix what you do not acknowledge.

Introduction: The Transition No One Prepares You For

You just got promoted. Congratulations. Now comes the hard part.

Most new technology VPs fail within the first year. They fail because they don’t understand that being a VP is a fundamentally different job than being a director.

Before (Director)

You knew the answer
Optimized for technical excellence
Shipped clean code

Now (VP)

You ask the right questions
Optimize for business outcomes
Protect margin & enable revenue

⚠️ The Cautionary Tale of Sarah
Sarah was the best architect at a Series B SaaS company. Promoted to VP, she kept doing what she knew: reviewing code and being the technical expert. At her 90-day review, the CEO said: “Sarah, you’re doing the job of a senior director, not a VP.” She was let go at six months.

Phase 1: Days 1–30

Internal Audit & Shadow Mapping

Exercise 1: Stakeholder Sentiment Interviews

Your first job is not to change anything. It is to listen strategically. Identify the 8-12 people who actually matter and schedule 30 minutes with each.

💡 The “Magic Wand” Question
Ask this verbatim: “If technology were 100% reliable tomorrow and you could wave a magic wand, what would you do to increase revenue?”

Theme 1: What are the top 3 business goals everyone agrees on?

Theme 2: Where is the biggest friction between Tech and the Business?

Exercise 2: Stakeholder Power Map

Titles do not equal power. Map the people who can actually block or greenlight your success.

Name	Influence (1-10)	Stance	Strategy

Exercise 3: Technical Debt Reality Audit

Executives don’t fear bugs. They fear business risk. Any system with Criticality ≥ 9 and Health ≤ 3 is an executive-level risk.

System Name	Criticality (1-10)	Health (1-10)	SPOF?

Phase 2: Days 31–60

Authority, Wins, and Talent

Exercise 5: Your VP README

Your team cannot meet expectations they do not understand. Draft this here and share it with your direct reports by Day 45.

MY ROLE:

I am accountable for:

MY TOP 3 PRIORITIES:

ESCALATION PROTOCOL:

DO Escalate if:

☐ It impacts revenue
☐ It blocks a deadline
☐

DON’T Escalate if:

☐ Interpersonal conflict
☐ Reversible decision
☐

Exercise 6: The Quick Win

You need one visible, low-effort, high-impact win. Use this matrix to choose.

Idea	Effort (10=Easy)	Impact (10=High)	Total Score

Exercise 7: 9-Box Talent Audit

Identify who scales with you, who needs coaching, and who needs to exit.

Name	Performance	Potential	Action

Phase 3: Days 61–90

Strategy, Scale, and Executive Presence

Exercise 8: EBITDA-First Roadmap

Translate engineering tasks into business value.

Language Translation Guide:
❌ “Refactoring” → ✅ “Reducing operational failure risk”
❌ “Cloud Migration” → ✅ “Reducing infrastructure COGS by 20%”

Initiative	Business Outcome (Rev/Risk)	Sponsor

Exercise 9: Capacity Gap & The Ask

Executives don’t fund complaints. They fund trade-offs.

Current Capacity: hrs

Committed Demand: hrs

GAP: hrs

Option A: Reduce Scope (Cost: $0)

What do we cut? Impact?

Option B: Strategic Investment (Cost: $$)

If we add resources, what is the ROI?

Exercise 10: Executive KPI Dashboard

Select the 4 metrics that actually matter to the Board.

Category	Your Metric	Target
Revenue & Growth
Cost & Efficiency
Risk & Stability

Exercise 11: Emergency Incident Playbook

A major incident will happen. Your job is communication and calm, not heroics.

Phase 1 (First 15 Mins):

☐ Acknowledge publicly (“We are aware…”)
☐ Alert CEO/CFO (“FYI, team is responding…”)
☐ Designate Incident Commander (Not you)

Phase 2 (Post-Incident):

☐ Blameless Post-Mortem
☐ Executive Brief (Business Impact + Prevention Plan)

Exercise 12: Board Update Outline

1. Current State Snapshot:

2. Three Key Wins (Business Impact):

3. Critical Risks:

4. The Ask / Next 90 Days:

What Now? (Day 91+)

You have survived the first 90 days. You have built your foundation. Now the real work begins.

1. Archive This Document.

Save this workbook. In one year, pull it out. Look at your “Power Map” and “Talent Audit.” If your answers haven’t changed, you aren’t growing.

2. Operationalize the Tools.

Take the KPI Dashboard and make it real. Take the Incident Playbook and drill it with your team. These shouldn’t live on paper anymore; they should live in your operations.

3. Scale Yourself.

Your first 90 days were about proving you belong. The next 90 days are about proving you can scale. Focus on: Developing leaders, delegating outcomes, and thinking 3 years out.

“The first 90 days set the trajectory for the next three years. Act like an owner, and you will become one.”