30-60-90 day plan for VPs of engineering
On this page
- How is a VP of engineering different from a CTO or an engineering manager?
- What does the 30-60-90 day plan look like?
- Which numbers should a new VP of engineering baseline?
- Which employment rules shape an engineering hiring plan?
- What does "on track" look like at day 30, 60 and 90?
- A filled example
- How should the CTO or CEO use this plan in the final interview?
- What should the CTO or CEO ask at the check-ins?
- What the hiring executive owes a new VP of engineering
- Common mistakes
- Adapting the plan
- Questions people ask
A 30-60-90 day plan for a new VP of engineering should map the engineering organization and how work actually gets delivered in the first 30 days, use days 31-60 to fix the operating rhythm with product and the engineering managers, and present an org, hiring and delivery plan at day 90. The VP of engineering runs the organization that builds the product (teams, managers, planning, on-call, hiring and the career ladder), while the CTO, where there is one, owns technical direction. Hiring rules affect the plan's budget too: the federal overtime exemption for computer employees and the status of the H-1B payment requirement are summarized below as of October 2026.
This page is for the CTO, CEO or founder hiring a VP of engineering who leads several engineering managers. For the technical strategy role, see the 30-60-90 day plan for CTOs; for the managers who report to the VP, see the 30-60-90 day plan for engineering managers.
How is a VP of engineering different from a CTO or an engineering manager?
| Area | Engineering manager | VP of engineering | CTO |
|---|---|---|---|
| Scope | One team | The engineering organization: teams, managers, budget | The company's technology and technical direction |
| Delivery | The team's sprint and on-call | Predictability across teams and the planning process with product | Architecture choices that make delivery possible |
| People | Hires and coaches engineers | Hires and coaches managers; owns the career ladder, hiring loop and performance cycle | Senior technical leadership and staff-level engineers |
| Risk | The team's incidents | On-call health, attrition and delivery risk across the org | Security, reliability strategy and technical debt priorities |
Where the company has no CTO, the VP of engineering picks up part of the CTO column; add the architecture and security review from the CTO plan to the first month.
What does the 30-60-90 day plan look like?
30-60-90 day plan — [Name], VP of Engineering, [company]
Reports to: [CTO / CEO] Start date: [date]
Engineering: [N] engineers in [N] teams; managers: [names]
Open roles: [N] Engineering budget: [amount]
Planning cycle: [quarterly / half-yearly] On-call: [rotations]
DAYS 1-30 — Learn the organization and how work gets delivered
Goals:
- One-to-one with every engineering manager and staff-level
engineer; skip-levels with a sample of every team
- Map teams: services owned, headcount, open roles, manager span,
on-call rotation and load
- Sit in each team's planning and retro; join one incident review
- Baseline delivery (DORA measures), commitments met in the last
two quarters, incidents and out-of-hours pages per shift
- Review the hiring funnel, interview loop and offer data with the
recruiting lead
- Read the career ladder, the last performance cycle results and
regretted exits from the last 12 months
Deliverables by day 30:
- Org map showing ownership gaps and overloaded teams
- Delivery and health baseline, with how each measure is built
DAYS 31-60 — Fix the operating rhythm
Goals:
- Agree one planning process with product: capacity, a fixed share
for maintenance and security work, who decides tradeoffs
- Weekly managers' meeting; monthly delivery review with product
- Fix the worst on-call rotation or the slowest step in the
delivery path, with the team that owns it
- Rebuild the interview loop: structured questions, a scorecard
per level, trained and calibrated interviewers
- Coach or change the weakest management situation, with HR
Deliverables by day 60:
- Written planning agreement with product
- Hiring plan matched to the roadmap and budget
DAYS 61-90 — Present the org and delivery plan
Goals:
- Present the org design for the next two quarters: teams,
managers, hires, budget
- Report the quarter's delivery against the commitments made at
its start, with causes for each miss
- Prepare the next performance cycle on the career ladder
Deliverables by day 90:
- Org and hiring plan approved by the CTO or CEO and finance
- One measured improvement in on-call load or delivery
Check-ins: weekly with [CTO / CEO]; day 30, 60 and 90 reviews.Which numbers should a new VP of engineering baseline?
The measures below are examples. DORA names five software delivery measures, grouped as throughput and instability, on its metrics guide; the rest come from the company's own planning, paging and hiring data. Write the definition next to each number.
| Area | Example measures (examples only) | The question behind it |
|---|---|---|
| Throughput | Change lead time, deployment frequency, failed deployment recovery time | How quickly can a change reach customers, and recover when it fails? |
| Instability | Change fail rate, deployment rework rate | How often does shipping create more work? |
| Predictability | Share of quarterly commitments delivered | Can product and sales rely on engineering's dates? |
| On-call health | Out-of-hours pages per shift, by rotation | Which teams are being worn down? |
| Hiring | Time to fill, offer acceptance, interviewer hours per hire | Can hiring keep up with the plan? |
| People | Regretted attrition, manager span of control | Are managers stretched, and are good engineers leaving? |
Use measures to find problems, not to rank individual engineers. A plan that ties individual performance to deployment counts usually gets more, smaller deployments and nothing else.
Which employment rules shape an engineering hiring plan?
The VP of engineering usually owns the hiring plan and works with HR on how roles are classified and posted. Checked against official sources as of October 2026; this is not legal advice.
| Item | The rule | Source |
|---|---|---|
| Overtime exemption for software roles | Computer employees whose primary duty is systems analysis or the design, development, testing or modification of programs can be exempt if paid a salary of at least $684 a week or an hourly rate of at least $27.63; job titles do not decide it | 29 CFR 541.400 |
| Roles the exemption does not cover | Employees who manufacture or repair computer hardware, and engineers or drafters who use software heavily but are not primarily doing systems analysis or programming | 29 CFR 541.401 |
| Stricter state rules | The federal rule is a floor; state or local laws with higher standards still apply | 29 CFR 541.4 |
| H-1B petitions | USCIS's H-1B page describes a $100,000 payment that a September 19, 2025 proclamation attached to certain new H-1B petitions; it also says a federal court in Massachusetts vacated the implementing guidance on June 8, 2026, the First Circuit denied a stay on July 24, 2026, and DHS will comply while it considers next steps. Check the page before budgeting | USCIS |
| Pay ranges in job ads | Several states require a pay range in job postings, and some reach remote roles that can be done from the state | Our pay transparency laws by state page |
On-call work matters for any engineers who are not exempt, such as some support or operations roles: confirm with HR how on-call time is paid before redesigning rotations. For sponsored hires, the Form I-9 guide for H-1B workers covers the onboarding paperwork.
What does "on track" look like at day 30, 60 and 90?
| Checkpoint | On track | Worth a direct conversation |
|---|---|---|
| Day 30 | Has met every manager and done skip-levels; org map and baseline done; knows which rotation is worst | Has spent the month in code or architecture debates; no baseline |
| Day 60 | Planning agreement with product in writing; interview loop rebuilt; one fix under way with its team | A reorganization announced before the baseline; product still learns dates from Slack |
| Day 90 | Org and hiring plan approved; quarter reported against commitments; on-call or delivery measurably better | Hiring plan with no link to the roadmap; misses reported without causes |
A filled example
VP of engineering: Hannah Kowalczyk (invented), joining a 70-engineer software company with eight teams and six managers, reporting to the CTO.
Day 30: The org map showed two teams sharing ownership of the billing service and both paging on it. One rotation averaged several out-of-hours pages a shift. The last two quarters had delivered about half of what was committed, mostly because unplanned maintenance had no capacity set aside.
Day 60: Product and engineering agreed a fixed share of each team's capacity for maintenance and security work. Billing ownership moved to one team, which fixed its noisiest alerts. The interview loop got structured questions and a scorecard per level.
Day 90: Out-of-hours pages on the billing rotation fell sharply and held for a month. The CTO and finance approved a plan for one new team and two manager hires, tied to the roadmap.
How should the CTO or CEO use this plan in the final interview?
Give finalists the same brief: team map, headcount, open roles, delivery history and one known problem. Ask for a two-page plan and score it with the rubric in how to evaluate a 30-60-90 day plan in an interview. The interview guide for engineering managers covers the people-leadership questions, and the software engineer interview scorecard shows what a rebuilt loop should produce. Questions that test the plan:
- "Product says engineering never hits dates. What do you look at first?"
- "One team's on-call is burning people out. What do you do in your first 60 days?"
- "How would you decide whether we need another team or a better planning process?"
- "A manager is well liked but their team misses every commitment. What do you do?"
What should the CTO or CEO ask at the check-ins?
- Day 30: Where is the organization stuck, and how do you know? Which manager needs the most support?
- Day 60: What did product agree to? What changed in the hiring loop?
- Day 90: What did the quarter deliver against its commitments? What does the org plan cost?
What the hiring executive owes a new VP of engineering
- Clear decision rights between the VP and the CTO: who decides architecture, who decides org design and hiring.
- Access to the paging, deployment, planning and recruiting data from day one.
- A product counterpart with the authority to agree the planning process.
- The history: promised dates, past reorganizations, and managers already on performance plans.
Common mistakes
| Mistake | Result | Fix |
|---|---|---|
| Reorganizing in month one | Teams lose context before anyone knows what was wrong | Org changes only after the day-30 map and baseline |
| Becoming the strongest engineer again | Managers stop growing; the VP becomes the bottleneck | Spend the time on managers, planning and hiring |
| Hiring to fix predictability | More people inside the same broken planning process | Fix the planning agreement first, then size teams |
| Ignoring on-call | Strong engineers leave quietly | Baseline pages per rotation and fix the worst one |
Adapting the plan
- First VP after a founder-CTO: agree decision rights in writing in week one; the founder will keep architecture, and the VP needs the org.
- Distributed teams: add time zones and handoffs to the org map, and rotate meeting times.
- Rapid hiring: move the interview loop rebuild to month one; the 30-60-90 day plan for software engineers shows the ramp new hires need.
The general 30-60-90 day plan template for new hires covers the structure for any role.
Questions people ask
What should a new VP of engineering do in the first 30 days?
Meet every engineering manager and senior engineer, hold skip-levels with each team, map which team owns which services and how loaded each on-call rotation is, sit in planning and incident reviews, and baseline delivery, predictability, hiring and attrition. Hold structural changes until the baseline shows where the organization is actually stuck.
How is a VP of engineering's 30-60-90 day plan different from a CTO's?
A CTO's plan centers on technical direction: architecture, security, technology choices and the technical strategy. A VP of engineering's plan centers on the organization that delivers: teams and managers, planning with product, delivery predictability, on-call health, the hiring loop, the career ladder and the engineering budget. Many companies have both roles, with the VP of engineering reporting to the CTO.
Which metrics should a VP of engineering track in the first 90 days?
DORA's five delivery measures (change lead time, deployment frequency, failed deployment recovery time, change fail rate and deployment rework rate), the share of quarterly commitments delivered, on-call pages per shift, hiring funnel measures and regretted attrition. Baseline them in the first month with the definitions written down, and set targets with the CTO or CEO rather than importing them.
Are software engineers exempt from overtime?
Under the federal rule at 29 CFR 541.400, as of October 2026, computer employees whose primary duty is systems analysis, programming or software design can be exempt if paid a salary of at least $684 a week or an hourly rate of at least $27.63; job titles alone do not decide it, and hardware repair roles are not covered. State law can be stricter. This is not legal advice.