The "First 90 Days" Strategist
Create a strategic plan for a new role to ensure early success and impact
Starting a new role can feel like drinking from a fire hose. There's so much to learn, so many people to meet, and pressure to prove yourself quickly. The first 90 days are crucial—they set the tone for your tenure and shape how others perceive your capabilities.
But here's the thing: you don't have to figure it all out alone. AI can be your strategic thinking partner, helping you craft a thoughtful plan that balances quick wins with long-term impact. Today, we'll explore how to use AI to create a comprehensive 90-day plan that positions you for success from day one.
Task
Transform AI into your personal strategic advisor by using this prompt framework:
The Prompt: "I'm starting a new role as [position] at [company type/industry]. Help me create a strategic 90-day plan broken into three 30-day phases. For each phase, identify:
Key learning objectives
Relationship-building priorities
Quick wins I can achieve
Metrics to track progress
Potential pitfalls to avoid
Context: [Add 2-3 sentences about company size, team structure, or specific challenges]"
Sample Problem
Let's say Sarah just landed a role as VP of Product at a Series B fintech startup. She's joining a team of 15 product managers and needs to balance immediate product improvements with longer-term strategic planning. Here's how she might use our prompt:
"I'm starting a new role as VP of Product at a Series B fintech startup. Help me create a strategic 90-day plan broken into three 30-day phases. For each phase, identify:
Key learning objectives
Relationship-building priorities
Quick wins I can achieve
Metrics to track progress
Potential pitfalls to avoid
Context: The company has 150 employees, just raised $50M, and is looking to expand from B2C payments into B2B solutions. The product team has been without a VP for 3 months, and there's some tension between product and engineering teams."
Solution
Chat GPT 4o
Congratulations on your new role! Here's a strategic 90-day plan tailored to your situation as the new VP of Product at a Series B fintech startup with 150 employees, a recent $50M raise, and a goal to expand from B2C into B2B — amid recent leadership gaps and product-engineering tension.
🗓️ First 30 Days: Listen, Learn, Diagnose
Key Learning Objectives
Understand the company’s vision, strategy, and goals — especially around B2B expansion.
Deep dive into product portfolio, roadmap, customer segments, metrics, and feedback loops.
Learn the org structure, team dynamics, past OKRs, and key rituals.
Understand current engineering processes, resource allocations, and pain points.
Clarify why the VP role was vacant for 3 months and its downstream effects.
Relationship-Building Priorities
Build trust with CEO/founders and clarify your charter and success metrics.
Host 1:1s with all product team members (PMs, designers, researchers).
Start forming connections with engineering, data, marketing, and sales leads.
Begin relationship-building with key customers or power users, especially B2B prospects.
Reassure and align with the engineering leadership to begin repairing trust.
Quick Wins
Provide clear visibility into your 30/60/90 plan to calm uncertainty.
Identify and unblock a low-effort, high-impact feature or issue.
Clarify and enforce product rituals (e.g., weekly standups, roadmap review).
Metrics to Track Progress
% of team 1:1s completed.
Engagement in onboarding docs, product reviews, retros.
Identification of 3–5 product areas needing urgent attention.
Stakeholder feedback on product/engineering alignment (qualitative for now).
Potential Pitfalls to Avoid
Jumping to solutions without context.
Taking sides in product vs. engineering tensions.
Over-indexing on B2B while neglecting B2C stability.
Acting like a "fixer" too early and disrupting morale.
🗓️ Days 31–60: Align, Strategize, Energize
Key Learning Objectives
Validate and refine product vision and strategy with exec and cross-functional teams.
Deepen understanding of B2B customer needs, market trends, and competitors.
Assess team capabilities, gaps, and processes (hiring needs, skills, velocity).
Map friction points in product-engineering collaboration.
Relationship-Building Priorities
Establish tighter working rhythms with engineering, design, and data science.
Meet with sales, customer success, and support to gather frontline insights.
Host a cross-functional offsite or working session on product priorities.
Start engaging directly with 1–2 strategic B2B pilot customers.
Quick Wins
Launch or refine a product development framework (e.g., RICE scoring, PRDs).
Build a shared roadmap artifact that improves transparency.
Refactor or kill a legacy feature/product that’s dragging team focus or morale.
Initiate a B2B discovery sprint or pilot validation effort.
Metrics to Track Progress
Completion of strategy/roadmap refresh.
Roadmap alignment score across product/engineering/design (via survey).
of internal process improvements implemented (e.g., grooming, specs).
Time-to-decision on key product/tech debates.
Potential Pitfalls to Avoid
Over-planning and under-delivering.
Making too many org/process changes at once.
Prioritizing short-term wins at the cost of long-term strategy.
Letting existing silos persist without intervention.
🗓️ Days 61–90: Deliver, Empower, Extend
Key Learning Objectives
Translate strategy into execution — measurable bets with clear ownership.
Develop a hiring roadmap and org structure for growth, especially for B2B.
Build a product culture of accountability, autonomy, and experimentation.
Start forming a longer-term product vision narrative for fundraising, hiring, and alignment.
Relationship-Building Priorities
Empower and elevate PMs and designers to drive their product areas.
Partner with finance and ops to align on budgets, hiring plans, and analytics.
Engage with investors or board members to represent product confidently.
Formalize feedback loops with internal teams and customers.
Quick Wins
Kick off or deliver a flagship B2B product initiative or beta.
Improve speed and quality of product/eng handoffs and planning cycles.
Create career ladders or development plans for the product org.
Share a vision deck that aligns the org around long-term aspirations.
Metrics to Track Progress
B2B pilot adoption, feedback, and early retention indicators.
Product development cycle time and defect rate.
NPS or internal satisfaction surveys from engineering/design.
Org health: team engagement, attrition risk, clarity of roles.
Potential Pitfalls to Avoid
Burning out the team to "prove" impact too fast.
Setting unrealistic B2B expectations before infrastructure is ready.
Undercommunicating vision or strategy as you shift into execution.
Failing to establish clear ownership and process sustainability.
Final Tips
Communicate frequently and clearly. Narrate your thinking and plans often to reduce anxiety during transition.
Balance urgency with long-term orientation. Everyone wants momentum, but they also want to trust the foundation being built.
Make space for tension repair. The product-engineering rift may require workshops, facilitated sessions, or deeper listening to mend.
Let me know if you'd like this in a slide format or a Notion-ready outline.
Gemini 2.5 Pro
Claude Opus 4
Your 90-Day Strategic Plan as VP of Product
Days 1-30: Listen, Learn, and Stabilize
Key Learning Objectives
Your first month should focus on deep discovery. Map the current product portfolio, understanding both the existing B2C payments infrastructure and the early B2B initiatives. Conduct thorough reviews of product metrics, user research, and competitive landscape. Most importantly, understand why the previous VP left and what gaps emerged during the three-month vacancy. Document the current product development process, tech stack, and any technical debt that might impact your B2B expansion.
Relationship-Building Priorities
Start with one-on-ones with every member of your product team to understand their strengths, concerns, and career aspirations. Given the tension with engineering, prioritize meetings with the VP/Head of Engineering and their key leaders. Schedule regular coffee chats with sales, customer success, and operations leaders who will be crucial for B2B expansion. Connect with the CEO and other C-suite members to align on strategic vision and understand board expectations post-funding.
Quick Wins
Address the most pressing pain points from the leadership vacuum: restart any stalled decision-making processes, clear product backlog ambiguity, and establish regular team meetings if they've lapsed. Create a simple team charter that clarifies roles and responsibilities. Begin hosting joint product-engineering standups to improve collaboration. Share a weekly "VP Update" email to increase transparency and show active leadership.
Metrics to Track
Monitor team morale through informal pulse checks and 1:1 feedback. Track the number of cross-functional meetings held and relationships established. Measure any immediate improvements in product velocity or decision-making speed. Document current baseline metrics for product KPIs like user engagement, revenue per user, and feature adoption rates.
Potential Pitfalls
Avoid making dramatic changes or strategic pivots before fully understanding the context. Don't pick sides in the product-engineering tension; instead, position yourself as a bridge-builder. Resist the urge to immediately hire new team members or restructure the organization. Be careful not to over-promise on the B2B expansion timeline to eager stakeholders.
Days 31-60: Build Bridges and Define Strategy
Key Learning Objectives
Dive deep into the B2B market opportunity through customer interviews, competitive analysis, and partnership discussions. Understand the technical and operational changes required to serve enterprise customers versus consumers. Analyze the unit economics of B2B versus B2C to inform resource allocation. Map the skills gaps in your team for B2B product development.
Relationship-Building Priorities
Strengthen the product-engineering partnership by establishing joint planning sessions and shared OKRs. Build relationships with key B2B prospects and early adopter customers. Connect with board members or advisors who have B2B fintech experience. Engage with the data team to ensure you'll have the analytics infrastructure for B2B insights. Start building external relationships with other product leaders in the fintech space.
Quick Wins
Launch a product-engineering "peace summit" workshop to address tensions and create joint working agreements. Deliver your first strategic presentation outlining a preliminary B2B product vision and roadmap. Implement a more structured product development process that both teams support. Create a B2B pilot program with 3-5 friendly customers to validate assumptions. Establish clear communication channels and escalation paths between teams.
Metrics to Track
Measure improvement in product-engineering collaboration through sprint velocity and fewer escalations. Track progress on B2B pilot customer acquisition and early feedback scores. Monitor team retention and engagement scores. Begin tracking B2B-specific metrics like average contract value, sales cycle length, and enterprise feature requests.
Potential Pitfalls
Don't rush the B2B strategy without proper validation; premature scaling is dangerous. Avoid favoring B2B initiatives so heavily that B2C customers feel neglected. Be cautious about making firm commitments to enterprise customers before understanding delivery capabilities. Don't let the improved product-engineering relationship become dependent solely on your mediation.
Days 61-90: Execute and Scale
Key Learning Objectives
Understand the resource requirements and timeline for successful B2B scaling. Learn from pilot customer feedback to refine the B2B product strategy. Assess the team's readiness for rapid growth and identify hiring needs. Develop expertise in B2B sales cycles and enterprise purchasing processes. Master the balance between maintaining B2C growth while investing in B2B expansion.
Relationship-Building Priorities
Solidify your leadership team relationships to ensure aligned execution. Build connections with potential B2B implementation partners and integration platforms. Strengthen relationships with finance and legal teams who'll be crucial for enterprise contracts. Engage with current B2C customers who might become B2B buyers. Deepen board relationships to secure support for your strategic vision.
Quick Wins
Close your first B2B paying customers from the pilot program. Ship a major feature that demonstrates improved product-engineering collaboration. Present a comprehensive B2B go-to-market strategy with clear milestones. Launch an internal product management excellence program to upskill the team. Achieve at least one significant improvement in a core product metric.
Metrics to Track
Track B2B pipeline growth, pilot conversion rates, and early revenue indicators. Monitor improvements in product team performance metrics like feature delivery speed and quality. Measure cross-functional collaboration health through formal surveys. Track progress against OKRs established in month two. Begin forecasting resource needs based on growth trajectories.
Potential Pitfalls
Avoid declaring victory too early on cultural improvements; sustainable change takes time. Don't overcommit to aggressive B2B revenue targets without proven product-market fit. Be careful not to burn out the team with simultaneous B2C maintenance and B2B building. Resist pressure to hire too quickly without clear role definitions and cultural fit assessment.
Critical Success Factors
Throughout your first 90 days, maintain a balance between strategic thinking and tactical execution. Your success will largely depend on healing the product-engineering divide while simultaneously navigating a complex market expansion. Remember that in a post-funding environment, there's pressure to move fast, but building the right foundation for scalable growth is more important than quick, unsustainable wins.
Regular communication with all stakeholders about progress and challenges will build trust and buy-in for your longer-term vision. Most importantly, your ability to bring stability to a team that's been rudderless for three months while charting an ambitious new course will set the tone for your entire tenure as VP of Product.
Extra Credit
Take your 90-day planning to the next level:
Create a Stakeholder Map: Ask AI to help you identify and categorize all key stakeholders, then develop specific engagement strategies for each group.
Design Your Communication Cadence: Have AI draft templates for your first team meeting agenda, 1:1 introduction emails, and weekly update formats.
Build a Knowledge Repository: Use AI to create a structured list of questions to ask in your first 30 days, organized by topic and stakeholder.
Scenario Planning: Ask AI to help you prepare for common challenges new leaders face, with specific response strategies for each scenario.
Cultural Integration: Request AI's help in identifying cultural norms and unwritten rules you should understand, based on the company's industry and stage.
General Takeaways
Why This Works:
Structured Thinking: AI helps you avoid the overwhelm of a new role by breaking down your approach into manageable phases
Comprehensive Coverage: The prompt ensures you're thinking about all dimensions of success—not just delivering results, but building relationships and avoiding common mistakes
Customization: By providing context, you get advice tailored to your specific situation rather than generic onboarding tips
Pro Tips:
Be specific about your context—the more details you provide, the more actionable the plan
Use follow-up prompts to drill deeper into any phase or aspect that needs more detail
Revisit and refine your plan with AI every 30 days based on what you've learned
Save the initial plan to compare against your actual experience—it's a great learning tool for future transitions
Remember: AI isn't just for tactical tasks. It can be your strategic thought partner, especially during critical career moments like starting a new role. The key is asking the right questions and providing enough context for meaningful guidance.