Succeeding in Your First 90 Days as a CXO
A practical guide for new CROs, CMOs, CCOs, and RevOps leaders in B2B tech
"What got you here won’t get you through what’s coming." — Sam Jacobs
TL;DR
What This Guide Covers
You just landed a new GTM leadership role — congrats. Now the real work begins.
There’s no shortage of onboarding advice for new executives. But most of it is generic, theoretical, or built by consultants — not the people who’ve lived the job.
This guide is curated from Pavilion’s global community of 10,000+ B2B leaders, and refined over the past decade through real-world experience. Every insight here comes directly from operators — CROs, CMOs, CCOs, RevOps leaders — who’ve walked into high-pressure executive roles and figured out what actually works.
This is for newly appointed VPs and CXOs in Sales, Marketing, Customer Success, and RevOps navigating the high-stakes first 90 days at B2B tech companies. Inside, you'll find:
- A proven Diagnose → Strategize → Execute onboarding framework
- Common missteps that sink early momentum (and how to avoid them)
- Peer insights from the Pavilion community
- Role-specific 30-60-90 templates that you can download and customize
This isn’t theory. It’s operator-grade onboarding — built by the people doing the work, for the people doing the work.
Use it to lead with confidence from day one. And if you’re ready to go deeper, Pavilion is here to support your next 90 days — and beyond.
Don't have time to read it now? Get the PDF
Whether you’re stepping into a CRO, CMO, CCO, or RevOps role, one thing is true: the expectations have never been higher — and the path has never been less clear.
The old playbook no longer applies. Linear careers, siloed teams, predictable buyers — they’ve been replaced by rapid org shifts, AI-native workflows, and shared revenue accountability across Sales, Marketing, CS, and Ops. GTM leaders today aren’t just running functions. They’re orchestrating systems, influencing product, partnering with finance, and building cross-functional trust in environments defined by volatility.
At Pavilion, we’ve worked with thousands of GTM executives who’ve made this leap — some successfully, some painfully. This guide distills what we’ve learned. It’s not just a checklist. It’s a strategic roadmap for your first 90 days: one that helps you diagnose clearly, align strategically, and execute with purpose.
It’s also just the beginning. If you want access to the frameworks, templates, and community support that can help you thrive beyond day 90, we’ve got that too.
Let’s get started.
Why the First 90 Days Matter More Than You Think
Your first 90 days aren’t just about proving yourself — they’re about positioning yourself.
As a new GTM executive, you’re stepping into a role defined by volatility:
- Median CRO tenure: 18 months
- Median CMO tenure: 21 months
- 46% of companies missed revenue targets in 2024
- Only 3% of companies increased growth three years in a row
As a newly-hired executive, you are stepping into a position of opportunity and of risk. The clock is ticking, with limited time before your performance is judged. But here’s the twist: most execs don’t fail because they’re bad at the job — they fail because they misread the job they’ve actually been hired to do.
First time as a CXO? Hear first-hand what it's like as Walnut CRO Catie Ivey shares her experience in "Confessions of a First Time CRO" on The Revenue Leadership Podcast
Common Misreads:
- You think the mandate is “fix revenue” → it’s actually “restore cross-functional trust.”
- You think the problem is pipeline → it’s actually churn, GTM misalignment, or product-market noise.
- You try to score early wins → but erode trust by moving too fast, with too little context.
Modern GTM execs are inheriting roles with no map. Playbooks from the last decade — linear funnels, siloed functions, predictable buyer journeys — have collapsed and what got you here won’t necessarily get you to the next stage in your career journey.
To thrive now, you need to:
- Learn across silos: sales, marketing, CS, ops
- Build influence fast (especially with peers and product)
- Balance speed with context: quick wins without reckless change
- Speak fluently about AI, the P&L, and GTM efficiency from Day 1
That’s what this guide helps you do.
Theme: Listen deeply. Map reality. Build credibility.
The first 30 days of a new GTM executive role aren’t about being brilliant. They’re about being accurate.
It’s tempting to view your onboarding as a race: meet your team, find the biggest problem, fix it fast. After all, you were likely brought in to drive results. Maybe there’s pressure to “shake things up,” or to implement a methodology that worked at your last company. But jumping into execution mode too quickly is the most common—and costly—mistake new GTM leaders make.
Why? Because what’s broken on the surface is rarely the root issue. That shaky pipeline? It might trace back to misaligned messaging, not rep performance. That churn problem? It might originate in the sales motion, not customer success. That high CAC? Could be a downstream effect of marketing’s lack of influence over product positioning. If you try to solve the symptom without understanding the system, you’ll misfire.
This first month is your window to see clearly. And clarity is your most valuable currency.
But here’s the real challenge: you’re walking into a complex organizational machine with multiple stakeholders, implicit expectations, and years of entrenched behavior.
Onboarding well means listening on three levels simultaneously:
- To your team — What they say, what they don’t, and what they fear will change.
- To your peers — How they view your function, what support they expect, and what they’ve learned to work around.
- To your CEO — The political and financial subtext behind their goals for you.
You may have inherited a mess. You may have inherited a minefield. Or you may have inherited a quietly functional team that no one else truly understands. The only way to know which is to pause long enough to gather the real story — not the sanitized version, not the pitch deck version, but the truth from the inside out.
It’s during this phase that you also begin to build your leadership brand.
People are evaluating not just your knowledge, but your judgment. Are you reactive or thoughtful? Are you a listener or a fixer? Do you respect what came before you, or are you eager to replace it? These judgments start forming in the first few weeks — and they’re hard to reverse once they calcify.
That’s why the best GTM executives treat their first 30 days as a diagnostic sprint. Not passive observation, but intentional inquiry. Not just information gathering, but relationship mapping. They don’t jump into solutions. They investigate, synthesize, and narrate what they’re learning — building trust as they go.
Especially critical in this period is building alignment with your executive peers. GTM success is rarely functional. It’s cross-functional. You’ll need the head of RevOps to buy into a new forecasting model, the CFO to support changes in incentives, the Head of Product to prioritize integrations your team needs to close deals. None of that happens without trust — and trust is earned through empathy, clarity, and momentum.
Ultimately, your ability to lead through change will depend on the foundation you lay here. You’re not just onboarding. You’re studying the battlefield, mapping the allies, and clarifying the mission.
Get it right, and the next 60 days become a platform for durable change. Get it wrong, and you’ll be fixing misunderstandings well into month six.
What This Phase Is Really About:
- Building cross-functional trust fast — especially with your peers on the ELT
- Understanding the true GTM mandate (not just the job description)
- Diagnosing what's actually broken vs. what’s politically expedient to fix
- Listening for unspoken truths from your team, your customers, and your CEO.
The world's #1 private community for GTM leaders.
A trusted space for GTM professionals to learn, share, and grow.
| Priority | What It Looks Like | Why It Matters |
|---|---|---|
| Clarify your mandate |
Ask your CEO and board: “What will make you say I’ve succeeded here?” and “What would failure look like?” | Prevents you from over-indexing on a specific challenge that may be out of alignment with CRO or board priorities (ex. focusing on pipeline if churn is the real crisis.) |
| Map the power structure | Identify formal and informal centers of influence across Sales, CS, Product, Marketing, Finance. | You can’t move fast if you don’t know where the landmines are. |
| Build trust with your ELT peers | Book 1:1s with each — CRO, CMO, CFO, COO, Head of Product — with a goal of understanding how you can help them win. | Peer alignment is the #1 predictor of early exec success or derailment. |
| Connect with your direct team | Meet individually and as a group. Ask for personal context, team observations, and unfiltered advice. | Sets a tone of respect and high standards from Day 1. |
| Assess GTM mechanics | Look under the hood: pipeline quality, funnel conversion, channel-level performance, unit economics, churn segments, CSAT/NPS, team comp plans. | You'll uncover the disconnects between reported vs. experienced performance. |
| Listen to customers | Shadow calls, join QBRs, read churn interviews, review lost deals. | Reveals what your company thinks it’s selling vs. what buyers actually value. |
- What’s the biggest misunderstanding people have about your team?
- Where do you feel friction with other departments?
- What do we say we do that we don’t really do?
- What’s one sacred cow we’re afraid to kill?
- If I could fix one thing in my first 90 days, what should it be?
| Pattern | What It Signals |
|---|---|
| Lots of projects, no clear metrics | Execution theater; lack of GTM clarity |
| Multiple teams claiming pipeline ownership | Misaligned revenue architecture |
| Leaders referring to “them” instead of “us” | Functional silos and broken trust |
| Hero reps or CSMs doing work outside process | Broken systems being masked by individuals |
| Budget surprise or tech sprawl | GTM-finance disconnect, poor operating rhythm |
- Rushing to restructure your team.
You might be right — but until you understand the power dynamics, you’ll lose buy-in and trigger fear. Pause, diagnose, then act. - Assuming your peers trust you because the CEO hired you.
They don’t — not yet. Build credibility by asking how you can support their goals, not just pushing your own. - Over-indexing on performance data without cultural context.
The dashboard might say the problem is win rate. The real issue? The CS and
Don’t default to proving your value in the first 30 days. You were hired for a reason. Listen. Observe. Understand the business model, the personalities, and the power dynamics.
Then go deep on two things: (1) building trust with your direct team, and (2) aligning with your CEO on what success actually looks like. Most missteps happen when new execs confuse activity for impact.”
Kyle Lacy
CMO, Docebo
Leadership Execution Excellence
Pavilion University
Offered on demand to Pavilion Executive members, learn how to enhance your skills in implementing accountability frameworks, developing effective leadership cadences, and optimizing execution within your teams to drive growth and efficiency.
Theme: Align, prioritize, and set the foundation for change.
If your first 30 days are about listening, your second month is about translating what you heard into a coherent strategy.
This is the moment when the fog should start to lift. You’ve built relationships with your peers, clarified your mandate with the CEO, and diagnosed the critical points of failure (and possibility) in your GTM system. Now, your stakeholders are expecting a point of view. That doesn’t mean presenting a finished plan. It means outlining a thoughtful, focused path forward — one that earns trust by balancing ambition with realism.
What separates great GTM leaders from merely good ones during this phase is their ability to navigate ambiguity while still driving alignment. Your CEO might want pipeline acceleration. Your CFO may be pushing for efficiency. Marketing may be focused on brand repositioning while Sales is asking for new enablement. These aren’t conflicting goals, but they do require orchestration. Strategy in month two isn’t about knowing everything — it’s about setting the right priorities and getting people moving in the same direction.
You also need to define what will be true if you’re successful. What metrics will move? What behaviors will shift? How will the GTM engine function differently? Strategy without a hypothesis for how change happens is just theater.
This is also when you start to pressure-test your early insights with data. Were the problems you identified in churn supported by expansion metrics? Is the messaging you flagged as unclear actually reflected in win/loss notes? Are teams underperforming because of skill gaps — or structural misalignment? You’re not just defining the strategy; you’re building the case for it.
At the same time, this is a critical period to socialize, not sell your plan.
Cross-functional buy-in isn’t granted — it’s built. Meet with peers 1:1 before you present anything to a broader group. Ask for input. Reflect their priorities in your recommendations. Your peers don’t need to agree with every decision — but they do need to feel seen in the strategy.
A final note: this is often the most emotionally complex phase of your onboarding. You’re no longer new enough to ask naive questions. But you’re also not established enough to make sweeping changes without pushback. You’ll likely feel both pressure to move and uncertainty about when to pull the trigger. That’s normal. Your job is to find the right pacing — to act without overreaching, and to lead without isolating.
Strategizing well now gives you the credibility and clarity to execute decisively in month three.
PEER LEARNING: Listen to Kyle Norton's Revenue Leadership Podcast interview on "Strategic Planning and Executive Alignment with Eric Gilpin, CRO at G2" to hear first-hand how G2 is solving for executive team alignment.
- What are the 1–2 bets we’ve made as a company that most affect GTM?
- What’s a recent change that went well — and why?
- Which metric do you trust the least in our reporting stack?
- If we could only fix one GTM process this quarter, which would it be?
- What’s the “third rail” topic no one wants to talk about?
| Priority | What It Looks Like | Why It Matters |
|---|---|---|
| Translate findings into strategy |
Identify 2–3 core GTM challenges and their root causes. Draft a directional plan tied to business outcomes. | Shows you're not just diagnosing — you're here to lead change. |
| Align with peers and the CEO | Share early drafts, listen to feedback, and revise accordingly. Seek pre-alignment before group presentation. | Prevents derailment and builds buy-in before the big reveal. |
| Define GTM operating rhythm | Establish a cadence for forecast reviews, deal reviews, pipeline health, and QBRs. | Builds execution consistency and visibility across functions. |
| Clarify metrics and accountability |
Design or refine KPI dashboards, scorecards, and definitions of success. | Keeps the team aligned and helps identify early progress or drift. |
| Plan early wins and pilots | Launch 1–2 small, scoped initiatives that build momentum and demonstrate your approach. | Builds confidence in your leadership and your strategy. |
- What are the 1–2 bets we’ve made as a company that most affect GTM?
- What’s a recent change that went well — and why?
- Which metric do you trust the least in our reporting stack?
- If we could only fix one GTM process this quarter, which would it be?
- What’s the “third rail” topic no one wants to talk about?
| Pattern | What It Signals |
|---|---|
| Strategy conversations stay vague | People are avoiding tradeoffs or political tension |
| No peer pushback or questions | They’re checked out or letting you fail on your own |
| Metrics aren’t consistently defined | You’ll struggle to align performance and accountability |
| Sales, CS, and Marketing calendars don’t align | GTM execution is happening in silos |
| Requests for “quick wins” from every corner | Organization is used to short-termism over systemic change |
- Presenting a strategy without socializing it first — peers need to feel included, not surprised
- Making everything a priority — dilutes focus and undermines credibility
- Building in isolation — GTM strategy must reflect Finance, Product, and CS realities
- Defining success without defining behaviors — KPIs don’t matter if the org doesn’t know how to act
- Trying to “own” the plan too tightly — influence beats control in this phase
Focus 80% of the time on learning and networking. No assumptions. Work across your team, cross-functional teams, and with customers.
Learn first. Take the time to understand what people care about, how they are measured, what's working, what's not, where are they stuck, and ask - how can I help?."
Mike Simmons
Speaker & Facilitator, Catalyst A.C.T.S.
- A strategic brief that includes your synthesis, priorities, and hypotheses
- A draft GTM operating cadence with cross-functional alignment
- Updated scorecards or KPIs with clear definitions and owners
- A plan for the next 30 days: what launches, who leads it, and what success looks like
- Signal moments: peer endorsements, quiet early wins, or changes already underway
Theme: Build momentum. Drive alignment through action. Establish your leadership.
The final phase of your onboarding is where strategy becomes reality. This is when your ideas start to live in the wild — tested not in decks or memos, but in calendars, dashboards, conversations, and results.
But execution in this phase doesn’t mean launching everything at once. It means proving your model works — through smart prioritization, clear ownership, and visible wins. It means reinforcing trust, not burning political capital. And it means taking the first steps in a new GTM operating rhythm that will ultimately outlast you.
The best GTM executives in this phase are defined by two traits: focus and follow-through. By now, you’ve likely surfaced a dozen things you could fix. Your job is to narrow that list to the highest-leverage opportunities — the initiatives most likely to demonstrate early impact, clarify your leadership style, and reinforce the new direction.
This is also the point where communication becomes your primary tool. You’re no longer the new exec “in learning mode.” You’re now seen as a change agent — and change is uncomfortable. What you say, what you ignore, what you celebrate, and how you react when things go sideways — these become the blueprint for how your team and your peers interpret your leadership.
Crucially, this is when your leadership brand starts to set. The early goodwill from your hiring fades. Performance expectations rise. People start deciding what kind of executive you really are.
So use this time to:
- Cement alignment with your executive peers
- Make your team feel momentum and stability
- Reinforce your culture through rituals, cadences, and accountability
Do this well, and by Day 90 you won’t just be onboarded — you’ll be seen as a leader who gets things done.
What This Phase Is Really About
- Translating your strategy into visible action and impact
- Delivering early wins that validate your leadership
- Building consistent communication and operating rhythms
- Reinforcing new standards for performance and accountability
- Creating a culture of ownership and follow-through
PEER LEARNING: How do top-performing CXOs build high-performing teams? Check out Brex CRO "Sam Blond's Blueprint for Building Exceptional Leaders and Teams" on The Revenue Leadership Podcast.
What Great GTM Execs Focus On in Month Three
| Priority |
What It Looks Like | Why It Matters |
|---|---|---|
| Deliver early wins | Execute 1–2 high-priority initiatives (e.g. revamped pipeline review, churn initiative, team restructure, messaging refresh). | Builds credibility and shows your strategy isn’t theoretical. |
| Operationalize your GTM cadence | Kick off a new operating rhythm (eg. weekly forecast reviews, marketing standups, QBR prep, or CS renewal reviews). | Turns GTM into a system — not just a series of fire drills. |
| Reinforce performance culture |
Share expectations, inspect KPIs, give feedback early. Hold your leaders accountable. | Your standards become the team’s standards. |
| Communicate consistently |
Weekly notes, team standups, 1:1s, and peer updates. Transparency beats perfection. | Aligns the org and reduces uncertainty during change. |
| Identify what's next |
Begin planning for the next quarter. What needs to scale? What needs to stop? | Ensures your momentum carries into long-term impact. |
The world's #1 private community for GTM leaders.
A trusted space for GTM professionals to learn, share, and grow.
Five High-Leverage Questions to Ask
- What early indicators tell us this is working?
- Where are people still confused about priorities?
- Who’s showing real leadership under this new model?
- What have we started that we may not have capacity to finish?
- What will it take to scale this progress sustainably?
Patterns to Watch For
| Pattern | What It Signals |
|---|---|
| Execution is happening, but messaging feels inconsistent | You haven’t aligned the “why” across teams |
| Some leaders are passive-aggressively stalling | Political resistance or lack of true buy-in |
| KPIs are still not trusted | Dashboards may not reflect what people actually experience |
| Wins are happening, but no one’s celebrating them | Missed opportunity to build morale and culture |
| Your team is doing the work, but you’re still the bottleneck | Time to start delegating more decisively |
Common Mistakes to Avoid
- Launching too much at once — spreads your team thin and dilutes your message
- Assuming everyone remembers your strategy — keep repeating and reinforcing it
- Measuring progress too narrowly — look for leading indicators, not just lagging metrics
- Under-communicating — silence creates confusion; consistent updates build trust
- Neglecting your peers — alignment at the top drives alignment across the org
Expect the unexpected. Your first 90 days as a CXO will be filled with surprise priorities; flexibility and curiosity are your most critical assets."
Stephanie Valenti
VP of Sales, BILL
What to Deliver by Day 90
- A short summary memo to the CEO and ELT outlining:
- What’s been launched
- What’s working
- What’s next
- A working GTM cadence — meetings, dashboards, decision rights (ex. a RACI framework)
- Evidence of impact — improved metrics, culture shift, team feedback
- One or two high-impact results: a better forecast, a shorter cycle, a saved renewal
- A plan for Q2 — how you’ll scale what’s working and stop what isn’t
Additional Resources
The Evolution of GTM Strategy: Pavilion x Influ2
eBook
Growing revenue targets are putting intense pressure on GTM teams and increasing volume isn’t enough anymore. We talked to five GTM leaders who are shifting away from brute-force tactics and toward a more focused, aligned, and efficient approach — and uncovered four key opportunities to make your GTM strategy work.
The Playbook Is Dead. Now It’s Up to You.
You didn’t take this role to blend in - you took it to change the game.
But here’s the truth: the old playbook for GTM success is gone. The tidy funnel, the predictable buyers, the stable org charts — they don’t exist anymore. What you’ve stepped into isn’t just a job. It’s an arena.
And you don’t win in the arena by playing it safe.
At Pavilion, we know this because we’ve seen it firsthand. Our community includes thousands of executives across Sales, Marketing, Customer Success, and RevOps — operators who are navigating the same chaos you are. They’ve built the new mental models. They’ve tested the strategies. They’ve faced the pressure, and they’ve figured out what works.
That’s what we’ve distilled into this guide — not corporate theory, but hard-earned insight.
By operators. For operators. Sharpened over a decade, by people like you, for people like you.
So as you step into your first 90 days, don’t just survive them. Lead like the future depends on you — because it does.
If this guide helped you, we’ve got more:
- Download role-based 30-60-90 day onboarding plans for CROs, CMOs, CCOs, and Revenue Operations Executives
- Join Pavilion University programs like CRO School, CMO School, or our GTM Leadership Accelerator
- Connect with other GTM executives navigating the same challenges inside Pavilion’s global peer community
Your role is evolving. Your onboarding should too.
