10 Things the Best VPs of Sales and CROs Did in the First 90 Days
SaaStr has done deep dives with so many of the top CROs and VPs of Sales in B2B. We went back annd analyzed the first 90 days strategies of 18 of the world’s most successful Chief Revenue Officers and VPs of Sales—leaders who have collectively built over $100 billion in enterprise value.
This includes Matt Plank (Rippling CRO), Christian Smith (Splunk CRO), Jonathan Vassil (Toast CRO), Ron Gabrisko (Databricks CRO), Jameson Yung (Gong SVP Sales), Ashley Kelly (Rippling VP Global Sales Development), Sam Blond (former Brex CRO, Founders Fund Partner), Stevie Case (Vanta CRO), Loren Padelford (Slice CRO), and nine other revenue leaders who have scaled companies from startup to IPO and billion-dollar valuations. All the best practices they shared with SaaSt.
What emerged from this research is striking: the playbook for elite CRO success in the first 90 days is remarkably consistent. These aren’t theoretical frameworks—these are battle-tested strategies from leaders who have generated billions in revenue and built some of the fastest-growing B2B companies in history.
The first 90 days as a VP of Sales or Chief Revenue Officer are make-or-break. If your VP of Sales isn’t working out, you’ll know within 30 days—and if they haven’t shown real progress by 90 days, they likely never will. The best revenue leaders hit the ground running and deliver measurable impact within one sales cycle.
Here are the 10 critical things the most successful VPs and CROs do in their first 90 days:
1. Immediately Upgrade the Team with Proven Closers
The best VPs don’t waste time with underperformers. They immediately bring in 2-3 proven reps, often on Day 1, who know how to close at their stage and price point. Great VPs of Sales can’t afford to keep “Can’t Close Bob”—they immediately show underperformers the door.
What this looks like:
- Analyze the existing team within the first week
- Identify top performers and give them more leads/opportunities
- Stop giving leads to underperforming reps
- Recruit 1-2 strong reps within the first 30 days
Graham Moreno (VP Worldwide Sales at Windsurf) scaled their go-to-market team from 3 to 75 people in less than 12 months by immediately bringing in proven talent. Over 90% of their 73 GTM hires were sourced directly by the leadership team, and 7 out of 10 sellers who’ve been with Codeium 6+ months have already exceeded annual targets.
Ashley Kelly (VP of Global Sales Development at Rippling) emphasizes hiring people you trust first. When she joined Brex at $2M ARR to scale outbound, her first move was hiring three experienced in-network hires—all top-performing SDRs from her previous company, Lever. These were already experienced SDRs, and they were in-network, helping Brex scale outbound sales from $2M to over $300M in ARR.
2. Focus on Immediate Pipeline Improvement and Deal Velocity
The best VPs focus on improving what’s already in the pipeline rather than just building new pipeline volume. Multiple SaaStr speakers including VPs from Talkdesk, Zenefits, Showpad and GuideSpark all doubled sales in one sales cycle by optimizing existing opportunities and increasing close rates.
Key actions from successful SaaStr speakers:
- End endless pipeline discussions and charts—focus on actual deals that can close
- Increase close rates with the same number of leads and lead velocity
- Optimize conversion rates at every stage of the funnel
- Double revenue per lead as your core metric
Example from SaaStr speakers: Christian Smith (CRO at Splunk) emphasizes that pipeline should be treated as a “village activity”—no one person or sales rep owns a piece of the pipeline. The entire team owns the entire pipeline. The key insight: “It’s not about the pipeline volume. It’s about the quality of the pipeline. It’s about what pipeline actually converts and what are the characteristics of that pipeline and how do we do more of that?”
3. Master the Product and ICP Within 30 Days
By the end of the first month, they should be able to demo the product like a pro, handle the top 10-20 objections, and deeply understand your Ideal Customer Profile (ICP). If they’re still fumbling through the basics at this point, it’s a red flag.
What mastery looks like:
- Can deliver compelling product demos independently
- Understands top customer use cases and pain points
- Can handle objections confidently
- Has clear ICP definition and targeting strategy
- Can sell the product better than existing team members
Jonathan Vassil (CRO at Toast) emphasizes that incentive structure is the biggest lever a sales leader has to drive behavior across the business. Toast leverages a “flywheel concept”—when they reach density in a market, their win rates and productivity increase dramatically.
Jameson Yung (SVP Sales at Gong, now SVP Intl at Rippling) immediately raised quotas and compensation and hired a sales team one or two levels above what they initially thought they’d put in place when he joined. He hired people somewhere between the 20-years-in-a-suit and the year-or-two-on-the-job person to effectively sell to CROs and senior executives.
4. Create a Detailed 60-Day Action Plan with CEO Alignment
The best VPs create a real, detailed 60-day plan and force-rank their Top 5 priorities, getting the CEO to agree before they start. Priority dis-alignment is the #2 mistake with VP hiring and maybe the #1 reason VPs lose their job.
Essential plan elements:
- Clear priorities that align with CEO expectations
- Specific hiring targets and timeline
- Revenue improvement goals tied to sales cycles
- Process improvements that build on what’s working
- Cross-functional alignment requirements
5. Build Cross-Functional Relationships and Understanding
Successful CROs have deep discussions with all directs, conduct skip-level 1:1s with the revenue team and cross-functional leadership, and build relationships with customers, partners, and prospects.
Key relationship-building activities:
- Meet with every team member and stakeholder
- Understand marketing lead quality and alignment
- Partner with product on roadmap and customer feedback
- Align with customer success on retention and expansion
- Build relationships with key customers and prospects
Matt Plank (CRO at Rippling) emphasizes the importance of tight partnership between marketing and sales without caring who gets the credit. This allows allocation of budget towards things that generate outbound opportunities while maintaining marketing alignment.
6. Embrace Competition and Improve Win Rates
The best VPs embrace competition rather than running from it. They quickly learn relative weaknesses and strengths, and focus on areas where they can win. If you have competition (and 90% of SaaS companies do), a VP of Sales that doesn’t embrace it won’t work out.
Competitive strategies:
- Study competitors’ strengths and weaknesses
- Develop competitive battle cards and positioning
- Train the team on competitive selling
- Turn competition into a game to increase motivation
- Focus on deals where you have the best chance to win
Brendon Cassidy immediately embraced competition at Adobe Sign / EchoSign, turning it into a game for the team. Most of their prior reps had struggled with vendor competition, but embracing it helped them learn their relative strengths and weaknesses and improve win rates.
Example from SaaStr speakers: Jameson Yung (SVP Sales at Gong) notes that when Gong came along, they weren’t replacing something people previously used. Instead, they came onto the scene with a compelling story that the current world was broken, and they had the solutions to fix it. They immediately outsold Chorus from the start by leveraging a different marketing engine that gave Gong more credibility.
7. Show Measurable Pipeline and Revenue Impact Within One Sales Cycle. Yes, One.
By the end of the first full sales cycle (90 days), you should see clear signs of improvement: more demos, more contracts being drafted, and ideally, more closed deals. A great VP Sales will tune the engine they inherit immediately, showing faster revenue growth in just half a sales cycle.
Measurable improvements should include:
- Increased demo-to-opportunity conversion rates
- More contracts in negotiation
- Higher close rates with existing pipeline
- Faster deal velocity
- Improved revenue per rep metrics
Ron Gabrisko (CRO at Databricks) immediately hired 40 enterprise reps within his first quarter when he saw bigger dollars were in the enterprise. He leveraged investor networks (particularly a16z) to land early Fortune 500 deals by making specific, pointed asks rather than generic requests.
Ashley Kelly (VP of Global Sales Development at Rippling) helped scale Brex’s outbound from $2M to over $300M in ARR by immediately implementing structure and clear KPIs. She created calendar blocks for reps to make outbound calls, write emails, and follow up with accounts, with clear expectations on sales activity for each SDR.
8. Take Executive Ownership of Deals and Provide Hands-On Coaching
The best revenue leaders engage directly in deals to provide executive sponsorship and conduct initial assessments of funnel metrics and friction points. In the early days, a VP of Sales should be closing deals themselves to learn the product, sales process, and customer firsthand.
Hands-on leadership includes:
- Joining key prospect calls and negotiations
- Personally closing important deals
- Coaching reps on live opportunities
- Identifying and removing sales process friction
- Demonstrating best practices in real situations
Vanta CRO Stevie Case recommends getting multi-threaded early and qualifying buyers to de-risk deals, especially in the “messy middle” of mid-market where stakeholders can change rapidly during company growth.
Christian Smith (CRO at Splunk) emphasizes that in enterprise selling, building deep, long-term relationships is much harder to do remotely. “If you can meet with customers face-to-face more often, you’ll have a real competitive advantage because many organizations haven’t course-corrected back to in-person engagement post-pandemic.” Splunk sees 3x higher conversions when they show up in person.
9. Assess and Improve People, Process, Systems & Culture
Top CROs conduct comprehensive assessments of people, process, systems, and culture, developing a revenue/sales operating model that defines new ways of working. If a VP doesn’t do something you expect them to do in the first 90 days—they never will.
Assessment areas:
- Team performance and skill gaps
- Sales process effectiveness and bottlenecks
- CRM and sales tooling optimization
- Compensation and incentive alignment
- Team culture and motivation drivers
Loren Padelford (CRO at Slice) emphasizes that the role of CRO is pure science, not magic. Most of his job is “in the foxhole with the team, looking at spreadsheets, watching input and output values, looking at the math, drawing trend lines, working out process steps.” He focuses on knowing the specific levers that make a difference, understanding that revenue is just an output of what people actually do—make calls, attend meetings, do presentations.
Stevie Case (CRO at Vanta) emphasizes developing a “killer discovery process to impose order in the chaos.” She advocates creating mutual close plans in writing, shared with buyers to force them to figure out their procurement process. Key questions include: “What problem are you trying to solve, and why is it a priority today?” and “What’s your process for purchasing once you’ve decided to buy?”
Matt Plank (CRO at Rippling) completely restructured their customer success approach. Instead of traditional CSMs only owning retention, he moved to sales-oriented account managers who own both revenue AND retention quotas. “If you have to choose between a CSM profile that owns revenue or an Account Manager profile that needs to be CS oriented, 100/100 times I’d choose an Account Manager that needs to be customer-oriented because you can teach a revenue-oriented person to have empathy for a customer.”
10. Develop a Multi-Quarter Achievable Roadmap
The best CROs create multi-quarter prioritized action plans with cross-functional alignment to ensure resources are available as needed. They don’t just audit or analyze—they bring people together around a roadmap for what the company needs to accomplish in the next quarter, two quarters, and beyond.
Strategic planning includes:
- 3-4 quarter revenue and hiring roadmap
- Scaling strategy for different market segments
- Technology and process improvement timeline
- Cross-functional resource requirements
- Risk mitigation and contingency planning
Kyle Norton (CRO at Owner.com) focused on fixing a “leaky bucket” in his first 90 days by saying no to 40% of prospects who previously would have been closed-won. He paused growth plans until churn was under control, demonstrating the importance of prioritizing sustainable economics over volume.
Christian Smith (CRO at Splunk) advocates for measuring everything because the more you measure, the more data slices you can create. “Measure everything you possibly can. Capture it and keep it because a whole bunch of the science behind pipeline is measuring at a specific point in time and comparing and contrasting so you can identify what’s changing and what’s not.”
The Bottom Line
The best VPs of Sales and CROs hit the ground running from their first week and even their first day. Within 30-90 days, they should be improving pipeline metrics, closing more deals, and showing tangible progress. If they can’t deliver results quickly, they won’t last long in the role.
Remember: great revenue leaders are world-class managers, not magicians. They succeed by doing “all” the fundamentals—hiring, managing, promoting, listening, iterating, and assisting—in their first 90 days.
The companies that get this right accelerate faster. The ones that don’t often lose a critical year of growth. Make sure your next VP of Sales or CRO has a plan to deliver on all 10 of these areas, and hold them accountable to measurable progress within their first sales cycle.
And … 10 Warning Signs Your VP of Sales/CRO Isn’t Going to Work Out
If you see these red flags in the first 30-90 days, it’s time to make a change:
• They’re still learning the product after 30 days – Can’t demo effectively, fumbles objections, or doesn’t understand core value propositions
• Pipeline discussions are all charts and no action – Endless spreadsheet reviews without focusing on which actual deals can close this quarter
• They haven’t upgraded the team – Still giving leads to underperformers instead of recruiting proven closers who can deliver results
• No measurable improvement in key metrics – Close rates, deal velocity, and conversion rates remain flat or decline after 60 days
• They avoid competition instead of embracing it – Runs from competitive deals rather than developing battle cards and competitive strategies
• CEO alignment is missing – No clear 60-day action plan or frequent disagreements about priorities and expectations
• They micromanage process over results – Focus on activity metrics instead of revenue outcomes and deal progression
• Cross-functional relationships aren’t developing – Poor collaboration with marketing, product, and customer success teams
• They don’t get in the trenches – Rarely joins customer calls, doesn’t coach reps on live deals, or closes deals themselves
• Strategic thinking is absent – No multi-quarter roadmap, scaling plan, or vision for how to grow beyond current constraints
Remember: If your VP of Sales isn’t working out, you’ll know within 30 days. Trust your instincts and act quickly—every month you wait costs you a quarter of growth.
This post is based on SaaStr deep dives withJason Lemkin, Brendon Cassidy (EchoSign/Adobe Sign), Matt Plank (Rippling CRO), Sam Blond (former Brex CRO, Founders Fund Partner), Kathy Lord (CRO at Zensai), Andrew Bothwell and Aaron Schilke (Talkdesk), Graham Moreno (Windsurf/Codeium VP Worldwide Sales), Jonathan Vassil (Toast CRO), Chris Merritt (Cloudflare CRO), Ron Gabrisko (Databricks CRO), Kyle Norton (Owner.com CRO), Loren Padelford (Slice CRO), Stevie Case (Vanta CRO), Ashley Kelly (Rippling VP Global Sales Development), Jameson Yung (Gong SVP Sales), Christian Smith (Splunk CRO), and dozens of other successful revenue leaders who have scaled B2B companies from startup to IPO.
