The First 90 Days: A Guide to Evaluating Your New VP of Sales
What to expect in the first few months and how to measure success (beyond pipeline).
DEAR STAGE 2: We are actively hiring for a VP of Sales and as part of the process my board asked me to share how we would evaluate the performance of this leader. Certainly we care about hitting the revenue targets and board plan, but I’m wondering what else we should be looking at in the first few months. What is expected? What is fair? ~EVALUATING NEW EXECS
DEAR EVALUATING NEW EXECS: Hiring the right VP of Sales is make or break during the scaling phase, as this leader will drive the revenue engine and influence your company's growth trajectory. A board member asking these questions has probably lived through some turnover in GTM leadership and knows catching a mis-hire quickly can save months of time. When the board asks how you plan to evaluate this leader's performance, they're not just looking for assurance on meeting revenue targets but guidance on how you plan to get this hire up to speed quickly, integrate them into the company culture, and give them room to run.
I collaborated with John Boucher, Stage 2 Capital Operating Partner, who has extensive experience hiring sales leadership and advising companies and boards on GTM. Here’s our guide to help you assess your VP of Sales holistically in the first few months:
In the initial 30 days your VP of Sales should…
Start looking for quick wins in process and operational efficiency. Early on, your VP of Sales should identify bottlenecks in current sales processes and propose improvements, and focus on unblocking and moving critical projects forward. A data-driven, detail oriented leader is going to want to free up the time of their team and will quickly figure out a few obvious ways to do that. Be wary of changes that disrupt workflows or fail to improve efficiency - a rinse and repeat “this is how we did it at my last company” is usually the cause.
Conduct a comprehensive Data Deep Dive on historical metrics. John Boucher, Partner at Stage 2 Capital, emphasizes the importance of this step: "The new hire should be diving into historical data on Bookings, Win/Loss, NDR Trends, Cross-Sell, and Upsell Data. This means reaching out to finance and revenue operations teams for detailed information. By doing so, they can share unique insights on the business early on." This data-driven approach allows the VP of Sales to make informed decisions and identify areas for improvement right from the start.
Demonstrate a deep understanding of the market, competitive landscape, and your unique value proposition. He or she should be asking insightful questions and bringing fresh perspectives (that align with your company's vision) to the table.
TIP: Make sure you, as the founder/CEO, are making yourself available to this new exec. It’s tempting to hire a leader and go hands off, but these early days set the tone for the relationship and you want to ensure that you are in lock step.
By the 60-day mark, expect a detailed plan of attack...
By this point your VP should have a pulse on the team's strengths and weaknesses and a clear view of top priorities. The quick wins move into a more organized strategic vision for the coming months. You’re looking for a balance of strategy and execution. A cohesive, data-driven plan signals early success, while a vague or overly ambitious strategy (often lacking in actionable detail) may be cause for concern - these hires can get stuck in analysis mode and never reach the pace of execution required for a startup. This plan might include a sales playbook, compensation plan adjustments, re-org proposal, hiring plans, and feedback on the plan for the year (how to achieve it or why it might need to change).
An important aspect to watch for, as John points out, is the VP's ownership of the forecast. "In the current quarter and the next, the forecast should be fully reviewed, with the new VP showing clear ownership vs. treating it as an inherited forecast with no accountability," Boucher advises. This level of engagement demonstrates the VP's commitment to driving results and their willingness to be held accountable for the team's performance.
Cultural fit and integration become clear within the first few months too. Positive signals include strong alignment with company values and effective cross-functional collaboration with departments like marketing, product, and customer success. If they foster inter-departmental collaboration and contribute to company-wide initiatives, it's a good sign they're integrating well. A great leader is also going to seek out feedback from you and peers during this period to make sure they understand the cultural norms.
To validate this integration, Boucher recommends a proactive approach: "Get direct feedback from cross-functional peers to validate that integration and communication is happening." This feedback loop ensures that the VP of Sales is not operating in a silo and is effectively collaborating across the organization.
Within the first 90 days, your VP of Sales should…
Have invested in team development through 1:1 face time with each team member, understanding their strengths and development areas, and building strong trust-based relationships. Additionally, they should have established relationships with top clients, gathered meaningful feedback, and translated this feedback to appropriate parts of the organization.
Have a meaningful impact on revenue targets. It's important to consider the quality and sustainability of the pipeline and customers coming through the funnel. Closing deals that align with long-term business goals indicates success, while focusing solely on short-term gains can be detrimental. The VP of Sales' ability to accurately forecast sales is another important factor and they should have a strong handle on the pipeline and forecast within the first quarter.
Develop and communicate a formal cadence for the sales business. As John emphasizes, "Within the first 90 days, you would want to see that a VP of Sales has developed and communicated a cadence to his/her business. This means establishing regular forecast calls, pipeline/coverage calls, a leadership meeting schedule, and a cross-functional cadence." This structured approach shows the VP's ability to create a rhythm for the sales organization, ensuring consistent communication, accountability, and alignment across teams.
Ultimately, evaluating a VP of Sales goes beyond hitting revenue targets. It’s about ensuring they are strategically aligned with your vision, effectively leading and developing the sales team, improving operational efficiency, engaging with customers, meeting sales performance metrics, and integrating well into your company culture.
The first few months are crucial for setting the tone and trajectory, so take the time to get this leader up to speed quickly.
Until next week!