First 90 Days in Sales Leadership: A Playbook by Tim Savage


Stepping into a sales leadership role or aiming to enhance your team’s performance? The first 90 days are critical. Just like in sports, the fundamentals are everything. This playbook outlines key steps to set you on the path to success during these pivotal early days.

Day 1-14: Understand Your Outbound Operations

Talk to Your Team Start by engaging with your outbound team. Understand their processes, challenges, and successes. Comprehensive engagement with everyone involved in outbound activities is essential to grasp current operations fully.

Evaluate Connection Rates Assess your current connection rates. If your calls are connecting at less than 20%, or if you can’t measure this metric, it’s an immediate optimization opportunity. Review your outbound emails for low open and engagement rates as well, indicating areas ripe for improvement.

Get the Data Right Outbound activities are the lifeblood of your sales engine. Ensure all activities are meticulously tracked within a robust system. Accurate data is critical for pinpointing areas needing improvement and measuring progress.

Day 15-30: Analyze Your Funnel

Review Every Opportunity Delve deep into your sales funnel. Examine every opportunity for the current and next quarter. Review the last update, the last set of notes, and the next action for each deal.

Team Huddle If there are gaps in the data, gather your team for a huddle. Export all notes into a spreadsheet and utilize tools like ChatGPT to quickly analyze the data. This brute-force method provides a clear picture of your funnel’s health.

Day 31-45: Mid-Funnel to Bottom-Funnel Insights

Mid-Funnel Focus Apply the same scrutiny to mid-funnel opportunities as you did at the top. Understand the stages where deals are stalling and identify ways to accelerate them.

Bottom-Funnel Evaluation Evaluate your bottom-funnel deals. Look at closing rates, last and next conversations, and notes associated with each opportunity. This highlights bottlenecks and provides insights into effective closing strategies.

Day 46-60: Deployment and Engagement

Post-Sale Analysis Even if you’re not directly responsible for post-sale engagement, understand what happens after the sale. Analyze deployment and engagement processes to gather feedback that can be looped back into your sales strategies.

Collaborate with Teams Work closely with customer success and support teams. Their insights are invaluable for refining your sales approach and improving customer retention.

Day 61-90: Optimize and Report

Run Revenue Retention Metrics By this point, conduct a comprehensive analysis of your net revenue retention (NRR). NRR measures the percentage of recurring revenue retained from existing customers over a specific period, including upsells and cross-sells. Determine whether you are at, above, or below 100%. Use this data to inform your optimization plans.

Create an Optimization Plan Develop a detailed plan to improve your metrics. Focus on areas identified in your first 60 days and implement strategies to address them. This plan should be actionable and data-driven, targeting improvements in NRR by ensuring customer satisfaction and loyalty.

Show Results At the end of 90 days, demonstrate tangible results. Highlight improvements in connection rates, engagement metrics, and revenue retention. Your goal is to show a clear trajectory towards 200% NRR with a solid plan to achieve it.

Continuous Improvement

Training Opportunities Identify training needs within your team. Whether it’s improving sales techniques or better utilizing technology, continuous development is key.

Tech Stack Optimization Evaluate your technology stack. Ensure it’s optimized for efficiency and effectiveness. Invest in tools that provide real-time data and insights.

Plan for the Future The first 90 days are just the beginning. Use the foundation you’ve built to continuously refine and enhance your sales strategy. Keep the momentum going and strive for excellence in every aspect of your role.

Reflection of Net New Solutions Core Values and Deliverables

At Net New Solutions, our core values and deliverables are reflected in this playbook’s focus on preparation, data-driven strategies, and continuous improvement. We believe in:

Excellence and Integrity The emphasis on thorough preparation and execution aligns with our commitment to excellence and integrity in all our client interactions. We ensure our strategies are both effective and ethically sound.

Data-Driven Decision Making The focus on analyzing connection rates, funnel metrics, and NRR reflects our dedication to data-driven decision making. We provide our clients with robust tools and insights to make informed decisions that drive growth and retention.

Customer-Centric Approach Understanding and improving customer engagement and retention is at the core of our solutions. We focus on ensuring our clients deliver exceptional post-sale experiences, reinforcing our customer-centric approach.

Continuous Improvement The identification of training opportunities and tech stack optimization mirrors our commitment to continuous improvement. We evolve our strategies and tools to meet the ever-changing needs of our clients.


In sales leadership, preparation and execution are paramount. Follow this playbook to navigate your first 90 days with confidence and set the stage for long-term success. Success comes from knowing you did your best to become the best you are capable of becoming.

For more insights and support, reach out to me at Let’s elevate your sales game together.

Tim Savage
NET NEW Solutions


Connection Rate: The percentage of outbound calls that result in a meaningful interaction with a potential customer.

Engagement Rate: A measure of how many people interact with an email or content, indicating their interest.

Net Revenue Retention (NRR): A metric that measures the percentage of recurring revenue retained from existing customers over a specific period, including upsells and cross-sells.

Top-of-Funnel (TOFU): The initial stage of the sales funnel where potential customers first become aware of your product or service.

Mid-Funnel: The middle stage of the sales funnel where potential customers evaluate your product or service and consider making a purchase.

Bottom-Funnel: The final stage of the sales funnel where potential customers are close to making a purchase decision.

Outbound Activities: Sales efforts that involve reaching out to potential customers, such as cold calls, emails, and social media outreach.

Tech Stack: The combination of software and technologies used by a company to manage and improve its operations.

ChatGPT: An AI tool developed by OpenAI that can analyze text data and generate insights, summaries, and recommendations.