Navigating the First 90 Days as a Customer Success Leader: A Strategic Playbook for Startups and Mid-Size Companies
Navigating the First 90 Days as a Customer Success Leader: A Strategic Playbook for Startups and Mid-Size Companies
Explore a detailed guide for Customer Success leaders in startups and mid-size companies, focusing on a strategic 30/60/90-day plan for team building, strategy development, and customer engagement, crucial for business growth and customer retention.

Stepping in as a Customer Success (CS) team leader in today's business landscape, particularly in a startup or mid-size company, presents a challenging and rewarding journey. Customer Success is more than just a department; it's the heartbeat of any thriving company. In this new role, you must establish trust and credibility with your team, company, and customers. Therefore, a solid CS strategy is essential, and it is imperative to start quickly. This is where your 30/60/90-day plan comes in. Think of it as the roadmap for laying down a rock-solid foundation for your Customer Success team and ensuring your company's success.  Days 1 - 30 are the information-gathering stage.  Days 31- 60 are all about analysis, and Days 61 - 90 are about establishing and beginning the execution of your Customer Success Program. So, let's roll up our sleeves and dive in!


The First 30 Days: Knowledge Collection


This phase is all about gathering data and laying a solid foundation. First things first: You've got to get up close and personal with your company's products, services, processes, goals, personnel, and, most importantly, your customers. This isn't just about knowing what you sell but understanding the why behind it. 


There will be a lot of meetings in this phase, and you need to tackle them with enthusiasm so you can get to the analysis and planning stages as quickly as possible. Your first few weeks will be about scheduling time with almost everyone in the company. You’ll need to meet with your team and the executive team and then set up specific meetings with sales, finance, marketing, product, etc. You can use the guide accompanying this article to prepare for these meetings. It contains lists of questions that you’ll need to answer to complete your analysis. 


The purpose of all these meetings and all the questions in the guide is to prepare you to understand the company’s objectives, processes, KPIs, and your team’s strengths and weaknesses. What do you already have in place and what do you need to put in place? 


Finally, you’ll need to prepare to meet with your customers and should follow the Initial Customer Meeting Prep Guide. The main objective of those meetings is to see if we’ve identified the customer's business objectives and goals for using the company products and discover if the measurements we have in place are correct. If the measurements are correct, how well are we performing against them, and what are the next steps based on these discussions?



Days 31-60: What’s Working, What’s Not, What’s Needed?


While you’re probably not finished gathering information and still have customer meetings, you should have gathered enough information to move into your analysis phase. It's time to roll up your sleeves and get into the nitty-gritty of developing your Customer Success strategies and processes. This is where you start building your objectives and actionable plans, but you can’t build fully formed plans without analyzing and prioritizing the needs.


Where you start will depend on the company’s position and what is already in place, but we’ll begin discussing the Customer Success strategies and team for this plan. At this stage, your focus should be two-fold: Firstly, if customer segmentation and journey mapping still need to be implemented, prioritize establishing these critical elements. Secondly, focus on developing specific onboarding, retention, and growth plans. These plans should be adaptable and scalable to meet your business’s evolving needs and consider its expected growth. Establishing these plans will contribute to your organization's structure and help validate the processes that still need to be added. Finally, this exercise should provide a set of KPIs specific to the customer journey you want to show successful execution against.  


With the Customer Journey and information you’ve gathered about your company's goals, you’ll need to look at your organizational needs to determine the team’s current staffing and what is required to achieve the projected growth. How much additional work can your existing team achieve? What work are they doing today that shouldn’t be done or should be done by other teams? What work should be automated? With these questions answered, what processes, technology, and staffing are needed to achieve the projected growth? You’ll need to implement a profit and loss statement (P&L) for your team. You’ll use it to show ROI on process, technology, and perhaps most importantly, human investment.  


In the final analysis, the change management process demands your attention. Your initial 30 days should include gathering insights on existing change management practices. Assess whether a formal process is in place and if it's well-documented. If not, establishing a robust change management framework is essential for the success of your initiatives across the team, company, and customer base. Effective change management involves several key steps: defining the nature of the change, securing agreement and buy-in for the change, effectively communicating it across relevant stakeholders, implementing the change, and finally, measuring and ensuring its adoption. This comprehensive approach is crucial for smoothly navigating and managing organizational transitions.



Days 61-90: Action Plan


You're now entering the home stretch of your 90-day plan – the phase where you define the execution of the remaining 275 days this year and establish the initial 2, 3, and 5-year plan for the Customer Success organization's growth.


You’ve spent time gathering information about your team and company and considering your organization's needs. It’s an intense process. Now it’s time for the fun part when you get to execute, but it can be a critical mistake to begin execution without a complete vision and plan. 


We can’t say precisely what your plan will be because it will be different in every company. What we can highlight is what the critical concerns are in building this plan. Such as:

  • Clear and concise objectives
  • Timelines and costs associated with planned changes
  • List of processes and playbooks needed
  • Specific milestones to measure against
  • Evaluate and update compensation based on new goals.
  • Gain buy-in from your team, organization, company, and customers. 
  • CS-related Technology projects - Digital CS Program details
  • You’ll need to build your resource plan against this execution plan as well. You must plan to scale with your company's growth. This means preparing to scale your team in a way that maintains the quality and personalization of your customer interactions. Develop scalable processes and training programs that can accommodate this growth without losing the essence of what makes your approach successful.
  • Don’t forget you’ll want to build out your reports and dashboards and be sure to set up reporting to your executive team and board.

This exercise is about building the infrastructure for your program. As you implement and execute this plan, you’ll breathe life into your organization and ultimately grow your company's value. 


Unlike a project plan, this is a strategic plan built to mature your Customer Success organization. Therefore, you’ll want to execute this plan, iterate on it periodically, and adjust it to achieve your goals.  


This plan is like a charted course for a sailing trip. The course assumes blue skies and avoids any known storms, but in life and business, as in sailing, the weather changes, and you have to rechart your course. The goal is to create a continuous improvement cycle where you're constantly learning from your experiences and adjusting to serve your customers better.


Beyond the plan, remember that building a customer-centric culture is crucial to success. Customer Success shouldn't just be your team's responsibility; it should be a company-wide ethos. Encourage practices that put the customer at the heart of everything your company does. Share customer success stories and key learnings across the organization. This not only boosts morale but also ensures everyone understands the impact of their work on customer success.



Conclusion

As we wrap up this “playbook,” it's evident that this period is pivotal in shaping the future of your team and the broader organization. The journey from understanding to action, from analysis to execution, requires discovery, planning, and action. It involves establishing a robust Customer Success program and embedding a customer-centric culture. 


In the final 30 days of your initial plan, you translate your insights and strategies into tangible actions and long-term plans. This phase involves detailed execution while remaining agile enough to adapt to new challenges and opportunities. Your focus should be on building a scalable and efficient Customer Success organization that aligns closely with your company's goals and the evolving needs of your customers. The business world is ever-evolving, and so are your customers' needs. Staying agile, being open to feedback, and being willing to pivot your strategies are essential to a successful Customer Success function. This is not a one-time effort but an ongoing journey of improvement and adaptation.


I encourage you, as leaders, to use this playbook as a starting point and tailor it to fit the unique needs of your industry and company. Every business has challenges and opportunities; your Customer Success strategy should reflect that uniqueness.


Creating a successful Customer Success team is a journey, not a destination. It's about building relationships, understanding needs, and continuously striving to provide value to your customers. With the right approach, mindset, and tools, you're well on your way to laying a solid foundation for client success in your startup or mid-size company. Good luck, and here's to your success!