Creating A Six Months Winning Plan for a New Head of CS

In the first six months as a new CS Leader, the executives who hired you will be looking for significant changes in team structure, operating processes, and improvements to the bottom line across the board. The question is: where do you start?

As the VP of Customer Success in a SaaS software company for the past 5 years, I have learned many things, both good and bad. I made many mistakes, but I learned from them in order to leverage my experiences in creating a six month winning plan for a new Head of Customer Success. If you’re trying to launch a new organization at an existing company, or looking to transition your team into new practices, here’s a simple 10 step checklist, with milestones to make sure you’re hitting all the right marks.

Step 1 – Learn the Product

Timeline – First 10 Days

Understand the problems the product solves and how customers use it. You need deep understanding of your personas, use cases, and pain points. Talk to other executives to understand their perspectives on the product. Engage the Customer Support team to learn workarounds, issues, and successes with the product. Own the product as an expert.

Step 2 – Get to Know the Team

Timeline – Next 20 Days

When you’re hired to manage an existing team, the first thing to do is understand who they are as people. What are their strengths, passions, and desires? What jobs are they doing that they’d prefer not to? What are their personal histories, and what makes them tick? What additional roles do you need to hire to augment your current staff to create a high-performing team? Learn if it makes sense to split the team according to strengths (e.g. onboarding, day to day CSM, upgrades & renewals etc.).

Milestone: By the end of the first month, you should have a deep understanding of the team and the product.

Step 3 – Take a Hold of the Budget

Timeline – Next 10 Days

How much of the annual budget is left, and what has already been spent? What commitments have been made (and how firm are they)? What budget is available for completely new projects, and what is your plan for how to achieve your goals? Understand the past metrics and the ROI of all of the projects. When are discussions open for a new budget, and what is missing?

Step 4 – Talk to Customers

Timeline – Next 20 Days

Start joining the customer calls that your team has scheduled; it may be a QBR, onboarding, feature webinar, training calls or just a friendly check -in call. Speak with a large variety of customers and prospects about their needs and ideas. Include a few onsites to watch your customers use your product, and to encourage them to be candid about their experiences and needs. The goal is to understand what sticks, what needs more work, and what is going to likely encourage them to renew or put them in danger of not renewing.

Milestone: By the end of the second month, you understand your customers and your budget flexibility.

Step 5 – Evaluate and Optimize the Processes

Timeline – Next 30 Days

First, you should understand why things were the way they were before implementing changes. Meet with your team and understand reasons behind the current process (Onboarding, QBR, Hand-offs, Renewals). You may not get the entire story, so you will need to analyze the data that has currently been captured. Use the tools that are already in place – communication, collaboration, measurement, platforms, project management tools, and more. The key objective with your tool set is to ensure you have visibility into your customer base.

Milestone: By the end of the third month, you now have a grip over the processes and your style is visible in the processes.

Step 6 – Build an Action Plan

Timeline – Next 20 Days

From the data collected, start writing a plan for what to do. Take stock of what items were off track. The plan should have ideas at higher level, and tasks at tactical level. These should include engagements, CSM day to day, weekly and quarterly plans, budgets, and tools needed to get the job done. See what’s been done historically, and learn from those mistakes and wins.

Step 7 – Present to Your Team

Timeline – Next 10 Days

Let your team know about your track record including background & experiences. It’s crucial early on to communicate with your team your initial thoughts and ideas. Let the team provide feedback. At the end, everyone in your team should have an understanding of the team goals and a bit about your personal style.

Milestone: By the end of the fourth month, you are ready to present your plan broken down into short term (quarter) and long term (yearly).

Step 8 – Execute Your Plan

Timeline – Next 30 Days

Execute your plan, and optimize the resources and work allocation. Now it’s time to structure the winning team to focus on the right set of customers and the processes in which their strengths are reflected. For example, if somebody is good at motivating customers to renew and upgrade then that strength needs to be leveraged across the customer base. Similarly, if a resource is highly competent in training, then that’s highly important skill to help customers moving on the product.

Milestone: By the end of the fifth month, your ideal team is beginning to take shape, (you may still have gaps), and almost all the roles are covered.

Step 9 – Put Metrics in Place

Timeline – Next 30 Days

Without metrics, you will never be able to impact revenue and see what needs improvement. If you are not able to impact revenue, you will always be under stress. Focus on the metrics that highlight where the team needs to improve. Segment your customer base based on the revenue. Track your top 20% customers daily, your next 30% customers weekly, and rest of the 50% monthly. I would highly suggest using a tool specific for Customer Success Professionals that integrates with your existing SF. That way, you can clearly manage the metrics and share what is needed with key players.

Milestone: By the end of the sixth month, you are ready to show small wins and the modified yearly plan to executives and the board.

Step 10 – Post Six Months

Timeline – Going Forward

Post six months should be focused on getting metrics north, and establishing working relationship with key stakeholders – CEO, CFO, CRO, Product heads, and your customers. Each quarter, you should be adjusting any flaws or weaknesses in your plans and constantly improving. Just like you hold QBRs with your customers, make sure that you’re meeting the stakeholder’s expectations so that you ensure expanded budgets in the future.

Moving Forward

This plan is meant to be a breakdown of how you can structure your process and growth. Customers Success is still a relatively new role and career, but it’s swiftly gaining prevalence. As always, deviations will be made to your plans based on company, customer, executive, and product variations. Creating and maintaining a plan your first six months will not only ensure you don’t miss anything, but will propel you forward to creating a successful team and meeting your goals.

Kim Oslob has worked as VP of Customer Success for over 5 years. She has extensive experience in building CS teams, gathering metrics, and developing processes to drive retention, cross-sells and upsells. She is skilled at leading and guiding teams in creating solid customer connections and trust. In September, Kim will join Whisbi to lead and start up their U.S. CS team as Vice President of Operations.

Kim Oslob

Customer Success Consultant, Linnea Consulting