The CS Leader 'First 90 day' Plan
- Russ
- Sep 18
- 7 min read
Updated: Sep 19

In a previous company I was in, a new leader came into the business and talked about the ugly green lamp. He said, "when you move into a new home you see an ugly green lamp, but over time you get used to it, forget it's there, so don’t bother to change it. When anyone comes into your home, they notice the ugly green lamp". There is an ugly green lamp in every business and how you go about handling it is crucial so as to have the right and appropriate response to it. Do you change it? Do you accept it?
In a new Customer Success leadership getting a fast start is important, but getting the right start is even more important. You only get one first impression, and can only play the ‘new person’ card for so long before you become part of the furniture. Every time I have been in a new role for a few months, I always think, “I must remember to do this next time.”
Some call it a 90 day plan. Others call it an onboarding plan. Whatever you call it, you will essentially be planning what to do now, next and later, in whatever period of time you need to make your impact.
To focus the plan, split the focus into 6 core areas; Commercial, People, Process, Product, Performance, Tools
Here’s what a first 90 day impact plan would look like.
By end of Week 1 (day 5)
Objective: Watch, listen, learn. Don’t make assertions, assumptions or decisions.
As the newest person in the room, listen to everything said, make notes, keep an open mind, don’t make decisions. Go into every situation with a Shoshin mindset, an attitude of openness, eagerness, and a lack of preconceptions, ready to learn. Make sure you seek out multiple data points and opinions.
Commercial
Review lists customers by cohorts and revenue to identify top/important customers
Identify renewals due in the next 30 days
Identify top risk customers
Have someone deep dive on the commercial strategy, pricing structure, and Sales philosophy and methodology
Watch at least 1 customer call recording every day
People
Meet with direct reports 1:1 to learn about them as individuals, and learn about their approach to the role. Establish a weekly cadence.
Attend/schedule a team meeting and establish a weekly/regular cadence
Set a regular cadence meeting with my line manager and establish their early expectations and deliverables of me
Identify key individuals across the company to meet. Prioritise senior leaders across all functions, first-line leaders, Product Management, and Sales reps
Attend Company All-Hands/identify when the next one is.
Process
Locate existing company/process documentation and review those that pertain directly to CS and Sales. Prioritise processes for onboarding new customer and handling churn risk
Product
Get full access to the product and identify the best customer-facing person to give a walkthrough Q&A/demo
Connect with Product Managers and schedule 1:1s for 1st month
Performance
Identify the company’s current goals, OKRs and where to locate current performance metrics
Review the last Company All-Hands
Tools
Get access to core tools used in the company; CRM, CS platform, billing system, data/analytics tools, Support system, call recording system, company documentation site
Speak to the owner of each of the above tools and get a whistle-stop tour of how each is used, and identify key dashboards and views for visibility
By end of Month 1 (day 30)
Objective: Build relationships and trust, skill up, be visible.
Connect with key individuals and establish priority relationships, learn the ropes and understand what works, what doesn’t work, and where opportunities for improvement will have the greatest impact. Don’t be afraid to keep asking questions, but with an equal balance of taking action. Block and tackle for your direct reports where needed, and be present and ready to assist on anything. You may have already identified quick wins, in the form of high impact/low effort tasks that can be executed with minimal disruption. Do them.
Commercial
Review each CSM’s book of business to understand top/important customers, at risk customers, new customers, customers that haven’t been contacted in a while.
Ensure a plan of positive proactive engagement is in place to address renewals due in the next 30 days that are at risk
Meet personally with key contacts at top customers to listen, learn and identify action opportunities. Start to produce a Champion Score metric
Attend weekly Sales team meetings.
Produce a forecast of renewals due this quarter and next quarter
Ensure all renewals are completed before the renewal date. Maintain that expectation
Watch/attend at least 1 customer call recording every day
People
Continue to meet direct reports, with a goal to establish formal or informal social contracts
Plan for team all-hands to communicate personal principles, vision, and plan, based on learnings in first 30 days
Meet with key individuals across the company. If the company is < ~100 people, meet with everyone!
Process
Locate existing company/process documentation and review those that pertain directly to CS and Sales. Prioritise processes for onboarding new customer and handling churn risk
Meet with SMEs for processes to understand what’s working and not
As learning and onboarding begins, validate existing process documentation for accuracy. Where process documentation doesn’t exist, write learnings in the form of process documentation
Product
Take available product training and get demos from individuals who know it well.
Learn the product demo, pitch and value sell. Demo internally and to a customer.
Meet with all Product Managers 1:1 to understand what their area of ownership is
Read/watch/listen to latest Product Roadmap and identify key product development areas for near future and their positive customer impact
Review content of customer feedback repository. If there isn’t one, establish a process and repository
Performance
Review company metrics and performance and trends of the last 4-8 quarters. Deep dive into the company metrics, performance successes and challenges
Review current and past CS metrics and performance
Tools
Review the content held in the CS platform and CRM tools in depth
Review the usage of all tools that CS uses or needs in order to produce a ‘minimum viable tech stack’
By end of Quarter 1 (day 90)
Objective: Provide meaningful impact and value, and set longer term vision, strategy and goals
Having learnt about the business, built relationships, established principles and operational norms, the first quarter gives you an opportunity to make a really valuable impact. Bring your experience and knowledge without being tempted to lift and place playbooks, programs and operations that have succeeded in past companies. Respect the history and culture of the company, and be mindful of the journey existing team members have been on to get the company to where it is today.
Commercial
Produce a rolling forecast of renewals for the next 3 quarters
Establish regular cadence for reviewing and communicating at risk customers
Establish internal top account forum
Make necessary changes to cohort engagement strategy and CS assignments/books of business.
Standardise Renewal execution. Codify renewal processes and operations, pricing philosophy & legal/finance guardrails.
Review the proactive approach to land and expand. Ensure there are plans for appropriate supporting strategy, messaging, enablement, messaging, quotas/goals
Watch/attend at least 1 customer call recording every day
People
Review existing role profiles and adjust/update as needed with a view to establishing clarity on role and performance expectations
Identify future headcount needs which result in coaching and development, promoting, hiring, or departing
Establish career and progression plans for interested team members
Establish a form of internal quarterly business reviews
Invest heavily in peer relationships. Ensure regular cadence with leadership peers exists for alignment and that you have clarity of understanding of their goals
Learn the companies approach to performance reviews
Ensure a culture of celebrating wins, successes and best practices exists, where giving and recognising credit worthy work is in place.
Process
Have someone walk me through the end to end customer journey
Resolve and codify missed steps, gaps, in existing documentation. Ensure familiarity and adherence is consistent.
Have process documentation created for all key CS processes pre-sales, post-sale onboarding, engagement, revenue/finance/billing related, upsell/expansion, renewal
Plan in place for next quarter/phase, outlining longer-term projects and CS operations backlog of work to be done
Product
Ensure a Product/CS Partnership Agreement is in place with alignment on expectations and value adds
Ensure regular cadence of forums for CS and Product org exists
Review product usage data with Product Managers and CSMs to identify PQL triggers and process improvement opportunities
Performance
Review and validate current and next quarters CS goals
Review and align CS compensation for the following quarter based on company and sales goals. Review/introduce incentives aligned with company key metrics.
Tools
Review Enhance, consolidate, or acquire tools that will achieve standardised use, greater visibility, and revenue growth.
Ensure tool specific expectations and guidelines are understood and documented
Review the commercial agreements for all tools CS owns
It’s important to note that the ‘by end of quarter’ portion of your plan will be heavily driven by what you learn and discover in the first weeks and months you are in the new role. Coming into the business with assumptions, learnings, pre-conceived notions and biases can be dangerous if not properly tested and validated. The later parts of your 90 day plan will be heavily assumption based and, hopefully, you will be pleasantly surprised enough to be able to change much of that later on.
My plan above is by no means extensive and certainly cannot be lifted and shifted into your first 90 days in a new business without considerable amounts of listening, learning, assimilation, and qualifying. Your business and role will come with its own nuances, politics (unfortunately), business priorities, performance and successes, go-to-market strategies and customer dynamics.
I think in structures, strategies, and principles, that I can apply to a new role, and adapt according to the surroundings, so that I can both listen and learn, but also provide early impact and value.
If you want a couple of academic voices for further reading, consider reading Good Strategy, Bad Strategy by Richard Rumelt or The First 90 Days by Michael D Watkins. These texts will undoubtedly give you your own inspiration and guidance, in the same way they have me as I have built my own 90 day plan.
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