Michael Maday

As a Customer Success leader, there are a handful of alignments that I have prioritized. Sales - Aligning CS & Sales is the most important thing an organization can do and if you be the tie that binds these groups, it will pay significant dividends. Support - Bugs happen, tickets and escalations are part of our day-to-day but if you do not have a strong relationship with Support you will not have a lifeline when you need something prioritized, or eyes on an issue impacting your customer. Services - Most SaaS companies are dependent on Services to stand up the instance and make incremental improvements through the lifecycle. Building relationships with the team will make tricky situations easier to work through and will also you to offer procedural improvements that they would otherwise not appreciate. Getting in the trenches with Support and Services is something a great CSM / CS Leader does but you also need to know when to get out of the way! Product teams - No one knows the way your product is used and the gaps that exist like Customer Success and Product teams thirst for this knowledge. Either through technology or a spreadsheet, find a way to aggregate feedback and get it to Product. Also, invite them to meet with your customers! Most Product teammates love seeing their work in the hands of customers, but do not have the relationships, make it happen for them! Once this relationship is built, then you can introduce a little scope creep into their backlog :)

Always try teaching them someone that they don't already know about the business, product, or customers. Keep your communications tight, both verbal and written! Never let them walk into a risky/negative situation unprepared Remember that they are people too! Establish yourself as a go-to person that they can count on in key situations. Be hungry and aggressive!

This is a tough one! In this situation, I would do my best to flex my diplomatic skills. Draft up communication that includes both Execs (with some other relevant stakeholders if possible) and do your best to lay out the pros and cons of both options, doing your best to appear as neutral as possible and then push these execs to make a decision one way or the other. If you feel very strongly that one option is the correct one, and you have facts to back this up, do not walk away from an opportunity to appear decisive and in control. I would much prefer to be fast and wrong (and then course correct) than taking too long to make a decision, or even worse never making one at all!

To understand what initiatives are critical to focus on within your business, you need to take a data-driven approach. A quick strategy would be to understand the financial changes within your customer base (add-on dollars, churn dollars) and then review the activities that occurred with these customers. Analayze this data to understand trends, and how the CS team is driving outcomes and then eliminate non-crucial tasks.

Senior Executives love to learn things that they do not already know about the company, your product, or your industry. When an opportunity arises for you to interact with them, give them an opportunity to learn from you! Additionally, these leaders despise walking into a difficult conversation unprepared and it is your role as the CSM to make sure this NEVER happens within your book of business. When you have an Executive joining your meeting, over-index on the prep you put together for them. Recently my team has started recording quick videos so the execs can get their prep that way (in addition to email) Do not be afraid to speak up at an All-hands or company-wide meeting but be sure your question/opinion is razor-sharp. While your CEO will obviously answer a softball question about expansion into a new geography or potential acquisition, you will not stand out to them. 

In this current economic landscape, the only teams that are going to be allocated resources are the ones that are able to show and substantial return on investment (ROI) to the organization. For example, Customer Success teams must be able to project how adding resources or technology will positively impact Retention Rates, Drives Expansion, or Reduces churn. Additionally, these requests must be as data-driven as possible and not hypothetical scenarios. Be critical in your assessment and if your ask is not going to bring a 5x-10x return, it will not be accepted. 

1. Customer Success Managers (CSMs) are grouped into segments based on either Product Type or Annual Recurring Revenue (ARR). 2. Each CSM reports to a CS Director responsible for leading their respective segment. 3. CS Directors report to the VP of Customer Success, who manages all CSMs. 4. The VP of CS reports to the Chief Customer Officer (CCO), who oversees all post-sales teams, including Renewal Managers. 5. The CCO, in turn, reports to the CEO of the company

To scale a Customer Success function effectively, it's crucial to demonstrate its financial impact and how additional headcount can amplify this effect. A simple method is to analyze renewal and expansion rates for accounts managed by Customer Success. By applying this financial model, you can determine the potential growth and retention value that an additional CSM could bring when engaging with currently uncovered accounts. This approach provides a clear rationale for expanding the team while showcasing the function's tangible contribution to the organization's bottom line.

Understanding and quantifying the value customers receive is paramount for a new CSM function. Once identified, it facilitates the construction of a CS framework to expedite time to value recognition and provide tangible proof to the customer. Growth of this value becomes the cornerstone for aligning with stakeholders, conducting Executive Business Reviews, and other operational motions.

When interviewing new Customer Success Managers, I prioritize strong communication skills and professionalism as fundamental requirements for the role. Additionally, I seek evidence of their proven track record in essential role-related skills. I also inquire about instances where they've demonstrated "Extreme Ownership" of accounts and situations, along with lessons learned from past missteps, whether internal or with customers.