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9 June 2022

The Why, What & How Of Hiring A Transformational Customer Success Operations Leader

by Emily Ryan Reading time: 8 mins
operations leadership

Are You Missing The Mark On CS Operations?

If you’re a CCO or CRO at a B2B technology company, ask yourself these 3 critical questions:

  • Is your existing Customer Success management team struggling to keep up with your customer’s needs and your business goals?
  • Is collecting, analyzing and acting on critical customer data a challenge in your organization?
  • Are your internal systems facing low adoption or being used inefficiently, blocking the team’s ability to scale?

If you answered yes to any or all of the above questions, then you urgently need to hire a senior-level Customer Success Operations Leader. 

Customer Success Operations is an exploding domain within the realm of Customer Success (CS) yet few companies are leveraging this function to its full potential. More often than not, CS Operations is a dispersed function with Director-level and below folks. While having these on-the-ground folks is certainly important, this leaves a glaring gap within your CS organization. With only a Director of Operations who answers to your VP of CS, you have no one to focus on the strategy driving your CS Operations, the engine that powers your entire Customer Success organization. In order to drive best-in-class Net Dollar Retention (NDR), you need seasoned CS Operations leadership with the right amount of strategic expertise, seniority, and influence that can act as a partner within your organization and across your business. This leader must be empowered to coalesce all of your operations momentum into a strategic direction that brings your customers and your company closer to value realization.

In this article, we outline 3 critical reasons why you must hire a Senior CS Operations Leader, what skills and qualities you should look for in a first-rate candidate, and how to prove the organizational, economic and business impact of your Senior CS Operations leadership.

The Business Impact Of Senior Customer Success Operations Leadership

1. They Drive Economic Growth

The goal of your Customer Success Operations function is to improve the efficiency of your team, tools and processes to ensure maximum net dollar retention. By fulfilling this important charter, a Senior CS Ops leader will directly impact 3 critical metrics that drive your company’s growth: Customer Lifetime Value (CLV), Cost-to-Retain Customers (CRC) and Cost-to-Expand Customers (CEC). If you hire first-rate CS Ops leadership and fully empower them with proper funding and resources, they will help your organization increase CLV, decrease CRC, and reduce CEC. Ultimately, your Senior CS Ops Leader will be able to determine and decrease your Cost-to-Serve per $1 million of revenue, while simultaneously impacting profitability and your ability to drive best-in-class Net Dollar Retention.

From an investment standpoint, hiring a Senior CS Operations Leader provides exceptional ROI. The primary goal of CS Operations leadership is efficiency. For every improvement they make and every person they hire, you’re increasing your ability to serve more customers; often, this impacts hundreds or even thousands of additional customers served versus just a dozen from hiring another Customer Success Manager.

2. They Optimize The Customer Lifecycle

Inevitably, everything related to the customer lifecycle falls under the purview of your CS Ops team and Senior CS Ops leadership. From tool selection and optimization to CS strategy development and implementation, a Senior CS Ops Leader will impact everything related to your customer and your ability to drive and scale value across the customer lifecycle. Luckily, this impact isn’t limited to your CSM team – given a broader scope of Customer Success Operations, your Senior CS Ops Leader will work closely with team leaders in Sales, Marketing, and Revenue Operations to collaborate on customer data analysis, platform integration and customer engagement strategies in order to create a unified customer journey and deliver a seamless experience to your customers.

3. They Derive Insights For Data-Backed Decision Making

As the nexus for all customer data, CS Operations leadership Leader plays a key role in generating data analysis and deriving key insights that strongly influence the direction of your organization at large. By determining the efficacy of your processes and customer engagements, your CS Operations Leader will undoubtedly impact the effectiveness of your CS team. The valuable insights they derive, the KPIs they measure and the data story they tell will be used by your executive leaders to support company operations, develop effective strategies, create new programs, diagnose existing issues and influence the overall direction of the business. Having a competent and empowered Senior CS Ops Leader will help you make data-driven changes that streamline your teams and processes and influence Executive Leaders to steer business strategy.

3 Key Qualities To Look For In A Top-Rate Customer Success Operations Leader

1. Leadership & Business Strategy Expertise

There are some qualities essential to any and all senior leaders which your Operations Leader should also possess, including strong communication skills. While this may seem obvious, this trait is especially important in a Senior CS Ops Leader because this person needs to be able to communicate effectively with cross-functional department leads in Sales, Marketing and Product, as well as with Senior Leadership and the C-Suite. Strong leadership skills also intersect with another essential skill for this role; organizational change management. CS Operations as a function is responsible for constant change in the organization through continuous optimization and improvement. The ability to successfully enact change, especially in people and their behavior, is an often underestimated and overlooked skill that is critical to the success of a Senior CS Ops Leader.  

As this is a relatively new position for even the most advanced B2B technology organizations, an entrepreneurial mindset and get-stuff-done attitude is a must. There’s a lot of foundational work to be done in CS Operations without clearly outlined processes or best practices, which may feel overwhelming to some. You need a transformational leader who is able to move the needle by charting a clear strategy and direction while also taking tactical steps to achieve that strategy.

2. Customer Expertise

In order to deliver optimal customer value, your candidate for a Senior CS Ops Leader should have prior experience with customer management and the Post-Sales ecosystem. Oftentimes, companies will turn to Sales or Marketing Operations leadership to fulfill CS operational roles, which can backfire; the demands and requirements of a Senior CS Operations Leader are distinct and entirely different from these functions. In order to optimize and scale customer engagement and activities, relevant experience in a role like Customer Success Manager or as a CSM leader is essential. As a bonus, look for someone who also has experience leading digital engagement strategies and methodologies as this expertise will help them successfully scale value across your customer base.

3. Technical Expertise

While your Senior CS Operations leadership may not get involved in the finer details of your technology and data, they will oversee both aspects. As such, they should have previous exposure to and a solid understanding of system administration strategy, including software development tools, practices and methodologies. They should also have a deep understanding of customer data and a proven ability to analyze and evaluate this data to tell a compelling story that is relevant to Senior Leadership and highlights key gaps and opportunities for organizational development. 

How To Measure The Success Of Your Senior CS Ops Leader

Once you’re able to communicate the criticality of Senior CS Operations leadership and hire someone for this position, you need to measure their progress and show ROI to your Executive Leaders. To do this successfully, there are a number of key factors that can help you measure their impact: 

  • Economic & Satisfaction Criteria – First and foremost, your Senior CS Operations Leader should be measured by their impact to Net Dollar Retention. Additionally, measure their ability to drive efficiency and scale, their impact on Cost-to-Serve per $1 million, gross margins, customer satisfaction across all tiers and employee satisfaction across Customer Success. 
  • Key Customer Success Criteria – while the specifics of these may differ based on your business model and product, some metrics that you can measure your Senior CS Operations Leader against include Time-to-Value, product adoption, health score and expansion win rates.

Operational Excellence With The Right Leader

Customer Success Operations is an integral component of all growing B2B technology companies. In order to unify your customer lifecycle and your CS organization, you need a seasoned CS Operations Leader with the right blend of strategic direction and operational expertise that can lead your customers to success and your business to best-in-class Net Dollar Retention. 

At the heart of a powerful CS Operations function is actionable customer data. Here are 5 steps to unlocking the power of revenue-driving Customer Intelligence that will boost your operational efficiency and your impact as an organization.

Emily Ryan

Emily has nearly 15 years’ experience coordinating teams across Sales, Post-Sales and Product/Delivery to ensure successful customer interactions. Her unique expertise applying Customer Success Strategy to effectively establish, analyze and scale great customer-centric teams means her impact is not only to corporate revenue and retention, but to the health and productivity of the teams she empowers.