Let's face it. It's tough out there for first-time Customer Success leaders. Having excelled as individual contributors, they now navigate a complex leadership landscape where the rules of success have fundamentally changed within the last few years.
What is expected is a commercial focus, to be a mentally strong superhuman and an AI hero.
I have created a CS Leadership Freewheel to help first-time leaders navigate the world.
The CS Leadership Challenge
Over the past year, while speaking with CS leaders in various SaaS companies, I’ve noticed some common struggles that everyone faces:
First: Increasing NRR while keeping costs low. Urgent demands and crisis situations often throw off schedules. Managers must juggle customer relationships, team leadership, and revenue targets, like AI, while dealing with rapid tech changes. Welcome to our world.
The complexity is growing daily, and gaps in knowledge exist, especially when it comes to digital CS and AI implementation and creating commercial strategies.
Time management is a big hurdle, with competing priorities leading to constant decision fatigue. Without enough time to reflect, strategic thinking suffers, resulting in reactive management instead of proactive leadership.
I created the CS Leadership Freewheel to help with these challenges and speed up the success process for first-time CS leaders. Let's explore it.
The CS Leadership Freewheel
The Freewheel identifies five critical areas where CS leaders must develop mastery to succeed in today's complex environments:
1. Team One Realignment
Most first-time CS leaders continue to prioritise their direct reports (as they did as individual contributors) rather than building relationships with their peer leadership team—what Patrick Lencioni refers to as "Team One."
This area focuses on developing the strategic relationships with fellow directors or VPs necessary to reposition CS as a revenue driver rather than a cost centre. It involves creating executive-friendly narratives demonstrating CS's impact on revenue metrics, building cross-functional alliances that elevate CS in the value chain, and developing influence tactics that work in boardroom settings.
Without this realignment, CS leaders remain isolated, fighting for resources and recognition rather than collaborating strategically across functions.
2. IC to Leader Evolution
The transition from exceptional individual contributor to effective leader represents one of the most challenging professional evolutions. Many first-time CS leaders continue to rely on the problem-solving skills that earned them promotion, drawing them into tactical firefighting at the expense of strategic leadership.
This area focuses on transitioning from a reactive problem-solver to a strategic enabler by developing delegation systems that withstand urgent demands. It includes creating crisis management frameworks that do not require leader intervention, building team autonomy through structured decision-making models, and establishing reflection routines that protect strategic thinking time despite daily pressures.
I am not a big fan of the Coach-Player role. Instead, leaders should master this evolution by building scalable teams rather than continuing to be involved in IC role-play.
3. Metrics & Business Impact
CS leaders face mounting pressure to demonstrate financial impact with inadequate measurement systems. Traditional customer satisfaction metrics like NPS or CSAT no longer suffice in boardroom discussions about budget allocation and strategic importance.
This area focuses on creating sophisticated measurement frameworks that connect CS activities directly to Net Revenue Retention and other financial outcomes. It involves developing predictive health scoring systems, implementing ROI models for CS initiatives, and creating commercial strategies that increase the value of customer relationships.
Leaders who develop this mastery transform perceptions of CS from a cost centre to a revenue driver, securing the resources and influence required for departmental success.
4. Organisational Influence
Even with compelling metrics, CS leaders often struggle to establish their function as strategically important amid competing organisational priorities. Many find their departments positioned as reactive support functions rather than proactive value creators.
This area focuses on building systematic approaches to extend CS influence beyond traditional boundaries and into product, marketing, and sales decisions. It includes developing internal advocacy strategies, creating compelling cross-functional business cases, and establishing CS as a strategic insights centre through data-driven customer intelligence sharing.
Leaders who master organisational influence ensure customer perspectives inform key company decisions, enhancing product-market fit and go-to-market effectiveness.
5. Tech & Innovation
The increasing complexity of CS technology stacks adds another layer of pressure, as leaders must evaluate, implement, and optimise tools while ensuring adoption across their teams. This technical burden can feel overwhelming, particularly for leaders who have risen through relationship-focused careers.
This area focuses on developing a structured approach to digital CS. It includes creating AI implementation roadmaps, establishing tech adoption frameworks, and strategies that maximise ROI on tech investments.
CS Leaders who excel here create an advantage for their own career progression. This will help ignite conversation with the Team One alignment and create a freewheel that can spin freely and fast.
The HOW - My ADAPT Coaching Framework
When coaching first-time CS leaders through this framework, I utilise the ADAPT methodology to create a structured transformation.
Access
Establish a baseline at any stage and identify counterproductive patterns in decision-making and time allocation.
Design
Co-create personalised leadership development plans with practical frameworks for delegation, crisis management, and strategic thinking.
Activate
Provide structured accountability with real-time guidance for implementing new leadership behaviours amid daily pressures.
Perform
Together, establish metrics and scorecards to track progress and demonstrate tangible leadership growth.
Transform
Create a resilient system that enables CS leaders to shape their department's future rather than merely survive daily pressures.
The Journey Ahead
The transition to CS leadership has never been more challenging—or more crucial for organisational success.
The CS Leadership Freewheel provides a structured approach to navigating this critical transition, helping first-time leaders avoid common pitfalls and accelerate their development across all dimensions of effective leadership.
In future newsletters, I will explore each dimension of the Freewheel in greater depth, sharing practical strategies and frameworks you can implement immediately in your leadership journey.
Please reach out if you are a first-time CS leader and need help—I am always open to help!
Responses