This scenario comes up regularly in my work with European scale-ups: “Gordon, we need an interim CCO or an Interim Head of Customer Success. Our current leader started as our first support hire five years ago. He’s brilliant with customer support and the team loves him, but he’s struggling with data analytics and strategic proactive customer success. The board keeps asking why our expansion revenue is flat.”
Sometimes the situation is more pressing: “She’s going on maternity leave in two months, and we see this as an opportunity to bring in interim customer success leadership to evolve the role while she’s out.” Or: “Our investors have given us six months to show measurable improvement in customer metrics, and we need fractional customer success expertise that can deliver results quickly.”
Here’s what I’ve found working with companies in this situation: the question isn’t whether you need to fix your customer success operation — it’s whether you develop your existing leader whilst transforming the function, or start over completely.
Why Replacing Good People Feels Wrong (And Usually Is)
Most CEOs I speak with hate the idea of replacing someone who’s been loyal, works hard, and genuinely cares about customers. And they should — it usually backfires.
I’ve seen companies lose valuable customer relationships when they bring in external “strategic” hires who don’t understand the nuances of their customer base. The new hire spends months figuring out what the previous leader already knew, while customers notice the difference in service quality.
Your existing leader knows which customers are actually happy versus just polite. They know who the real decision-makers are behind the official contacts. They understand your product’s quirks and how customers actually use it versus how you think they should use it.
That institutional knowledge has real commercial value. The question is whether you can combine it with strategic customer success expertise fast enough to meet your business timeline.
What I Do Differently
When I work with companies in this situation, I don’t come in to replace anyone. I come in to build capabilities — both in the operation and in the people.
Here’s what that looks like in practice:
I spend my first month working alongside your existing customer success leader, not above them. We analyze customer health data together. I show them how to spot expansion opportunities they’ve been missing. We build playbooks for different customer segments based on their relationship insights and my process frameworks.
Instead of taking over customer relationships, I help them have better strategic conversations with their existing contacts. Instead of implementing my systems, we design processes that work with their customer knowledge and company culture.
The transformation happens faster because I’m not starting from scratch — I’m amplifying what already works and filling in the strategic gaps.
When Development Makes Most Sense
The development approach through interim leadership is particularly effective in several scenarios:
Leadership Development Opportunities When your current leader has strong customer relationships and team loyalty but lacks strategic customer success experience with data analytics, expansion strategies, and proactive account management.
Natural Transition Periods When your customer success leader is going on parental leave, sabbatical, or extended absence, creating an opportunity to bring in interim strategic leadership while preserving their role and ensuring they return to a more strategically evolved organization.
Board-Mandated Rapid Change When investors or board members are demanding measurable improvements in customer metrics within specific timeframes that don’t allow for gradual internal development but still value preserving institutional knowledge.
Cultural Preservation Priorities When company culture values internal development and you want to send a message that growth and skill development are supported rather than replaced, while still achieving transformation results quickly.
Customer Intimacy Advantages When your existing leader’s deep customer knowledge provides competitive advantage, and losing that relationship capital would be more costly than the time investment required for strategic development.
The Development-Focused Approach
The most effective strategy often combines interim transformation with internal leader development:
Phase 1: Assessment and Quick Wins (30 days) Interim leader conducts rapid assessment of current customer operations while working closely with existing Head of Customer Success to understand customer relationships, team dynamics, and operational challenges.
Phase 2: Implementation and Mentoring (6-12 months) Deploy proven customer success frameworks while mentoring the existing leader on strategic customer success concepts: roles and profiles, customer health analytics, expansion playbooks, cross-functional alignment, and data-driven decision making.
Phase 3: Sustainable Handoff (3-6 months) Gradually transition strategic responsibilities to the developed internal leader while ensuring processes, systems, and capabilities are fully embedded in the organization.
This approach provides immediate transformation benefits while building sustainable internal leadership capability and preserving valuable institutional knowledge.
Economic Considerations
While interim leaders command premium daily rates, the total cost often compares favorably to permanent hires when you factor in:
Speed to value – Interim leaders typically deliver measurable results within 90 days, compared to 6-12 months for permanent hires to reach full effectiveness.
Reduced hiring risk – No long-term compensation commitments or severance obligations if the leadership approach doesn’t deliver expected results.
Transformation expertise – Access to specialized change management skills that most permanent customer leaders don’t possess.
Immediate impact on revenue – Faster improvement in customer retention and expansion can quickly offset higher daily rates through improved financial performance.
For a company with €50M ARR, a 5% improvement in net revenue retention driven by interim leadership could generate €2.5M additional annual revenue — easily justifying the investment in transformation expertise.
Making the Decision
Consider interim development leadership when:
- Your current customer leader has strong relationships but lacks
strategic customer success experience - Natural interim opportunities exist (parental leave, sabbaticals)
that allow for strategic evolution - Board or investors are demanding rapid customer performance
improvements with specific timelines - Preserving institutional knowledge and team stability is important
- Company culture values internal development over external replacement
- Customer intimacy and relationship knowledge provide competitive advantages
Consider replacement when:
- Current leadership lacks both strategic skills and development potential
- Board mandates are so urgent that development timelines are impossible
- Cultural change requires completely fresh leadership perspective
- Existing leader doesn’t want to develop new strategic capabilities
- Customer relationships are already strained and fresh perspective is needed
- (An interim leader could still fill the gap here and get you started today)
The Strategic Opportunity
The real opportunity isn’t just about solving immediate customer success challenges—it’s about building sustainable strategic capabilities while addressing urgent business needs. Whether driven by natural transitions, board mandates, or internal development priorities, interim leadership can deliver both immediate transformation results and long-term organizational capability.
For companies with customer leaders who have grown from support backgrounds, interim strategic leadership offers a path to evolution rather than replacement. For organizations facing board pressure for rapid improvements, it provides a way to achieve urgent results while building internal capabilities for sustained performance.
The most successful approaches recognize that customer success transformation isn’t just about implementing better processes—it’s about developing strategic thinking, analytical capabilities, and commercial focus while preserving the customer relationships and institutional knowledge that provide competitive advantage.
Ready to explore whether interim customer leadership could accelerate your transformation timeline? The decision requires careful assessment of your specific situation, timeline, and transformation requirements.
Let’s discuss the approach that makes most sense for your organization.
