What Leading a Business Unit P&L Has Taught Me About Customer Success

After nearly seven years as a customer success leader, I recently stepped into a role overseeing a business unit with P&L responsibility—managing cross-functional teams across sales, product, customer success, solution engineering, and research. Being responsible for delivering a product to market has shifted my perspective on the optimal role of customer success.

The Traditional CS Dichotomy

While at its core, customer success is primarily focused on retaining customers and revenue, in my experience, customer success teams typically lean toward one of two orientations:

Sales-Driven CS: These teams focus on identifying new use cases, building executive relationships, and partnering with sales to execute on new opportunities. They often support renewals planning, negotiations, and drive expansion revenue.

Product-Driven CS: These teams serve as the voice of the customer within the company while acting as product specialists externally. They drive adoption, gather feedback, and ensure the product delivers value.

While both of these focuses should continue to have a retention target (both in terms of revenue and customer logos), retention is ultimately a lagging indicator. In both a sales and product focused role CS role, client value must be the first consideration in order to help drive that revenue retention.

Both orientations come with inherent challenges. Sales-driven CSMs risk being perceived as "too salesly" and focused on growth at the expense of customer value. Meanwhile, product-driven CSMs can easily fall into reactive support roles, troubleshooting issues without moving customers forward strategically.

The Product Maturity Connection

Ultimately, CSMs (as with any other role within the company) should be aligned to the company objectives and value. However, as I have taken on overseeing across multiple functions, including driving new product development to market. I realized when shaping the function and priorities of the CSM team, a fundamental consideration is:

"How mature is your product?"

This question has significant implications for how customer success teams should be structured and operate.

The Product Maturity Continuum

The right balance between sales and product focus should shift based on where your product sits on the maturity spectrum:

Low Maturity (Early-Stage Products)

• You have an initial MVP or immature product

• CS Role: Product Focused 

• CSMs should heavily emphasize gathering customer feedback, identifying product gaps, and ensuring early customers achieve baseline value

• They become critical conduits to product teams shaping the roadmap

Medium Maturity (Growing Products)

• Your product is in the market but still refining its product-market fit

• CS Role: Product/Sales Mix

• CSMs balance championing product improvements while beginning to identify expansion opportunities

• They help validate new use cases while ensuring existing capabilities deliver value

High Maturity (Established Products)

• You have an established product and are focused on market expansion

• CS Role: Sales Focused 

• CSMs can lean more heavily into identifying new use cases, driving account growth, and supporting renewals

• Product feedback remains important but becomes more incremental than transformational

Beyond Maturity: Additional Considerations

While product maturity provides a strong foundation for CS role definition, several other factors influence the optimal balance:

• Team Resourcing: Larger organizations may support specialized CS roles while startups often need versatile generalists

• Product Complexity: More sophisticated products may require greater product-focused guidance regardless of maturity

• Customer Segment: Enterprise customers typically demand more strategic engagement than SMB customers

• Competitive Landscape: Highly competitive markets may necessitate more sales-oriented CS to prevent churn

For more considerations about setting up your CS team, check out my Customer Success Organizational Assessment Form (coming soon). 

Breaking Up Is Hard to Do: When and How to Let a Customer Go

In the quest for growth, many businesses adopt the mantra that the customer is always right. But after years of leading customer success teams and now overseeing a business unit with P&L responsibility, I've learned a difficult truth: not every customer relationship is meant to last forever.

Some customer relationships, despite everyone's best intentions, may actually be holding your business back.

The Misalignment Challenge

During my time leading customer success at a Fortune 500 technology company, we encountered numerous customers who didn't align with our evolving go-to-market strategy. These customers often consumed disproportionate resources, generated minimal margins, and pulled our product roadmap in directions that benefited few other clients.

Identifying and addressing these misalignments isn't about being callous—it's about making deliberate decisions that serve both your business and your broader customer base.

The Customer Fit Assessment Framework

Before making any decisions about customer relationships, it's critical to perform a thorough assessment using these key dimensions:

1. Strategic Alignment with Go-to-Market Strategy

Start by evaluating how well each customer aligns with your current and evolving go-to-market strategy:

• Are they in your target industries?

• Do their use cases match your product's core strengths?

• Will they benefit from your strategic roadmap?

Customers who fall outside your strategic focus may become increasingly difficult to serve as your product and services evolve to meet the needs of your target market.

2. Customer Margin Analysis

Understanding the true profitability of each customer relationship is essential:

• Calculate all costs associated with serving the customer (COGS)

• Include implementation, support, and maintenance costs

• Compare against revenue to determine actual margins

This analysis often reveals surprising insights—some of your largest revenue customers may actually be your least profitable when all costs are considered.

3. Resource Consumption Assessment

Beyond direct costs, consider the opportunity cost of resources dedicated to each customer:

• Engineering and product development time

• Support ticket volume and complexity

• Customer success management hours

• Executive attention and firefighting

These opportunity costs can be substantial when challenging customers divert resources from strategic initiatives that would benefit your broader customer base.

4. Logo Value Consideration

Some customers provide value beyond direct revenue:

• Industry recognition and reputation benefits

• Reference potential for prospective customers

• Strategic market positioning

• Industry insights and product feedback

A customer with exceptional logo value might justify lower margins or higher resource allocation if they genuinely help you attract and retain other customers.

Check out my template for assessing this value. (coming soon)

Turning Poor Fits into Value-Add Relationships

Before proceeding with a breakup, explore whether the relationship can be salvaged:

Margin Improvement Opportunities:

• Evaluate pricing adjustments at renewal

• Consolidate or eliminate custom features

• Transition to newer, more efficient product versions

• Adjust service level agreements

Expectation Reset:

• Clarify support boundaries and escalation processes

• Establish more realistic implementation timelines

• Define product roadmap influence parameters

• Set communication cadences that work for both sides

In my experience, some of our most challenging customer relationships were transformed through honest conversations about expectations and boundaries. Sometimes, a reset is all that's needed.

The Art of the Customer Breakup

If you've determined that parting ways is the right decision, how you handle the separation matters tremendously:

1. Contract Review

Start with a thorough legal review:

• Understand termination clauses and notice periods

• Identify any breach risks or penalties

• Prepare data transition requirements

• Document all compliance obligations

2. Executive Involvement

Having a senior leader involved in the process is crucial:

• Demonstrates respect for the relationship

• Conveys the strategic nature of the decision

• Provides authority when discussing alternatives

• Prevents the account team from becoming scapegoats

3. The Breakup Conversation

The actual conversation should be:

• Direct but compassionate

• Focused on mutual best interests

• Specific about transition support

• Appreciative of the relationship history

I've found that framing these conversations around your company's evolving direction—rather than customer shortcomings—preserves dignity while still being honest.

4. Transition Support

Offer meaningful transition assistance:

• Provide data export assistance

• Recommend alternative solutions

• Allow reasonable time for migration

• Maintain support during the transition period

Successful "breakups" can result in the customer returning under different circumstances or even sending referrals later because of professionalism during the separation.

Here is a template for having that conversation. (coming soon) 

The Organizational Benefits

When handled properly, parting ways with misaligned customers can yield substantial benefits:

• Resource Reallocation: Teams can focus on customers who align with your strategy

• Improved Morale: Staff burnout decreases when challenging relationships end

• Product Focus: Development resources concentrate on features with broader impact

• Enhanced Reputation: Professional separations can actually build respect in the market

• Margin Improvement: Overall profitability increases as you focus on better-fit customers

Conclusion: Strategic Customer Portfolio Management

Building a sustainable business requires viewing your customer base as a portfolio that needs active management. Just as investors rebalance their portfolios, businesses must occasionally reassess their customer relationships.

The most successful companies I've worked with regularly evaluate their customer base against their strategic direction, making deliberate decisions about which relationships to invest in, which to restructure, and which to gracefully conclude.

Breaking up can indeed be hard to do—but when executed with care and professionalism, it can lead to better outcomes for everyone involved.

Bridging the Gap: How AI-Powered Prototyping is Revolutionizing Customer Success and Product Collaboration

Customer Success teams sit at the epicenter of customer feedback—fielding feature requests, processing complaints, and translating user pain points into actionable insights. Yet one of our greatest challenges remains: effectively communicating customer needs to product teams in a way that drives meaningful development.

Too often, customer feedback arrives as vague requests: "I don't like this feature" or "I want something different." While these statements signal dissatisfaction, they rarely illuminate the underlying problem or desired outcome. The knee-jerk reaction? Build exactly what the customer asks for. But this approach overlooks critical considerations like development effort, broader market impact, roadmap alignment, and resource allocation.

The Translation Challenge

Product managers are trained to probe deeper, asking the right questions to uncover true customer needs. However, they don't always have direct customer access, and when they do, their technical focus can sometimes miss the emotional and operational context that CSMs naturally understand.

On the flip side, Customer Success Managers excel at building relationships and understanding customer pain points, but may struggle to extract the specific technical requirements that product teams need to prioritize and scope development work effectively.

The traditional solution—getting product teams in front of customers more frequently—helps but creates its own challenges, pulling developers away from building and extending feedback cycles.

Enter AI-Powered Prototyping

Artificial Intelligence presents a game-changing opportunity to bridge this communication gap. CSMs can now leverage AI as a rapid prototyping tool, transforming abstract customer feedback into tangible concepts that spark productive conversations.

Here's how it works in practice:

Imagine you're a CSM at an e-commerce platform, and a key customer complains that their storefront feels "too busy and overwhelming." They want a "simplified experience" that makes it easier to repurchase frequently ordered items. Rather than passing along this vague feedback, you can prompt an AI tool like Claude to generate visual mockups in under a minute.

Sample prompt: "Create a simplified e-commerce storefront mockup focused on repeat purchases, with clean design and easy reorder functionality for frequently bought items."

Within moments, you have concrete prototypes to share with your customer.

Turning Prototypes into Insights

These AI-generated mockups become conversation starters that help you ask the right questions:

• What specifically appeals to you about this design approach?

• How would this improved functionality change your daily workflow?

• What business outcomes would this enable for your team?

• What time, cost, or resource savings do you anticipate?

• How might this impact user adoption across your organization?

Through this structured dialogue, you're not just gathering feature requests—you're uncovering the business case and ROI that product teams need to make informed prioritization decisions.

From Conversation to User Story

The process doesn't stop at customer validation. By recording and transcribing these prototype feedback sessions, you can leverage AI again to generate comprehensive user stories for your product team.

Follow-up prompt: "Based on this customer feedback conversation about storefront simplification, create a detailed user story including the use case, desired outcome, and business impact for our product development team."

The result? Rich, contextual requirements that go far beyond "make it simpler" to explain the who, what, why, and expected impact of the requested functionality.

Real-Time Collaboration

Perhaps most exciting is the potential for real-time collaboration. AI prototyping is fast enough to happen live during customer calls. With screen sharing, you can iterate on designs in real-time, getting immediate feedback and refinement until you reach alignment on the desired solution.

This dynamic approach transforms customer feedback sessions from complaint resolution into collaborative design sessions.

Expanding the CS-Product Partnership

While AI already supports traditional Customer Success functions—account research, Executive Business Review preparation, risk analysis—its application to product development represents a new frontier. As AI continues to democratize design and development capabilities, it creates unprecedented opportunities for CSMs to become more strategic partners in the product development process.

The traditional handoff from "customer wants X" to "product builds X" evolves into a collaborative process where CSMs arrive with validated concepts, clear business cases, and detailed user stories that make product teams more effective and customer-focused.

Implementation Considerations

Before diving in, ensure your AI prototyping approach aligns with both your organization's and your customers' privacy policies. When incorporating screenshots or product information, use private enterprise AI tools or limit content to publicly available information.

The Future of Customer Success

AI-powered prototyping represents more than just a new tool—it's a fundamental shift in how Customer Success teams can contribute to product strategy. By transforming vague feedback into visual concepts and business cases, CSMs become strategic translators who bridge the gap between customer needs and product execution.

The organizations that embrace this approach will find their Customer Success teams driving not just retention and expansion, but actual product innovation that delivers measurable business value for both their customers and their company.

Jack/Jill of All Trades to Specialized Roles: When and How to Evolve Your Customer Success Team

The Evolution of Customer Success Teams

In less mature organizations, customer success often involves wearing multiple hats - from support and implementation to training and renewals. This approach makes sense when you're establishing your customer base and operating with limited resources.

However, as your business scales, creating specialized roles becomes essential for both operational efficiency and team satisfaction. Clear role definitions and responsibilities are critical not just for customer outcomes, but for employee success and retention.

Two-Pronged Approach to Specialization

1. Understanding Customer Needs Through Journey Mapping

The foundation of effective specialization starts with thoroughly mapping your customer journey. This means documenting:

• The ideal pathway through your product lifecycle

• Key touchpoints that influence customer satisfaction

• How marketing, sales, and customer experience functions should align

• Critical milestones for successful product adoption and value realization

Creating a comprehensive customer journey map highlights natural breakpoints where specialized roles can add significant value. You can utilize my customer journey template here: [LINK TO TEMPLATE]

2. Auditing Your Current Team Activities

Equally important is understanding how your post-sales team currently spends their time. Conduct a thorough audit to identify:

• Breakdown of key activities of your post-sales team

• Support requirements and trends

• Training expectations and delivery methods

• Retention-focused activities and their effectiveness

• Balance between proactive and reactive efforts

• Identification of revenue-generating activities vs. overall team costs and margins

This audit will reveal opportunities to redistribute responsibilities based on:

• Team members' natural strengths and interests

• Potential efficiency gains through specialization

• Activities that could benefit from automation or self-service options

• Opportunities to reset customer expectations based on paid vs. unpaid engagements

Leverage my post-sales role audit here: [LINK TO TEMPLATE]

Implementation Strategies for Specialization

When transitioning to specialized roles, consider these approaches:

• Create centers of excellence for key functions like implementation, training, and support - explore opportunities for on-demand training and education, AI agents or centralized support models, and repeatable implementation and onboarding approaches

• Develop clear handoff protocols between specialized teams - never lose track of the customer journey and the intended end goal of your approach; when you specialize, you create more hand-transitions that need careful management

• Establish shared success metrics that prevent siloed thinking as you specialize into different segments

• Leverage specialization to update recruitment, hiring, onboarding, and training for employees

Managing the Human Element

Any transition from generalized to specialized roles requires thoughtful change management. Success depends on:

• Transparent communication about the business rationale

• Involving team members in defining new specialized roles

• Aligning specialization with individual career aspirations

• Providing training and development for new specialized functions

Conclusion

The evolution from jack-of-all-trades to specialized customer success roles marks a critical maturation point for growing businesses. By basing this transition on both customer needs and team capabilities, you can create a specialized structure that enhances both customer outcomes and employee satisfaction.