Crash the Cost of Revenue Via Land & Expand
Holistic Customer Success serves your company via your clients by serving your clients via your company,
increasing Net Recurring Revenue (NRR) while producing assets for Marketing, Sales, and Support.
Product-Led Growth (PLG) and Customer Success-Led Growth (CSLG)
lower the viscosity of making and growing a sale, and are
powerful tools in expediting Sales-Led Growth (SLG).
Case Studies
CloudSploit: Holistic Customer Success
CloudSploit: Holistic Customer Success
$40 MRR to Exit
The Challenge
CloudSploit started as a bootstrapped open-source CSPM tool with just $40 in MRR. The challenge was to scale revenue efficiently while maintaining a customer-centric approach that would drive expansion and retention without traditional funding.
The Approach
Using a holistic Customer Success strategy, we combined quantitative analysis with customer engagement to scale effectively:
Customer Expansion & Retention: We identified key inflection points using usage data and relationship value analysis. A critical moment, for example, was when the first user invited additional users—this was a natural expansion trigger.
Customer Success as a Revenue Driver: While CSMs didn’t own quotas, they were accountable for leading indicators of expansion, ensuring users moved through the funnel towards higher engagement and spending.
Customer-Driven Product Development: We tracked 100% of customer suggestions, even if nominal or antithetical, ensuring all feedback was considered. Our open-source model allowed technical users to debug, contribute, or feel ownership of the product.
Scaling with Automation & Thought Leadership
Onboarding Automation: We used micro-targeted email campaigns to create “Empathy at Scale,” ensuring high-touch experiences at low cost.
Content as a Sales & Marketing Tool: Support docs and technical blogs doubled as customer marketing, traditional marketing, sales, and social media content, reinforcing our brand as a security thought leader.
Bottom-Up to Top-Down Sales (SLG): We focused on users first, knowing that adoption at the individual level would drive enterprise adoption later.
The Outcome
This approach helped CloudSploit land its first $100/month deal, scale to seven figures, and ultimately exit successfully to Aqua Security—all without external funding.
By integrating Customer Success, Product-Led Growth (PLG), and Sales-Led Growth (SLG), CloudSploit built a low-friction, high-impact growth engine that positioned it for acquisition.
Takeaway
Contrast Security: Building Customer Success
Contrast Security: Building Customer Success
Organizing for Success
The Challenge
Contrast Security, an IAST application security startup, had no Customer Success infrastructure when I joined. The challenge was to build a scalable, strategic CS function while ensuring adoption and expansion in a security-conscious market. Our primary focus was driving adoption and revenue growth from the outset; defining and standardizing processes was a secondary priority.
The Approach
I implemented key initiatives to drive adoption and revenue growth and documented what worked.
- Customer Maturity Model & Standardization: After building a CMM, I developed a CS maturity model that aligned best practices with customer stages, allowing us to guide adoption and expansion based on customer needs.
- Champion Development & Adoption Acceleration: Focused on creating customer champions within organizations. Setup was designed to be as simple as installing “an app on a phone,” with the key metric being Time to First Value (TTFiV)—installing the agent and receiving immediate security insights.
- Aligning CS with Sales for Growth: Shifted CSMs from a support mindset to technical engagement leaders, driving expansion revenue instead of simply maintaining accounts. This revenue-focused approach significantly increased Net Revenue Retention (NRR).
- Automated QBRs for Scalable Insights: Built a Quarterly Business Review (QBR) template generator that auto-filled slides with customer usage data, allowing CSMs to efficiently personalize reports and drive deeper discussions.
- Security as a Value Driver: Encouraged customers to install the Contrast agent to generate an inventory of their insecure libraries and applications. Once set up, they could enable IAST and RASP to improve security testing and remediation strategies.
- Cross-Functional Collaboration: Created assets that supported Marketing, Sales, and Support, ensuring a consistent message across all customer touchpoints. This helped position CS as a revenue driver, not just a support function.
Scaling with Automation & Thought Leadership
- Empathy at Scale: Used micro-targeted email campaigns to provide personalized, high-touch onboarding experiences at scale.
- Leveraging Content for Multiple Teams: Support documentation, technical blogs, and security insights were reused across Marketing, Sales, and Customer Success, reinforcing Contrast Security as a thought leader in application security.
- Bottom-Up to Top-Down Sales (SLG): Focused on technical users first, knowing that widespread adoption at the user level would eventually drive enterprise-wide adoption.
The Outcome
By integrating CS best practices early, Contrast Security achieved:
- Increased adoption through champion enablement & seamless onboarding.
- A structured maturity model that improved engagement & expansion potential.
- Greater alignment between CS and Sales, leading to significant NRR growth.
- Efficient, data-driven QBRs, improving customer insights and retention.
- Security integrations that simplified adoption and improved long-term engagement.
Takeaway
Adding Customer Success best practices early sets the foundation for long-term growth. Aligning CS with Sales and structuring technical engagements creates expansion opportunities long before scaling becomes a challenge.
Customer: Land & Expand
Customer: Land & Expand
From Skeptic to Advocate
The Challenge
An international content publishing giant initially landed at $50k ARR, but faced skepticism from its key engineer, “Patrick”. He saw security as a distraction from development and resisted Contrast Security’s tooling because he didn’t want to be a “tool monkey”. The challenge was to expand adoption and demonstrate business value in a way that would drive executive buy-in and long-term growth.
The Approach
Using a strategic Customer Success approach, I worked alongside Sales to expand the account:
- Understanding the Customer’s Priorities: While Patrick wasn’t interested in security, we took time to understand his career goals and work priorities. By aligning with peers who cared more, we ensured our message reached key stakeholders.
- Making the Business Case with Data: Used Contrast’s Inventory Mode to showcase real-time security risks, demonstrating how severe OWASP Top 10 vulnerabilities had remained unaddressed for nearly a year.
- Quarterly Business Reviews (QBRs): Formalized security discussions with executives, leveraging a QBR automation tool to highlight risk exposure and security improvements.
- Multi-Threading Engagements: Expanded relationships beyond Patrick to connect with decision-makers like his Managing Director (MD), who recognized the critical security gaps and championed Contrast’s adoption.
- Training & Enablement: Provided hands-on training sessions that made it easy for teams to understand the product, implement fixes, and see the value firsthand.
The Outcome
By focusing on strategic engagement and executive buy-in, Contrast Security achieved:
- Expansion from $50k to $500k ARR, and later to $800k ARR.
- Strong executive advocacy from the MD, even as Patrick remained disengaged.
- Improved security awareness and response times, with Contrast’s Inventory Mode providing real-time visibility into vulnerabilities.
- Repeatable QBR-driven engagement models, later used successfully with other enterprise customers.
- Immediate impact during the Heartbleed vulnerability, where Contrast’s tooling enabled the customer to quickly assess affected applications and libraries.
Takeaway
Skeptical users don’t need to be converted—success comes from engaging the right stakeholders. By leveraging data-driven risk assessments, multi-threaded relationships, and executive engagement, CS can drive expansion even when the initial users are unmotivated.
Product Led Growth
Invite trials and drive adoption by iteratively adding value
Target Your First Movers
Hone your messaging to the persona that you want the trial to “land” with.
Minimize Time To First Value
Engage!
Continue Driving Value
Draw an adoption road map to Full Value, including waypoints. This may involve other stakeholders.
Customer Success-Led Growth
Align desired outcomes with capabilities