I work with B2B SaaS and fintech companies—typically founder-led or PE-backed—where post-sale performance is critical to growth, but the organization is:– Under cost pressure
– Experiencing renewal risk, forecasting issues, or uneven expansion
– Struggling with unclear ownership across Sales, Customer Success, Support, and Product
– Operating with tools and data, but without a reliable operating rhythmThese companies often need CCO-level outcomes, but don’t need—or can’t justify—a full-time executive.
I’m usually engaged when leaders say things like:
- “We don’t trust our renewal forecast.”
- “Churn isn’t catastrophic, but it’s unpredictable.”
- “Customer Success is busy, but impact is unclear.”
- “Sales hands deals off and disappears.”
- “We bought the tools, but they’re not changing outcomes.”
- “We’ve had smart people here—things just don’t stick.”This is less about talent and more about operating design.
I help leadership teams design and run a post-sale operating system that:
- Makes retention and expansion visible and forecastable
- Clarifies ownership across Sales, CS, Support, and Product
- Aligns metrics to decisions (not dashboards for their own sake)
- Scales judgment, not heroics
- Holds up under real-world constraints: headcount limits, executive time, and change fatigueI stay long enough to ensure the system is working—not just documented.
This is not advisory theater and not slideware consulting.My approach is:
- Operator-led — built from patterns that worked in enterprise SaaS, fintech, and AI-driven platforms
- Practical — frameworks are only useful if teams actually use them
- Embedded — I work alongside leaders until behaviors and cadence change
- Candid — I’ll say when the issue isn’t tooling or process, but alignment or incentivesI’m often most valuable when leaders want truth, clarity, and follow-through, not consensus.
Engagements typically begin with a focused diagnostic and progress based on need, without obligation to proceed to the next phase.
1. Post-Sale Diagnostic (30 days)
A focused assessment of:
- Renewal pipeline health and forecast credibility
- Churn and expansion drivers
- Segmentation and coverage model
- Decision rights and handoffs
- Metrics that matter vs. metrics that distractOutcome: A clear diagnosis and a 90-day operating plan leadership can actually execute.2. 90-Day Operating System Build
Hands-on work to:
- Define segmentation, ownership, and escalation paths
- Establish renewal and risk cadence
- Align Sales, CS, Support, and Product expectations
- Implement executive-level visibility that drives decisionsOutcome: A functioning post-sale system—not a binder.3. Fractional CCO / Senior CS Leadership
Ongoing leadership presence to:
- Stabilize retention and expansion
- Coach Customer Success leadership
- Partner with CRO, Product, and Finance
- Prepare the organization for scale, restructuring, or a full-time hireOutcome: Executive-level results without executive-level headcount.
I’m a good fit when:
- A CEO or CRO is concerned but not panicking
- Leadership wants change, not just validation
- The business depends on a small number of meaningful customers
- There’s willingness to align incentives and behaviors, not just rename rolesI’m not a fit when:
- The goal is cosmetic change
- Leadership expects CS to “fix things” without changing upstream behavior
- There’s no appetite for candid discussion
If helpful, a simple introduction like this works best:“We’ve been talking about retention and post-sale execution.Aaron specializes in building practical post-sale operating systems for companies under cost pressure.No pitch—just a useful conversation.”
I’ve led and built Customer Success and Operations organizations across enterprise SaaS, fintech, and AI-driven platforms, working closely with Sales, Product, Engineering, Risk, and Finance.My work has focused on turning customer usage into durable revenue, especially in complex, regulated, or high-stakes environments.I believe in building systems through people, not replacing judgment with process.
No pitch. Just a candid conversation.[email protected]
Exploratory conversations are confidential and informal.