Your 10-Second Sterling Cooper Opportunity Review
CloudNinja is a strategic mid-market / enterprise customer with $5M in ARR under contract, renewing on 02/12/2026. The account is managed by Alex Martinez (Account Manager) and has been a customer for two years.
Primary stakeholders:
- Leah Kim — VP, Customer Success (executive sponsor / budget owner)
- Brandon Ortiz — Director, Support Operations (day-to-day owner, strong user advocate)
- Emily Rogers — RevOps Manager (data and workflow integration)
Overall sentiment is mixed but recoverable. CloudNinja sees clear potential value in surfacing churn-risk and expansion signals from CS and Support conversations, but:
- Usage is low and inconsistent across teams and regions.
- Pricing and term length are being questioned, given under-adoption.
- There is ongoing friction around workflow fit, Salesforce routing, and reporting/roadmap expectations.
The renewal is moderately at risk. Leadership is open to continuing, but will need:
- a sharper, quantified value story,
- a credible adoption plan, and
- a convincing commercial structure.
Customer expects a clear adoption and value-realization plan across all CS and Support pods before committing to a new term.
By reframing pricing within a value narrative (i.e., feature enhancements, improved support), Yellowsail could mitigate churn and rebuild trust
Customer expects improvements to signal routing into Salesforce and alignment with their existing QBR workflows.
“Some of the signals are still landing in a generic queue. We need tighter routing into Salesforce and our QBR views if we’re going to call this a core part of our CS stack.” — Emily, email, Dec 4, 2025
Vendor has committed to a joint 6‑month “renewal success plan” with specific adoption, usage, and impact targets.
“We’ll put together a 6-month success plan with adoption targets, key workflows we’ll improve, and the specific metrics we’ll track together.” — Alex, QBR call
Vendor has promised targeted enablement for underutilizing teams (APAC CS, Tier 2 Support) to address low usage.
“We’ll run targeted enablement with your APAC CS team and Tier 2 Support so they’re using signals consistently in their workflows.” — Alex, follow-up email, Nov 22, 2025
Customer expects transparent roadmap timelines for two reporting/analytics enhancements previously discussed.
“We’ve been asked internally about better roll-up reporting on signals by segment and product area. I need to know when that’s coming.” — Brandon, QBR call
Low Usage / Under-Adoption
Overall usage is low; some regions and teams barely use Sturdy.ai, diluting perceived ROI and making renewal harder to justify.
“If only half our teams are leaning on this, it’s hard to justify an increase or a multi-year commitment.” — Leah
Pricing & Contract Structure
For a $5M ARR account, leadership is sensitive to paying for unused capacity and is cautious about a longer term without clear value.
“I’m not opposed to a longer term, but I’d need a clearer link between the license count and outcomes we’re seeing.” — Leah
Workflow Fit & Integration Friction
Signals are not yet cleanly routed into Salesforce or fully embedded in QBR/renewal workflows, creating manual work and weakening value perception.
“Right now, Emily’s team is still doing some manual triage to get these into the right places.” — Brandon
Roadmap Expectations
Lack of clarity on delivery timing for reporting enhancements is eroding confidence in long-term partnership.
“We’ve talked about roll-up analytics a couple of times. I just need to know if it’s coming this half or not.” — Brandon
Tool Consolidation / Competitive Threat
CloudNinja is reviewing their CS stack and may consider consolidating tools or leaning on in-house analytics instead.
“We’re looking across our CS stack to see where we can consolidate or lean more on what we already have.” — Leah
Multi-Year Renewal with Value-Based Structure
By tying license levels to actual impact (expansion pipeline captured, churn-risk accounts identified, manual hours saved), there is room to secure a multi-year renewal with aligned economics.
Drive Usage in Underutilized Teams
A focused push in APAC CS, Tier 2 Support, and Customer Marketing can materially improve usage metrics and strengthen the renewal story.
Executive NRR Narrative
Positioning Sturdy.ai as a core Net Revenue Retention (NRR) lever (not a reporting tool) raises the perceived importance of retaining and potentially expanding the partnership.
Workflow & Reporting Wins
Delivering concrete improvements to Salesforce routing and roll-up reporting before renewal can visibly reduce friction and rebuild trust.
Internal Champions & Success Stories
Turning CloudNinja’s best-performing pod into a visible internal case study arms Leah with proof points to justify renewal to finance and leadership.
Inbound (CloudNinja → Vendor)
~3–4 notable inbound comms in the last month (QBR, follow-up questions, roadmap/security/usage discussions).
Inbound is focused on strategic value, adoption, and roadmap — this is good engagement but also indicates pressure to prove impact before 02/12/2026.
Outbound (Vendor → CloudNinja)
Regular but mostly reactive follow-ups to QBR items and feature questions.
Outbound has answered questions but hasn’t fully shifted to a proactive, executive-level “here’s the plan for the next 6 months” narrative.
- Immediate (Next 7 Days): Deliver a Concrete Renewal Success Plan
- 2–3 pages, shared with Leah, Brandon, and Emily:
- Current usage snapshot (by team/region, highlighting low usage).
- Adoption targets for the next 6 months (e.g., % of teams using signals weekly, # of users logging in weekly).
- 3–5 measurable outcomes:
- expansion opps created from signals,
- churn-risk accounts flagged and acted on,
- hours of manual triage/reporting eliminated.
- 2–3 pages, shared with Leah, Brandon, and Emily:
- Short-Term (Next 2–3 Weeks): Usage & Enablement Sprint
- Run focused enablement for APAC CS and Tier 2 Support with concrete workflows:
- “How to use signals in daily standups and case reviews.”
- “How to prep QBRs using Sturdy.ai signals.”
- Track and share quick usage wins back to Leah as proof of motion before renewal.
- Run focused enablement for APAC CS and Tier 2 Support with concrete workflows:
- Short-Term: Fix 1–2 High-Impact Workflow Frictions
- With Emily, redesign key Salesforce routing paths (e.g., specific signal categories → owners/queues → QBR dashboards).
- Ship at least one meaningful routing improvement and a basic roll-up view prior to 02/12/2026, then highlight this in a recap email.
- Short-Term: Transparent Roadmap + Interim Solutions
- Provide a clear update on the two requested reporting enhancements (ETA, dependencies).
- If timing is post-renewal, offer interim: custom reports/views or manual roll-ups supported by your team.
- Pre-Renewal (Late January / Early February): Executive Review + Commercial Proposal
- Host an executive business review (Sturdy.ai exec + Leah + CloudNinja leadership) focused on:
- NRR impact,
- specific saves/expansions influenced by signals,
- trajectory of adoption since the success plan started.
- Present structured options:
- 1-year renewal at current footprint, anchored to agreed success plan.
- 2–3 year term with incentives (pricing stability, roadmap / advisory access, ongoing enablement) conditioned on achieving adoption and value milestones.
- Host an executive business review (Sturdy.ai exec + Leah + CloudNinja leadership) focused on: