Company Background

You are joining CloudKite, a B2B SaaS company selling a cloud cost optimization platform to mid-market and enterprise engineering teams. CloudKite’s product monitors AWS/Azure/GCP spend, flags anomalies, and recommends savings actions. The company is Series C, has $85M ARR, and is growing ~28% YoY. Gross margin is 82%, and the board is pushing for $120M ARR within 18 months to support an IPO path.

CloudKite’s go-to-market model is sales-led with a strong top-of-funnel motion. The commercial org includes 42 SDRs (split across inbound qualification and outbound prospecting), 28 AEs, and 12 CSMs. The CRM is Salesforce, with Outreach for sequencing, ZoomInfo for contact data, and Gong for call recording. Marketing generates ~35% of pipeline; outbound generates the rest.

Over the last two quarters, pipeline creation has slowed. The CRO believes the SDR team is underperforming because they are “not making enough calls.” The SDR manager argues the opposite: SDRs are spending too much time on manual data entry and “CRM hygiene” tasks, leaving less time for selling activities. Attrition in SDR roles has ticked up from 18% annualized to 27% annualized, and exit interviews frequently cite “busywork” and “tools that don’t talk to each other.”

Strategic Situation

The CEO has asked you (acting as Strategy & Ops lead for Revenue) to run a 3-week diagnostic and propose a plan. The decision is not simply whether to buy a new tool; it’s whether CloudKite should:

1. Optimize the current stack (Salesforce + Outreach + ZoomInfo) with better workflows, automation, and governance.
2. Adopt a new revenue automation platform (e.g., a modern “revenue OS” that promises auto-logging, enrichment, and AI-generated notes).
3. Re-architect the SDR operating model (e.g., shift some tasks to RevOps, introduce specialists, change KPIs/comp plans, or reduce required fields).

The board cares about near-term pipeline impact, but the CFO is concerned about tool sprawl and rising SaaS spend. The CISO is concerned about customer data leakage and the use of generative AI on call transcripts.

Current Performance Signals (Provided Data)

CloudKite has pulled a snapshot of SDR activity and funnel metrics.

A) SDR Time Allocation (self-reported + limited time-study)

B) Funnel Metrics (last quarter)

C) CRM Hygiene Requirements (selected)

• SDRs must populate 18 required fields on a Lead before converting to Contact/Account.
• SDRs must log every call outcome with a disposition code (12 options).
• SDRs must create a follow-up task for any “No Connect” call.
• SDRs must attach meeting notes to every meeting record.

D) Tooling and Integration Context

• Outreach syncs emails and some activity to Salesforce, but call outcomes often require manual updates.
• ZoomInfo enrichment is available, but SDRs report duplicates and stale titles.
• Gong provides transcripts and summaries, but they are not consistently pushed into Salesforce fields.

Market & Vendor Context (for competitive analysis)

Revenue automation vendors are actively selling into CloudKite’s segment. You have early quotes and benchmarks:

Competitors (two direct rivals) have recently announced “AI SDR copilots” and claim 15–25% productivity gains. Your CEO worries CloudKite will fall behind in sales efficiency and employer brand if it doesn’t modernize.

Your Deliverables (What you must do)

As the candidate, you will present a structured approach and recommendation:

1. Root-cause investigation plan: How will you determine why manual data entry is high? What data will you gather, and what hypotheses will you test?
2. Quantify the opportunity: Estimate the cost of manual data entry today and the upside if it is reduced (e.g., meetings booked, pipeline $, or headcount efficiency). Include a simple market-sizing style estimate.
3. Solution options: Propose 3–4 solutions across process, tooling, and operating model. For each, explain expected impact, cost, and risks.
4. Competitive and build-vs-buy view: How should CloudKite evaluate vendor solutions vs improving existing tools? What would you benchmark against competitors?
5. Recommendation and rollout plan: Choose a path, justify it, and outline a phased implementation with success metrics.

Constraints

• Timeline: 3 weeks for diagnosis; 90 days to show measurable improvement.
• Budget: incremental $250K annualized tool spend is pre-approved; anything above requires CFO approval.
• Compliance: Must meet SOC 2 controls; cannot send customer call transcripts to unapproved third-party LLMs.
• Change management: SDR leadership is supportive, but AEs are skeptical of “automation that creates bad data.”
• Data quality: RevOps reports Salesforce has ~14% duplicate leads and inconsistent account matching.