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.”
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:
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.
CloudKite has pulled a snapshot of SDR activity and funnel metrics.
| Activity | Avg hours/week per SDR | Notes |
|---|---|---|
| Calling + live conversations | 12.5 | Includes connect time |
| Email/LinkedIn outreach | 10.0 | Mostly through Outreach |
| Manual CRM updates | 9.0 | Logging calls, updating fields, creating tasks |
| Research + list building | 6.0 | ZoomInfo + LinkedIn |
| Internal admin (meetings, enablement) | 4.5 | Team meetings, training |
| Metric | Inbound SDRs | Outbound SDRs |
|---|---|---|
| Leads worked per SDR per month | 420 | 260 |
| Meetings booked rate (lead → meeting) | 2.8% | 1.9% |
| Meeting → SQL conversion | 54% | 47% |
| SQL → Closed-won (AE-owned) | 18% | 16% |
| Avg sales cycle (days) | 74 | 92 |
Revenue automation vendors are actively selling into CloudKite’s segment. You have early quotes and benchmarks:
| Vendor Type | Example Vendors | Typical Pricing | Claimed Benefit |
|---|---|---|---|
| CRM workflow automation | Salesforce add-ons, low-code tools | $20–$60/user/month | Reduce manual field entry, enforce governance |
| Revenue engagement suites | Outreach/Salesloft add-ons | $30–$90/user/month | Better activity capture + sequencing |
| AI note-taking + auto-logging | Gong/Clari/Wingman-style | $80–$140/user/month | Auto summaries, auto CRM updates |
| Data enrichment + dedupe | ZoomInfo/Clearbit-style | $10–$40/user/month | Reduce research time, improve data quality |
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.
As the candidate, you will present a structured approach and recommendation: