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Pipeline Review: Sterling Cooper
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High-Level Summary & Obstacles

Sterling Cooper is evaluating Yellowsail as part of a broader effort to reduce software supply chain risk introduced through open-source dependencies and internal artifact repositories. The CISO has acknowledged growing exposure and internal friction between security and engineering, but urgency remains situational rather than institutional.The primary obstacle is status quo tolerance: while Sterling Cooper recognizes the risk, there is no active incident or regulatory forcing function driving immediate action. Consensus is forming within security, but engineering leadership has not yet internalized the cost of inaction. Procurement and budget timing are still loosely defined, pushing this deal into “potentially real, but not yet inevitable” territory.

Opportunity Snapshot
Attribute
Detail

Account

Sterling Cooper

Opportunity Name

Sterling Cooper – Strategic – 2026

Type

Net New

Economic Buyer

Alfred Bachman, CISO

Stage

02 – Consensus Building

Age

46 days

Amount

$185,000 ARR

Forecast Probability

30%

Close Date

02.23.2026

Key Value Drivers / Pain Points

Core Problems They Are Trying to Solve

1. Lack of control over what enters internal repositories

  • Sterling Cooper currently relies on scanning after packages are introduced, not at ingestion.
  • This creates blind spots around compromised or malicious open-source components.

Buyer verbatim:

“Once something lands in Artifactory, we’re basically trusting that it’s clean unless it trips something later. That’s not a great place to be.”

2. Security slowing engineering without actually reducing risk

  • Security policies are seen as reactive and disruptive.
  • Developers often bypass controls to keep velocity high.

Buyer verbatim (CISO):

“We keep telling ourselves we’re reducing risk, but all we’re really doing is adding more checks after the fact — and engineering hates us for it.”

3. Inability to confidently address zero-day exposure

  • Sterling Cooper lacks a proactive control to stop malicious packages before they spread internally.
  • Current tooling is dependent on known CVEs and delayed intelligence.

Buyer verbatim:

“Zero-days are the ones that keep me up at night because by the time we see them, they’re already everywhere.”

Internal Consequences if Unresolved

  • Increased breach likelihood through transitive dependencies introduced silently into production.
  • Organizational friction between security and engineering leadership is reducing trust and slowing future initiatives.

Buyer verbatim:

“If something happens and we have to explain why we let it in at the front door, that’s on me.”

Economic Impact

Cost / Risk Mentions

  • CISO referenced breach impact in the context of incident response costs and board scrutiny, not specific dollar amounts.
  • No fines mentioned, but SOC 2 and enterprise customer audits were cited as pressure points.

Buyer verbatim:

“The cleanup cost isn’t even the worst part — it’s explaining to the board how it happened.”

Budget Signals

  • Security budget exists for 2026 planning; not yet locked.
  • Buyer initiated conversation about pricing ranges and contract structure.

Buyer verbatim:

“If we do this, it has to come out of preventative controls, not incident response.”

Tradeoffs Discussed

  • Potential reallocation from:
    • Additional SAST tooling
    • Manual security review headcount

Buyer verbatim:

“If this actually stops bad stuff from getting in, I’d rather invest here than hire another analyst to chase alerts.”

Buying Process at Sterling Cooper
  • Security evaluates and recommends
  • Engineering leadership must sign off on workflow impact
  • Procurement involved post–technical validation
  • Final approval rests with CISO

Timeline

  • No fixed decision date
  • Buyer referenced Q4 planning for 2026 initiatives
  • No external forcing event (breach, audit deadline) currently driving urgency

Assessment:
Process is understood but not yet time-bound.

Competition & Alternatives
  • Primary competitor: Status quo (existing scanning + manual review)
  • Secondary: Native repository tooling upgrades
  • No direct head-to-head competitive bake-off underway

Buyer verbatim:

“We’re not unhappy enough yet to rip everything out — this has to be meaningfully better.”

Risk: High likelihood of delay due to “good enough for now” thinking.

  • Engagement is moderately strong but security-heavy
  • Buyer participates consistently in calls
  • Engineering leadership has attended one session but remains cautious
  • Follow-ups are mostly rep-driven

Pattern observed:

  • Security agrees conceptually
  • Engineering asks “how disruptive is this?”
  • Momentum slows after technical discussions

Assessment:
This is not a one-sided deal, but the buyer is not yet pulling the deal forward.

Close Prognosis

Will this opportunity close?

Possibly — but not without a shift in urgency and internal alignment.

This deal is real in the sense that:

  • The problem is acknowledged
  • Budget is plausible
  • Buyer is engaged

However, it will stall or slip unless:

  • Engineering leadership internalizes the cost of inaction
  • A concrete decision timeline is established
  • The value is reframed as risk prevention, not tooling improvement
What Must Happen to Increase Close Probability
  1. Engineering impact must be validated
    • Demonstrate how Yellowsail blocks malicious packages without slowing developer workflows
  2. Cost of inaction must be quantified
    • Translate risk into scenarios that leadership can’t ignore
  3. Buyer must own the timeline
    • Tie the decision to the planning, audit, or risk review cycle
Recommended Next Steps (Salesperson)
  1. Facilitate a security + engineering working session
    • Focus on real repository workflows
    • Surface objections early
  2. Create a one-page “before vs after” risk narrative
    • Show how bad code enters today vs. how Yellowsail blocks it
  3. Pressure-test urgency with the CISO
    • Ask directly what would cause this to slip to “next year”
  4. Secure a buyer-owned milestone
    • Example: internal recommendation meeting or budget earmark

Would you like me to provide a probability of this closing based on the close date and other listed factors?