GTM Live: What a $500M SaaS Company Saw When Their Full Funnel Became Visible

Hosts: Carolyn Dilks & Trevor Gibson, Co-Founders of Passetto
Date: December 9, 2025
Episode Type: Case Study Breakdown

Episode Overview

In this episode, Carolyn and Trevor share a candid case study about a $500M cybersecurity SaaS company that underwent a 14-day "sprint" with Passetto to diagnose and optimize their go-to-market (GTM) funnel. The episode is aimed at revenue leaders and focuses on extracting real insights from pipeline data, shifting away from "last lead source" attribution and short-sighted demand capture toward unit economics, efficiency, and long-term growth.

Key Topics and Insights

1. Case Study: Setting the Stage [02:10 – 04:07]

• Company Profile:

  • $500M+ ARR cybersecurity SaaS company
  • Recently restructured, new CMO onboarded
  • Engagement led by the Head of Performance Marketing—keen to modernize demand generation

• Key Pain Points:

  • Pipeline generation was inconsistent and lacked insight.
  • The marketing team's performance was evaluated on “last lead source,” resulting in a myopic view focused on paid search and product trial conversions.
  • Past year focused on tightening opportunity pipeline and forecasting, but wanted answers on true pipeline creation and conversion bottlenecks.

• Quotable Moment:

  • "We’re basically running paid search to drive product trials, and it doesn’t feel like responsible or modern marketing." – Carolyn, [04:07]

2. The State of the Funnel and Data Visibility [05:49 – 09:40]

• Legacy Metrics and Limitations:

  • Company’s measures—last lead source and opportunity pipeline—lacked granularity, making it hard to track demand creation ROI.
  • Notable issue: $2M recently shifted from marketing to SDR outreach, reflecting a trend toward dialing up outbound efforts to manufacture pipeline.

• Tech Stack:

  • Salesforce (CRM), Marketo (automation), Outreach (sales automation), Chat tool (Qualified/Drift), and a not-yet-implemented attribution platform.

• The Passetto Approach:

  • Integrated all available data into Passetto’s app, building a unified “GTM Factory” pipeline across engagement, prospecting, and closing stages.
  • Focused specifically on inferring prospecting triggers and mapping every opportunity’s true path.

3. The Diagnostic Rubric: Scoring the Funnel [09:40 – 12:46]

• Visibility Scores (Out of 100%):

  • Engagement Stage: 67% (decent tracking of digital/offline events, inconsistent UTM use)
  • Prospecting: 0% (no prospecting triggers or activities tracked)
  • Closing: 70% (issues with opportunity definition, instant opportunity creation regardless of qualification)

• Key Insight:

  • Most companies, regardless of size, severely under-track the prospecting stage.
  • "We have yet to see a company that really tracks prospecting comprehensively." – Amber, [09:40]

4. Findings: The Reality of Opportunity Creation [12:46 – 18:31]

• Lost in the Funnel:

  • 40% of annual opportunities had no identifiable trigger—they simply appeared in the CRM with no traceable precursor event.
  • The majority of attributable opportunities (60%) originated from product trial signups.

• Product Trials: The Misguided Focus:

  • 55% of SDR load triggered by product trials from paid search campaigns.
  • Critically low win rate on product trial-sourced opportunities: 5% vs. expected 10-20% for strong PLG programs.
  • Product trial deals produced the lowest ACV ($2-3k vs. peak ACV of $10k).
  • “Auto-creation” of opportunities led to pipeline contamination with unqualified, quickly rejected product trial leads.

• Memorable Quote:

  • "You're having to work a shitload of those [trials] for very little yield." – Carolyn, [17:00]

5. Hand Raisers vs. Product Trials [18:31 – 22:24]

• Hand Raisers:

  • Lower overall volume compared to trials, but 2x the win rate and 2x the deal size (higher ACV).
  • Hidden hand-raiser forms (contact/quote request) resulted in missed opportunities.
  • Immediate client action: testing new CTA positions and driving more high-intent leads.

• Sales Feedback:

  • Sales had repeatedly raised the alarm: “Trials don’t convert. Stop sending us these.”
  • Data from Passetto finally gave marketing the evidence needed to justify shifting away from the trial-first mentality.

6. Funnel Health, Signal Analysis, and Strategic Shifts [22:24 – 26:37]

• Company Win Rate:

  • Overall win rate around 6-7%, far below mid-market SaaS benchmarks (25-30%).
  • Win rate has been decelerating in tandem with marketing’s declining influence.

• Signal Analysis:

  • Only 35% of opportunities touched by any first-party signal (even something as simple as a page visit).
  • Trend toward more "cold" opportunities as paid search and outbound dominated the GTM machine.
  • Strong correlation between fewer signals and declining win rate.

• Moving Forward:

  • Client recognized the need for mature demand generation and began plans to hire a Head of Demand Generation.
  • Outbound (SDR) motion lacked proper tracking: 200,000+ leads worked with a 3% conversion to opportunity—ripe for optimization with better data.

• Memorable Quote:

  • "If they can do it as a $500 million company, no excuses—you can do it too." – Amber, [26:37]

7. Takeaways and Client Impact [26:52 – End]

• Key Stakeholder Quote:

  • "Passetto Sprint brought a level of inspection beyond what we do internally, but exactly what we require to be strategic. They compressed what would normally take months into two weeks and gave us a clear roadmap forward. It was the forcing function we needed to move from analysis to action." – Client Head of Performance Marketing, [26:52]

• Hosts’ Reflections:

  • Hosts proud to see that rapid, actionable insights yielded immediate shifts in marketing and sales strategy.
  • Plans for ongoing retrospective episodes to help other SaaS leaders learn from real-world transformations.

Notable Quotes & Timestamps

• "We’re basically running paid search to drive product trials, and it doesn’t feel like responsible or modern marketing."
  — Carolyn, [04:07]

• "You're having to work a shitload of those [trials] for very little yield."
  — Carolyn, [17:00]

• "Passetto Sprint brought a level of inspection beyond what we do internally, but exactly what we require to be strategic. They compressed what would normally take months into two weeks and gave us a clear roadmap forward. It was the forcing function we needed to move from analysis to action."
  — Client Head of Performance Marketing, [26:52]

• "If they can do it as a $500 million company, no excuses—you can do it too."
  — Amber, [26:37]

Episode Flow / Timestamps

• [00:11] – Case study introduction & context for pipeline anxiety going into 2026
• [02:10] – Breakdown of client company profile and their current challenges
• [04:07] – GTM pitfalls: Last-lead-source and over-indexing on paid search trials
• [09:40] – Visibility scores: Engagement, Prospecting, Closing
• [12:46] – Black holes in prospecting and the problem with untracked outbound
• [15:25] – Deep dive into product trials: High volume, low win, low ACV
• [18:31] – Hand raisers outperform trials on both win rate and ACV
• [22:24] – Funnel deceleration, signal drought, and the cost of ignoring true demand gen
• [24:56] – Takeaways for shifting PLG strategy and improving prospecting visibility
• [26:52] – Spotlight quote from client stakeholder and hosts' closing thoughts

Tone & Style

• Direct and candid: No sugarcoating—a strong focus on what the data truly says.
• Pragmatic: Heavy emphasis on actionability, unit economics, and sustainable pipeline growth.
• Supportive: Hosts highlight successes, learning opportunities, and next steps without resorting to blame.

For Listeners

This episode is invaluable for revenue leaders rethinking their GTM approach, especially those stuck in legacy models chasing vanity metrics. It’s a master class on diagnosing pipeline health and pivoting swiftly from data blindness to high-leverage action.