Company: Fieldline
Fieldline is a B2B SaaS platform that helps revenue teams at 50–500 person companies manage their sales pipeline more effectively. The product integrates with CRMs and communication tools to surface deal risk signals, coach reps through stalled opportunities, and automate pipeline reporting for sales managers.
Fieldline charges $120 per user per month and competes in a market with several established players. The company has 14,000 free-trial users, a team of 9 sales reps, and a marketing team of 4. They are 60 days from launching their first AI-native feature: Fieldline Coach, which uses conversational AI to give reps real-time guidance on their active deals.
What's happening right now
The Head of Growth has just left the company. You are stepping in for your first 30 days. The VP of Marketing has given you two problems to address simultaneously:
Problem 1 — Trial Conversion Is Falling
Trial-to-paid conversion has dropped from 18% to 11% over the past two quarters. The VP suspects three possible causes but isn't certain which is the primary driver:
Trial users who reach the 'Pipeline Health' dashboard within 72 hours convert at 3× the rate of those who don't — but only 24% of trial users ever reach it
Outbound email sequences to trial users have an average open rate of 31% but a click-through rate of only 4% — the emails aren't driving action
A competitor, Pipestack, launched 5 months ago with a similar feature set at $79/user/month and has appeared in 6 of the last 14 head-to-head sales evaluations
Problem 2 — Fieldline Coach Launches in 6 Weeks
The engineering team will ship Fieldline Coach in 6 weeks. The feature is ready; the go-to-market is not. Specific gaps:
Fieldline's current positioning is built around 'pipeline visibility' — it doesn't yet reflect AI coaching capability
The 9 sales reps have been using the old positioning in prospect conversations. They haven't been briefed on what changes
Pipestack is also rumored to be launching an AI feature in Q2, which could undercut Fieldline's first-mover window
What the VP of Marketing has asked for
Before your end-of-week-one sync, she wants a single integrated brief that covers:
Your diagnosis of the trial conversion problem and a prioritized plan to address it
A repositioned messaging framework for Fieldline Coach — including who you're writing for and how the launch connects to the conversion problem
A 6-week GTM plan for the Fieldline Coach launch
How you'll measure whether this is working
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