Clearpath — a 40-person B2B SaaS company — was handling every trial signup with manual emails and spreadsheet tracking. Two SDRs were spending 12 hours a week on tasks HubSpot should have owned. We automated the full trial lifecycle in four weeks.
“We were doing 12 hours of weekly emails by hand before Mark rebuilt our trial flow.” Clearpath · Head of Revenue Operations
Clearpath sells workflow-automation software to mid-market operations teams. When a prospect started a free trial, two SDRs manually sent a welcome email, then a check-in on day three, then a features walkthrough on day seven — all from Gmail, all tracked in a shared spreadsheet. There was no enrollment logic, no personalization, and no way to know which emails had actually been sent.
The manual workload had grown to roughly 12 hours per week split between two SDRs. As the team scaled, this wasn't going to hold. More critically, the process had invisible gaps: if an SDR was out sick, trials went dark. If a trial user hit a key milestone — creating their first workflow, inviting a teammate — no one knew, so no one followed up at the right moment.
The CSM team had no CRM visibility into product engagement. Sales couldn't prioritize follow-up based on who was actually using the product versus who had signed up and never logged in. Every Monday the team held a manual pipeline review to decide which trials to pursue — a meeting that existed entirely because the data didn't surface the answer automatically.
The engagement ran over four weeks as a fixed-scope HubSpot implementation covering four interconnected workflows that together automated the full trial lifecycle:
Workflow 1 — Trial Welcome Series. Enrollment trigger: Contact lifecycle stage = MQL AND form submission = "Start Free Trial". A 5-email sequence fires over 14 days (day 1, 3, 6, 10, 14), personalized by industry using HubSpot personalization tokens — Operations teams get content about process bottlenecks, Finance teams see compliance and reporting angles, HR teams see headcount and onboarding use cases. Previously, every one of these emails was sent by hand by an SDR.
Workflow 2 — In-App Milestone Triggers. HubSpot was connected to Clearpath's product event data via a webhook endpoint — each time a trial user completed a key action (first login, first workflow created, team member invited), the event updated a custom contact property called onboarding_milestone. A branch in the workflow then fired: milestone hit → send a "congrats + next step" email immediately; milestone missed after 48 hours → create a HubSpot task for the assigned CSM. This replaced the spreadsheet entirely. The CSM team went from checking a Google Sheet every morning to having their day's priorities appear automatically in their HubSpot task queue.
Workflow 3 — Lead Scoring + Sales Handoff. Built a HubSpot Lead Score using 12 criteria weighted by signal strength: product engagement events (high weight), email engagement — opens, clicks, reply (medium), and firmographic fit — company size and industry (lower, but still present). When a contact's score reached 60, HubSpot automatically updated the lifecycle stage to SQL and created a task for the assigned AE with a summary of the trial activity. This eliminated the Monday pipeline review meeting. The AE team no longer needed to spend 45 minutes deciding which trials were worth pursuing — HubSpot surfaced the answer in real time.
Workflow 4 — Trial Expiry and Re-engagement. Three days before a trial ended, a workflow checked the onboarding_milestone value and branched based on engagement depth. Contacts with two or more milestones hit were routed to their AE for a "you're ready to convert" call — a warm handoff, not a cold close attempt. Contacts with zero or one milestone received a 30-day extension offer email and were enrolled in a win-back sequence. Previously this step was ad hoc at best: many trials simply expired with no follow-up at all, representing pure churn that was never measured or recovered.
Time-to-close dropped 40% quarter-over-quarter after go-live, measured from trial-start to closed-won. The primary driver was workflow 3: AEs were now contacting the right trials at the right moment rather than working a prioritized list built once a week. High-score trials that previously sat in a queue for days were now being contacted within hours of hitting the SQL threshold.
The 12 hours of weekly manual email and tracking work — split across two SDRs — was fully eliminated. Both SDRs reallocated that time to outbound prospecting, which contributed to a measurable increase in top-of-funnel volume in the same quarter. The cost of the four-week engagement was effectively covered within six weeks by the time recovered.
Trial-to-customer conversion improved 2.1× compared to the prior two quarters. The change wasn't attributable to any single workflow — it was the cumulative effect of no trial going dark, every milestone being followed up on, and every expiring trial receiving a tailored next step rather than silence.