From Trial to Expansion — B2B Infrastructure SaaS, Canada — $2M ARR — 12-month engagement

Challenge

I joined the company during a growth stage where marketing-led leads were increasing, but product trial sign-ups and paid conversions had gone flat.

The company operated in a very competitive infrastructure software space, up against much larger players with deeper feature sets and stronger brand recognition. That made it hard to win on product breadth, so the real lever had to be a frictionless onboarding experience.

When we looked at the funnel, the issue was clear: people were signing up for the 30-day freemium product but not activating. Demand existed, but the path from registration to revenue was broken.

Solution

1. Data Gathering & Market Research

I started with a deep dive into CRM data (Salesforce) to map out real user behavior end-to-end and identify the exact drop-off points where friction existed.

From there, I worked with the executive team to rebuild buyer personas from scratch. We defined key markets, company size, revenue bands, buying triggers, and pain points.

To validate this, the team ran anonymous interviews with users of competing products. Simultaneously, I worked with product and support teams to define the value proposition: the software's strengths and gaps versus competitors.

That combined view shaped both the go-to-market strategy and how we positioned the software in a crowded market.

2. Creating Product Materials

Together with the marketing team, I then rebuilt the core sales and marketing foundation:

• Wordpress landing pages and product messaging
• Sales decks and spec sheets
• Email nurture and Pardot drip campaigns
• Webinars and product demos
• Google Ads and blog content

3. Onboarding Journey

The biggest shift was designing the full onboarding experience inside Salesforce, from first touch to paid conversion. The system included lead scoring and grading, segmentation, behavioural triggers, and clearly defined lifecycle stages from MQL to trial, activation, and paid.

We aimed to account for diverse customer scenarios, reduce friction, and help users realize value faster through clear milestones, guided steps, and timely support touchpoints. The architecture was iterated multiple times based on customer feedback and collaboration with the software team.

I delivered a hands-on workshop for the sales team, along with key stakeholders, to walk them through the full flow, so everyone had a shared understanding of how leads moved through the funnel.