Ready When

Sachin (CMO/Co-founder) was working in corporate at Car after TradeRab was acquired, running international marketing for a 15,000-person organization. While successful, he missed the startup hustle and wanted to bet on himself. In late 2019, his co-founder Jesse Bade—a BC notary with 15+ years of experience and former president of the BC Notary Public Society—approached him with an idea for Ready When. The timing was personal: both Sachin's parents had passed away, and navigating his role as executor of their estate was grueling. He realized there was a massive gap in the market and no Canadian solution existed that combined guided estate planning with document storage.

Sachin came on as CMO and co-founder from day one, handling naming, branding, and UX. Jesse took the CEO role based on his business experience. They officially launched Ready When as a beta in November 2020, then launched their MVP in spring 2021. The product was specifically built for Canada, leveraging Jesse's legal expertise to create a guided journey for estate planning—not just will-writing, but a comprehensive hub for financial assets, digital assets, health information, and informational inheritance. Unlike US competitors like Trust & Will, Ready When was built from the ground up to handle Canadian probate requirements and could reduce estate settlement from 2-3 years to months if filled out correctly, potentially saving families thousands of dollars and hundreds of hours.

Ready When's go-to-market strategy hinged on partnerships rather than paid acquisition. They identified three core customer segments: proactive planners organizing their affairs, aging parents and their adult children, and B2B2C channels through professionals. By the time of this interview, they had partnered with around 20 notaries who became their primary customer acquisition engine. These notaries recommended Ready When to their clients, and the model worked: the company hit over 1,000 customers with over 1,200 items (documents and information) stored across accounts. Most importantly, more than 70% converted to paying customers.

Their acquisition costs were remarkably low because most volume came through organic social and the B2B2C notary channel with minimal spend. They tested three pricing tiers: $5/month, $50/year, and a $500 lifetime membership. The lifetime option was deliberately used to drive near-term revenue and gather market data on customer appetite—a pragmatic trade-off for a cash-conscious startup. They'd raised $100,000+ in 2020 (friends and family) to build the prototype, then closed a strategic raise of close to $1 million in 2021 from legal and financial professionals, selling 10-20% equity. The Canadian focus proved to be a moat: Trust & Will and Willful.co were either US-only or focused on will-writing alone, leaving Ready When's guided estate planning and document hub uncontested in Canada.

With roughly $4,000 in MRR and a $48,000 ARR run rate, Ready When was preparing to launch VC fundraising in January 2022 with a target funding close by May. The team had grown to 11 people, including 3 engineers. Sachin noted that the partnership strategy—working directly with 20 notaries who had brought in customers—was their engine, and users were actively engaging, uploading documents and organizing their affairs. The company's north star was clear: reduce the burden of estate settlement and give families peace of mind during the worst of times.