Randy Gilling, Founder of RDG Digital Holdings Inc.

Founder

Randy Gilling.

Operator-investor. Builder of a private portfolio of digital health and wellness businesses — quietly compounding from a single 2017 cheque.

Queen's BCom. Chartered Accountant. The discipline of audit and capital structure married to a long-only operator's patience. Either started or bought every company in the portfolio — and still runs the room.

LinkedIn →

The Path

Either started or bought.

From a CA designation in 2007 to a quietly compounding moated digital health portfolio. No fund. No LPs. Two decades of operator decisions, one at a time.

  1. 2005 — 2008

    Deloitte & Touche LLP · Auditor and Senior Consultant

    Joined Deloitte after completing the Queen's BCom (Smith School of Business). Earned the Chartered Accountant (CA) designation through the Ontario Institute in 2007. Audit, tax, and capital structure discipline that still anchors how the portfolio is run today.

  2. 2008 — 2015

    Enterprise Sales · Director → SVP

    Eight years leading enterprise sales organizations from Director to SVP. Repeatedly handed underperforming books and territories — converted them into top-performing teams through hands-on rebuilds, talent re-grading, and disciplined operating cadence. The same playbook later applied to acquired businesses.

  3. 2015 — 2016

    Kognitiv Corp · Chief Commercial Officer → CEO

    Promoted into the CEO seat at Kognitiv Corp — a collaborative commerce, data, and AI platform serving the global travel and leisure industry. Ran the commercial organization end-to-end, then took the chief executive role. The bridge from operator-leader to acquirer-operator.

  4. 2017

    Acquired Clinio · Founded AlignWellness

    Acquired the Clinio location network using BDC debt; repaid the bank in ~11 months. Restructured the asset base into AlignWellness — the start of the private portfolio.

  5. 2023

    Founded SilverBirchGrowth.com

    Launched the operator-network thesis. Restarted late 2024; scaled from zero to seven-figures in recurring revenue with no outside capital, alongside a 120+ senior operator network and Jon Inada developed into co-founder. Incubated Scale Health inside SBG and created Birch Reserve as the SBG-owned automated ad-buying brokerage and recovery-economy media channel. Advertising revenue flows to Scale Health. Now functions as the value-creation engine for the wider portfolio: building moats around owned businesses and de-risking acquisitions in the pipeline.

  6. 2024

    AlignWellness restructuring · Clairvoyant Holdings

    Took full operational control of Align in mid-2024. Embedded new leadership, overhauled digital systems, deployed a managed-services model. Network grew from 19 to over 80 active locations (tracking 90+ by YE 2026) in under 18 months.

  7. 2025

    Reforged · Pilot

    Stood up Reforged (getreforged.org) — a technology-powered platform that scores overlooked talent for six-figure operator roles inside SBG portfolio companies. Pilot showed strong institutional interest. Public launch sequenced after Scale Health, mid-to-late Fall 2026, with B Corp certification planned thereafter.

  8. 2026

    AIforHealth Alliance

    Launched the industry-wide horizontal layer linking clinics, coaches, creators, supplement brands, and the agencies serving them — pooling buying power, intelligence, and AI-forward playbooks across the H&W operator base.

  9. 2026

    Scale Health launch

    Building Scale Health as a private, invite-only digital health network with AlignWellness as its exclusive in-person physiotherapy network and initial fulfillment nucleus. Brand demand and clinic supply are being curated now; activation will happen in stages and audience traffic will ramp with a lag; Birch Reserve brokers advertising across the inventory created as hubs activate, and advertising revenue flows to Scale Health. Targeting 100MM+ recurring page views/month by December 2026 — a forward plan, not current or guaranteed traffic.