Jason Bennett

Founder & CEO @ Brilliantly.OS

About

You’ve proven you can build. $1–5M ARR. Customers in market. A team on payroll. But now the pressure is real: ↓ Revenue still runs through you. ↓ Hires are flying blind. ↓ CRM is a database, not a system. ↓ Investors are asking questions you can’t answer with confidence. I’ve lived this. → 2× SaaS founder with exits → Raised millions, scaled GTM and ops to \$10M+ ARR → Ex–SpecOps and Fortune 50, no patience for fluff What I do now: I partner with impatient CEOs to get them out of sales and install the GTM + RevOps foundation their business can actually scale on. In about a quarter, we deliver: ✅ Predictable deal flow (validated ICP, messaging, and channels) ✅ Sales enablement (new hires productive from Day 1) ✅ Investor-grade RevOps (dashboards, workflows, operating cadence) Model: Done-with-you execution leadership. Not an agency. Not a guru. A system your team owns. Proof: 🚀 Venture-backed payments SaaS → 20+ early adopters closed, \~5 opps/week by Week 10, ≈\$18M outlook, founder out of sales. 🚀 Multiple CEOs retained us post-install to continue as executive partner and fundraising advisor. If you want to be scale-ready in Q1 ’26, the window is now. 📌 DM me "KPI" and I’ll send you the <<Scale Ready Step-by-Step>> we use to get boards leaning in.

Country

United States

City

Vancouver

Industry

Management Consulting

Skill

Board Relations, Sales Operations, Digital Strategy, Corporate Advisory, Sales Management, B2B Marketing Strategy, Organizational Leadership, Revenue Generation, Fundraising, Pricing Strategy, Possess strong analytical, Contract Negotiation, Customer Analysis, Marketing Analytics, Marketing Automation, Customer Segmentation Strategy, Customer Journeys, Content Strategy, Brand Strategy, Communication

Experience

Founder & CEO

Brilliantly.OS

2022 - Present · 4 yrs

Vancouver, Washington, United States

We help seed stage tech-savvy founders attract dream customers and close more deals at scale with proven processes and systems - while having more time to run your business. Real experts, no bullshit, just results.

Chief Revenue Officer

Holios

2025-10 - Present · 1 yr

Worcester, MA

Fractional CRO at Holios, owning GTM strategy and execution to own our niche and and scale up through repeatable deal flow engine. I lead revenue ops cadence (pipeline, conversion, and forecast hygiene) and partner with the CEO, Product and Marketing to turn post-launch friction insights into deals.

Lead Mentor

Founders Network

2021 - Present · 5 yrs

United States

Chief Revenue Officer (CRO)

Lüt

2024-4 - 2026-2 · 1 yr 11 mos

Vancouver, Washington, United States

Lüt is a next-generation payments processor designed to eliminate middleware, reduce fees, and drive smarter transactions for businesses and consumers. Unlike traditional providers, Lüt is 100% cloud-based, PCI & SOC2 Type 2 compliant, and built with a robust API-first infrastructure, ensuring seamless adoption and maximum security.

Chief Growth Officer

Advanze

2024-1 - 2026-2 · 2 yrs 2 mos

Vancouver, Washington, United States

Advanze is the client-first digital transformation company helping CIOs meet business goals and together, reimagine how P/C insurance works, globally. As CGO, I am responsible for leading strategic growth initiatives, unifying growth lever teams, client relations and acquisition, and 200%+ annual growth.

Board Of Directors

Jasper Benefit Solutions, LLC

2020-12 - 2024-1 · 3 yrs 2 mos

Vancouver, Washington, United States

Active board member responsible for advising and contributing to strategy, innovation, and growth

C-Suite Network Executive Leader

The C-Suite Network

2020 - 2024-1 · 4 yrs

Vancouver, Washington, United States

Founder & CEO

GSD Growth Labs

2021 - 2022-6 · 1 yr

Vancouver, Washington, United States

Leading a private investments group with over 120 years of combined experience. Our mandate is simple: save small employers 50% on health and other employee benefits thru opportunistic buyouts and digital transformation of underperforming Third Party Administrators.

Fractional Chief Growth Officer

Limitless Venture Group Inc (LVGI)

2020 - 2021 · 1 yr

Vancouver, Washington, United States

Fractional CGO engaged to develop new market(s) and position LVGI (OTC: LVGI) for raising capital. Leveraging skills in strategy, marketing, executive coaching, business development, and deal flow advisory to successfully enter a healthcare vertical, qualify for RegA funding, and raised stock price nearly 600% (Feb 2021).

Founder & CEO

Unna

2018 - 2020-9 · 2 yrs

Portland, Oregon Area

We started Unna to give Family Caregivers peace of mind when it comes to the health and wellness of aging loved ones thru comprehensive, smart, and user-friendly technology. As the founder and leader, I instilled a growth mindset and agile principles, established key relationships, raised some capital, and drove customer development.