Jason Bennett

Founder, 2x exits, 3x flops — Scaleup operator for CEOs ready to think and do different | ex-Fortune 50 | Ex-SpecOps | Dad x4 | SoberLife

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.

Founder

We are Fractional Chief Growth Officers (CGO) positioning Enterprise SaaS Companies for A-Round and we love it. 

I help high-achieving SaaS founders like you position for A-Round or that next big milestone thru scaling your perfect, exceptionally happy customer. High revenue customers who enthusiastically adopt features.  Customers who are excited to be a part of the journey; who evangelize your product as if it was their own.   - That's growth.

✅ Strategies that actually work
✅ 33% - CEO's time savings
✅ 2x - MRR in just months not years
✅ >70 NPS - Customers and employees
✅ 60% - Savings & Benefits of a Fractional Partner


Easy to follow strategies, Integrated Teams & Processes, Strategic Alliances, Happy Customers.
#B2B; #FinTech; #HealthTech; #InsurTech; #MarTech

How i’ve turned around founder-led sales

Founder-led sales will collapse for one simple reason: nobody is tracking anything.

My problem in sales was never skill.
It was discipline.

The moment I started using a daily scorecard with founders, everything changed.
There’s nothing mystical about it.
It works because I’m finally paying attention to what matters.

The biggest behavior shift?
Getting shit done.
Hard stop.

The founders I work with show up to the morning huddle knowing I’ll grill on missing numbers.
Every. Single. Morning.
So they get it done.

And >90% start seeing results within 24–48 hours
Then they repeat the process.
Momentum isn’t motivation.
It’s accountability. 👀

And the metrics that actually matter?
Not replies.
Not clicks.
Not open rates.
No vanity metrics.

We track:
-Daily outbound (per channel)
-Meaningful conversations
-Qualifying meetings booked
-Qualifying meetings **held** (the metric that actually predicts intent)
-Sales calls booked
-Proposals sent
-Proposals value
-Closed/Won
-Wins (YTD)
-Wins ($)

The moment founders stop tracking “activity theater” and focus on real commercial motion, pipeline appears.

And the biggest lie I tell myself (and my clients do this all the time):
“I’ll catch up tomorrow.”
Except tomorrow’s 20 calls turn into 40.
Then 60.
Then a black hole they never dig out of.

I let my scorecard become the boss.
Not my mood.
Not my excuses.
Not my calendar.

If you’re tired of having no pipeline and want real momentum going into 2026, let’s talk. 📍

Your move.

-----------------------------------
Start in 2 days, GTM in 5, real deal flow in about 3 weeks.

Founder, 2x Exits | Systemizing sales and elevating investor confidence for impatient CEOs looking to scale 1 to 10

Brilliantly

Customer Experience Manager

Marketing Manager/Project Manager

Marketing Coordinator

Director of Marketing Operations

ALLEN CHIROPRACTIC CLINIC

Chiropractic Assistant

Chiro One Wellness Centers

Store to Door PDX

Direct report to Executive Director and sub to Program Manager I coordinate executive daily activities and scheduling, manage operations, work directly with key vendors, manage logistics and volunteers, reconcile receivables, contribute in strategic planning, present/advocate mission, and acting Voice of Customer.

•	Executive Assistant: Meetings and status, reporting, communications, scheduling, oversight
•	Program Coordinator: Primary contact; vendor & client relations, procurement, logistics
•	Office Management: Vendor management, scheduling, activities coordination
•	Productivity Tools: MS Office suite, proficient in Access (reports and queries), Giftworks

Program Coordinator

Coordinate daily activities, scheduling, manage logistics, volunteers and vendors

Program Assistant

Service delivery to the elderly & home-bound, mission advocacy and client relations

Volunteer Staff

Beaverton Oral Surgeons

Physician’s assistant, data entry, filing, patient intake, scheduling and supply reconciliation

Surgical Assistant & Office Administrator

Mountain View Medical Group

Pre & Post surgical assistance, coordination and instrumentation oversight.  Other responsibilities included basic office administrative duties, supply management, scheduling, phone coverage and data entry.

Surgical Technologist & Office Assistant

South Bay Hospital

Surgical technologies and key case administrator supporting directors of interdisciplinary surgical teams over 125 clinical cases

Surgical Technologist & Administrator

Largo Medical Center

Surgical Technologist (Intern)

I am the Customer Experience Manager leveraging growth marketing and business operations experience in B2B SaaS. Working along side the CGO, together we produce value by following a simple cadence:

— Align vision and goals to what’s most important this quarter;
— Define the perfect customer, partners, and winning strategies;
— Get stakeholders, shareholders, and customers on the same page; and
— Execute, measure results, iterate, and keep going.

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