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

Team Rays, LLC

AI prototypes, Training AI models, statistical analysis, Prompt engineering, data analysis, AWS, Azure, Citrix SME 
Architect/ design Google Cloud, Citrix solutions (all versions), Azure Virtual Desktop AVD and AWS solutions
MS Azure security, Governance using MS Purview, NIST and CWE compliance
Migration from Citrix to AVD 
On-Prem to cloud migrations, BigQuery, GCP, Data-lakes, Docker containers, data warehouse, Machine learning, Python, JIRA and VersionOne for managing user stories, Software development life cycle SDLC, Agile methodologies, SCRUM, structured, unstructured and semi structured data, data science models, Citrix and VMWare solutions for upgrading and cloud management.

Sr Solutions Architect/ Director/Project Manager/Product Owner

- Management consulting for all types of businesses 
- Agile coach 
- Experience with creating stories in JIRA, VersionOne. 
- Scrum, PI planning, release trains, sprint retrospective, sprint review, backlog refinement. 
- Python Scripting
- Google cloud, Azure, AWS architect 
- Design and implement solutions (MS Azure and AWS)
- Experience working with AI/ML, Datalakes, data warehouse, Docker containers
- Design and implement load balancing solutions (NetScaler, F5)

https://fedlinks.com/profile/Team-Rays-LLC-Rockville-MD
http://teamraysllc.com

Senior Architect & Product Owner

Independent

-Online tutor at Wyzant 
https://www.Wyzant.com/Tutors/Hajra19
- Online technology trainer Microsoft (since 2003) and Citrix NetScaler (2014-2016)
- Agile coach (2019-Present) 
- Social media marketing 
- Business development 
- Marketing strategies

Technology Trainer

Academy of Management

-Management manuscripts reviewer for 2018 annual Academy of Management meeting in Chicago, IL for the Technology & Innovation Management (TIM) and Healthcare Management (HCM) divisions.

Management Manuscript Reviewer (Volunteer)

U.S. Census Bureau

-Designed/ architected VDI environment for Decennial Census 2020 project to accommodate 25k users
-Provided engineering leadership and subject matter expertise in the evaluation, development, and documentation of the Virtual Desktop Infrastructure and hosted/streamed applications
-Maintained knowledge of relevant hardware and software applications as assigned.Participates in special projects as required 
-Assisted in the development of requirements, design specifications, and security considerations for the field office physical architecture
-Led the definition of the direction and strategy for VDI design to ensure the operational needs are being addressed against aggressive schedules

Technical Lead/ Virtualization Consultant Architect for Decennial Census 2020

Element Fleet Management

-	Architected and engineered unique project of providing remote access through Citrix on headless devices HP Moonshot appliances
-	Architected and engineered load balancer high availability and redundancy solutions to provide reliability and dependability of environment for off shore users

Sr. Solutions Architect

AECOM

Lead Consultant Engineer /Architect

U.S. Department of the Treasury

Lead Consultant Virtualization Architect

AstraZeneca

Sr. Network/ Virtualization Consultant

Citrix

-Led VDI and NetScaler projects in public and private sector in US and Canada at following locations: 
-University Health Network (UHN), Canada 
-St. Joseph's Hospital, Syracuse, NY
-University of North Carolina at Chapel Hill, NC 
-Defense Security Cooperation Agency (DSCA), VA 
-National Science Foundation (NSF), VA
-Consumer Product Safety Commission (CPSC), MD 
-Ropes & Gray LLP, NY 
-Executive Office of the President (EOP), MD 
-University of Missouri Health Center, MO
-St. Anthony's Medical Center, MO
-Federal Trade Commission (FTC)

Lead Technical Consultant

Office of the Comptroller of the Currency Contractor

Technical Lead Sr. Citrix Engineer

Hands-on Architect and IT Management specialist with extensive experience in actively working with AI, Data Science, Citrix, Azure, AWS, and Virtual Desktop AVD. Proven expertise in federal government, healthcare, retail, real estate, and finance sectors. Proficient in project management, complex technical problem-solving, and ensuring client satisfaction. Strong background in hands-on security and monitoring.

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Jason Bennett

Dr. Hajra Kirmani Cloud Architect(Azure/AWS/Artificial Intelligence)

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The Battle

Jason Bennett

Dr. Hajra Kirmani Cloud Architect(Azure/AWS/Artificial Intelligence)

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jason Bennett's LinkedIn Performance

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