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

EP Claims Services

VP of Strategic Partnerships

Acorn Claims

Vice President of Business Development

ION - Insight. Onsite. Now.

Director of New Business

CCMS & Associates

Director Of Business Development

RYZE Claim Solutions

National Sales Representative

Premier Adjusting and Catastrophe Services, Inc.

National Marketing Director

Envista Forensics

Envista Forensics. Launched in January 2017 and formerly known as PT&C|LWG Forensic Consulting, Envista satisfies the growing demand by insurance claims and legal professionals for a global, multi-disciplinary and highly-skilled forensic engineering partner. Our new identity is rooted in our strength in investigation, and conveys our global, comprehensive capabilities. Stronger than ever, the over 300 professionals located in 30 offices on 4 continents that comprise the Envista team are industry leaders committed to providing the best possible service, vast experience, thought leadership, and Certainty in an Uncertain World.

Regional Account Executive

Helicon Foundation Repair

Business Development and Sales

•	Responsible for developing business relations within the insurance industry
•	Maintained high level of contact with clients to identify and resolve customer problems
•	Acquired business from large insurance carriers and engineering firms
•	Participated in industry events to increase company branding and recognition

Business Development Manager

ClaimCor - Insurance Claim Solutions

•	Executed business development strategies around new growth within high profile accounts including key decision-makers
•	Acquired new accounts with regional and national insurance carriers 
•	Maintained a high level of contact with existing clients to increase customer satisfaction, thereby increasing revenues within each account
•	Coordinated and handled marketing events and activities to boost company visibility
•	Created marketing collateral for the company and  implemented an online presence through social media: Facebook, LinkedIn and Twitter
•	Developed and maintained positive working relationships with insurance carriers and vendors to leverage contacts/connections within the industry

Business Development Specialist

Total Title Solutions

•	Increased revenue of sales (company numbers doubled within one year) through relationship-building and branding
•	Created marketing collateral for the company
•	Developed a solid referral resource through networking: BNI, realtor boards of Pasco and Pinellas, and chamber events
•	Implemented an online presence through social media: Facebook, LinkedIn, Twitter, YouTube and Constant Contact 
•	Put into practice the use of online tools and web-based platforms for the sales team to help develop their organizational skills
•	Guided sales team and determined the focus of their efforts
•	Coordinated and reviewed activities in sales and service areas

Marketing Director

Hi, I’m Jay Knight Guasco and I’ve always believed that business success is directly related to the ability to cultivate strong, productive relationships with every stakeholder in the sales pipeline. Over the course of my career, I’ve maintained a laser focus on relationship-building and have established a reputation as a hands-on sales & marketing professional with a knack for developing innovative account management and business development strategies that accelerate growth and improve sales performance.
 
For the past decade, I’ve been fortunate to have acquired a diverse skill set, while providing sales, marketing and business development services to the property & casualty insurance industry. In addition to sales, marketing and business development, my background also encompasses extensive experience that includes – account management, lead generation, social media marketing, brand development, event planning, networking and more. I also possess strong negotiation and diplomacy skills and have a proven track record of success exceeding target sales goals and increasing customer satisfaction. My ability to leverage this experience with exceptional strategic planning, communication and cross-functional collaboration skills, has allowed me to make significant contributions to sustainable growth and revenue for the teams I’ve served.

Jay Knight Guasco

taplio

The Battle

Jason Bennett

Jay Knight Guasco

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