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

At Brilliantly, I serve as the Chief Strategy Officer and as a Fractional Chief Growth Officer for the InsurTech industry. In this capacity, I specialize in generating revenue growth and business expansion by devising and implementing distinctive growth strategies. Leveraging my extensive 30-year career as an executive sales leader, actuary, and leader in digital transformation within the InsurTech sector, I bring a wealth of expertise and an expansive network to drive our success.

Co-Founder, CSO & CGO

Xplore Consulting, LLC

Xplore Consulting provides a comprehensive suite of services customized for the life insurance industry. Our offerings encompass growth strategy development and execution, business development, digital product strategy, InsurTech advisory services,  strategic partnership matchmaking, and executive coaching. What sets us apart is our ability to leverage three decades of experience and industry insight from a variety of leadership positions, allowing us to deliver practical and innovative solutions that drive success. Our commitment to excellence and a deep understanding of the industry landscape make us a trusted partner for achieving your business objectives.

Parachute Digital Solutions Inc.

Led US Business of Munich Re’s new Life Innovation Company, PDSI, with goal to digitize insurance and provide the ultimate customer experience. Parachute, a digital insurance company "in a box” that included everything except Carrier paper (distribution, marketing, digital products, enrollment, billing, admin, call center, customer portal), was a turn-key solution for Carriers & Distributors. Started in Canada and exploring the US market.

COO, Head of US Business

Munich American Reassurance Company

Lead the market assessment, strategy, development and implementation of innovative products and services in the US Life and Health market through unique partnerships, new ventures and distribution channels.

Vice President, New Ventures

Oversaw US Individual Life Business Development and Marketing Actuary teams.  Cultivated relationships with nearly every large Carrier and vendor in the US.

Vice President, Reinsurance Marketing - Head of US Business Development

International assignment working with the leadership team to develop strategies that address significant challenges in the Australian living benefits market and to lead the project team responsible for developing and implementing the Control Cycle risk management framework.

Vice President & Actuary

CDR Optimal Consulting Group

Product Development Consulting Actuary in entrepreneurial firm responsible for pricing and developing direct carrier Term product portfolios and brokering the portfolios to the reinsurance marketplace.

Consulting Actuary

Canada Life

Principal life and health actuary in US Individual business unit.  Responsible for pricing, product development, state and SEC filings, illustration development, reinsurance placement, and actuarial support.  Also held position of Southeast Sales Director, developing the regional PPGA sales force and wholesaling variable products.

Assistant Vice President - Head of Product Development

Transamerica Reinsurance

Consultant developing VUL, UL, and Term product portfolios for direct insurers and structuring/pricing the reinsurance backing the deals.

Product Consulting Leader

The Hartford

Individual life product development actuary.  Also held positions in Group and Special Risk financial reporting.

Actuarial Associate

Southwestern Company

Attended intensive entrepreneurial / sales skills training, established own business 2600 miles away from home.  Sales volume ranked in top tier nationwide. Gained unique life experience and entrepreneurial fundamentals - learned how to enter an unknown market and build a successful business.

Salesman

As an accomplished executive actuary seasoned in launching new businesses and innovative products, I am passionate about developing and executing creative marketing strategies and leveraging and expanding my broad industry network to form partnerships and relationships that accelerate and maximize growth. 

I've been recognized for being a collaborative visionary adept at attracting, developing, and inspiring high-performing teams to exceed objectives.  I invest in relationships, giving relevant feedback with the goal of maximizing potential and developing future leaders.

I'm known for being a forward-thinking leader with an entrepreneurial mindset, one that designs & builds solutions by strategically viewing the business holistically.  I instinctively challenge the current state, looking for continuous improvement to drive the organization forward.

taplio

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