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

RedMountain Advisors

Provide Fractional-CMO and Advisory services to companies in Insurtech and Fintech, specializing in Strategy, Branding, Go-to-Market, Product, and Digital Growth.  Recent client engagements, virtual and on-site (Toronto, Miami, NYC, Tampa, Chicago, Des Moines, Calgary, Romania, and Las Vegas), include:
•	Strategic planning process creation and leadership workshop moderation
•	Market-entry strategy and focus group facilitation
•	New product ideation and product development
•	Executive staff development and recruiting
•	Branding strategy and name-creation
•	Carrier relations and partner introductions & development
•	Investor prep advisement and presentations (leading to 9-digit funding)
•	Speaker and moderator at Industry conferences
•	Webinar strategy, content creator, and featured panelist/speaker
•	Value proposition and market positioning development & commercialization
•	Establishment of growth-initiatives, business plan creation, and Go-to-Market
•	Marketing asset audit, review, and updating
•	Corporate website strategy and development
•	Executive mentoring and coaching

Founding Principal - Strategic Growth Advisor

Optimity

Provide Strategic Advisory guidance to Optimity founders and executive leadership, with a primary focus on strategy, growth, marketing, pricing, channel development, and geographic and market expansion.
  
Optimity is a mission-driven technology company that enables a healthier population and fosters the industry vision of insurability for all -- serving Insurance Carriers and Distributors, Corporate Wellness, Healthcare Providers, Financial Service Companies, and their customers, employees, and partners.

Strategic Advisor

ClientUp

Consultative advisory services to the ClientUp founder and executive leaders; principally focused on strategy, market positioning, growth, partnerships and alliances, and market expansion.

ClientUp operates in the Lead-Generation and Sales-Enablement space within a number of sectors and markets, with an expanding focus in Insurance.

Insurance Supermarket International Canada

Provided strategic advice in areas regarding growth, product, leadership development, recruiting, new market development, investments, carrier-relations, and more.  Work spanned multiple countries, engaging with the founders and executive leadership across the organization.

Farmers Insurance Group of Companies - Life Insurance

Farmers Life Insurance, a subsidiary of Zurich Insurance Group and part of the Farmers Insurance Group of Companies -- Reaching consumers directly and through our 13,500 agents.

Leadership and oversight of Marketing, Consumer Insights, Digital Strategy and Execution, CRM / Campaigns, Content, Advertising, NPS, Market Research, and Consumer Direct and Omni teams for Life company.  -- Managing direct (staff of 12), indirect/matrixed teams (remote and on-site), and vendors/partners in fluid, agile, and at-times ambiguous organizational structures.

Executive leadership engagement beyond direct-report teams spans:  Product Strategy and Development, Annual-planning, Distribution Strategy, Pricing Strategy, In-force Management, Corporate Strategy, Digital Transformation.  Regular presentations to US and Zurich Board of Directors and Executives.

Active involvement in industry associations as Committee Chair, Speaker, Panel Moderator -- LIMRA and Society of Actuaries (SOA).

Head of Marketing

Global Visionaries

Empowering youth to be global leaders in creating a just and sustainable future.

Global Visionaries is a staff and youth-led organization that challenges and empowers young people to become socially and environmentally conscious global leaders. Through Global Visionaries’ unique three part learn-participate-lead approach, its participants are motivated and prepared to maximize their potential. Formed in 1995, Global Visionaries is a nonprofit organization based in Seattle, Washington and welcomes participants from across the U.S.

Member Board Of Directors

T-Mobile

Directed Product Development/Management team, focused on driving messaging services, cloud text, group communications, contextual mobile advertising, and voice-integration across mobile devices, their associated apps, and cloud and web access.

Led the creation of new brand for Communications Services - Bobsled by T-Mobile.  Developed products and services targeting T-Mobile and general-market consumers worldwide.  Branded as Bobsled, products span mobile, web, and tablet, allowing consumers to reach anybody, anywhere, on any device.

Senior Management, Product Management & Development

Strategic Growth Consulting

Specializing in applying big-company rigor and MBA focus together with entrepreneurial savvy, tenacity, and resourcefulness to enable companies, large and small, start-up and established, to realize their growth potential.

Principal / Consultant

JPMorgan Chase & Co.

Positions: 
• First Vice President Channel Strategy, Consumer Direct - Mortgage {Washington Mutual, now JPM}
• First Vice President Product Development & Management - Mortgage {Washington Mutual, now JPM}

Built and led a $900 million-producing Business Unit.  Scope encompassed go-to-market strategy, product development and management, operational design, general management, and overall unit P&L accountability.
• Ramped up business from start-up stage to volume of $92mm per month.

Formed the Product Development department for 1,500 person $32B division while reporting directly to Division President.  Managed product management, market research, analytics and reporting, and implementation staffs.
• New product activity helped contribute to record-setting volume in excess of $3.0 billion/month; new product line accounted for 51% of total division volume
• Presented concept and plan for new innovative product directly to WaMu Chairman and Executive team – breakthrough product line generated profit of $165mm during initial release

WaMu Corporate Innovation Center
• Member of Innovation Center Brainstorming Team; selection based on enterprise-wide Creativity testing

Awards:
• President’s Club Honoree

FVP Channel Strategy (D2C); FVP Product Development (B2B/wholesale channel)

WorldCash Technologies

Conceived, implemented and managed WorldCash, an intrapreneurial start-up at UPFC.  WorldCash created a proprietary cost-effective system/solution for the global (largely Hispanic) electronic money transfer / remittance market.
• Built the consumer service business from an idea into a separate wholly-owned subsidiary
• Identified and implemented all technology platforms and operational partnerships in the US and abroad  – Directed the development of payment systems; managed contract and in-house technology personnel
• Developed and executed all aspects of sales and marketing plan for market launch  – Established affiliation with BP’s Arco for initial placement in more than 1,000 am/pm locations
• Oversaw all relationships and contracts with partners, advertising agency, investment firms, and regulators

Intrapreneurial Start-up Founder / GM

Provide Fractional-CMO and Advisory services across a range of Industries and Channels.  
Prior Corporate and Start-up Expertise includes:  Lead diverse teams in achieving growth and profit by identifying and implementing innovative business opportunities, and leveraging products, infrastructure, and market potential.  In often-ambiguous and fluid corporate environments, develop and introduce products, pioneer distribution channels, establish new divisions, build new ventures, and re-focus organizations toward customer-centricity and digital transformation.  Proven success in start-ups, intrapreneurial divisions, Fortune 100 and international.

LEADERSHIP IN NEW PRODUCTS AND MARKETING INNOVATION:
•	Formed and led Product Development, Marketing, Promotions, Business Development, and Strategy teams across multiple industries and in diverse channels

CREATING NEW CHANNELS OF DISTRIBUTION:
•	Developed, launched, and managed new consumer-direct (D2C) divisions for established B2B businesses

ESTABLISHING “INTRAPRENEURIAL” & START-UP VENTURES:
•	Conceived, developed, and ran technology-driven payments service start-up, utilizing parent-bank’s core assets to innovatively capture market opportunity in a new business area
•	Developed start-up mobile digital service; initiated new products, corporate ID/branding, and market launch

Specialties: Consumer Services, Technology, Mobile, Prepaid, Consumer Products (CPG), Financial Services (Payments, Lending, Insurance), Digital Media, Business Services, Concept to Introduction, Market Research, Customer-Centric Operations, Diverse Sales Channels, Market Segmentation, Advertising, NPS, Customer Innovation, Strategic Planning, B2B and D2C Focus, “Intrapreneurial” Ventures, Operational Leadership, E-commerce, Technology Solutions, Digital Transformation, P&L Management, Start-ups

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Jason Bennett

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