# FutureSight — Co-Founder & CEO - AI-Native Mortgage Origination

- Generated: 2026-08-31 11:54:54 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/4461032293/
- Posting time: approximately 2026-08-30 04:54 PM EDT (estimated from LinkedIn's '19 hours ago' at capture)
- Applicants: Be among the first 25 applicants
- Work model/location: United States; work model not independently verified as remote; LinkedIn location: United States
- Compensation: Founder equity only; explicitly not a salaried executive role
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 38% evidence coverage
- Explicit override: Keith explicitly authorized generation despite the hard fit-gate failures on August 31, 2026.

## Fit decision

FAIL remains the correct fit-gate outcome. The role is explicitly equity-only, and its central mandates include fundraising, capital close, B2B SaaS sales conversion, and direct mortgage-origination/lending-operations experience. Keith explicitly overrode the gate and authorized application-material generation. The resume therefore foregrounds only supported founder, product, engineering, customer-discovery, commercialization, and team-building evidence without claiming mortgage expertise, venture-backed founding, or completed fundraising.

## Weighted evidence map

| Requirement | Weight | Evidence score | Evidence |
|---|---:|---:|---|
| Set venture direction and execute as co-founder/CEO | 3 | 3 | Direct Intelligent DataWorks co-founder/CEO ownership of strategy, product, architecture, team, and commercialization. |
| Build and ship an AI-native V1 | 3 | 3 | AssistX shipped in eight months; 70+ automations across 20+ workflows. |
| Customer discovery, pilots, pricing, and product positioning | 3 | 2 | Direct discovery, pilots, pricing analysis, demonstrations, partnerships, and value modeling; limited proof of repeatable paid conversion. |
| Recruit and lead the founding team | 3 | 3 | Recruited and led 11 engineers selected from 400+ applicants; repeated team-building evidence. |
| B2B SaaS go-to-market and sales success | 3 | 1 | Adjacent commercialization, customer engagement, and pilots; required sales success is not documented at the target depth. |
| Fundraising fluency and capital close | 3 | 1 | Fundraising support is documented; direct seed-raise ownership and capital close are not. |
| Mortgage origination and lending operations | 3 | 0 | Unsupported mandatory domain experience; not claimed. |
| Equity-only compensation | 3 | 0 | Explicit hard conflict with Keith's standing compensation requirement. |

Weighted evidence result: 36 of 72 possible points = 50% on this evidence map; the original batch score remains 38% because the hard functional and compensation gaps dominate the decision.

## Direct-match strengths

1. Current AI startup co-founder/CEO ownership spanning vision, product, architecture, team, customer discovery, and commercialization.
2. Quantified 0-to-1 production delivery: eight-month release, 70+ automations, 20+ workflows, up to 50x acceleration, and hundreds of launch signups.
3. Repeated product and engineering organization building in startup and enterprise settings.
4. Enterprise customer credibility from advising 200+ AWS organizations and shipping five commercial SaaS products.

## Material gaps and caveats

1. Founder equity only and explicitly not salaried; this remains a hard compensation conflict.
2. Direct mortgage-origination and lending-operations experience is required and unsupported.
3. Repeatable B2B SaaS sales conversion and seed-capital close are central but not documented at the required depth.
4. The work model is not independently verified as remote; travel is undisclosed.

## Full normalized job description

The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Closeline, an AI-native mortgage origination venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Closeline is building the AI-native infrastructure for mortgage origination, purpose-built for brokers and mid-market IMBs. The agent owns the full loan file lifecycle: reading documents, checking them against investor and agency guidelines, and routing each loan through to a decision, acting rather than waiting on a human, and earning more autonomy as trust builds loan by loan. Customer discovery validates a real, recurring cost problem in this segment: lenders spend thousands of dollars to originate a single loan today, a cost that's climbed roughly 35% over the past three years, with up to 80% of that time spent on manual document review. The US mortgage market processes roughly 6.5 million loans a year across close to 5,000 lending institutions, an estimated $3.25B in addressable software spend at Closeline's pricing. Brokers and mid-market IMBs alone originate about 5.3 million loans a year, representing a $2.65B segment, our initial target market. At target pricing, firms see an estimated 8 to 10x return on what they're currently paying to originate a loan. About FutureSight FutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale. You'll co-create with a proven venture building team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth. The Partnership Founder equity with meaningful ownership from inception Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding Venture building resources, including embedded design, engineering, growth, and fundraising support from day one Investor and advisor network across fintech and early-stage capital markets A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner What You'll Own As Co-Founder & CEO, you will set the venture's direction and lead its execution. Strategy — Refine the ICP, pricing model, and product positioning Customer Development — Lead pilots with underwriters, processors, and operations leads, convert them to paid engagements, and build the go-to-market motion Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback Capital — Lead the seed raise, supported by FutureSight's network and traction Team — Recruit and lead the founding team, and establish the cultural foundation of the company Co-Founder Profile Previous founding experience at a venture-backed company Demonstrated success in B2B SaaS go-to-market, including sales and customer engagement Fundraising fluency, with the ability to develop investor narratives and close capital Proven ability to attract, develop, and retain top talent Clear-eyed understanding of the risks and demands of co-founding a venture-backed company Direct exposure to mortgage origination and lending operations How to Apply Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate. FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.

## Artifact metadata

- Resume: https://bit.ly/4xwKFL2
- Cover letter: https://bit.ly/4gLPLvD
- Direct resume: https://files.keithsteward.com/FutureSight/Keith_Steward_Co_Founder_CEO_AI_Native_Mortgage_Origination_Resume.pdf
- Direct cover letter: https://files.keithsteward.com/FutureSight/Keith_Steward_Co_Founder_CEO_AI_Native_Mortgage_Origination_Cover_Letter.pdf
- Archived JD capture: https://files.keithsteward.com/FutureSight/Keith_Steward_Co_Founder_CEO_AI_Native_Mortgage_Origination_JD_capture.md
- Validation: 2-page resume (982 words); 1-page cover letter (248 words); profile 89 words; 41 supported technologies; PDF geometry, annotations, bounds, text extraction, and public links verified.
- Google Drive used: No