FutureSight

Co-Founder & CEO - AI-Native Mortgage Origination

Canada full-time Executive Salary not listed
full-time Executive level Technology & IT Curated
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About the role

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.
Originally posted on Himalayas

Interview prep

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Executive
Technology & IT Operations Sales Founder Ceo Native Executive level

Likely questions

  1. Tell us about work you have done that is close to the Co-Founder & CEO - AI-Native Mortgage Origination role.
  2. How would you approach your first 30 days at FutureSight?
  3. Which of Operations, Sales and Founder have you used recently, and what did it help you achieve?
  4. How have you led people, improved a process, or made a hard decision in a previous role?
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Operations, Sales and Founder.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Co-Founder & CEO - AI-Native Mortgage Origination role because I can bring practical experience in Operations, Sales and Founder, learn the team quickly, and contribute to the outcomes FutureSight needs from this hire.

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