Co-Founder & CEO – AI Property Tech

FutureSight; Chicago (IL); On-site; USD 180,000 - 320,000; Full time

Benefits offered by this job

Equity stake

Job summary

FutureSight is seeking an experienced Founding CEO to launch an AI leasing and workflow orchestrator for multifamily property management. You will lead vision, build the founding team, and drive a 0-to-1 journey in a $20B+ PropTech market.

You will pilot pilots with customers, shape pricing, and lead seed fundraising while building a world-class product and go-to-market motion. This is a full-time leadership role with significant equity.

Qualifications

• Proven ability to build and lead a new venture from concept to market
• Strong fundraising fluency and investor storytelling
• Track record of GTM success in B2B SaaS, preferably PropTech

Responsibilities

• Lead the vision and strategy for FutureSight's AI leasing platform
• Build and shepherd the founding team and culture
• Raise seed capital and manage early investor relations
• Own P&L and drive product/market fit from V1 rollout to early traction

Skills

Founding CEO

Fundraising

GTM strategy

People leadership

B2B SaaS

PropTech knowledge

Industry experience

Job description

FutureSight is seeking an experienced and visionary Founding CEO to lead the launch of a new AI leasing and workflow orchestrator serving the multifamily property management industry.

Today, leasing and operations teams at property management companies spend hours chasing documents, sending follow-ups, and coordinating between site staff and head office to expedite the approval process for applicants. The result: lost applicants, compliance risk, and slow move-ins.

Our venture is reimagining this critical workflow with an intelligent orchestration platform that connects leasing, screening, and compliance steps into one automated, trackable process — helping teams move faster, stay compliant, and provide a seamless experience for residents and staff alike.

As Founding CEO, you’ll shape the vision, build the team, and lead this transformation across the $20B+ PropTech market.

As Founding CEO, you will

• Win customers — Run pilots, shape pricing, and validate retention + expansion


• Build the product — Work with FutureSight’s product/engineering pod to launch V1


• Raise capital — Lead the seed round with our initial investment


• Build your team — Hire your founding team and set the cultural foundation

About FutureSight

FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage — pairing hands-on studio support with early capital, thereby reducing risk and increasing the odds of success by 10x.

We’re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.

What We Bring

• Validated problem — You will enter a venture with a proven market need and strong momentum toward building and scaling


• Studio bench strength — Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1


• Capital commitment — Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network

What You Bring

• Founder-level drive — You’re motivated to co-found a new venture as the CEO. With or without us, this is your calling


• Startup scrappiness — You know what you’re signing up for. You’re familiar with the scrappiness of owning something from start to finish


• Previous founding experience — You have co-founded a product company or B2B SaaS venture, or have been at a venture-backed company


• Risk appetite and capacity — Read more on our post on the Entrepreneurial Risk Profile


• GTM chops — Proven success in B2B SaaS sales, marketing, and customer engagement


• Fundraising fluency — Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities


• People leadership — Magnet for top talent; coach and culture carrier


• Industry experience — Background in property management, real estate operations, or proptech solutions

What You Can Expect

• Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise


• Full P/L ownership of the new entity


• A significant equity stake in the business


• This is a full-time role; we are seeking someone to dedicate themselves full-time and exclusively to building and owning a new SaaS venture

FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.