FutureSight

Co-Founder & CEO - AI Content Intelligence for Professional Services

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 an AI-native content intelligence and publishing venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
Orbitwell is an AI-first content workflow that turns a professional's own judgment and stories into a consistent, firm-approved public presence. The platform captures private input through conversation, audio, and dictation, drafts voice-matched content grounded in that person's real expertise, and routes every draft through configurable firm guardrails and human verification before it reaches a ready-to-publish queue. Rather than another point solution for capture, writing, or scheduling, Orbitwell is designed to be the system of record for expert-driven publishing inside professional-services firms.
The venture begins with an initial product, 30+ validation interviews, and a working prototype to accelerate iteration and go-to-market. We are now seeking a founder to lead the venture from here.
Market Context

~500,000+ US professional-services firms in wealth and legal alone (33,000 RIAs, 418,000–463,000 law firms), most under 10 people

Professional-services AUM/revenue is growing and consolidating: RIA assets under management +22.3% YoY to $176.8T; RIA M&A hit a record 322 deals in 2025, up from 272; law firm employment +1.4% in 2025

The category proving willingness to pay for this workflow, personal/employee advocacy software, is a $0.5B–$2.2B market in 2026, growing at double-digit CAGR through the early 2030s

Generative AI content creation, the underlying technology wave, is a $14.8B market in 2024 projected to reach $80.1B by 2030 (32.5% CAGR)

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 vertical AI 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 execution.

Strategy — Define the ICP wedge (creators vs. teams vs. agencies), pricing model, and product positioning

Customer Development — Expand from internal design partners to external users (creators, teams, agencies), validate retention and willingness to pay, and build the go-to-market motion through creator-led distribution

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 the creator economy, marketing tech, social platforms, or knowledge work tooling, with familiarity in AI agents/LLMs

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

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Executive
Technology & IT Figma Sales Writing Founder Ceo Executive level

Likely questions

  1. Tell us about work you have done that is close to the Co-Founder & CEO - AI Content Intelligence for Professional Services role.
  2. How would you approach your first 30 days at FutureSight?
  3. Which of Figma, Sales and Writing 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 Figma, Sales and Writing.
  • 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 Content Intelligence for Professional Services role because I can bring practical experience in Figma, Sales and Writing, learn the team quickly, and contribute to the outcomes FutureSight needs from this hire.

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