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§ Private Profile · San Francisco, CA, USA
The AI Workspace for Guided Selling
Outlit has raised $500K across 1 funding round.
Key people at Outlit.
Outlit was founded in 2024 by Josh Earle (Founder) and Leo Paz (Founder).
Outlit has raised $500K in total across 1 funding round.
Outlit is a guided selling experience for founders and early stage sales teams.
Track all your deals and always know: what to do next, who to follow up with, and what to send.
Key people at Outlit.
Outlit was founded in 2024 by Josh Earle (Founder) and Leo Paz (Founder).
Outlit has raised $500K in total across 1 funding round.
Outlit's investors include Sunset Ventures, Y Combinator.
Outlit is an AI-native workspace designed to enhance guided selling for founders and early-stage sales teams, particularly in B2B enterprise environments. It helps deal desk and revenue teams close better deals faster by leveraging historical deal data—terms, pricing, clauses, and redlines—to automate deal reviews and surface upsell, cross-sell, and renewal opportunities. This AI-powered approach eliminates the traditional trade-off between speed and accuracy in sales cycles, increasing deal size and improving deal hygiene[1][4].
Outlit serves sales and revenue leaders by providing a comprehensive view of the customer journey from first touch to paid, enabling smarter, more personalized sales proposals and deal management. It addresses the problem of losing up to 40% of deals during proposal, negotiation, and closing phases by guiding sales reps and deal desks on what to do next and who to follow up with, thus improving sales efficiency and revenue outcomes[1][4].
Outlit was founded by Josh Earle (CEO) and Leo Paz (CTO), both experienced in building and scaling SaaS and enterprise web applications. Josh has over six years of experience designing SaaS products used by over a million users, while Leo has built diverse enterprise applications, including no-code website builders and computer vision tools. The idea emerged from their deep understanding of the challenges in enterprise sales, particularly the tension between sales teams’ need for speed and deal desks’ need for accuracy. Their combined expertise led to creating an AI-driven solution that transforms deal history into actionable insights for sales teams[1].
Outlit rides the growing trend of AI-guided selling, which integrates AI into the sales process to enhance decision-making, personalization, and forecasting. The timing is critical as B2B sales cycles become more complex and competitive, with enterprises seeking tools that can reduce deal losses and accelerate revenue growth. Market forces such as the increasing adoption of AI in sales enablement, demand for automation, and the need for data-driven sales strategies work strongly in Outlit’s favor[1][2][3].
By automating deal reviews and surfacing upsell and cross-sell opportunities, Outlit influences the broader ecosystem by setting new standards for sales efficiency and deal accuracy. It also contributes to the evolution of sales technology by embedding AI deeply into the deal desk and revenue operations workflows, helping companies unlock hidden revenue potential and improve customer retention[1][3].
Outlit is positioned to become a key player in the AI-driven sales enablement space, with potential to expand its capabilities in predictive analytics, real-time coaching, and deeper integration with CRM and revenue operations platforms. As AI adoption in sales continues to accelerate, Outlit’s influence will likely grow, shaping how enterprises approach deal-making and revenue growth.
Future trends shaping Outlit’s journey include increased demand for personalized, data-driven sales strategies, the rise of AI in forecasting and deal intelligence, and the need for seamless collaboration between sales and deal desk teams. Outlit’s ongoing innovation and strong founding team suggest it will continue to refine its product to meet evolving market needs, potentially becoming a standard tool for guided selling in enterprise sales[1][2][3].
Outlit has raised $500K across 1 funding round. Most recently, it raised $500K Seed in March 2025.
| Date | Round | Lead Investors | Other Investors | Status |
|---|---|---|---|---|
| Mar 1, 2025 | $500K Seed | — | Sunset Ventures, Y Combinator | Announced |
