Outlit

What do they actually do

Outlit provides an AI workspace that helps sales teams run structured, guided selling conversations. It brings playbooks, product rules, and AI suggestions into one place so reps can qualify needs, navigate complex options, and assemble correct proposals for configurable products.

Teams set up guidance and rules, then use step‑by‑step flows during live calls to recommend bundles or configurations, surface talking points, and generate concise follow‑ups or draft proposals. The goal is to shorten time to an accurate proposal, reduce reliance on ad‑hoc spreadsheets and tribal knowledge, and make selling more consistent across reps.

Who are their target customer(s)

• Account Executive at a mid‑market or enterprise B2B company with configurable products: Deals stall or go sideways because pricing and options are complex and junior reps can’t confidently assemble correct proposals. They waste time switching between docs, spreadsheets, and the CRM instead of running a smooth conversation.
• Solutions Engineer / Pre‑sales: They repeatedly rebuild demos and custom configurations and manually enforce rules, which slows cycles and introduces errors. Critical know‑how lives in spreadsheets and a few experts’ heads, making coverage hard to scale.
• Sales Manager or Revenue Operations lead: They can’t see whether reps follow qualification steps or playbooks, so coaching is reactive and onboarding is slow. Forecasts are noisy, and managers must closely babysit deals to hit targets.
• Customer Success Manager focused on renewals/expansions: It’s hard to recommend the right add‑ons or renewal options because pricing/compatibility rules are scattered. Upsell opportunities are missed and proposal prep is slow, frustrating customers.
• Enablement or Product Marketing owner: Keeping playbooks and examples current is manual and field feedback is slow. Reps ignore stale guidance or create inconsistent versions that dilute intended positioning.

How would they acquire their first 10, 50, and 100 customers

• First 10: Founder‑led outreach to YC/network contacts and warm intros to AEs and SEs at mid‑market configurable‑product companies, offering a short hands‑on pilot where founders help set up playbooks and run initial calls; capture ROI notes and a brief testimonial post‑pilot.
• First 50: Use early case studies and templates to target similar companies via outbound (sales and RevOps) and short technical webinars for SEs; offer a low‑friction trial with templated playbooks, and begin lightweight partnerships with CRM/RevOps consultancies for implementation and leads.
• First 100: Formalize reference accounts and referrals, then scale direct sales with a small mid‑market AE team doing named‑account outreach. Expand channel by partnering with implementation firms and listing integrations in major CRM marketplaces to speed procurement and win larger deals.

What is the rough total addressable market

Top-down context:

Outlit sits at the intersection of sales enablement and CPQ/configurators for mid‑market and enterprise teams selling configurable products. Budget typically comes from sales, pre‑sales, enablement, or RevOps lines.

Bottom-up calculation:

Illustrative example: N = 40,000 target companies (US+EU mid‑market & enterprise with configurable B2B offerings), P = 25% that need guided selling/configuration, A = $50,000 ACV. TAM ≈ 40,000 × 25% × $50,000 = ~$500M annually (scope and inputs adjustable).

Assumptions:

• Scope is US+EU mid‑market and enterprise companies with configurable B2B products.
• Penetration (P) estimated at 25% needing guided selling/configurators.
• Average ACV (A) of ~$50k including seats and basic integration.

Who are some of their notable competitors

• Highspot: Sales‑enablement system that centralizes playbooks and content with adoption analytics. Overlap on playbooks; less focused on real‑time configuration or in‑call AI for specific SKUs/prices.
• Seismic: Enterprise sales‑enablement and content automation (templates, personalization, versioning). Strong in content operations; not primarily a conversational guided workspace for qualification + configuration.
• Salesforce CPQ: CPQ that enforces product/pricing rules and generates quotes and proposals. Great for rules and document output; not designed as a lightweight, AI‑driven, in‑call guidance workspace.
• Consensus: Buyer‑engagement platform with on‑demand, tailored demos and guided buyer journeys. Buyer‑facing and demo‑centric; Outlit is positioned as rep‑facing guided selling.
• Gong: Conversation intelligence for call recording, transcription, and coaching insights. Focuses on post‑call analysis rather than real‑time guidance, configuration, or quote assembly during a live sale.