Skwill - 2026 Pricing, Features, Reviews & Alternatives

Skwill is a cloud-based AI sales performance coaching platform built for B2B sales teams across startups, scaleups, and enterprises. It combines a proprietary Sales Book of Knowledge (SBoK), a fine-tuned large language model (Ask Willy GPT), behavioral psychology models, and conversation intelligence to deliver personalized, business-contextual coaching across the full sales cycle. Core capabilities span meeting preparation with buyer-specific insights and do's and don'ts, AI-driven pitch practice against simulated buyer personas with real-time feedback on language, tone, structure, and emotional delivery, and post-call analysis that maps performance to competency models. The platform integrates natively with Microsoft 365 (Teams and calendar) and supports Gmail and Google Calendar, with CRM, LMS, and SSO available as add-on integrations. Data is secured with AES-256 encryption at rest and TLS 1.2+ in transit.

Conversation intelligence captures buying signals, objection categories (price, timing, features), commitment tracking, and talk-to-listen ratio from meeting transcripts automatically. Pipeline velocity monitoring surfaces live data and predictive risk and opportunity alerts, giving sales leaders early visibility into deal health through behavioral and emotional signal analysis. The on-demand AI coach (Ask Willy GPT) provides B2B sales-specific Q&A and prospect insights drawn from publicly available data, including LinkedIn profiles assessed through behavioral psychology models to infer personality and decision-making style.

Skwill serves solo sales leaders and founders, small teams of up to five members, and large enterprise organizations, with a primary industry focus on IT and technology, B2B SaaS, and brand protection. Coaching prompts are customizable to team sales methodology, industry, and product. A credit-based usage model is tracked via a team dashboard, with a free 14-day trial and flexible upgrade or downgrade options, making the platform accessible regardless of team size or growth stage.