AskBibi: AI-Powered Sales Assistant
By Alex Bukowski
Client: Bobit Business Media
Industry: Media & Marketing
Product: AI-Powered Sales Assistant
Overview
Gambit partnered with the team at Streetwise Consulting to build AskBibi for Bobit Business Media. With services offered across multiple business units, Bobit needed a more consistent way to guide discovery and uncover cross-selling opportunities.
Gambit implemented AskBibi, an AI-powered sales assistant that helped structure those conversations and supported a smoother handoff to sales. The result was a 38% lead capture rate and an increase in sales opportunities.
Challenge
Bobit’s sales teams were missing cross-selling opportunities due to a lack of structured lead nurturing and warm introductions. Early conversations were happening, but important context was not always captured in a way that made follow-up easy or consistent across the team.
Bobit needed a solution that could guide prospects through discovery, ask the right questions, and help connect customers with the right services across multiple business units.
Solution
Gambit implemented AskBibi, an AI-powered sales assistant designed to capture intent and uncover customer needs through conversation. The assistant asked strategic questions based on each user’s responses, helping surface what prospects were looking for while keeping the experience conversational.
As users responded, AskBibi dynamically generated cross-service marketing packages that pulled from multiple business units. This helped ensure the right services were positioned at the right time, and supported a more consistent discovery experience across the sales process.

Results
AskBibi helped create stronger handoffs to Bobit’s sales team by passing AI-generated conversations directly to sales reps. This gave reps warmer introductions and reduced friction in moving deals forward.
Sales teams also benefited from access to chat histories, making it easier to personalize follow-ups and continue the conversation without losing context.
Overall, Bobit achieved a 38% lead capture rate, significantly increasing sales opportunities and expanding their pipeline.

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