Journey Mining + AI: TheyDo’s Path to Bigger, Faster Deals

Description:  

In this episode of Sound Bites, host Bill Binch from Battery Ventures talks with Matt Peloso, Head of Global Revenue at TheyDo, about how his team used journey mining, AI-enriched call and CRM data and improved qualification to dramatically shorten sales cycles, increase deal sizes and elevate overall rep productivity.

Key Takeaways/Key Moments: 

(00:00) Identifying Deal Stage Bottlenecks Through Journey Mining

Matt explains how TheyDo analyzed Gong calls, Salesforce notes and internal insights to map their sales journey and uncover stage-level weaknesses slowing down deal progression.

(03:09) Using AI to Spot Qualification Gaps and Surface Deeper Pain

By aggregating and enriching data inside TheyDo, the team identified where reps weren't digging deep enough into business-level pain, leading to better qualification and earlier “qualify out” decisions.

(03:38) Coaching Reps on True Pain vs. Surface Pain

AI-driven insights revealed when reps were dealing with coaches rather than champions, enabling targeted coaching on follow-up questioning and linking technical pain to executive-level business outcomes.

(05:40) Major Impact: Deal Cycles Cut in Half While Deal Sizes Increase by 3x

Negotiation-to-close shrank from 101 days to 54 days, overall deal cycles dropped from 5.5 months to 71 days and average deal size jumped from ~20K to ~65K.

(08:55) Why the Inspection Started: A Need for Scalable, Productive Growth

Matt shares that TheyDo’s shift from PLG to sales-led growth, and board pressure to scale efficiently, prompted a deep inspection into productivity models, exposing wasted cycles and long-stalled deals.

Disclaimer: This material is intended for an audience of entrepreneurs and provided for informational purposes, and it is not, and may not be relied on in any manner as, legal, tax or investment advice or as an offer to sell or a solicitation of an offer to buy an interest in any fund or investment vehicle managed by Battery Ventures or any other Battery entity. The information and data are as of the publication date unless otherwise noted. Content obtained from third-party sources, although believed to be reliable, has not been independently verified as to its accuracy or completeness and cannot be guaranteed. Battery Ventures has no obligation to update, modify or amend the content of this post nor notify its readers in the event that any information, opinion, projection, forecast or estimate included, changes or subsequently becomes inaccurate. The information above may contain projections or other forward-looking statements regarding future events or expectations. Predictions, opinions and other information discussed in this video are subject to change continually and without notice of any kind and may no longer be true after the date indicated. Battery Ventures assumes no duty to and does not undertake to update forward-looking statements. For a full list of all Battery investments, please visit https://www.battery.com/list-of-all-c...