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Jake Cronin

Jake Cronin

Co-Founder & Co‑CEO building AI coaching for field sales

jakecronin
New York, New York, United States
Joined August 2025
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Network

7.8K connections
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McKinsey Alumni
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Sales & GTM Leaders
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Venture Capital Investors
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Siro GTM & Ops
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Siro Product & Eng
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Summary

Founder & operator focused on bringing AI to a neglected sales segment: Jake co-founded Siro (2020) to build conversation-intelligence and coaching tools for in-person/field sales reps, and has led fundraising, product and R&D as Co-Founder & Co-CEO. Under his leadership Siro has raised a Series B and scaled the product into numerous verticals. siro+2
Hands-on sales experience shaped product mission: early work selling Cutco and running a Vector Marketing branch informed Jake's view of coaching scarcity in field sales and directly inspired Siro's product focus on making coaching abundant and actionable. siro+1
Technical background plus consulting discipline: a B.S. in Math & Computer Science (Emory) and time as a McKinsey Business Analyst gave Jake both product/engineering chops and a data-driven, strategy-oriented approach to building and scaling a startup. emory+1
Early founder experience and rapid product iteration: prior co-founding of Queue (2016) and early traction/testing (Alchemist Accelerator, Grand Central Tech cohorts) reflect a pattern of building lightweight products, testing with hundreds to thousands of reps, and iterating to product-market fit before scaling. siro+1

Work

Education

Projects

Writing

Letter from the CEO: Announcing Siro's Series B

June 1, 2025

Company blog post by Jake announcing Siro's $50M Series B, describing Siro's mission (AI coaching for in-person sales), product impact metrics (close rates, turnover, coaching speed), and the company's roadmap.

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Siro's Top Secret Master Plan

January 1, 2023

Long-form company post describing the origin story, mission, product approach (scaling coaching via conversation intelligence), early traction (users, ARR), and the founders' sales background (Cutco/Vector Marketing) that inspired Siro.

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Hobbies

Running and soccer; also active in coding and product/engineering. linkedin+1

Notes

MCMichael Caldwellsaid
JCJake Cronin
has demonstrated a strong ability to turn AI research into impactful products that interact with the physical world.

Mar 4, 2026