Matt Dubois
Brigham Young University
Pearl
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I'm the Cross-Sell Manager at Pearl AI, where I've built the company's cross-sell function largely from the ground up — designing comp structures, routing rules, hiring profiles, and quota models for a growing team of AEs and SDRs selling AI-powered products into existing dental practice customers. I operate as a player-coach, which means I'm not just setting strategy from the sidelines; I'm in the data, in the calls, and in the 1:1s helping reps close more and sell smarter. What sets my coaching apart is how I use AI to do it. I've built tools that score and surface trends across rep calls, systems that flag performance issues before they become quota problems, and individualized coaching plans grounded in real data rather than guesswork. I care about structured, direct feedback, no fluff, no generic advice, because that's what actually moves reps forward. Outside of work, I'm a Denver sports fan (Broncos, through thick and thin), a sci-fi reader, and someone who still finds time for D&D and Pokémon Go. I believe good coaching looks a lot like good sales management: clear expectations, honest feedback, and a genuine investment in the person's growth, not just their numbers.
Work with Matt
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Work Experience
Cross-sell Manager
Pearl
July 2025 - Present
Hiring Manager
I use AI extensively to run my sales team, not just to sell it. We built a call review tool that scores reps' calls against our sales framework and surfaces trend insights across calls over time, giving me an objective, scalable way to coach beyond what I could catch by spot-checking calls myself. I've paired that with an automated daily briefing system pulling from HubSpot, Slack, Gmail, and our calendar for a real-time read on pipeline and rep pacing, plus AI-driven analysis of our CRM data to diagnose performance issues at the root — like catching that one rep's low MRR came from an overreliance on low-value deals rather than a broader skill gap — which feeds directly into individualized coaching plans grounded in our sales methodology. I also used AI to build our quota model, keeping ramp schedules and seasonality data-driven rather than gut-feel. I happen to sell AI products too (I lead cross-sell for an AI-powered dental SaaS platform), but the more relevant experience for coaching is this: I've used AI as an operating system for managing people, not just a talking point in a pitch.
Director of Sales Development
Pearl
July 2024 - August 2025
Executive Producer
No Agenda Show
May 2021 - May 2021
Account Executive
Weave
June 2019 - July 2024
Analytical Skills, SaaS Sales and +1 skill
Account Executive
Weave
November 2018 - June 2019
Analytical Skills, SaaS Sales and +1 skill
Sales Development Representative
Weave
December 2015 - November 2018
Analytical Skills, SaaS Sales and +1 skill
Marketing Intern
Partner Fusion
May 2015 - December 2015
I was tasked with increasing customer retention for an Online Travel Agency by the name of ReservationDesk.com. As part of that task I created content and assisted in SEO, I handled the website analytics, and I assisted in social media customer care. I also was in charge of verifying the validity of the data coming through the call centers used by the company. Analytical Skills
Director of Clubs Events
Brigham Young University
April 2014 - April 2015
I am a member of the BYUSA presidency and as such I am a figure head for the university. I am in charge of all clubs on campus. This includes approving charters, events, and new organizations, as well as running a team of volunteers who serve as a resource to on-campus clubs and club presidents.
Director of Clubs Events
Brigham Young University
June 2013 - April 2014
I am in charge of all advertising for clubs on BYU campus. I also facilitate designers, club presidents and administration on campus.
Education
Brigham Young University
Bachelor's degree, Business Management- Marketing Emphasis
2009 - 2015
Activities and societies: BYU Student Service Association, BYU Marketing Association. Marriott School of Management Analytical Skills
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Matt has helped Leland clients get into TeligentIP