HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Description: In this episode, Guillaume speaks with Rick Rattray, MPPM, CEC, an executive coach and former EdTech C-suite leader who has helped multiple PE-backed companies scale, refocus, or turn around at critical inflection points. Rick brings a rare operator-advisor perspective: he knows how to coach leaders, but he also knows how to run the business. For consultants working with growth-stage or PE-backed clients, Rick’s insights on alignment, focus, and GTM execution show exactly where advisory work creates real commercial impact. ********************************************************** Links: StreamYard (for guest): https://streamyard.com/tvqp2xtsq8 YouTube (for sharing): https://www.youtube.com/watch?v=hOD4U5l0Lcs Apply to be a guest: https://ghapodcast.com/application-to-be-a-guest-on-consulting-leaders/ ********************************************************** Rick's Bio: Rick Rattray, MPPM, CEC is an executive coach and transformational EdTech operator with deep experience in PE-backed growth environments. As Managing Director of Varroom LLC and Principal at The Parliament Group, he works with leadership teams facing scale challenges, growth plateaus, or high-stakes strategic decisions. He’s held senior roles at Kaplan, Vista Equity’s ReliasLearning, QuadPartners’ ILSC GlobalFoundations, Shorelight, Barbri Professional, and AltaClaro, where he helped scale the business to ~$3M ARR, formalized operations, strengthened GTM, and supported a successful seed round and enterprise expansion. Rick holds an MBA from Yale SOM, is a CEC-certified executive coach, an ICF member, and an active mentor in innovation and commercialization ecosystems including Yale’s Tsai CITY. ********************************************************** Show Notes: Rick has built and transformed organizations across the EdTech and higher-ed ecosystem, from Vista Equity and Leeds Equity portfolio companies to Kaplan Ventures and emerging ventures like AltaClaro. He’s spent his career stepping into environments where clarity is missing, growth has stalled, or the team is struggling to align around what matters most. Through Varroom LLC, Rick now coaches founders, CEOs, and leadership teams while also advising growth-stage companies that need deeper support, from refining product-market fit to stabilizing operations to preparing for a fundraising round or exit. His approach blends grounded coaching with the hands-on experience of someone who has actually run and grown businesses. For consulting firm owners, Rick is a powerful model: he has created repeatable client value across industries, built long-term engagements anchored in clarity and results, and supported companies through meaningful revenue growth, including taking AltaClaro from ~$0 to $3M ARR while helping secure institutional funding and major enterprise clients. ********************************************************** Proposed Interview Structure 1. What led you from running PE-backed businesses to building your own coaching and advisory practice? 2. When a CEO or leadership team brings you in today, what’s the underlying problem they’re usually trying to solve? 3. Who do you work with today through Varroom and Parliament Group, and who’s typically the decision-maker who brings you in? 4. Most consultants struggle with pipeline. For you, what consistently brings in new coaching or advisory clients? 5. When a potential client is at a major inflection point, how do you scope the engagement and move from first conversation to a clear mandate? 6. You’ve built long-term relationships across several companies, how do you keep clients coming back and make sure the relationship continues to grow over time? 7. Where do you find yourself most stuck right now as a coach and advisor, if at all? Is it capacity, ideal client fit, evolving your offer, or something else that you’re currently working through? 8. Looking ahead, where do you see the biggest opportunities in your field over the next few years?
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