Jason Roswig
LinkedIn Copy
Hey Jason — congrats on launching LeftRight. Similar IB → PE background here — been deep in middle market origination lately. Would be good to connect.
Hey Jason, similar background, weirdly — I'm from Zimbabwe, did growth equity in London, not scaling a middle market fund like LeftRight. most funds I talk to have a database — PitchBook or Grata — maybe a CRM, and then the origination setup is mostly Excel and email from there. but proprietary deal flow still feels thin. thesis, network, and intelligence never sync into one system — so origination resets every cycle instead of compounding. does origination look different at LeftRight? — Russ
Hey Jason, similar background, weirdly — I'm from Zimbabwe, did growth equity in London, not scaling a middle market fund like LeftRight. most funds I talk to have a database — PitchBook or Grata — maybe a CRM, and then the origination setup is mostly Excel and email from there. but proprietary deal flow still feels thin. thesis, network, and intelligence never sync into one system — so origination resets every cycle instead of compounding. does origination look different at LeftRight? — Russ
hey Jason — was thinking about this more. after hitting this wall myself doing growth equity, I ended up building origination infrastructure for funds full-time — Mentmore Capital, Axiom Equity, Noble Rock, a few others. at my old fund we had a solid stack and smart people, and origination still restarted from scratch every cycle. the funds who systematise it early end up compounding deal flow — the ones who don't keep resetting. curious if LeftRight has cracked that or if it's the same pattern. — Russ
hey Jason — appreciate the connect either way. we documented the origination infrastructure we've built across funds — tech stack, workflows, prompts. free to share if it'd be useful at LeftRight. either way, I'm around if origination ever becomes a conversation worth having. — Russ
Email Copy
Hi Jason, looks like we share a similar PE path — though I'm from Zimbabwe and ended up doing growth equity in London, not scaling a middle market platform like LeftRight. most funds I talk to have a database — PitchBook or Grata — maybe a CRM, and then the origination setup is mostly Excel and email from there. yet the off-market pipeline stays weirdly thin. the intelligence is all there but it's scattered across tools and inboxes — so nothing compounds into a real origination edge. does origination look different at LeftRight? Russell searchloop.ai linkedin.com/in/russellt23
hi Jason — been thinking more about origination. after hitting this wall myself doing growth equity, I ended up building origination infrastructure for funds full-time — Mentmore Capital, Axiom Equity, Noble Rock, a few others. the pattern I keep seeing is that the funds who systematise it early end up compounding deal flow in a way that's really hard to replicate later. happy to compare notes on what's actually moving the needle if you're interested. Russell searchloop.ai linkedin.com/in/russellt23
hi Jason — something about this keeps rattling around. when I was doing growth equity we had every subscription going — PitchBook, CRM, enrichment tools, the lot — and I still spent half my time manually pulling origination together across all of it. always wondered if that was just us being disorganised or if it's genuinely universal. imagine LeftRight has a way more dialled setup — but figured I'd ask. Russell searchloop.ai linkedin.com/in/russellt23
hi Jason — completely separate from all that. we put together a playbook on PE origination — the tech stack, the workflows, some of the prompts and automations that actually move the needle. happy to send it over if it'd be useful at LeftRight. Russell searchloop.ai linkedin.com/in/russellt23
hi Jason — I'll leave it here. the origination playbook is yours whenever — no expiry on that. I'm deep in this space all day, so if it ever becomes a conversation worth having, I'm around. Russell searchloop.ai linkedin.com/in/russellt23
Prospect Research
## PROSPECT INFORMATION: Name: Jason Roswig Title: Partner Fund: LeftRight Capital Background: Prospect Summary: Jason Roswig Current Role: Partner at LeftRight Capital (since February 2024). Background: Jason is an experienced finance and operations executive with 25 years of experience in strategy, corporate development, and M&A. He previously served as President and CFO of Skillz Inc., where he led a major two-year restructuring. Prior to that, he was a Managing Director at The Blackstone Group, focusing on asset management for the firm's technology and financial services portfolios. His early career included significant leadership roles at McKinsey & Company (Associate Partner) and General Electric, with international experience in both China and Germany. He holds an MBA from Columbia Business School and a BA from Bowdoin College. Core Expertise: Mergers & Acquisitions, Corporate Development, Financial Modeling, Strategic Planning, Performance Improvement, and Post-Merger Integration. He has overseen or been involved in 100+ transactions with deal sizes ranging from $2 million to $27 billion. Recent Activity & Hooks: - On May 5, 2025, in a post regarding a website collaboration, it was noted: "We partnered with LeftRight Capital to create a splash page that reflects their structured, long-term approach to investing, balancing engaging design with social proof." and "Shoutout to Jason Roswig and Richard Jones for their collaboration and insight." - On January 2, 2024, Jason shared a post from Skillz: "#happynewyear everyone from all of us at Skillz! May it be filled with lots of fun, play and wins! #2024 #winningtogether" - On December 14, 2023, while at Skillz, a post mentioned: "Aarki is making major investments in it's ML performance engine with some groundbreaking optimizations and enhancements... Aarki was ranked #1 for retargeting for Android for performance and volume in the 16th edition of AppsFlyer performance index for 2023." - On November 5, 2023, he posted: "We are thrilled to share that we’ve been featured as CIO Review's Top Platform for Competitive Mobile Games in 2023!" - On October 30, 2023, he wrote: "At the very core of human competition lies the indispensable concept of fairness... We are resolute in our commitment to ensuring that the deployment of bots for any nefarious purposes that could defraud players is unequivocally prevented." - On August 29, 2023, regarding hiring, he noted: "We're hiring a Head of Talent Acquisition who can help us continue to build our team of passionate innovators dedicated to bringing fair and fun competition to all." Relevant Publications: - "Going, going, gone: A quicker way to divest assets" (McKinsey on Finance, August 2018) - "Negotiating a better joint venture" (McKinsey on Finance, May 2016) Fund details: - Description: We are the catalyst to the broader middle market. We scale and professionalize lower middle market companies, unlocking their full potential for customers, employees, and future owners. Typically, founder-led and family-owned, our targets have strong margins and growth in markets where we have a proven record. With disciplined execution and strategic expansion, we build businesses primed for sustained success. - Website: https://www.leftright.capital/ - Location: Dallas, Texas, United States - Lead qualification: Research: - Query: =LeftRight Capital Jason Roswig recent investments fund thesis - Answer: Jason Roswig leads LeftRight Capital, focusing on growth equity for middle market companies, and has a history of driving significant EBITDA growth. He previously served as President and CFO of Skillz and Managing Director at Blackstone Group.