Rahul D.

Rahul Desai

5.0

(1)

BizOps Expert | 1000+ Coached | Former GM at BizOps Network

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Admissions Committee at McDonough School of Business (Georgetown)

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Worked at Newfront Insurance

Successful clients at

Available tomorrow at 10:30 PM UTC

Questions? Start chatting with this coach before you get started.

Rahul's Coaching Offerings

Custom hourly · $149/hr

Get help with Cover Letters, Business Strategy Development, and .

Rahul also coaches for Private Equity, Management Consulting, and Chief of Staff. View all.

Rahul’s Business Operations & Strategy Qualifications

Coaches professionally

Experience level: Executive

100+ people coached for Business Operations & Strategy

I bring a wealth of experience from my roles as COO at Saddletree Partners and Executive in Residence at Cintrifuse Capital. My journey includes founding and scaling businesses, such as Upslope, which was acquired within 45 days of incorporation, and being an operating partner at Sylva, where I achieved a 41% increase in top-line revenue for my business units. As an author and consultant via my training firm AI America, I've guided companies on AI best practices and automation. I was the first BizOps hire at Pathpoint ($100M valuation) and second BizOps hire at Newfront ($1B exit). Whether you're looking to optimize your business operations or develop strategic growth plans, I'm here to help you navigate the complexities of the business world. Let's connect and explore how I can support your journey to success!

Rahul can help with:

Cover Letters

Business Strategy Development

Operations Management

Networking Strategy

Process Improvement

LinkedIn Review

Resume Review

Negotiation Skills

Rahul also coaches for Private Equity, Management Consulting, and Chief of Staff. View all.

About Rahul

My career has spanned strategy consulting, BizOps / Chief of Staff at tech startups, and private equity / search funds. I'd love to help you with those topics. I am CEO of AI America, an AI training firm. I am simultaneously COO of Saddletree Partners, a search fund roll-up in the luxury group travel industry. I also serve as an expert-in-residence at VC fund Cintrifuse Capital, supporting portfolio companies with operations and AI. I am the author of the upcoming book The Invisible Advantage: How A-Players Navigate the Job Market in the Age of AI. I most recently worked at a micro-cap PE fund called Sylva, as Operating Partner / GM of their Operations training businesses, growing 40%+ YoY for 3 years. I also founded Upslope, an online business school focused on tactics & tools, not just theory & networking, which I sold to Sylva. Before that, I was the first BizOps hire and served as Chief of Staff at Pathpoint ($100M valuation, Max Levchin's bet on insurance) and was the second BizOps hire at Newfront ($1B exit), working on regulatory compliance, finance, HR, IT, process design & automation, revenue ops, and more. Prior, I helped household names (e.g. Uber, Google) set corporate & product strategy to spur top-line growth as a consultant at Frog Design / Fahrenheit 212; prior to that, I was the CEO of Trendify, a machine learning startup to predict startup exits for VCs. I studied Full Stack Web Development at Lambda School. I am also a magna cum laude graduate of Georgetown University, where I studied Business Administration and English.

Why do I coach?

Coaching is the most gratifying thing I've ever done. If I can raise people's ambition and help them earn more and be more valued, that's what it's all about. As part of running the BizOps and Chief of Staff Networks for Sylva, I offered complimentary coaching to 1000+ members over 3 years. I supported people with business problems around vendor selection, strategy, process improvement, and more. I also helped with career coaching around promotions, negotiations, job search, networking, etc.

Work Experience

Cintrifuse Capital Logo

Executive in Residence

Cintrifuse Capital

October 2025 - Present

I help Cintrifuse Capital portfolio companies think through operations and automation challenges. I have coached 10+ firms on matters including marketing automation, GTM strategy, process improvement, HR incentive design, and more.

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COO

Saddletree Partners

January 2024 - Present

Hiring Manager

Raised $1M search fund, successfully acquired luxury travel business, currently searching for additional firms to roll-up. 15% growth in Y1, expected 30% growth in Y2. Profiled on the popular ETA podcast Acquiring Minds.

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Consultant

Self Employed

February 2015 - Present

• Train companies on AI best practices and automation, including Goldman Sachs, Meta, Microsoft, etc. • Serve as an outsourced IT & web services director for the largest youth soccer club in NJ, building websites, COVID screening systems, doing graphic design, and creating communications collateral. • Built a no-code COVID screening & alert system for a school district in NJ, processing thousands of submissions daily. • Worked with a seed stage company as their first Product Operations person, creating in- and out-of-app touch-points to help convert users during their free trial. The startup exited a few years later. • Recruited by a successful VC to aid in the launch of her new consumer-focused seed / A fund; developed narrative and pitch deck for fundraising. Successfully raised a $XXM fund • Recruited by Dr. David Walker (Georgetown University) to build financial models for a lawsuit between between two companies in the risk management sector. Directed my own legal and financial research in order to determine how to value & benchmark the defendant in the suit, a private company; made the final determination that such modelling would be inaccurate, and therefore unusable in court.

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Author

Self Employed

June 2010 - Present

• Wrote The Invisible Advantage: How A-Players Navigate the Job Market in the Age of AI (published Apr 2026). • I blog about strategy, operations, technology, and psychology at The DesAI Digest (rahuldesai.beehiiv.com) and formerly at ThoughtDistiller.com. • Wrote The First 30%, an ebook covering the class Sam Altman & YC taught at Stanford; this book has had thousands of downloads with zero marketing effort. • Wrote Soft Control, an e-book about surviving in the knowledge economy. Represented by Agnes Birnbaum at Bleecker St. Associates.

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GM / Operating Partner

Sylva

September 2022 - October 2025

Hiring Manager

Sylva is a micro-cap PE fund that buys training companies. - I ran a portfolio of affinity-group businesses catering to operations professionals. - My responsibilities included product strategy and development, customer experience, sales & BD, recruiting & people management, and P&L ownership. - I increased top-line revenue 41%YoY with 0 marginal spend on sales.

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General Manager

Chief of Staff Network

September 2022 - October 2025

Hiring Manager

I ran this business on behalf of Sylva: - Serve 1000 customers with only 2 FTE staff. - Deliver 150+ events with a total unique audience of 4000+ attendees, while maintaining customer satisfaction of 4.8/5. - Grow paid membership by 35% via 1.3x growth in blog traffic, doubling applications for membership, and achieving close rate of 39%.

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Founder

Upslope

August 2022 - September 2022

- Created an online business school focused on tactics & tools, not just theory & networking; we offer lessons, apprenticeships, and job search help. - Finalist in the September 2022 Pioneer Tournament, reaching rank of #2 in US East and #22 globally. Offered a spot as a Pioneer, but declined it. - Upslope was acquired by Sylva within 45 days of incorporation.

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Business Operations

Pathpoint

May 2020 - June 2022

Interviewer

• First BizOps hire, interim Chief of Staff as well as functional leader in Compliance, Finance, HR - direct report to the CEO. • Focused on vendor selection, process automation, analytics, regulatory compliance, & company strategy. • Selected Pathpoint's first agency management system and payment processor, enabling the firm to store comprehensive policy and endorsement data, complete servicing activities in a structured way, and invoice retail agents scalably for the first time. • Built a regulatory compliance apparatus to cover all 50 states, including license & education management, SOS registration & renewals, and E&S taxes, fees, and reporting. • Picked a CRM to enable sophisticated sales operations and automation for the first time. Worked with our Sales Operations lead to build out our first sales reporting.

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Business Operations & Strategy

Newfront Insurance

May 2019 - April 2020

Interviewer

• Managed a cross-functional project between Operations, Product, and Engineering to implement a workflow management system for our 100+ operators. The project consisted of vendor selection, workflow documentation & validation for 50 internal workflows, system implementation, and launch within 12 weeks. • Built an anomaly detection system to flag issues within our data; then wrote resolution guides and trained our operations team to correct problems, making our data an order of magnitude cleaner. • Directed our commissions review process: did root cause analysis of issues in conjunction with Finance, looped in cross-functional stakeholders to rectify issues, and drove errors from 400+ per month to under 100 per month.

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Consultant

frog

August 2016 - August 2018

Interviewer

• Reimagined the e-commerce experience for a celebrity's CPG brand from the ground up by doing consumer intercepts, developing a new strategy, and laying out potential building blocks for a new UI / UX. • Guided a client in the Rent-to-Own retail space through a full product lifecycle from initial design sprint to MVP launch of a new customer-facing app. Beyond design sprint coaching and PM responsibility, crafted training materials for the company's 8000 employees regarding the app. • Managed & mentored 9 interns over 2 summers as they deliver thesis-driven "Future Of" research on various categories including banking, life sciences, brick-and-mortar retail, the sharing economy, DNVBs, e-sports, telecom. • Developed new product proposals for a Big 4 Tech Company, in order to help mitigate technology addiction in society at large. These proposals were based on the latest in academic research as well as consumer observation. Some of these product proposals have been shipped to the public. • Led initial research efforts and prepare presentation materials for new client pitches, helping to close deals worth over $1M; helped close one of the firm's most politically important deals, involving 7 separate groups within Capgemini. • Created new driver support offerings for a large ridesharing company, in order to re-envision and re-build driver support centers, thereby organically improving driver sentiment in the midst of broader corporate turmoil. • Conducted primary research and distilled cutting-edge behavioral science research to craft a doctor acquisition strategy for a pharmaceutical client introducing a new “digital” drug. Read 1000+ pages of existing research in the pharmaceutical space within 24 hours to create a core body of knowledge for the project team.

Education

Bloomtech Institute of Technology Logo

Bloomtech Institute of Technology

Full-Time (Cohort 14), Full-Stack Web Development

DESCRIPTION I figured out how to graduate a CS bootcamp without paying tuition due to a loophole in their contract. Lambda School is a Computer Science & Software Engineering bootcamp that provides an immersive hands-on curriculum with a focus on computer science, software engineering, & web development. FINAL PROJECT • Created a shift scheduling SaaS in 5 weeks with a team of 4 others, using modern web technologies and Git workflows. This was before vibe coding.

McDonough School of Business (Georgetown) Logo

McDonough School of Business (Georgetown)

B.S., Business Administration

2013 - 2016

Admissions Committee Experience

Graduated magna cum laude from the McDonough School of Business undergrad program in 3 years.

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Overall Rating

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