Sales Masterclass: Closing Your First 6-Figure Deals
This masterclass is designed for founders and early sales leaders who are ready to land high-value customers and move beyond small, transactional sales. You’ll learn how to sell to serious buyers, run high-impact discovery, navigate multiple stakeholders, and close larger deals with confidence.
You’ll walk away with proven frameworks to qualify real 6-figure opportunities, position your offer for larger budgets, handle objections, and close without heavy discounting.
Perfect for founders, first sales hires, and B2B operators looking to make 6-figure deals repeatable.
Featuring insights from exited founder Rachael Craig and sales coach
About Rachael Craig:
Rachael Craig is an enterprise technology executive and exited founder with a track record of applying artificial intelligence to scale solutions in highly regulated, complex environments. She specializes in building decision-making and coordination systems that unlock productivity, accelerate innovation, and drive meaningful progress.
She is the CEO and Founder of MotionHall, a vertical AI company enabling global strategic transactions in the life sciences sector, which was acquired by Clarivate (NYSE: CLVT).
About Kevin: Kevin Ramani is a founder coach who helps B2B startups go from early product-market fit to predictable, scalable revenue growth in a post-AI world.
He has coached 75+ startups, helping generate over $500M in ARR and more than $6B in enterprise value. His approach blends rigorous go-to-market frameworks with deep psychological insight, grounded in his belief that “the founder journey is 80% psychology, 20% tactics.”
Before coaching, Kevin built and led sales organizations at high-growth SaaS companies including Close.com and Fleet Space Technologies. His career began as a mechanical engineer working on NASA missions — a foundation that shapes his first-principles approach to revenue strategy and systems thinking.
Today, Kevin helps founders build repeatable sales engines, hire and scale high-performing teams, and lead with clarity in uncertainty. His work sits at the intersection of emotional resilience, communication mastery, and tactical execution — enabling founders not just to hit revenue targets, but to evolve into leaders capable of scaling enduring companies without burning out.
About Pilot:
Pilot provides expert bookkeeping, tax, and CFO services tailored to startups and small businesses. Headquartered in San Francisco and Nashville, Pilot combines U.S.-based finance experts with powerful software to deliver trustworthy financials and actionable insights—helping founders focus on what they do best: building their businesses.
About JustPaid.ai:
Co-hosted by JustPaid.ai — an AI-powered revenue operations platform for founders and B2B teams. We automate invoicing, payment tracking, and accounts receivable straight from your contracts, so you collect faster and scale without the engineering headaches. billing for startups that you can use with Slack + Stripe and any other tools you are using! Backed by Y Combinator (W23) and trusted by innovative startups.