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Your first six-figure deal can expose every weak spot in your sales process.
You chased the wrong buyer. Priced from fear. Followed up too late. Let one internal champion carry the whole deal.
Then the contract lands. You celebrate. The next question hurts more: can you do it again?
This Ugly Talk gets into the hard calls behind closing a major customer. You will hear what founders got wrong. You will see what made the deal move. You will leave with a clearer path from one big win to $1M ARR.
Why you should be in this room.
Spot the sales mistakes that quietly kill large deals.
Find the buyer with budget, urgency, and enough power to move.
Learn what changes across pricing, pitching, negotiation, and follow-up.
Build a sales motion that can survive beyond one lucky contract.
Understand what needs to break before your company reaches $1M ARR.
What's on the table.
Choosing the right deal: Which customers deserve months of your runway.
Reaching the real buyer: How to navigate stakeholders and build an internal champion.
Closing six figures: The decisions that move a large deal across the line.
Owning the mistakes: Where founders lose ground on pricing, pitching, negotiation, and follow-up.
Getting past one win: How to turn an early contract into repeatable revenue.
Featured speakers.
TJ Allison - Sales Advisor & Coach
TJ Allison is an NYC-based sales advisor focused on helping founders transition from founder-led sales to a revenue-generating sales team. He draws on early stage sales experience at DocuSign (IPO), Socrata (sold to Tyler Tech for 140m), and Drishti (Sold to Apple).
Over the last four years he has worked with over 50 founders and regularly speaks and conducts workshops at Lerer Hippeau, Forum Ventures, FFVC, NYU, Blue Ridge Labs and Gener8tor.
Who's hosting it.
Manan Modi - Founder, B2B NYC
NYC B2B is the premier community for 10,000+ B2B startup founders, operators, and investors in NYC.
Who's getting in.
Seed-stage founders pushing toward $1M ARR.
Founders chasing their first major B2B or enterprise customer.
Sales and revenue operators working inside early-stage companies.
Investors and advisors helping founders close and expand large accounts.
Who's backing this.
B2B NYC
Join 5,000+ founders, operators & VCs in NYCs top B2B startup communityget NYC startup events, resources & deal flow.
About Ugly Talk
Started in 2019, Ugly Talk has been transforming business setbacks into breakthrough \
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