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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, & enough power to move.
Learn what changes across pricing, pitching, negotiation, & 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 & 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, & 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), & Drishti (Sold to Apple).
Over the last four years he has worked with over 50 founders & regularly speaks & conducts workshops at Lerer Hippeau, Forum Ventures, FFVC, NYU, Blue Ridge Labs & Gener8tor.
Manan Modi - Founder, B2B NYC
NYC B2B is the premier community for 10,000+ B2B startup founders, operators, & investors in NYC.
Who's getting in.
Seed-stage founders pushing toward $1M ARR.
Founders chasing their first major B2B or enterprise customer.
Sales & revenue operators working inside early-stage companies.
Investors & advisors helping founders close & expand large accounts.
Who's backing this.
B2B NYC
Join 5,000+ founders, operators & VCs in NYC's top B2B startup community-get NYC startup events, resources & deal flow.
About Ugly Talk
Started in 2019, Ugly Talk has been transforming business setbacks into breakthrough "aha!" moments by hosting unfiltered, no-nonsense events where battle-tested entrepreneurs share their raw lessons & insights.
With a growing presence in cities like New York, Chicago, San Francisco, & Miami, we've built a vibrant community of thousands of founders & industry leaders making a profound impact on the entrepreneurial landscape.
Official Website: UglyTalk.com
Important Notice for Ugly Talk Attendees
Admission & Confirmation
Attendance is by approval only. Approved guests will receive a confirmation email along with a calendar invite. Invitations are non-transferable. Additional event details will be shared as the event approaches.
Code of Conduct
By attending, you agree to:
Maintain respect & professionalism, adhering to all venue rules, policies, & applicable laws.
Refrain from harassment, discrimination, unwelcome sexual advances (verbal or physical), intimidation, or inappropriate photography/recording.
Report any violations to the event hosts immediately.
Violations may result in immediate removal from the event & exclusion from future invitations.
Liability & Risk
Participation is voluntary & at your own risk. The event organizers, hosts, sponsors, & venue are not liable for personal injury, lost or stolen belongings, or any other damages incurred during the event.
Media Consent
By attending, you grant the event organizers & affiliated entities the right to capture, use, & distribute photos, videos, & audio recordings of you for promotional, marketing, & other lawful purposes, including digital & print media, advertising, & social media. You waive any right to inspect or approve the final materials & release all claims related to their use.
Communications
By registering, you agree to receive marketing & promotional communications from Ugly Talk & its co-hosts, partners, & sponsors. You may unsubscribe at any time.
Agreement
If you do not agree to this Code of Conduct, please refrain from attending the event.
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