Hiring Pains: Founders Panel (ProperRoom NYC · Series A+)
An invitation-only panel for Series A founders, growth-stage operators and executives navigating one of the most expensive parts of scaling a company:
People.
The first ten hires can be instinctive.
The next fifty usually are not.
As companies raise capital and move beyond founder-led execution, hiring decisions become capital allocation decisions. Compensation gets more complicated. Equity starts carrying meaningful dilution. Senior hires become harder to evaluate. And one wrong executive can cost a company far more than their salary.
Hiring Pains & Equity Comp brings founders together for a candid conversation about what happens when building the team becomes as consequential as building the product.
How much ownership should employees receive?
When is a company actually ready for a VP?
When does hiring accelerate growth, and when does it simply accelerate burn?
And how do founders build a high-performance organization without creating bureaucracy around themselves?
This is the next conversation in the ProperRoom NYC founder series.
Topics We’ll Explore
Equity Compensation: Options, ownership, dilution, vesting and using equity intelligently to recruit and retain exceptional people.
Executive Hiring: Knowing when the business actually needs senior leadership and avoiding premature executive layers.
Scaling Teams: Moving from a small founder-led company into functional teams without losing speed or accountability.
Compensation Strategy: Balancing salary, bonus, equity and long-term incentives as the company matures.
Option Pool Planning: Understanding how hiring plans affect founder dilution and future financing.
Founder-Led Recruiting: Why the best founders often remain deeply involved in recruiting long after a talent function exists.
Retention & Performance: Keeping the people who matter while addressing underperformance before it becomes cultural debt.
The Panel
Moderated by Jack Payne, CFP®, CEPA®, Pre-IPO & Equity Compensation Advisor at UBS
He will be joined by three founder and operator perspectives
Together, they will examine the people decisions founders rarely understand fully until the consequences are already inside the company.
A Series A Founder: A founder who has scaled beyond the early team and experienced the hiring decisions that come with institutional growth.
A Growth-Stage Founder: A founder managing executive hiring, compensation, retention and organizational complexity at meaningful scale.
A Founder / Operator: An experienced company builder who has seen both successful and failed approaches to building high-performance teams.
Together, they will examine the people decisions founders rarely understand fully until the consequences are already inside the company.
Evening Schedule
6:30 to 7:00 PM
Private rooftop arrival, reception, small plates and drinks
7:00 to 7:05 PM
Opening remarks and introduction to Hiring Pains
7:05 to 7:50 PM
Founder panel on hiring, equity compensation and scaling teams
7:50 to 8:05 PM
Audience questions and moderated discussion
8:05 to 9:00 PM
Curated founder conversation and private networking
This gathering is designed for:
Series A founders actively expanding their teams
Seed founders preparing for institutional scale
Growth-stage founders hiring senior executives and functional leaders
Founders making equity compensation and option pool decisions
Operators responsible for scaling high-performance teams
Select investors and advisors working closely with venture-backed companies
This is not intended to be a recruiting conference or broad HR event.
Attendance will be curated around founders and operators making real decisions about how to translate capital into talent.
Why Hiring Pains?
ProperRoom NYC was created around the founder decisions that become increasingly expensive when handled too late.
Our recent programming has included our private UBS Rooftop Panel on Exit Regrets, examining what founders wish they had structured differently before a liquidity event became imminent.
That gathering followed our New York Tech Week flagship brought together 345 startups representing more than $1.15B in venture backing, alongside founders, investors and family offices.
The series then moved into Bootstrap vs. Venture, examining the tradeoffs between ownership, speed, control and institutional capital.
And The Vanderbilt Problem explored what happens after wealth has been created, including estate planning, trust structures, preparing heirs and preserving wealth across generations.
Each conversation addresses a different stage of the founder journey.
Hiring Pains turns the lens back inside the operating company.
Because after the financing closes, founders face a deceptively simple question:
What do we do with the capital?
For many companies, the answer is people.
And few decisions are easier to get wrong.
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