Name: The Operator’s Playbook: How to Scale Your Team and Secure Funding
Start: 2025-12-09T18:00:00-05:00
End: 2025-12-09T21:00:00-05:00
Location: The Yard: Herald Square

Most early-stage founders treat hiring as a fire drill. They hire fast in order to fill gaps, only to face culture cracks and churn six months later.

Richard Hughes doesn't work that way. 🙅

As Operating Partner at Gutter Capital, he rolls up his sleeves and recruits directly alongside his portfolio companies. As a result, Gutter portcos see more than 80% employee retention at 18 months (significantly higher than the industry average).

On December 9th, we’re sitting down with Richard to dismantle the standard startup recruiting playbook. We’ll cover his philosophy on hiring fewer people, hiring them better, and keeping them longer.

WHAT YOU'LL LEARN

Cross-Functional Evaluation: How to assess and validate candidates in areas outside your own expertise (e.g., a non-technical founder hiring their first lead engineer).
The Closing Framework: A structured approach for decision-making during late-stage negotiations to secure top prospects without losing leverage.
Lo-Fi Talent Magnets: Scrappy, low-cost methods to position your company as a destination for top-tier talent, even before you have the brand recognition.
The "Curve of Excellence": How to structure an interview process that builds conviction over time rather than just checking functional boxes.

Special Focus: The Elbow Grease Accelerator.&nbsp;Richard is also spearheading Gutter's new AI accelerator, Elbow Grease, which offers $300k in funding and runs locally in NYC.&nbsp;

If you are building in AI and looking for more than just cash, you need to be in the room to hear what they are looking for as they start recruiting for cohort #2.

WHO SHOULD ATTEND

Pre-seed/Seed founders building their founding teams.
Operators looking to transition into high-growth startup roles.
AI builders interested in the Elbow Grease accelerator program.

Tickets for this event include food and drinks, as well as exclusive access to this VC who will change the way you're building teams.

You'll also meet dozens of other high-performing entrepreneurs who are creating their next big thing. Seriously, it's some of the best founder networking in the city.

Getting a ticket guarantees admission. No waitlisting.

AGENDA

6:00 PM: Networking, Food & Drinks
7:00 PM: Fireside Chat with Richard Hughes
8:00 PM: Meet the Speaker

And don't miss our other monthly tech events. They are great opportunities for builders, founders, and operators to network with each other to share best practices and find new resources to grow your startup the right way. See our full event lineup here.

Agenda

6:00 PM: Networking, Food & Drinks

7:00 PM: Fireside Chat with Richard Hughes

8:00 PM: Meet the Speaker

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Speaker

Richard Hughes - Gutter Capital (Operating Partner)

Richard Hughes is an Operating Partner at Gutter Capital, where he has supported hiring over 100 people across the entire portfolio. Richard joined Gutter after a career of building winning teams at ZocDoc, Managed by Q, Primary Ventures and Alma.
Richard has mastered what many founders struggle with most: turning hiring into a competitive advantage. His systems achieve 80% retention at…

Hosted By

Joshua Ness, Director, Startup Grind

Joshua Ness is Executive Director at Startup Grind NYC and a Senior AI Advisor with the Fulbright Program. He provides opportunities and access for startups to build and scale their companies. He advises new entrants in tech-driven sectors from startup to scale-up, and provides guidance on enterprise partnerships and venture opportunities. He is an international technology development specialist with Fulbright in the field of AI in public sectors, and a Professor of Technology at City University of New York.

Tova Feldheim, Cofounder

I am a strategic advisor and marketing expert with 20+ years in B2B SaaS, brand building, and customer discovery. Specializing in aligning human behavior with technology to build products that resonate and marketing that converts. I've worked with enterprise clients and early-stage startups alike to refine messaging, strengthen go-to-market efforts, and accelerate growth

Prianka Ball,

Currently working in data at a early stage startup. Ex founder and looking for my next startup building adventure.

Paul GUILLARD, Chief of Staff / BizOps / Project Manager / BD

I moved to NYC in April 24. I am currently coaching and advising early-stage founders on ideation, Business Model x Ideal Customer Profile x MVP, GTM and Fundraising.
Received my authorization to work in Nov so now also looking for a full time job as BizOps / Chief of Staff / Strategic Project Management for B2B SMB or Series A+
Before that, an Engineering Degree and 2 years of SMBs consulting in France, 10 years in APAC doing Strategic Project Management, Sales and BD; and 4 years in Spain for an MBA at IESE (consistently ranked Top10 in the world by FT) and working on some startups.

Rebecca Liang,

Ex-founder | Ex-VC | 5 yrs @ Startup Grind Shanghai

Community over Competition

Shanghai → Hong Kong → Singapore → New York

Madison Simon,

I've spent the past 8 years working closely with startups in revenue-focused roles, and I genuinely love being in the trenches with bold, compassionate founders tackling real-world problems. There's nothing more energizing than teaming up with people who think differently, move fast, and build with heart. I believe being genuine, knowledgeable, and deliberate in business relationships is essential.

Business aside - I enjoy scuba diving, sailing, painting, cars, and all things going on at www.thegirlswhogather.com.

Daniel Silver, Owner

Creative, Thoughtful and Results-Driven Product Marketing Strategist Focused on Building, Launching and Optimizing New and Existing Products Across Their Life Cycle.

KT Goldthorpe,

I'm a NYC-based brand strategist and startup advisor with over 20 years’ experience guiding both global corporations and early-stage ventures.I specialize in foundational brand development—helping founders articulate their business’s inner narrative, align teams, and build brands that resonate from the inside out. I am a champion of helping early-stage startups strategically position themselves in crowded markets, using audience insights and agile frameworks like The Wayfounding Map to operationalize brand strategy for real growth.

After years advising corporate, agency, and startup teams—including roles like founding member and CMO at Thirstie—I’ve learned that standing out starts with building brand from the inside out. My programs are designed to help startups find their market fit and shape messaging that actually connects. I lead with practical coaching and actionable frameworks grounded in experience, and while my work hasn’t won awards, yet, it’s delivered meaningful impact and momentum for founders pushing their brands forward.

I’m also the creator of Champ, built to help founders and teams navigate brand development step-by-step. Outside of work, I’m a two-time NYC Marathoner, a steady runner, and an active community builder—focused on making healthy brand growth accessible, collaborative, and fun for those who want to move fast and make purposeful change.

Michaela Freedman,

As a freelance business consultant, I help companies go-to-market in highly regulated industries globally, advising an industry-agnostic clientele spanning AI/tech, healthcare, consumer goods, industrial manufacturing, and logistics.

I specialize in navigating regulatory compliance protocols and developing business action plans, including lead generation strategies and securing high-value partnerships that successfully expand revenue channels.

Payton Shafer,

Nabila Okudo,

Bhavnish Walia,

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Presentings

Codewalla (https://www.codewalla.com/startup-grind-offer)
Codewalla is a small product development studio dedicated to helping startup founders launch products quickly. As founders ourselves, we understand the challenges of traditional development: high costs, long timelines, and risks. We are a CTO-led studio of developers, designers, and project managers dedicated to building exceptional products. With expertise in startups, SaaS, fintech, and more, we bring creativity and experience to every project.

Snowflake Inc (https://www.snowflake.com/)
Snowflake is the platform for the AI era, making it easy for enterprises to innovate faster and get more value from data. More than 12,000 customers around the globe, including hundreds of the world’s largest companies, use Snowflake’s AI Data Cloud to build, use and share data, applications and AI. With Snowflake, data and AI are transformative for everyone. Learn more at snowflake.com (NYSE: SNOW).

Partner

The Yard (https://theyard.com/)
The Yard is a coworking space at the intersection of innovation, creativity, design, & play -- with locations in Manhattan, Brooklyn, Philly, and DC -- with a variety of shared and private workspace options.

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Startup Grind is a global startup community designed to educate, inspire, and connect entrepreneurs. We host monthly events in more than 600 cities and 125+ countries featuring successful local founders, innovators, educators and investors who share personal stories and lessons learned on the road to building great companies. Our monthly fireside chat interviews, startup mixers and annual conferences provide ample opportunities to connect with amazing startups and the people behind them, tap into a strong support network, form meaningful connections and gain inspiration for the startup journey ahead. For more information visit StartupGrind.com or follow us on twitter @StartupGrind.
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Complete your event RSVP here: https://www.startupgrind.com/events/details/startup-grind-new-york-city-presents-the-operators-playbook-how-to-scale-your-team-and-secure-funding/.

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The Operator’s Playbook: How to Scale Your Team and Secure Funding

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