How To Choose The Right GTM Opp
About The Event
The GTM landscape is evolving rapidly, and choosing your next role has never been more critical - or complex. Join us for an evening with some of SF's top GTM operators who've successfully navigated career transitions across different stages, industries, and business models - and will give you the tl;dr on what to look for (and avoid) in choosing your next breakout opportunity.
Some questions we'll tackle:
How do you evaluate the right stage company for your skillset and career goals?
What are the key signals to look for when assessing a company's GTM potential?
How should you think about compensation vs. equity vs. learning opportunities?
What questions should you ask during the interview process to truly understand the role?
How do you balance risk vs. reward when considering early-stage opportunities?
What are the biggest mistakes people make when choosing their next GTM role?
Expect honest conversations about career decisions, lessons learned, and frameworks for making your next move count.
Event Details & Schedule
Date: Wednesday, August 20th
Time: 5:30 PM - 8:00 PM PST
Location: Shown Once Approved
5:30 - 6:00 PM | Open doors & networking reception
6:00 - 7:00 PM | Panel discussion
7:00 - 8:00 PM | Drinks & general networking
Moderator
Chris Balestras | Co-Founder of GTMBA & VibeScaling
After working in sales at BigCo (Salesforce), growth (Celonis), and early-stage (Metronome), Chris founded an advisory and recruiting firm called VibeScaling, helping seed through series B crack sales 0->1 along with helping hire their founding GTM team. He also started/writes for GTMBA (one of the fastest growing blogs on all things GTM + AI + startups).
Featured Speakers
Cailen Dsa | First GTM @ 6 Unicorns (Box, Dropbox, & others)
Cailen DSa is a seasoned go-to-market executive and startup advisor who was the first GTM hire at major companies like Dropbox, Box, and Front, helping scale them from early stages to IPOs and billion-dollar valuations. He currently runs VibeScaling, an advisory firm that supports founders and executives from $0 to $100M+ in ARR, with an impressive portfolio of 60+ companies including 6 unicorns.
Mana Anvar | Head of Sales @ Pylon
Multi-industry GTM leader who transitioned from academia (UC Berkeley, UCSF) to build successful sales motions across fast-growing biotech and B2B SaaS. Consistently overachieving quotas, often doubling targets. Her success is fueled by a genuine passion for paradigm-shifting products and the opportunity to collaborate with exceptional teams.
Chelsea Palmer | Enterprise GTM @ Anthropic
Chelsea partners with AI's earliest enterprise adopters at Anthropic. A former Division 1 athlete, she brings unwavering commitment and passion to sales excellence and building high-performing team cultures. With nearly a decade in API sales and fintech, she's scaled teams at industry leaders like Stripe and built sales organizations from the ground up at early-stage companies like Check.
Nicole (Nikki) Wemple | Enterprise GTM @ Hex
Nikki started her career in tech by accidentally thinking Zenefits was somewhere she could put her Psychology degree into practice. She later realized Sales was a much better fit and joined Segment where she transitioned into a purely Sales role and later led a team of sellers in the West. She’s currently at Hex, and back in an Enterprise IC role. She has a unique take on career transitions and the path from IC to VP back to IC back to Director and now happily, back to an IC role.
Why Attend
Whether you're actively looking for your next opportunity or planning your long-term career trajectory, this event brings together practitioners who've successfully navigated multiple GTM roles and can share real insights on what works (and what doesn't). Come for the frameworks, stay for the connections with like-minded operators who understand the unique challenges of building a GTM career.
Private, invite-only event - limited spots available to keep discussions focused and networking meaningful.
Hosted & Sponsored By
Pylon - Support platform built for B2B companies. One tool for your ticketing, chat widget, knowledge base, AI support, customer portal, and more.
VibeScaling - GTM advisory & recruiting firm helping seed through series B startups grow from 0 to $20M in ARR and help build out founding GTM teams
GTMBA - The community for early & growth stage GTM operators
Questions? Contact the organizing team for more details.
This event is designed for GTM professionals and sales leaders. The thoughts, comments, and views said by panelists reflect their own stances and not those of their company. By signing up for or attending this event, you consent to being photographed and/or videotaped and grant permission for the use of your likeness in any media related to this event.