Placing High-Slope Founding GTM Talent for Seed Through Series D Startups

We work with early-stage teams to place their first GTM hires.

Our Recruiting Team

Led by Operators Who've Done It Before

Our recruiting team brings firsthand experience building and scaling GTM teams at high-growth startups.

Cailen Dsa

Partner & CEO

Cailen has a proven track record of scaling revenue operations from early-stage to $100M+ ARR. As a fractional CRO, he helps companies build and execute revenue strategies that drive sustainable growth.

Experience:

Dropbox - First GTM hire, Series A to Series C (IPO, $12B market cap)

Box - First GTM hire, Seed to Series C (IPO, $5B market cap)

Front - First 8 employees & Head of Sales, Seed to Series B ($1.7B valuation)

RevenueCat - First GTM hire & VP Sales, Series A to Series B ($500m valuation)

Truework - First 10 employees & VP Sales, Seed to Series B ($550m valuation, Acquired by Checkr)

Chris Balestras

Principal, Head of GTM Engineering & Recruiting

Chris brings extensive experience in building and optimizing go-to-market strategies for high-growth companies. He specializes in creating scalable sales processes and engineering effective GTM motions.

Experience:

Founder of GTMBA (gtmba.ai) - GTM + AI Blog & AI/Clay Consultancy

Metronome - Early GTM hire, Series B to C

Celonis - Enterprise Sales, Series C to D

Salesforce Alum - Enterprise Sales

Former Founder & CPA

Community

We host monthly private events for the top GTM operators in SaaS & AI in both NYC & SF

GTMBA panel discussion on GTM & AI - Selling in the AI Era

Audience members engaged in the GTMBA event

Networking and discussions during the community event

Community members connecting over refreshments

One-on-one conversations at the GTMBA gathering

Companies We've Helped

We've helped build founding GTM teams at some of the most successful startups across SaaS, fintech, AI, and enterprise software.

Testimonials

What Candidates Are Saying

Hear from professionals who found their perfect roles through VibeScaling.

"Coming from an accounting background at Deloitte, I knew I wanted to pivot to an early-stage startup in NYC but had no idea what role or company would be the right fit. Chris and VibeScaling helped me understand how to evaluate different opportunities and quickly identified that accounting tech would be perfect for my background. He made the intro to my top startup, and within weeks I landed exactly what I was looking for - his guidance on both strategy and connections was invaluable."

Sarah

Business Ops, Series A Startup, Khosla Ventures

"Coming from a banking and consulting background, I had little knowledge on to navigate the tech sales world or which companies to target. Chris and VibeScaling helped me analyze the right opportunities and made warm intros to my top firm, Hebbia. Within days, I was in the interview process at Hebbia and landed exactly the role I was looking for in only a few weeks - their guidance and network was super helpful."

Hunter

GTM, Hebbia (Series B, a16z, Index)

"Working with Cailen has been fantastic. As an SDR, he helped me make the leap into an AE role at Front. Later, I partnered with him again to join RevenueCat as the Founding Account Executive. Both moves were pivotal for my career, and I wouldn't have found or navigated these opportunities as successfully without Cailen's insight and support."

Dylan

GTM, Linear (Series B, Accel)

"Coming from an accounting background at Deloitte, I knew I wanted to pivot to an early-stage startup in NYC but had no idea what role or company would be the right fit. Chris and VibeScaling helped me understand how to evaluate different opportunities and quickly identified that accounting tech would be perfect for my background. He made the intro to my top startup, and within weeks I landed exactly what I was looking for - his guidance on both strategy and connections was invaluable."

Sarah

Business Ops, Series A Startup, Khosla Ventures

"Coming from a banking and consulting background, I had little knowledge on to navigate the tech sales world or which companies to target. Chris and VibeScaling helped me analyze the right opportunities and made warm intros to my top firm, Hebbia. Within days, I was in the interview process at Hebbia and landed exactly the role I was looking for in only a few weeks - their guidance and network was super helpful."

Hunter

GTM, Hebbia (Series B, a16z, Index)

"Working with Cailen has been fantastic. As an SDR, he helped me make the leap into an AE role at Front. Later, I partnered with him again to join RevenueCat as the Founding Account Executive. Both moves were pivotal for my career, and I wouldn't have found or navigated these opportunities as successfully without Cailen's insight and support."

Dylan

GTM, Linear (Series B, Accel)

"Cailen and the VibeScaling team were great to work with for my move into AI GTM. They helped me identify top companies, prepped me for interviews, made intros to the right hiring managers through their networks, and coached me on job offer negotiations. I highly recommend using them to break into early-stage GTM roles in AI and connected them to several of my peers."

Julian

GTM, Windsurf (Series B, Kleiner Perkins)

"Cailen brings the energy and expertise to help shape and fuel GTM growth. I was fortunate to work with him twice in my career as a first-time sales hire at two different companies. From strategy to execution, VibeScaling showcased just how valuable they can be, and they were never afraid to get into the weeds with me."

Prem

GTM, Render (Series C, Bessemer, General Catalyst)

"Cailen has a rare ability to deeply understand both business dynamics and the people needed to drive them forward. At Dropbox, he recruited and mentored me into one of the early GTM roles, setting me up for success in a high-growth environment. Years later, during my move to Miro, his guidance was instrumental—he helped me navigate the process, unpack compensation dynamics, and negotiate a strong, well-aligned offer. Cailen brings clarity, strategy, and heart to everything he does."

Rikav

GTM, Dropbox/Miro (Series B -> D, ICONIQ, Accel)

"Cailen and the VibeScaling team were great to work with for my move into AI GTM. They helped me identify top companies, prepped me for interviews, made intros to the right hiring managers through their networks, and coached me on job offer negotiations. I highly recommend using them to break into early-stage GTM roles in AI and connected them to several of my peers."

Julian

GTM, Windsurf (Series B, Kleiner Perkins)

"Cailen brings the energy and expertise to help shape and fuel GTM growth. I was fortunate to work with him twice in my career as a first-time sales hire at two different companies. From strategy to execution, VibeScaling showcased just how valuable they can be, and they were never afraid to get into the weeds with me."

Prem

GTM, Render (Series C, Bessemer, General Catalyst)

"Cailen has a rare ability to deeply understand both business dynamics and the people needed to drive them forward. At Dropbox, he recruited and mentored me into one of the early GTM roles, setting me up for success in a high-growth environment. Years later, during my move to Miro, his guidance was instrumental—he helped me navigate the process, unpack compensation dynamics, and negotiate a strong, well-aligned offer. Cailen brings clarity, strategy, and heart to everything he does."

Rikav

GTM, Dropbox/Miro (Series B -> D, ICONIQ, Accel)

"I've had the privilege of working with Cailen across multiple companies spanning several years - starting as the first SDR he hired at Front (seed stage), and continuing through Truework (acquired by Checkr), Neo.Tax and GoGo. He has an exceptional ability to identify talent, build foundational sales processes, and scale teams through critical growth phases. Cailen doesn't just understand the theory of early-stage GTM - he's been in the trenches executing it successfully time and again."

Ben

GTM, Multiple Startups

"I had a fantastic experience working with Cailen and the VibeScaling team during my job search. From our first conversation, the team was incredibly knowledgeable, responsive, and supportive. They took the time to understand my background, career goals, and what I was looking for in my next opportunity. What stood out most was their extensive network. They provided thoughtful guidance and made warm intros to the right folks—and ultimately helped me land a role I'm truly excited about at LiveKit. I'm grateful for their partnership and would highly recommend VibeScaling to anyone navigating a career move, especially those looking for a team that goes above and beyond."

Jonathan

BizOps, LiveKit (Series B, Altimeter & Redpoint Ventures)

"I've had the privilege of working with Cailen across multiple companies spanning several years - starting as the first SDR he hired at Front (seed stage), and continuing through Truework (acquired by Checkr), Neo.Tax and GoGo. He has an exceptional ability to identify talent, build foundational sales processes, and scale teams through critical growth phases. Cailen doesn't just understand the theory of early-stage GTM - he's been in the trenches executing it successfully time and again."

Ben

GTM, Multiple Startups

"I had a fantastic experience working with Cailen and the VibeScaling team during my job search. From our first conversation, the team was incredibly knowledgeable, responsive, and supportive. They took the time to understand my background, career goals, and what I was looking for in my next opportunity. What stood out most was their extensive network. They provided thoughtful guidance and made warm intros to the right folks—and ultimately helped me land a role I'm truly excited about at LiveKit. I'm grateful for their partnership and would highly recommend VibeScaling to anyone navigating a career move, especially those looking for a team that goes above and beyond."

Jonathan

BizOps, LiveKit (Series B, Altimeter & Redpoint Ventures)

A Process Built for Speed and Precision

How We Work

Align

We start by deeply understanding your culture, product, market, financial position, and target persona.

Search

Our team conducts hands-on, targeted outreach to operators who've done it before. We leverage our network of GTM professionals who have proven track records at early-stage companies.

Advise

We support you through the entire process, from candidate selection to advising on interviewing best practices and helping to close top candidates. From initial screening through offer negotiation, we ensure a smooth experience for both you and the candidate.

Let's Get In Touch

Whether you're a candidate looking for your next opportunity or a company seeking top GTM talent, we're here to help.

For Candidates

Looking for your next GTM role? Let's connect.

Placing High-Slope Founding GTM Talent for Seed Through Series D Startups

Led by Operators Who've Done It Before

Cailen Dsa

Experience:

Chris Balestras

Experience:

Community

Companies We've Helped

What Candidates Are Saying

How We Work

Align

Search

Advise

Let's Get In Touch

For Candidates

For Companies