From founder led to repeatable scale

GTM systems that drive repeatable revenue

About VerticalScale

VerticalScale partners with Vertical AI founders to evolve go-to-market from founder-led to scalable revenue systems. We bring deep domain expertise, repeatable process, precision messaging, and systems thinking to drive sustainable growth — without the bloat.

We believe that one of the hardest parts of company building is growing from Product Market Fit (<$1M ARR) to repeatable revenue ($20M+ARR). We derisk this stage by

  • Providing proven leadership for this stage of growth.

  • Focusing on B2B companies that sell complex enterprise products to regulated industries, and going deep to understand your business and customer.

  • Providing customer, candidate, and VC introductions from our tier 1 network

Testimonials

“Over the five years we worked together at AgentSync, I watched Robby win in one of the toughest and most risk-adverse markets to sell into: enterprise insurance providers. He paired elite selling skills with the ability to recruit and build a world-class team, taking our GTM organization from zero to over $40M in ARR. Robby drove us from a founder-led sales motion to a true enterprise saas machine; weaving structure, systems, and consistency into how we sold and scaled. He’s a legit CRO who is genuinely curious, loves vertical software, and knows how to make product market fit stick.”

Niji Sabarwhal, Co-Founder and CEO of AgentSync

“working with robby has been a huge unlock for us. he helped me level up how we think about sales, from hiring a great head of sales and defining what “good” looks like, to coaching our team and adding real rigor to our process. he ran pipeline reviews, built structure around stages and handoffs, and turned what was a pretty chaotic process into something consistent and accountable. he’s also been an incredible partner to me personally -- helping plan revenue targets, think through market capacity, and shape our go-to-market and account strategy for next year. overall, robby made our sales org sharper, faster, and more confident.”

Mike Yu, Co-Founder and CEO of Vesta

Working with Robby and VerticalScale was transformative for Garden. Robby helped us evolve from a founder-led sales motion into a scalable GTM system: building the processes, CRM structure, and early team foundations we needed to grow with confidence. His coaching challenged me to become a stronger operator and a more focused founder, while his structured frameworks brought clarity and predictability to our revenue efforts. I would recommend VerticalScale to any founder looking to win in the Enterprise!”

Adi Sidapara, Co-Founder and CEO of Garden

In good company:

How we’ll work together:

Advisory

From Founder led to First AE

  • Focus on ICP, repeatability, and closing your first $1M deal

    • Standing weekly coaching call with CEO/Founder

    • Available 7 days a week for support

    • Hiring Founding AE(s)

  • Fixed workstream and scope

  • Get you to the next stage of growth with repeatability and proof

  • Best for Seed and Series A founders

Fractional CRO

From First AE to First VP

  • Focus on systems, process, talent, and preparing to scale

    • Standing weekly workshop and call coaching with reps

    • Run forecasting & pipeline reviews

    • Interviewing, hiring and onboarding the team

  • Customizable workstreams and scope

  • Get you to the next stage of growth with a team and system that scales

  • Best for Series A, B and C companies between $2 and $50M ARR

Robby Allen, Principal

I’ve built revenue teams at AgentSync, Flexport, and Zenefits — three unicorns that scaled quickly. Most recently, I was CRO at AgentSync, where I led GTM through 10x, 4x, and 2x revenue years, helping raise $160M+ and reach a $1.2B valuation.

Along the way, I’ve built and led GTM teams of 75+, sold complex solutions into Fortune 1000 enterprises, closed dozens of $1M+ deals, and evolved GTM teams from transactional to strategic enterprise sales.

I’m a coach at heart. I care deeply about building strong teams, clear systems, and momentum that lasts.

That’s what I do now through VerticalScale — partnering with founders to evolve from founder led to systems led sales.

Past and present clients