Zenefits' Aggressive Growth: Robby Allen on growing a 250-rep sales team

01/15/24 • 43 min

Robby Allen, CRO of AgentSync, shares sales leadership stories from his time as Director of Sales Development at Zenefits.

Zenefits is one of the most infamous hypergrowth stories in SaaS history, growing to over $70 million ARR and a $4 billion valuation from 2013 to 2016.

But their hypergrowth came at a cost. Insurance compliance issues resulted in millions of dollars of fines, a leadership shakeup, and mass layoffs in 2017.

Robby Allen was there for all of it — bringing some key lessons from Zenefits to his next venture, leading sales at AgentSync.

On today's episode, Alex and Robby discuss:

Transitioning from SDR to sales leader
Spinning up Zenefits' outbound strategy
Why AgentSync hired scrappy AEs before enterprise reps
The difference between being a CRO and VP of Sales
Working with Jason Lemkin at SaaStr

Robby Allen, CRO of AgentSync, shares sales leadership stories from his time as Director of Sales Development at Zenefits.

Zenefits is one of the most infamous hypergrowth stories in SaaS history, growing to over $70 million ARR and a $4 billion valuation from 2013 to 2016.

But their hypergrowth came at a cost. Insurance compliance issues resulted in millions of dollars of fines, a leadership shakeup, and mass layoffs in 2017.

Robby Allen was there for all of it — bringing some key lessons from Zenefits to his next venture, leading sales at AgentSync.

On today's episode, Alex and Robby discuss:

Transitioning from SDR to sales leader
Spinning up Zenefits' outbound strategy
Why AgentSync hired scrappy AEs before enterprise reps
The difference between being a CRO and VP of Sales
Working with Jason Lemkin at SaaStr

Previous Episode

How Chris Orlob grew Gong to $200M (after they crushed his startup)

Chris Orlob shares his unlikely origin story as Gong's first marketer, sales leadership advice, and what it was like to transition entrepreneurship at Pclub.

In 2015, Chris faced tough competition when his newly founded company, Conversature, went up against Gong -- the eventual category winner.

Although he was forced to close his doors just one year later, a new one opened at Gong.

After joining as Gong's Head of Product Marketing, Chris started Gong Labs, one of the most successful content marketing programs in SaaS, and helped grow Gong from $200k to $200M ARR and a $7.2B valuation.

In 2022, he left Gong and leveraged his audience into co-founding Pclub.io — a sales learning platform, and QuotaSignal — a tech-enabled revenue team hiring service.

On today's episode, Alex and Chris discuss:

Going from competitor to Product Marketing Director at Gong
The explosive growth of Gong Labs
Transitioning from marketing to sales leadership
Co-Founding Pclub.io and QuotaSignal

Next Episode

Sprinklr's First AE: Jason Fishkind's 10-year sales journey at Sprinklr

Jason Fishkind recounts Sprinklr's sales journey from $5m to $500M in ARR.

Sprinklr is one of the biggest names in social media management, but it didn't start out that way.

As Sprinklr's first AE, Jason Fishkind helped the company 100x their growth from $5M to $500M ARR -- accelerating them through their IPO and earning a valuation of over $4 billion.

On today's episode, Jason joins us to talk about a decade of sales growth at Sprinklr, including: