Next NYC Spotlight: Building a World-Class Sales Team

Oct 26, 2023
Next NYC Spotlight: Building a World-Class Sales Team
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In 2018, Persona entered the game to become the identity layer of the internet. While they’ve been continuously expanding their talent and improving the product, it’s been imperative for the team to refine their GTM.

To get a closer look at how their sales engine operates, we talked to Ryan Libster, Head of Enterprise Sales at Persona. Ryan started his career in banking in the wake of the 2008 financial crisis. After that, he pursued startup life. After three years at Dropbox, he opened the New York City office as one of the first enterprise sales reps for Slack, then moved to Stripe to scale the new business organization, which exposed him to the identity space. He then joined Persona in 2022 when there were 200 people to lead the enterprise sales team. 

Here are his top lessons learned on hiring and culture:

Building a World-Class Sales Team is an Art

While dependent on the stage of the company, in the early days of forming a sales team, Ryan believes in hiring “renaissance reps,” aka individuals who may not have traditional sales backgrounds (e.g., banking, education), but possess key attributes of successful salespeople such as curiosity, passion, and discipline. 

He has also found that having impressive credentials or hype-y logos stamped on their resume, doesn’t necessarily translate to success in a new role. When looking at someone's experience, the specific moment in time spent at a company can outweigh the logo itself. For example, a “vintage rep” from the 2013 to 2015 days at Dropbox will have very different sales experience than someone who might be at Dropbox today. This also means that it can be more impressive to be a top rep at a startup with no name recognition than one at a name brand company.

To weed out the good from the great candidates, Ryan conducts “chronological interviews” in his hiring process. This typically entails an in-depth interview lasting 60 to 90 minutes with one hiring manager, two people from the sales team, and the candidate. The goal is to deep dive into each of the candidate’s previous positions, posing the same type of questions about their career arch. The process is meant to be thorough enough that it becomes nearly impossible for candidates to embellish their achievements. For each job, here are a few questions to ask:

  • What were you hired to do?
  • What accomplishments are you most proud of?
  • What were your low points during that job?
  • Who were the people you worked with? Specifically, what was your boss’s name? What was it like working for this person? If I were to call your boss (with your permission of course), what would they tell me your biggest strengths and weaknesses were?
  • Why did you leave that job?

A Culture of Trust is Critical in Startup Life

Startups are inherently characterized by their chaotic and fast-paced nature. In this type of environment, its critical team members feel supported and comfortable asking questions, and empowered to provide feedback. While the goal of any startup is to scale quickly, the “grow at all costs” and “move fast and break things” mentality has not only failed founders when it comes to fundraising, but has also led to the development of toxic cultures rooted in a fear of failure.

Two ways Ryan has created a culture of trust, include: 

  • Operating model: This is a written document that outlines the way Ryan operates –  his values, his culture normal, how he prefers to communicate, etc. – that he provides to all of his new employees. At Work-Bench, we do something similar. During onboarding, each team member fills out their own section and reviews others’ “user manuals.”
  • Journey lines: During company offsites, Ryan asks team members their emotional highs and lows, starting in high school in order to learn more deeply about each other and create closer bonds beyond day-to-day work. 

‍If you’re an early-stage enterprise founder or operator — connect with us directly or check out our events page to get involved with our Work-Bench community.‍