We are no longer accepting applications for this position.


Founding Sales Lead

New York, NY
Denver, CO

Build the sales program that dominates the next category of Internet commerce

Pico is building the infrastructure for the next big wave of Internet commerce – that which doesn't require a shipping label. You and the team you build will be in charge of building out a world-class sales operation focused on high-value SMB and small enterprise customers as well as agency partners.

You are:
  • Strategically patient. Many of our highest value relationships took years to create value for Pico. You'll have the foresight to focus on those that maximize long-term value.
  • Organized. You are able to manage and keep track of multiple processes across different customer and partner types.
  • Ambitious. You are eager to jump into a fast-moving environment to build an operation at Pico that reflects not just your experience to date but your potential to be one of the world's best at what you do.
  • High agency. You're comfortable with defining your own path amidst ambiguity. You figure out how to get done what needs doing even if all the pieces aren't in place.

You will:
  • Be responsible for growing and managing Pico's two primary sales pipelines: large customers and agency partners.
  • Work with our customer success team (including an account manager) to maintain key relationships over time and prevent churn
  • Be responsible for hiring and managing one BDR immediately and, if effective, replacing yourself within 6-9 months with additional hire(s)

Our ideal candidate will have:
  • 1-2 years experience hiring and managing direct reports or outside contractors
  • 7+ years work experience spanning sales or account management roles

As an experienced sales leader, you have 'seen it' a few times, with experience both closing sales as well as managing accounts and hiring and managing others. You are more incentivized by equity in Pico – building our long term success by landing and nurturing strategic partners and customers whose value compounds over months and years. That said, you'll be well compensated, with the opportunity to earn additional performance-based equity options as milestones are achieved.

Expect to be in close contact with Pico's founders, whom you'll be reporting to directly but who will give you wide latitude to own Pico's entire sales operation. They will make themselves readily available and deployable as strategic sourcing and closing assets but otherwise leave you to achieve your sales goals, hiring included, as you see fit.

This is not a traditional enterprise sales role.  Pico is building a new category, so many of our biggest customers don't yet exist! It's not uncommon for a small team to decide they're launching a startup, talk to us, launch 6-9 months later, and grow into one of our largest customers within 6 months (many of even our largest customers have grown 3-5x since joining Pico). That said, a substantial portion of our business does come from customers who migrate from competitor platforms or legacy payments solutions and will suit a more traditional sales process.

This position should appeal only to those with the ambition of building and leading a sales team from scratch in a category-defining company like Stripe, Shopify, or Square. You are comfortable being a 'pioneer', managing the ambiguity that comes with writing your own playbook for others to follow – and iterating constantly.

Why you should join us:

It's a rare opportunity to work on something you love, to have the power to improve the world around you, and to get rewarded for doing it. If protecting the press and elevating the standards of public discourse sound like interesting challenges to you, and if you’re in search of a startup that has de-risked upside and strong validation among the investor community, then working at Pico is that rare opportunity.

As an early employee, you have the chance to not just build an amazing platform, but to also help cultivate a company culture that reflects the type of community of which you want to be a part. Trust, mutual respect, and passion already run deep in our young company's DNA. Jason and Nick became friends in elementary school and started Pico several years after graduating from Stanford together. You'll fit right in if, like us, you're curious about the world, anxious to fix what's broken around you, and thoughtful about how you do it.

There's a lot of exciting work to be done to fulfill the vision and potential of Pico. Join our journey, and let's get there together.

We are no longer accepting applications for this position.

To apply for this role, please email your resume to [email protected].

Want to apply?

Please email your resume to [email protected] along with your answer (preferably in a Google Doc) to the following prompt:

In the show Unbreakable Kimmy Schmidt, Kimmy grows up and spends her young adulthood in a bunker underground where she is held prisoner. After being rescued from the bunker, she’s invited to a talk show in New York City. She’s given a plane ticket in the mail and told that a car will take her to the airport nearby in Indianapolis, but she has no idea what to do once she arrives at the airport. Explain to her in clear and concise instructions how to get on her flight to New York and how to get to the TV studio once she lands in New York. (There will be a limo driver waiting for her outside JFK. The driver will be holding a sign with her name on it.)

Want to apply?

Please follow the instructions in this homework assignment.

Apply for this role

Our Interview Process

We look forward to learning as much as we can about your skills and interests, but we also aim to be respectful of your time. Below are the 3 steps to joining the Pico team:

Apply for the role.

Email your resume (and portfolio, if applicable) to [email protected].


If we believe there is a potential fit, we will schedule an initial interview with you, after which you may be asked to complete a take-home assignment.


The top candidates for this role will then be invited to interview with other key members of the team. From the homework assignment to the job offer, you can expect the process to take 3-4 weeks.