Job Opening: Enterprise Sales - Courses

Location: Remote, must have a US work visa

Summary Description:

Out-Of-Pocket is trying to make the business of healthcare easier to understand. A big part of that has been courses to teach people about different parts of the industry, roles, and processes in fun and entertaining ways.

I’m looking to bring on someone that can help sell the courses to enterprises. Examples include F500 healthcare companies, F500 tech and retail companies interested in getting into healthcare, consulting/finance/services agencies with healthcare divisions, and mid-late stage health tech startups. This can be selling groups of seats for live courses, recorded versions of the course, bundling it with other services in the Out-Of-Pocket ecosystem, and more. 

This role is a great fit for someone hungry, who’s excited to build processes from 0-1, and is willing to work at a company that is growing slowly and intentionally.

Compensation and Benefits:

We offer a competitive salary including health insurance, retirement plans, and paid time off. Additionally, a portion of compensation will be directly tied to commission brought in from courses.

Skills needed:

  • Scrappy and can find ways to get in front of decision makers even if there isn’t a clear path to doing so

  • Creative - there are no playbooks or rules here, we’re really making it up as we go. There’s especially a lot of room to get weird with pricing, bundling, and more that can think just beyond “selling seats”

  • Excellent communication and interpersonal skills. I mean it’s a sales role. You can make a decent deck that’s concise and gets buyers excited

  • Organized - we need to be tracking budget cycles, personnel moves, etc. with documentation someone can land into and immediately know what’s going on. I’m already not a detail-oriented person, there can’t be 2 of us. 


Responsibilities can be bucketed into three areas


  • Develop and lead a sales process for the Out-Of-Pocket courses

  • Conduct outreach campaigns via cold outbound, champions, and inbound

  • Create assets and collateral to be used for the sales process


  • Collaboratively develop pricing and bundling strategies for courses and ancillary services with OOP leadership (which is…just Nikhil for now)

  • Work with other course instructors on best ways to leverage them and their networks for sales and offering other services to customers (e.g. custom modules)

  • Work closely with Founder/Thinkboi on outreach, go-to-market, messaging of courses, etc

  • Stay updated on industry trends to talk knowledgeably with prospects


  • Choose and build out the vendor stack required for succeeding in the role (CRM, reporting tools, invoicing, etc.)

  • Keep on top of payment and invoicing of customers

  • Build regular reporting on sales processes and flagging upcoming renewals for leadership


  • I do not care what level of education you have

  • 5+ years of sales experience, bonus points if it was selling corporate education

  • Some experience in sales management and building out a sales process from scratch

  • Can navigate through tools like notion, airtable, google suite, salesforce, etc.

  • Bonus points if you have a basic understanding of how the US healthcare system is organized

  • Bonus points if you’ve ever sold into F500 healthcare companies

  • Must be able to work in the US

To Apply:

Send the following to

  • Your resume

  • One paragraph about what you would want in the first 30 days to set you up for success in this role

  • One paragraph about your most fulfilling sale/close and why

  • Tell me how many ping pong balls would fit in a Boeing 747