VP, Sales

Do you want to be part of a movement to ensure that America delivers on its promise of equal opportunity for all, so that any entrepreneur, no matter what they look like, has the chance to chase their business dreams?

Title: VP, Sales

Reports to: CEO

Location: Remote / work from home (Note: there may be limited travel)

Salary: Base + commission

The direct impact of this role is huge - you will enable young people to build businesses, develop skills, gain confidence, and make money from their business ideas while creating jobs for themselves and others in the community. 

About Skysthelimit.org

At Skysthelimit.org (STL), we’re a highly-ambitious tech nonprofit. There aren’t too many like us - we combine the pace, feel, and Lean Startup approach of a tech startup with the business model of a mission-driven nonprofit. Our mission is to empower underrepresented young adult entrepreneurs to achieve their own goals for their businesses - resulting in new companies, new jobs, and new products & services that strengthen our local economies across the nation and eventually the globe. And the key to our work is developing our entrepreneurs’ social capital through meaningful, one-on-one support.

We have a diverse community of young entrepreneurs: 99% ages 18 to 29, 95% across the US in over 40 states, 70% female, 80% people of color, and the majority are low-income when they join our program. They are building businesses across many industries: clothing, food, beauty, the trades, and a large variety of services businesses. We primarily help our entrepreneurs build tech-enabled small businesses, although we do have freelancers and some high growth startups too. 

We’re backed by Accenture (NYSE: ACN) through a multi-million, multi-year grant to build & operate our own mentoring platform & program for underserved young entrepreneurs, while also whitelabeling our platform for other organizations who support entrepreneurs. We’ve got a completely remote team of 15 developers and five on the fundraising, marketing, and program teams across three states and three countries. Our board of directors includes:

  • Nicolas Cary, Co-founder and Vice Chairman at Blockchain

  • Fabio Rosati, former CEO at Upwork (Nasdaq: UPWK)

  • Rick Wade, VP of Strategic Alliances at US Chamber of Commerce

In this B2B SaaS sales role, the Vice President, Sales will build off of our successful pilot group of four global NGO customers, including one of Richard Branson’s Virgin companies, to license our business mentoring platform to other nonprofits/NGOs, accelerators, incubators, Chambers of Commerce, and higher ed institutions. In this niche market, our platform has a distinct advantage over other generic mentoring platforms in that it is custom built for entrepreneurs with intuitive UI and a superior user experience. This is a “founding” role -- you will be responsible for building from scratch a startup tech sales operation for a business mentoring platform with minimal support from the CEO and COO.


The Role:

  • With minimal support, build and lead a full B2B SaaS sales operation, based on the initial pilot work we’ve done. Build upon our initial market research, prospecting, positioning, sales deck, demo, etc.

  • Efficiently and effectively create and cultivate leads that translate into qualified opportunities

  • Shepherd qualified leads to close by selling strategically through a complex organization

  • Develop pricing, deal structure, proposal, and presentations to drive forward the sale

  • Negotiate terms and close 

  • Collaborate with the CEO, product, and tech team to continually improve the design of our solution and to best serve our long-term mission

  • Deliver compelling sales presentations and product demonstrations that highlight Skysthelimit.org’s competitive advantages, our value to entrepreneur development organizations, and the increased impact of our platform on entrepreneurs’ chances of success.

  • Build and maintain a high level of pipeline and CRM discipline and accurate customer and prospect interaction data (full disclosure: we’re currently at the spreadsheet CRM stage…)


  • B2B SaaS sales experience (required) Ideally, experience with deal size in the $10k-$50k ARR

  • Early stage tech startup experience (highly desired)

  • Nonprofit or Higher Ed industry experience (desired)

  • Experience being a mentor/mentored (desired)

Desired Skills and Mindset

  • “Hunter” salesperson, who will find and close deals, selling the platform we have now without custom feature development for each partner

  • Excellent communicator regardless of the medium (e.g., written communications, phone, etc.)

  • Passionate about building relationships with mission-driven organizations

  • Self-directed, disciplined, able to work on your own in a remote working environment, with the ability to work independently in a fast-paced changing environment, previous experience working remotely is highly desired

  • Experience starting or managing a small business

  • A desire to grow with our organization

  • A strong belief in our mission