Account Executive

Role Description

Uptrust is hiring an Account Executive to lead all revenue generating efforts and help us on our mission to keep people out of jail who should not be there. If you’re looking for an entrepreneurial role where you can have a huge impact on both your company and criminal justice reform, we’d love to talk to you.

About Uptrust

Uptrust is an innovative public benefit corporation supporting criminal justice reform. We’ve built the leading communication platform for helping people to successfully navigate the criminal legal system in both pretrial and post-incarceration situations. Our tools are already supporting more than 800,000 low-income individuals in 100+ jurisdictions across the United States. Uptrust helps reduce jail populations, allowing more people to live free and productive lives. Additionally, we are uniquely committed to never charging and never geolocating our users. 

Uptrust is currently a team of 16, distributed coast-to-coast in the US, with plans to continue growing our team throughout 2022. While the role will involve some travel, much of it can be done remotely and does not require relocation.

Uptrust is backed by several leading national foundations and investors and has received press from media outlets such as TechCrunch, the Associated Press, The New York Times, and the ABA Journal.

The Opportunity

We are looking for someone entrepreneurial who wants to apply their enterprise software sales skills to drive meaningful impact on Day 1. You will play a critical role in leading all sales opportunities. You will be responsible for understanding the buyer’s journey, facilitating complex, consultative sales, mapping diverse stakeholders, and deeply understanding the challenges our clients face and how Uptrust plays a critical role in helping them reform their field.

We need someone who is excited about evolving sales processes and has the demonstrated experience to implement new processes and procedures. We are a startup and things move fast. That means constantly evaluating the way we do things and making changes to our outreach, pitch, closing strategies, sales enablement tools, and more. You will be a crucial driver of these changes; and as the first Sales leadership hire, have the latitude to shape the Sales function at Uptrust. 

You will work alongside a close-knit team of passionate advocates, expert technologists, and legal professionals. Day to day, you’ll be collaborating closely with our CEO, Jacob Sills.


  • Drive strategic relationships with reform-minded probation / parole offices around the country
  • Develop outbound strategies to create and nurture opportunities
  • Partner with our Directors of Partnerships through the full sales cycle from lead to close 
  • Manage Uptrust’s sponsorships of local and national conferences 
  • Engage with company leaders in Product and Engineering to help drive product strategy
  • Design and implement strategic marketing campaigns (including virtual events, webinars, expert interviews, etc.)
  • Lead company use of Salesforce, MixMax, and other sales enablement tools


The ideal candidate has: 

  • 3+ years of Enterprise Software Sales Experience; at least 1 years in a revenue-closing role required
  • Track record of exceeding your quota
  • Start-up experience  
  • Interest in criminal justice reform and systems change, with a belief that technology can be a force for good 
  • Ability to develop and execute complex account plans
  • Collaborative, team player 

What We Offer

This is a full-time role reporting to the CEO with benefits and competitive salary/equity in the $80K-$120K range depending on experience, with OTE being 2x (i.e. $160-$240K). Our benefits package includes 401k, healthcare, vision, and dental coverage (all for you and your family). Lastly, while we are a tiny startup, we are also committed to helping all of our team maintain a healthy balance between work and personal life, especially during the pandemic when the line has been blurred for so many.

To Apply

If you would like to apply for this opportunity, please email your resume and a brief note to

Uptrust is an equal opportunity employer and we value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We strongly encourage members of historically underrepresented communities to apply.