Senior Account Executive

Roots Automation

Remote - United States


Roots Automation brings together machine intelligence and human ingenuity in the form of advanced, intelligent Digital Coworkers. Think of a Digital Coworker as your ideal team member – digitized. Our Digital Coworkers are built with AI and can think, read and intuit like humans. They are pre-trained to understand and interact with data, documents, systems, and processes commonly found in Insurance. Their knowledge base is perpetually expanding with learning federated across our Customers. Digital Coworkers are always on, ultra-secure, and deliver ROI from day one.

Roots Automation’s Digital Coworkers free Insurance Professionals from inefficient, repetitive, soul-destroying work, thus enabling them to be more creative, collaborative, and innovative.

Job Summary

Roots Automation is searching for a Senior Account Executive to join our growing Sales team. The person will partner with leaders across our team and with leaders at Fortune 1000 organizations to bring our AI-First, Industry-aware Digital Coworkers to market. As a Senior Account Executive, you will be responsible for full life-cycle sales. You nurture existing accounts and sales-qualified leads while prospecting and networking for new sales opportunities.

The ideal candidate has strong strategic and analytical thinking, experience working in or selling to Insurance companies, and has a solid track record selling SaaS or to Enterprise customers.

The role reports to the Head of Sales.


  • The Senior Account Executive position is a quota-carrying position; you will own the full sales cycle from building relationships with key stakeholders to negotiating and contracting
  • Develop authoritative knowledge of the Roots Automation, and effectively demonstrate the value of Digital Coworkers
  • Sell Roots Automation offering with a consultative approach in a high energy environment and skillfully deliver virtual/in person presentations while handling objections and relating to buyers
  • Lead a complex sales cycle while engaging customers in business, strategy, and ROI-based discussions to communicate how Roots can help deliver value/ROI
  • Pipeline development through a combination of outbound prospecting, Marketing Qualified leads, and high-value leads
  • Meets or exceeds assigned quarterly and annual revenue sales quota
  • Manage key customer relationships and find upsell/cross sell opportunities
  • Ensure 100% data entry/integrity across sales systems (i.e. HubSpot)
  • Become the go-to expert for prospects and customers alike for Digital Coworker as a Service solution
  • Work in tandem with Process Engineers to identify automation opportunities
  • Partner with marketing to develop materials for prospective customers
  • Attend Tradeshows/Events 


  • 10+ years of enterprise technology sales experience, SaaS selling a plus
  • Proven track record of selling into C-Suite executives
  • Capability to manage the entire sales process including lead generation, qualification, discovery, solution development/presentation, negotiation and close
  • Demonstration of ability to sell technical solutions emotionally (high EQ)
  • Accurately reporting on forecast/pipeline
  • Experience with opportunity and account planning
  • Ability to balance a competitive drive for exceeding goals with the collaborative culture of Roots Automation
  • Demonstration of consultative selling capabilities
  • Experience with CRM and related sales platforms (preferably HubSpot)
  • Ability to navigate complex enterprise organizations and persuade key decisionmakers

Preferred Qualifications

  • Collaborative, high-energy teammate with a passion for solution selling
  • Coachable – always willing to learn and adapt
  • Experience/knowledge in Insurance vertical
  • Hungry – ready to make an impact, excel, learn, and succeed
  • Determined – will do whatever it takes to attain quota
  • Automation software experience (RPA/OCR/IDP/ML)
  • Experience working in a startup environment
  • Background in remote, independent work


  • Work in a fast-growing, VC-backed startup with a clear upward trajectory
  • Base Salary + Competitive Quarterly Commission (with accelerators and new account kickers)
  • Full benefits (dental, health, vision, etc.)
  • Unlimited Paid Time Off
  • Fully remote work
  • Upward mobility for high performers
  • Potential equity opportunity

Interested Applicants