RegScale frees organizations from (digital) paper via its continuous compliance automation software. Our API-centric software platform integrates with your existing security and compliance platforms to dynamically manage security control state, shifting compliance left to deliver audit-ready documentation on demand while simultaneously visualizing compliance and operational risk. Heavily Regulated Organizations such as the U.S. Navy, Department of Energy and Fortune 500 Financial Institutions use RegScale to start compliant and stay compliant with the ongoing regulatory obligations such as NIST, SOX, PCI, ISO, and many many more.

Director of Sales

Boston, MA · Full-time

About The Position

RegScale [] is bringing the best practices of DevOps to Compliance to deliver RegOps – Continuous Compliance Automation. RegScale helps our customers shift-left compliance by digitizing, automating, transforming, and scaling their programs to generate cost savings, risk reduction, and faster time to value for delivering digital transformation.  RegScale is a fast-growing startup company with offices in Tysons Corner, VA (HQ) and Knoxville, TN (R&D). We offer an exceptional benefits package including comprehensive health insurance, 401k, stock options, and unlimited Paid Time Off (PTO) for full time W-2 employees. 


Do you love to build high performance teams? Do you still get your energy from being on sales calls with CISO’s? Are you a high activity leader who believes enablement and focus creates the repeatable outcomes?  If yes, we have the position for you in an innovative startup that is disrupting the compliance industry!  We are actively seeking an experienced SaaS sales leader responsible for establishing the Go to Market plan, building a team, and driving enterprise deals to closure while ensuring our customers achieve the most value out of their investment. If you have a passion for fast-paced team growth, a proven network of high-performance sellers, enjoy co-innovating with customers and R&D, and driving a market movement, then we would love to meet you.   

Position must be a US Citizen and is subject to a background check and unannounced drug testing requirements. Position is remote first or in our Boston or DC area offices but will require travel to customer sites as well as to RegScale offices and industry events.  We recognize that customer success is vital to our company’s success, and we have created a generous compensation package that includes a competitive OTE with significant stock options to help us recruit the most exceptional talent that is maniacally focused on delighting our customers.  If you’re ready to help redefine an entire industry, we are excited to have you on our team. 



  • Recruit, enable, and actively lead team of AE’s to build pipeline and close new ARR 
  • Accurately forecast and deliver results against territory plan; work closely with RevOps, Sales, and Finance as part of the leadership team 
  • Build and execute Go-to-Market plan for private sector accounts 
  • Work closely with the Customer Enablement team to ensure adoption of the platform and execute the land and expand strategy 
  • Leverage technology and integration partners to build market awareness, generate pipeline, and close business in a construct that delivers rapid time to value for customers 
  • Help shape future roadmap by establishing strategic relationships with prospects and customers and working closely with RegScale product teams to prioritize product capabilities 
  • Work with RegScale CISO to build the RegScale Community in target markets 


Proven Capabilities: 

  • Consistent record of building teams and exceeding team quotas with high team participation rates  
  • Repeated proof points of hiring and enabling top performers that will work for you again 
  • Verified commitment to delighting customers supported by referenceable customers 
  • Strong working knowledge of Cloud Computing infrastructure and the unique security and compliance challenges of the modern enterprise 
  • Successful experience in a Security and/or Compliance startup 
  • Track record of working cooperatively with a Partner ecosystem 
  • Willing to travel extensively in covering a large geographical territory 
  • Hard worker ready to put in the hours necessary to build the business and reap the rewards that come with doing so 
  • Proven ability to develop strategies, translate them into initiatives, and track successful delivery 
  • Able to be flexible and agile in responding to evolving business priorities and leading through change 
  • Able to collaborate across the organization and with external stakeholders 
  • Experience successfully working with senior (C-level) executives 
  • Strong operational skills with proven, repeatable, rhythm for achieving intended outcomes 
  • Willing and able to address escalated customer issues with speed and urgency 

Education/Training, Qualifications, and Certification: 

  • Bachelor’s Degree and 5+ years experience as a top AE in SaaS / Enterprise Software Sales  
  • 2+ years first line enterprise sales team leadership in SaaS / Enterprise Software Sales 
  • Demonstrable network of CISO & security contacts in F500 type accounts 
  • Demonstrated operational excellence in analytical thinking, process development and improvement, problem solving, communication, delegation and planning 
  • Ethical 
  • Excellent verbal and written communication skills  
  • Must be a US Citizen, able to pass a background check, and may be subject to random workplace drug testing 
  • Strong attention to detail with the ability to prioritize and multi-task 

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Ready. Set. RegScale

RegScale helps you stay continuously compliant with the vast number of growing regulations that govern your organization and industry - all in real-time.