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Senior Regional Sales Director – U.S. Federal

Washington, District of Columbia, United States

Position Overview:  

Diligent is seeking a high-performing federal sales professional to drive growth across the U.S. Federal Government. The Senior Regional Sales Director will be responsible for building and executing the federal go‑to‑market strategy for Diligent’s Governance, Risk, and Compliance (GRC) SaaS platform.

This role requires a seasoned federal sales professional with deep knowledge of government procurement, established relationships within federal agencies, and a track record of closing complex enterprise software deals. The ideal candidate combines strategic account leadership with disciplined pipeline execution and thrives in a fast‑growing SaaS environment.

You will work closely with Sales Engineering, Solution Architects, Marketing, Customer Success, and channel partners to develop opportunities, navigate federal buying processes, and deliver measurable mission value to federal agencies.

Key Responsibilities 

  • Own and execute Diligent’s U.S. Federal sales strategy, driving new revenue growth and expanding market share across civilian, defense, and intelligence agencies.
  • Identify, develop, and close complex enterprise SaaS opportunities within federal agencies through proactive territory development and strategic account planning.
  • Leverage existing relationships and federal market expertise to generate pipeline and accelerate sales cycles.
  • Navigate federal procurement processes, including contract vehicles such as GSA, GWACs, IDIQs, and agency-specific vehicles.
  • Build executive-level relationships with agency leadership, risk and compliance stakeholders, and procurement decision-makers.
  • Lead complex deal cycles using a disciplined qualification methodology (MEDDPICC) and value-based selling approach.
  • Partner closely with system integrators, channel partners, and distribution partners to drive co-sell opportunities and expand market reach.
  • Collaborate cross-functionally with Sales Engineering, Product, Marketing, and Customer Success to deliver compelling proposals, demonstrations, and customer outcomes.
  • Maintain accurate pipeline visibility and forecasting through Salesforce and sales engagement tools.
  • Represent Diligent in the federal ecosystem through industry engagement, events, and strategic partnerships.

Required Experience/Skills: 

  • 8+ years of enterprise software or SaaS sales experience with a demonstrated track record of success in the U.S. Federal Government market.
  • Proven ability to close complex, multi-stakeholder enterprise deals within federal agencies.
  • Strong understanding of federal procurement processes, budgeting cycles, and acquisition vehicles (GSA, IDIQ, GWAC, BPA, etc.).
  • Experience selling Governance, Risk, and Compliance (GRC), cybersecurity, audit, or compliance solutions into government organizations.
  • Established network of relationships across federal agencies, system integrators, and channel partners.
  • Demonstrated success working in partner-led or co-sell sales motions with SIs and distribution partners.
  • Strong strategic account planning, territory development, and pipeline generation skills.
  • High level of business acumen with the ability to translate mission challenges into technology-driven solutions.
  • Self-starter mentality with the ability to operate independently in a highly competitive market.

U.S pay range

$131,000 - $164,000 USD

About Us

Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, helping more than 1 million users and 700,000 board members to clarify risk and elevate governance. The Diligent One Platform gives practitioners, the C-Suite and the board a consolidated view of their entire GRC practice so they can more effectively manage risk, build greater resilience and make better decisions, faster. 

At Diligent, we're building the future with people who think boldly and move fast.  Whether you're designing systems that leverage large language models or part of a team reimaging workflows with AI, you'll help us unlock entirely new ways of working and thinking.  Curiosity is in our DNA, we look for individuals willing to ask the big questions and experiment fearlessly - those who embrace change not as a challenge, but as an opportunity.  The future belongs to those who keep learning, and we are building it together.  At Diligent, you’re not just building the future - you’re an agent of positive change, joining a global community on a mission to make an impact.

Learn more at diligent.com or follow us on LinkedIn and Facebook

 

What Diligent Offers You 

  • Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be differently both in our internal processes and to help our clients
  • We care about our people. Diligent offers a flexible work environment, global days of service, comprehensive health benefits, meeting free days, generous time off policy and wellness programs to name a few
  • We have teams all over the world. We may be headquartered in New York City, but we have office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney.
  • Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us. We foster and encourage diversity through our Employee Resource Groups and provide access to resources and education to support the education of our team, facilitate dialogue, and foster understanding.

Diligent created the modern governance movement. Our world-changing idea is to empower leaders with the technology, insights and connections they need to drive greater impact and accountability – to lead with purpose. Our employees are passionate, smart, and creative people who not only want to help build the software company of the future, but who want to make the world a more sustainable, equitable and better place. 

Headquartered in New York, Diligent has offices in Washington D.C.,  London, Galway, Budapest, Vancouver, Bengaluru, Munich, Singapore and Sydney.   To foster strong collaboration and connection, this role will follow a hybrid work model. If you are within a commuting distance to one of our Diligent office locations, you will be expected to work onsite at least 50% of the time. We believe that in-person engagement helps drive innovation, teamwork, and a strong sense of community.

 

We are a drug free workplace. Diligent is proud to be an equal opportunity employer. We do not discriminate based on race, color, religious creed, sex, national origin, ancestry, citizenship status, pregnancy, childbirth, physical disability, mental disability, age, military status, protected veteran status, marital status, registered domestic partner or civil union status, gender (including sex stereotyping and gender identity or expression), medical condition (including, but not limited to, cancer related or HIV/AIDS related), genetic information, or sexual orientation in accordance with applicable federal, state and local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. See also Diligent's EEO Policy and Know Your Rights. We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at recruitment@diligent.com.

To all recruitment agencies: Diligent does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, Diligent employees or any other organization location. Diligent is not responsible for any fees related to unsolicited resumes.

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