Director Sales, UK & Ireland New Business in London

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 reimagining 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.

Position Overview

The Director of Sales, reporting to the RVP Commercial Sales, will be responsible for overseeing the new business strategy for SMB and MidMarket in the UK & Ireland, managing a team of Account Executives for Diligent in the region. The Director of Sales is responsible for driving increased revenue from a new customer base. They will establish the operating rhythm for prospecting, pipeline creation, deal execution, and forecast rigor, ensuring predictable attainment and clear accountability as well as consistency across the team.

We're looking for an entrepreneurial sales leader who can set the tone for excellence, build a high-performing team, and execute a crisp go-to-market for their relevant segment. You'll develop and coach talent, bring discipline to forecasting, and partner cross-functionally including Product Marketing, Sales Development, and Marketing to generate and convert high-quality pipeline. You thrive on building repeatable processes, upleveling deal strategy, and winning new logos at pace.

Key Responsibilities

• Establish the operating rhythm for sales outbound prospecting, multi-channel pipeline creation, deal execution, and forecast accuracy to ensure predictable pipeline and bookings attainment.
• Deliver clear concise written and verbal communications including executive updates, deal reviews, and cross-functional alignment across the region.
• Lead complex negotiations to close strategic deals while setting a high bar for deal strategy execution discipline and team leadership.
• Own forecast accuracy and cadence providing precise weekly and monthly projections, risk/opportunity reviews, and action plans to close gaps.
• Own territory and market intelligence for the segment you are overseeing, tracking progress on market share capture, emerging opportunities, and competitor intelligence.
• Recruit, hire, onboard, train, and retain high-performing sales account executives; set clear expectations and coach for continuous improvement and accountability; and lead from the front by role-modeling sales excellence to the team.
• Define and execute the regional sales strategy in partnership with cross-functional stakeholders including territory design, commercial plays, and team enablement to achieve growth targets.
• Drive pipeline generation and inspection rhythms; partner with Marketing, Sales Development, and Revenue Operations to improve pipeline creation in target segments, shorten sales cycles, and increase win rates.

Required Experience / Skills

• Minimum 3 years of leading successful new business sales teams in SaaS/Software environments.
• Minimum 8 years of successful direct sales experience in SaaS/Software environments.
• Proven track record of achieving sales targets and driving revenue growth in the UK & Irish midmarket and SMB segments both as a leader and as an individual contributor; regular Presidents Club achievement for you and your teams.
• Excellent coaching, leadership, and management skills with the ability to motivate and inspire a team.
• Proven experience managing the sales funnel end-to-end leveraging data and metrics to inform strategy and systematically identify and resolve performance gaps with a data-driven focus on pipeline hygiene, activity quality, and rigorous deal inspection.
• Dedicated focus on forecasting accurate and achievable results.
• Expertise in sales methodologies including MEDDPICC, Force Management, Challenger Sales.
• Proficiency with modern sales tooling (e.g. Salesforce, Gong, Outreach, LinkedIn Sales Navigator) coupled with a deep curiosity about AI and demonstrable examples of leveraging AI to raise efficiency and outcomes for yourself and your team.
• Deep understanding of value drivers in recurring revenue business models.
• Strategic planning and implementation skills; ability to think ahead.
• Excellent communication and presentation skills.

What Diligent Offers You

• Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be different 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.

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, colour, 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.

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.