Director Sales, UK & Ireland - New Business

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.

The Director of Sales, reporting to the RVP Commercial Sales, will be responsible for overseeing the new business strategy for SMB and Mid‑Market 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.

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 mid‑market 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 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 programmes to name a few.
• Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us.

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.