Regional Vice President, Sales (uk/i, SMB & Mid - market)

Regional Vice President, Sales (UK/I, SMB & Mid-Market)

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.

The RVP, Commercial Sales, reporting to the VP Sales, UK & Ireland, is responsible for leading a team of Directors who manage the New Business and Existing Business sales teams for the SMB and Mid-Market segments across the UK & Ireland. As RVP, you will drive revenue growth through customer acquisition and expansion, while actively coaching front-line leaders and account executives, as well as attracting talent.

The RVP holds ultimate accountability for the segment's success, growth, reputation, and culture. They should be experienced in cross-functional engagement and have a natural interest in partnering with other GTM, G&A, and R&D leaders to align strategy and resources across the UK & Ireland and to advance Diligent's positioning in the SMB and Mid-Market segments. They institutionalize the operating rhythm for territory planning, multi-channel pipeline creation, deal inspection, and forecast governance — driving predictable attainment, clear accountability, and consistent execution across teams.

We're looking for an entrepreneurial sales leader who sets a high bar for excellence, builds a highly-performing team, and executes a crisp go-to-market across acquisition and expansion. The RVP ensures effective targeting and engagement of ICPs, clear articulation of Diligent's value proposition across solutions and multi-threading across target personas. In addition, they will drive improvements in tracking and reporting capabilities, along with commercial/industry knowledge specifically for the SMB and Mid-Market segment.

Key Responsibilities

• Own the segment bookings plan across New Business and Existing Business by institutionalising operating rhythms for territory planning, multi-channel pipeline creation, deal inspection, and forecast governance; ensure predictable attainment and accountability across teams.
• Define and execute the regional sales strategy for SMB/Mid-Market in partnership with cross-functional stakeholders, including territory design, commercial plays and team enablement to achieve growth targets.
• Foster a high-performance leadership culture by coaching Directors, setting clear expectations for sales execution, and driving continuous improvement and accountability
• Role model sales excellence, lead complex negotiations to close strategic deals while setting a high bar for deal strategy, execution discipline, and team leadership.
• Establish the operating rhythm for sales outbound prospecting, multi-channel pipeline creation, deal execution, and forecast accuracy to ensure predictable pipeline and bookings attainment.
• 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.
• Own territory and market intelligence for the segment you are overseeing, tracking progress on market share capture, emerging opportunities and competitor intelligence.
• Maintain oversight of pipeline reviews, forecast accuracy, and commercial reporting to ensure transparency and accountability to targets and OKRs, and hold Directors accountable for credible roll-ups, disciplined risk/opportunity management, and gap-closure actions tied to commercial plays.
• Drive executive-caliber communications and cross-functional alignment while owning forecast accuracy and cadence, delivering precise weekly/monthly projections, risk/opportunity reviews, and gap-closure plans.

Required Experience/Skills:

• Minimum 8 years of leading successful sales teams in SaaS/Software environments and ideally experience of managing managers.
• Minimum 12 years of successful direct sales experience in SaaS/Software environments
• Proven track record of achieving sales targets, 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 SMB and Mid-Market leadership at RVP (or equivalent) level, with a track record of scaling programmatic sales motions and partner/channel routes-to-market at volume including playbook governance, enablement, and performance management.
• 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

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.