Careers with
Drop Table

About Drop Table

Drop Table is a Cloud and DevSecOps consultancy focused on the Microsoft ecosystem. We help organisations design, secure, and operate modern cloud platforms, with deep expertise across Azure, DevSecOps, AI, Power Platform, application modernisation, and platform engineering.

Alongside our consultancy, we have built Drop Table Pulse, a SaaS platform providing continuous security, compliance, and governance visibility across Azure DevOps environments.

Our clients operate in complex, regulated environments across financial services, public sector, and enterprise. We position security as an enabler and deliver practical, engineering-led outcomes.

The Role

This is a commercial leadership role. We are looking for a Head of Sales to build and own a scalable, repeatable revenue engine across both consultancy services and SaaS (Drop Table Pulse).

This is not a manage-an-existing-team role. This is a build, shape, and lead position with full ownership of go-to-market strategy, pipeline generation, enterprise sales, and partner growth.

You will operate as part of the leadership team, directly influencing company strategy, positioning, and growth trajectory.

What You Will Be Responsible For

Sales Strategy and Revenue Ownership

• Define and execute the overall sales strategy across services and SaaS
• Build a structured, repeatable sales motion from early-stage pipeline through to enterprise close
• Own revenue targets, pipeline coverage, and forecasting discipline
• Improve win rates, deal velocity, and average deal size

Enterprise Sales Execution

• Personally lead high-value, complex enterprise sales cycles
• Engage C-level stakeholders (CTO, CIO, CISO, Head of Platform or DevOps)
• Navigate procurement, frameworks, and regulated buying environments
• Position Drop Table as a premium, engineering-led partner

Go-To-Market and Pipeline Generation

• Define target markets, ICPs, and vertical strategy (financial services, public sector, enterprise)
• Establish outbound, inbound, and partner-led pipeline engines
• Refine value propositions across Azure security, DevSecOps, and governance
• Work closely with leadership on messaging and positioning

Microsoft Ecosystem and Partnerships

• Build and leverage relationships across the Microsoft ecosystem
• Develop partner-led pipeline via CSPs, SIs, and resellers
• Align with Microsoft solution areas (Security, Azure, Identity, Data and AI)
• Identify co-sell opportunities and drive joint go-to-market activity

Building the Function

• Design and build the future sales team (AE, SDR, partnerships)
• Define sales processes, tooling, and operating cadence
• Implement CRM discipline and reporting standards
• Create a culture of accountability, ownership, and performance

What Success Looks Like (First 12 Months)

• Establish a repeatable, scalable sales process across consultancy and SaaS
• Build consistent pipeline coverage aligned to revenue targets
• Close high-value enterprise deals in regulated environments
• Develop a partner-led pipeline engine within the Microsoft ecosystem
• Clearly define and execute GTM strategy for Drop Table Pulse
• Improve conversion rates, deal velocity, and average deal size
• Lay the foundations for a scalable sales team and structure

What We Are Looking For

Experience

• Proven experience as a Head of Sales or Sales Director in a cloud, security, or DevOps consultancy
• Track record of building and scaling a sales function from early stage
• Experience closing complex enterprise deals (GBP 100k to GBP 500k+)
• Background in both services-led and SaaS-led sales models preferred
• Experience selling into regulated industries (financial services, public sector)

Microsoft and Cloud Expertise

• Strong understanding of the Microsoft ecosystem (Azure, Entra ID, Defender, DevOps, Fabric)
• Existing relationships within the Microsoft partner ecosystem are highly valuable
• Able to credibly position technical solutions to both business and engineering stakeholders

Commercial Capability

• Strong enterprise sales execution capability (multi-stakeholder, long-cycle deals)
• Experience building pipeline from zero and scaling revenue
• Commercially sharp with strong negotiation and deal structuring skills

Leadership and Mindset

• Builder mentality, comfortable creating structure from ambiguity
• High ownership and accountability
• Direct, disciplined, and outcome-focused
• Able to operate credibly with both executives and engineers

Why Join Drop Table

• Opportunity to own and shape the entire commercial function
• Work directly with leadership and influence company direction
• Blend of consultancy and SaaS with strong market relevance
• Access to complex, high-value enterprise environments
• Genuine opportunity to build something from the ground up

Package

• Competitive base salary plus uncapped commission (OTE aligned to senior leadership)
• Equity or long-term incentive structure
• Flexible remote working
• UK travel as required