Head of Enterprise Sales

About The Role

The Head of Enterprise Sales leads a team of outbound sales representatives across the US and UK, accountable for two revenue lines: new logo acquisition into white space accounts, and revenue growth within existing accounts through new seats, new products and new buying centers. Both motions are outbound. Reps prospect into a defined target list rather than working inbound leads or waiting on renewal timing.

The manager owns a dedicated outbound pipeline with its own sourcing, stages and forecast, held separately from renewals. Account Management retains the client relationship and the renewal in existing accounts; this team owns acquisition and growth.

Your main responsibilities will include:

• Outbound Sales Executive (New Business) — white space acquisition against a named target list of 180 to 220 accounts per rep, segment focused and region based
• Outbound Client Sales Executive (Expansion) — outbound growth inside assigned existing accounts, targeting new seats, new products and new buying centres
• Both roles carry individual quotas and neither carries renewal responsibility

• Lead, coach and develop a team of outbound reps carrying individual quotas across new business and expansion
• Hire and onboard into the team, and get new reps productive against a defined ramp
• Set activity and pipeline standards and manage performance against them consistently
• Work live deals alongside reps, particularly on commercial structuring and negotiation

• Own the new logo number for the team and the plan to deliver it, tracking progress against target list coverage and pipeline coverage ratios
• Define and allocate white space territory by segment and region, to a named target list per rep
• Drive account-based prospecting built on segment, firmographic and persona fit
• Hold reps to full-cycle execution from prospecting through negotiation and close

• Coordinate coverage so outbound activity is timed around renewal cycles and client sentiment, not against them
• Keep ownership clear: the Account Manager holds the relationship and the renewal, the rep holds the opportunity
• Escalate account health risk surfaced during outbound work, flagging early so Account Management can respond before renewal is at risk

• Own the expansion number across the team's assigned accounts, and the account-level plan to reach it
• Prioritize accounts by whitespace within the relationship: unserved teams and unattached products
• Drive outbound sourcing using product usage data, seat utilization, contract structure and engagement signals
• Hold reps to multi-threading beyond the current contact set into adjacent teams and functions
• Hand landed expansion back to the Account Manager once closed, with a clean handover of context so ongoing servicing isn't disrupted

• Build and govern a standing outbound pipeline with clear stages, definitions and hygiene standards
• Forecast new business and expansion separately so each line is visible on its own
• Run weekly pipeline reviews and monthly forecast reviews across both motions
• Maintain CRM discipline in Dynamics 365 and work with Sales Ops on funnel visibility

• Work with the deal desk on pricing, structure and approval
• Partner with Marketing on campaign design and lead generation, and with Product on positioning, packaging and objection handling
• Represent US and UK outbound performance in leadership forums and quarterly planning, bringing pipeline health and forecast confidence into the wider commercial narrative

• Track record managing outbound sales teams against carried quota, ideally across both new business and expansion motions, with a clear history of hitting or exceeding number
• Demonstrable ability to build pipeline from cold rather than manage inbound flow, including territory planning and account-based prospecting
• Strong commercial instinct on pricing, structure and negotiation, comfortable stepping into live deals alongside reps
• Experience coaching reps on multi-threading into complex organizations and…