Head of Sales, B2B New Business

Chegg Inc.

. Own new business bookings and the team number.

Posted 10/30/2026full-timeRemote • United Kingdom, Spain, France, Switzerland, Germany, ItalyLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in B2B SaaS sales leadership, with a strong focus on team performance management, coaching, and pipeline generation. Proficient in using MEDDPICC and CRM systems like HubSpot and Salesforce to drive strategic sales initiatives and maintain accurate forecasts.

Highest-signal resume keywords

B2B SaaS Sales LeadershipMEDDPICC Qualification MethodologyTeam Performance ManagementCoaching and DevelopmentCRM Systems Proficiency

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Quota-Carrying Sales ExperienceForecasting DisciplineSales MethodologiesPipeline GenerationData-Driven Decision Making

Soft Skills

High Emotional IntelligenceDirect Feedback CommunicationTeam LeadershipCollaboration

Tools & Technologies

HubSpotSalesforceOutreach

Industry Keywords

EdTechHR TechLearning PlatformsTalent ManagementPeople Functions

About the role

Key responsibilities & impact

Own new business bookings and the team number.
Set targets, track run rate and intervene when performance is off track.
Lead the shift to selling Busuu as a performance partner focused on outcomes rather than licences and lessons.
Coach the team weekly through deal reviews, call reviews and pipeline inspection.
Apply MEDDPICC as a working qualification discipline.
Run weekly and quarterly team forecasts.
Drive pipeline generation and help reps build repeatable outbound plays by market and segment.
Collaborate with regional SDRs on target account strategy execution.
Support strategic opportunities, including pricing, procurement, legal and internal deal-blocking issues, while keeping ownership with the rep.
Hire, develop and performance-manage team members.
Set expectations, run individual development plans and address performance issues.
Shape market, segment and ideal-customer-profile playbooks with the Director.
Lead a remote team through strong 1:1s, team cadence and written communication.
Travel regularly to spend time with the team and customers in person.
Coordinate with Marketing, Customer Success, Strategic Account Management, Revenue Operations, Finance, Product and Leadership.
Maintain clean HubSpot data, accurate forecasts and sensible commercial terms.
Provide leadership with honest, evidence-based views of team and pipeline performance.

Requirements

What you’ll need

10+ years in quota-carrying B2B SaaS sales, with at least 2 years leading a team of new business closers.
Track record of team attainment, with performance against target in each of the last four quarters.
Proven coaching ability, including hiring or developing reps who went on to outperform.
Forecasting discipline and fluency in MEDDPICC, MEDDIC or similar qualification methodologies.
Experience with sales methodologies such as Challenger, Value Selling or similar.
Experience leading remote or multi-country teams.
Commercial credibility with senior stakeholders, including CHROs, Heads of L&D or divisional MDs.
Data-driven approach and comfort using CRM systems such as HubSpot or Salesforce, plus tools like Outreach.
High EQ and low ego; ability to give and receive direct feedback.
Excellent written and spoken English.
Ability to travel across Europe as needed.
English and at least French, Spanish or Italian at C2 level.
Nice to have: experience selling into HR, L&D, Talent or People functions.
Nice to have: proficiency in additional European languages.
Nice to have: experience building or scaling a sales presence in a new market.
Nice to have: background in EdTech, HR tech or learning platforms, ideally through a repositioning or new-category launch.

Benefits

Comp & perks

A great Private Health Insurance scheme.
Flexible working hours and remote working, to support your work-life balance.
Enhanced maternity and paternity leave.
Socials and quarterly team and company events.