Head of Enterprise Sales, UpSlide

• 2+ years managing Enterprise AEs or senior sellers in B2B SaaS
• A strong personal track record selling large, complex enterprise deals
• Experience leading MEDDPICC-driven sales teams
• Rigorous pipeline management and forecasting discipline, with strong CRM hygiene
• Comfort with long sales cycles and multi-stakeholder, multi-threaded environments
• If you don’t tick all the boxes but you think you’d be a great fit, please apply and tell us why

Desirable

• This is a brand-new role, part of a broader simplification of UpSlide's go-to-market organization, with dedicated Enterprise Sales leadership now established across North America, EMEA & APAC, and a Global layer for Mid-Market and Professional Services
• You will lead the Enterprise Sales team across North America, reporting directly to Alexandra Chiaramonti (CCO), and Account Executives, experienced sellers handling large, complex, multi-stakeholder deals
• Own and scale UpSlide's Enterprise motion: large, complex deals with long sales cycles and multiple stakeholders, run with rigorous MEDDPICC discipline and reliable forecasting
• Team leadership & coaching (~40%)
• Lead Enterprise AEs across North America, driving new business targets using MEDDPICC
• Coach the team on large, complex enterprise cycles: deal strategy, multi-threading, executive engagement
• Set expectations on roles, territories, and performance bar
• Pipeline & forecast discipline (~40%)
• Run pipeline and forecast discipline across the team
• Maintain strong CRM hygiene as the standard for the team
• Map key accounts and whitespace; define cadences for pipeline reviews, deal reviews, and forecasting
• Cross-functional GTM execution (~20%)
• Partner cross-functionally on GTM execution
• Refine the sales playbook together with peers and RevOps: stages, MEDDPICC standards, handoffs
• Your goals
• 3 months: Team built and shaped. Accounts and whitespace mapped. Cadences and playbook in place. Coaching underway on live deals
• 6 months: Consistent, disciplined forecasting and CRM hygiene embedded across the team. Playbook adopted and driving more predictable cycles
• 9-12 months: Team collectively reaching 80% average attainment in Q4
• Beyond these milestones, this is a ground-floor opportunity: you'll be shaping how UpSlide's Enterprise motion runs across North America, with a direct line to the C-level

• Initial screening with Yann Mokoko (Talent Acquisition) — get to know your background and motivations, present UpSlide and its challenges, and answer your questions
• Interview with the hiring manager, ideally face-to-face — dive into your sales leadership experience and how you'd approach the role
• Task & case study with a panel including the hiring manager and other members of our Executive team — a hands-on exercise on a real Enterprise sales challenge
• Final conversation with a member of our Executive team — culture fit and final validation
• We'll conduct a reference check to learn how to help you thrive!
• On average, our process lasts 3 weeks