Head of Enterprise Sales (North America)

About the role

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.

Team goals

• 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.

Responsibilities

• 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.

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.

Requirements

• 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

Qualifications

• We'd love it if you've operated in a fast-growth B2B SaaS environment

If you don't tick all the boxes but you think you'd be a great fit, please apply and tell us why.

Recruitment process

• 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.

Benefits

• International environment with five offices (Paris, London, Berlin, New York, Singapore) and users in more than 60 countries
• Hybrid work: 3 days in-office per week
• Work-from-home budget: €500 WFH equipment budget
• Training & professional development through collaboration with our sister company, IPH, providing training on key soft skills and management
• Company events: Office socials and international company events (annual company seminar, team seminar, and sustainability actions throughout the year)
• Wellness package: $50 per month for physical and mental wellness activities
• Commuter allowance: $130 per month for commuting expenses
• Paid parental leave for the birthing/non-birthing parent and help for parents of children under seven
• Beautiful Manhattan office with stylish common areas and meeting rooms
• PTO: 20 days plus public holidays and health days
• Retirement plan: Opportunity to opt into a 401k plan
• Comprehensive healthcare plans

About UpSlide

• On top of exciting business challenges in a fast-growing market, you will find a friendly, caring, and challenging culture
• You will be met with opportunities to acquire new skills, learn from others in a multicultural environment, and grow as a person
• UpSlide employees have committed to making a positive impact on the world. We obtained B Corp certification in 2022 with strong commitments toward our employees, community, clients, suppliers, and the environment. UpSlide is now 30% owned by employees
• UpSlide was ranked #1 best place to work in 2019 and #1 best place to work in 2020 in the category "best company for remote work"
• As a B Corp-certified company, we have strong commitments toward our employees, community, clients, suppliers, and the environment. We strive to create an environment where everyone feels welcome. This commitment to diversity and inclusion is applied in our recruitment process and your employee experience once you've joined UpSlide