Head of Enterprise Sales (North America)

UpSlide

$160K — $200K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 2+ years managing Enterprise AEs or senior sellers in B2B SaaS
  • 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

Responsibilities

  • 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
  • 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 and deal reviews
  • Partner cross-functionally on GTM execution and refine the sales playbook

Benefits

  • International environment with offices in Paris, London, Berlin, New York, and Singapore
  • 3 days in-office per week
  • €500 WFH equipment budget
  • Training on key soft skills and management with sister company
  • Social events and international company seminars
  • $50 per month wellness package for physical and mental health
  • $130 per month commuter allowance
  • Paid parental leave for birthing/non-birthing parent and assistance for parents of young children
  • Stunning Manhattan office with stylish common areas
  • 20 days PTO plus public holidays and health days
  • Opportunity to opt into a 401k plan
  • Comprehensive healthcare plans
Full Job Description
The team

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.

Your 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


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.

You are a great fit if you have:
  • 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

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.

What we offer

International environment: Start-up 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: Collaboration with our sister company, IPH, who provides UpSliders with training on key soft skills and management

Company events: Office socials and international company events (e.g. annual company seminar, team seminar, and sustainability actions taken throughout the year)

Wellness package: $50 per month for physical and mental wellness activities

Commuter allowance: $130 per month for commuting expenses

Parental leave: Paid parental leave for the birthing/non-birthing parent and help for parents of children under seven

Beautiful office: A stunning Manhattan office with stylish common areas and meeting rooms

Holidays: PTO (20 days plus public holidays and health days)

Retirement plan: Opportunity to opt into a 401k plan

Healthcare: Comprehensive healthcare plans

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