Head of Enterprise Sales; North America) Job New York New York USA,Sales

UpSlide is the number one productivity solution provider for financial services. Our software dramatically improves the functionality of PowerPoint, Word, Excel, and Power BI and enables users at firms like Deloitte, KPMG, and BNP Paribas to focus on high-value tasks rather than formatting or copy-pasting. We’re scaling up with 180+ employees across our offices in New York, London, Paris (HQ), Singapore, and Berlin.

Our values

Our values guide our approach to work and are at the heart of our recruitment process. To join our team, we look for individuals who value:

Excellence: We think that every detail counts, and we place great importance on the quality of our deliverables.
Trust: We are passionate, committed, and free to act with autonomy.
Happiness at work: We enjoy looking on the bright side and we share our enthusiasm with our colleagues and clients.

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 Rev Ops: 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

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…