Head of Global Mid-Market Sales, UpSlide

• 2+ years managing junior-to-mid Account Executives, with 5+ years of total sales experience
• Proven experience managing a sales team with direct, personal accountability for results
• A track record of building or simplifying a sales process to drive speed and consistency
• Experience coaching a mixed-seniority team hands-on — shadowing calls, reviewing deals, leading by example
• Full professional fluency in English (mandatory) and comfortable with modern sales tooling (Salesforce, Gong, Power BI or equivalents)
• A direct, proactive, low-ceremony communication style — comfortable with autonomy and fast iteration
• ✨ 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. As UpSlide's go-to-market approach evolves, we're introducing a dedicated Mid-Market motion, distinct from Enterprise, each with its own team and process
• You will lead the Global Mid-Market Sales team, reporting directly to Alexandra Chiaramonti (CCO). It's a truly global scope: the team spans the UK, France, and the US - 10 to 15 Account Executives in total, a mix of experienced closers who chose to specialize in this segment, and more junior profiles recently promoted from BDR/SDR roles who are stepping into closing responsibility for the first time
• Team Goals: Build a fast, simple, scalable sales motion for this segment, with a shorter sales cycle, while freeing up the Enterprise team to focus where they matter most
• Team leadership & coaching (~40%):
• Own the team's aggregated ARR target across the UK, France, and US
• Get to know the team quickly and identify where improvement is needed
• Coach reps by leading through example: shadow calls, review calls, give direct, live feedback
• Run the team's rhythm: pipeline reviews, team meetings, 1:1 coaching, and hands-on sales challenges (e.g. cold-calling pushes)
• Process design & scale (~35%):
• Full mandate to rebuild the Mid-Market sales playbook, making it faster and easier for the team to navigate
• Design a simplified, repeatable process that significantly reduces the sales cycle
• Partner closely with RevOps on data, account segmentation, and territory definition
• Partner closely with Marketing on lead generation and pipeline
• Strategic partnership with leadership (~25%):
• Reporting directly to Alexandra, you will operate with full autonomy and move fast
• Bring an external benchmark: UpSlide is looking for outside perspective on what "good" looks like in Mid-Market sales
• Represent the Mid-Market segment in cross-functional planning
• Your goals ⚡
• 3 months: Team structure finalised. First routines and cadences running
• 6 months: Team hitting its revenue targets
• 9 months: Mid-Market segment scaling beyond its initial setup
• Beyond these milestones, this is a ground-floor opportunity: you'll be building a brand-new team and function from scratch, with a direct line to the C-level and real latitude to shape how UpSlide sells to this segment going forward

• 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 Alexandra Chiaramonti (CCO), ideally face-to-face - dive into your sales leadership experience and how you'd approach the role
• Task & case study with a panel including Alexandra and other members of our Executive team - a hands-on exercise on a real Mid-Market 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