🎭 Senior Enterprise Sales Executive | OnSinch | Prague | ESOP

Path to Head of Sales | Prague office-first | Direct partnership with founder

TL;DR

We're OnSinch: workforce management SaaS for events, festivals, crewing, hospitality. 200K+ users across 17 countries. 12M+ hours scheduled. 4.9/5 rating. 15+ years building one product. Clients run Formula 1, UEFA, and Europe's biggest festivals. Backed by Presto Ventures, Purple Ventures, and angels from Eskalator Capital.

We need a senior enterprise hunter who will:

• Close €4-10K MRR deals personally - with €10K+ MRR bespoke upsells stacked on top
• Build and lead the sales team from year two onwards
• Partner directly with the founder, no layers in between

🔝 Help us land the giants behind the world's biggest festivals, fairs, and productions

OnSinch is the workforce management platform for event staffing, crewing, security, hostessing, and catering. 15+ years building one product. 200,000+ people managed through our system across 17 countries. 12+ million hours scheduled. 4.9/5 rating with near-zero churn. Our clients run thousands of workers at events like Formula 1, UEFA tournaments, and Europe's biggest festivals.

We're a 15-person team based in Prague. Our co-founders started OnSinch because they ran their own staffing company - now Shameless, still the #1 stagehand provider in the Czech Republic, still running on OnSinch - and got tired of spreadsheets and chaos. That operator DNA is why we understand this industry end-to-end in a way generic workforce SaaS competitors cannot match.

ℹ️ Who's backing this

We're not a startup anymore. Bootstrapped for the first decade, then a strategic round from Presto Ventures and Purple Ventures in 2022, with angel support from Eskalator Capital. Today: 100+ paying customers, multi-year runway, no panic timeline. You're joining a company that has already proven it can survive without VC oxygen and is now choosing to scale.

❓ Why this role exists

Our founder has been running enterprise sales personally and built the business this way. He's good at it, and he's ready for a senior partner to build the next chapter with him, shoulder to shoulder. A peer who takes the sales function and runs with it.

This is a player-coach role. In year one, you personally close enterprise deals alongside the founder. From year two, you take over responsibility for the sales team: hire, coach, set the playbook, own the number. The existing small sales team becomes yours as the function grows.

🎯 Why now: from SaaS to solution provider

This is the bigger strategic shift behind the role. The pure SaaS environment is shifting, and it's time for us to bring our deep know-how and integration experience to bigger enterprises and key customers.

Our largest target customers don't want just a license. They want a partner: integrations, custom workflows, real expertise transfer, someone who actually understands their world from the inside. We can deliver that. Your deals will combine SaaS subscriptions with bespoke "subscription" packages on top, taking single accounts from €4-10K MRR base into €15-20K+ MRR territory. That's what you'll be selling.

📋 What you'll do

Year 1 - Hunt and close

• Target global staffing, crewing, hostessing, catering, security, festival production firms
• Open doors to COOs, Heads of Production, owners
• Run the full enterprise cycle: discovery → multi-stakeholder alignment → procurement → IT security audit → close
• Combine SaaS subscriptions with bespoke high-margin upsells

Year 2+ - Build and run

• Take over the sales function
• Hire, coach, set the playbook
• Own the number
• Existing team becomes yours

Always

• Work directly with the founder
• Extend and maintain our HubSpot CRM
• Use AI (Claude and others) properly - we use it to scale prospecting, personalise outreach, prep for calls

Markets to focus on

• Primary expansion focus: US and Canada - the natural next step for an English-speaking SaaS at our stage
• Strong core: UK, Czech Republic, broader Continental Europe, Middle East

We already have the foothold. We need a hunter to scale it.

🕵️‍♂️ Who we're looking for

Must-have

• 8+ years B2B SaaS enterprise sales
• Personally closed €50K+ ACV deals end-to-end (not "managed pipeline")
• Native or C1+ English
• Comfortable with 6-12 month enterprise cycles
• HubSpot fluency
• AI-assisted sales workflows in active use (or visibly hungry to learn)
• Prague-based or willing to relocate
• You finish what you start. You want responsibility, not a comfortable seat.

Nice to have

• Network in event / staffing / crewing / festival industry
• Czech language (for team integration)
• Additional European languages
• Prior experience scaling founder-led sales into a structured team

🎁 What we offer

Compensation

• Base: negotiable, seniority-dependent. Real money is in variable. If a big fixed base is what attracts you, this is not your role.
• Commission: 1.8x first-year MRRper deal
  • Example: €5K MRR deal = €9K bonus
  • Paid partially on close, balance across the deal's first year
  • Bigger deals → higher multiplier ceiling
  • Bespoke upsells stack on top
• ESOP / equity: real, meaningful, available after proven results. Partner-track role. We're deliberate about equity - earned, not granted.

Working setup

• Contract: IČO (Czech freelance), full-time commitment
• Reports directly to the founder
• Prague offices near Wenceslas Square
• Office-first. The partnership with the founder works best in the same room, regularly. Home office is available and used, but office is the default from the start. If you're looking for a fully remote role, we're not your fit.
• Multisport, laptop, phone, flexible hours, pet-friendly office
• Regular team activities, great team with a sense of humor

🧩 How we hire

We're not in a rush. We're looking for the right person, not the next person. Expect a thorough process: several conversations, a working session with the founders, references. The right candidate gets real autonomy and partnership. We want to make sure we're betting on the right person, and we want you to be sure too.

👉 Interested?

Send us:

1. The biggest enterprise deal you've personally closed end-to-end. Two paragraphs on what made it work.
2. How you actually use AI in your sales workflow today.
3. Pick one company in the global event industry and tell us in 3-4 sentences why they should pick OnSinch.