About Aspire Software
Aspire Software is an operating group of Valsoft Corporation, which is based in Montreal. Aspire buys and builds vertical market software businesses that their customers can’t run without. We invest for the long term and keep a decentralized model, so each business keeps its own team, brand and entrepreneurial pace. Each one also gets the capital, shared best practices and expertise of a global software group.
About Jazzware
Jazzware connects the systems that run a hotel. For 25+ years, premier hotel brands around the world have relied on our integrations and analytics to link phones, property management systems, voicemail and guest services.
We're now building a new generation of AI products for hotels, such as an AI auto-attendant and staff-safety alert routing. Jazzware is part of Valsoft's Aspire Software group, so you get the backing of a large software group with the speed of a focused team.
You'll own Jazzware's new-business number and build the engine behind it. This is a player-coach role: you'll close deals yourself while you write the playbook others will run. You'll build the sales motion, prove it works, and then hire the people to scale it. As the business grows, the team and the role grow with it.
What you'll do
• Own the number. Deliver net-new bookings across our AI and core products, plus revenue from partners.
• Sell, end to end. Run full-cycle deals with hotel groups, management companies and brands, from first call to signed contract.
• Lead the AI push. Take our new AI products to market, and shape packaging and pricing with the product team.
• Grow partnerships. Build channels with PBX and cloud phone vendors, carriers, managed service providers and PMS partners.
• Write the playbook. Define our ideal customer, messaging, discovery, demo, proposal and pricing guardrails so new reps can run them.
• Run the GTM machine. Set pipeline targets, keep the CRM clean, forecast accurately and report weekly to the Managing Director.
• Build the team. Hire, onboard and coach BDRs, AEs and partner managers as we grow.
• Work across the business. Partner with product, customer success and marketing so we win the right customers and keep them.
What success looks like
First 90 days
• You know our products, top customers and partners, and you've taken over the open pipeline.
• You've closed your first deals.
• Version 1 of the sales playbook and a go-to-market plan for our AI products are written and in use.
• Weekly pipeline reporting and a forecast cadence are running.
First 12 months
• You've hit your bookings targets across AI and core products.
• A new rep could ramp from your playbook without you in the room.
• Partners bring in a steady, measurable share of pipeline.
• Your first hires are on board and ramping.
Qualifications:
What we're looking for
• 4–8 years in B2B software or technology sales, with a record of beating quota.
• You've built sales process from scratch, such as a playbook, a new segment or a new product launch, not just followed one.
• Full-cycle closing experience with both technical buyers (IT, telecom) and commercial buyers (owners, GMs, brand teams).
• Some experience leading others, whether formally or by mentoring reps, and a real appetite to build a team.
• Disciplined in the CRM (HubSpot or Salesforce) and in forecasting.
• Hungry, self-directed and at ease with ambiguity. You'd rather build the road than wait for one.
• Clear, confident writing and speaking, from cold outreach to boardroom proposals.
Bonus points
• Hospitality technology experience: PMS, hotel phone systems (PBX or cloud), or guest-facing tech.
• You've sold AI products or opened a new category where buyers needed educating.
• You've built channel partnerships with telecom vendors, carriers or managed service providers.
• You've hired and ramped your first reps.
• You've worked inside a software group or a fast-growing startup.
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