Director of Sales (Player-Coach)

Job Description

About Valsoft

Valsoft builds and scales vertical market software companies. We partner with strong teams, invest for the long term, and run disciplined operating systems to drive sustainable growth across our portfolio.

About Aspire Software

Aspire Software, an operating group of Valsoft Corporation, acquires, builds, and grows vertical market software companies around the world. Each brand operates with entrepreneurial autonomy while benefiting from shared expertise, leadership, and collaboration across our global portfolio.

About Rentworks+

Rentworks+ is the next-generation platform being built on the proven foundation of one of Valsoft’s established US-based car rental software businesses. We serve rental operators who rely on software every day to run their operations - where uptime, reliability, and workflow depth matter.

We are investing in a modern platform designed to scale, alongside a growing suite of AI-powered products that expand the overall value we deliver to customers. This is a unique opportunity to join at a moment where the product roadmap, go-to-market motion, and revenue engine are being built for the next phase of growth.

The Opportunity

We’re hiring a Director of Sales (Player-Coach) to build and lead our North America revenue engine. This is a hands-on role for a proven seller who can personally close business, build repeatable outbound motions, and install a strong operating cadence across pipeline, forecasting, and performance.

You’ll sell two core pillars:

• Rentworks+, our new platform
• A suite of new AI-powered solutions (sold alongside the platform and as add-ons)

You’ll work directly with portfolio leadership and cross-functional stakeholders (Product, Customer Success, and Operations). You’ll also have the opportunity to build and grow BDR support to scale pipeline generation as the business expands. This role is designed for someone who thrives in a builder environment and wants real ownership.

What You’ll Do

Drive new business growth

• Own the full sales cycle: prospecting → discovery → demos → proposals → negotiation → close.
• Build and maintain a target account strategy by segment and customer cohort.
• Develop and iterate on talk tracks, competitive positioning, and objection handling.
• Share customer insights and inputs with internal stakeholders to develop a clear commercial plan to bring the platform and AI products to market

Build a repeatable outbound motion

• Lead outbound strategy and execution; coach BDRs to consistently generate a qualified pipeline.
• Create repeatable playbooks (segments, sequences, cadences, qualification, demo structure).
• Establish pipeline creation targets and inspection routines that translate activity into predictable results.

Implement the GTM operating system (RevOps discipline)

• Run weekly operating rhythms: pipeline inspection, deal reviews, and forecast calls.
• Define sales stages and exit criteria; maintain a clean CRM and reporting that leadership can trust.
• Track and improve conversion metrics (lead → meeting → SQL → win), cycle times, and win/loss learnings.
• Provide actionable inputs on pricing/packaging and commercialization over time.

Align cross-functionally to win

• Establish tight handoffs with Customer Success to ensure a consistent customer experience and closed-loop feedback.
• Share structured market feedback with Product (buyer needs, blockers, competitive themes).
• Coordinate internal resources to move deals forward and support successful launches.

What Success Looks Like

In the first 90 days

• Clear ICP/segmentation and outbound motion is live and producing qualified opportunities.
• CRM stages and reporting are reliable; forecasting is measurable and improving.

In 6–12 months

• A predictable GTM engine is running (pipeline generation → close) for the new platform.
• AI-powered solutions contribute meaningful incremental ARR via a repeatable attach motion.
• Coaching cadence, playbooks, and measurable improvements are in place across the funnel.
• You’ve hired and onboarded initial BDR support, set clear productivity/quality standards, and implemented pipeline hygiene that enables reliable forecasting.

What We’re Looking For

Required

• 5+ years of B2B SaaS sales experience with a strong record of closing new business.
• Demonstrated ability to generate a pipeline through outbound (not reliant on inbound-only environments).
• Experience building or materially improving a sales motion (process, messaging, cadence, forecasting).
• Strong deal leadership: disciplined qualification, multi-stakeholder selling, and negotiation.
• Player-coach mindset: you can lead and coach, while personally carrying and delivering on a quota.

Preferred

• Experience selling into car rental, fleet management, mobility, automotive, or transportation industries is a strong plus
• Experience in vertical market software and/or operationally complex environments.
• Experience selling multi-product suites, add-ons, or platform + modules.
• Strong familiarity with modern sales tooling and RevOps best practices (CRM, sequencing, analytics, forecasting)

Why Join

• Competitive base salary with uncapped commission and high OTE potential
• Build the GTM engine for a next-generation platform at the start of its growth curve.
• High ownership and direct partnership with a collaborative, driven and entrepreneurial management team
• Opportunity to shape commercialization and product strategy for both the platform and a suite of new AI products.

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