Sales Leader

This is a remote position.

About the Role

Grand Avenue Software is a SaaS-based electronic Quality Management System (eQMS) provider on a fast growth trajectory. We help our customers manage quality and compliance through modern, intuitive software — and we're building the sales organization to match the opportunity ahead. We're looking for a Head of Sales to lead and professionalize our sales function.

You'll take a small, capable team and optimize the structure, methodology, and discipline needed to get every seller ramped and consistently hitting goal — while staying close enough to the work to drive individual deals directly. This is a hands-on, player-coach leadership role reporting to the CEO, owning both Sales and Sales Development.

It's a rare opportunity for a rising sales leader looking for their shot to run a real team: someone who wants to build methodology and process from the ground up, but who leads from the front and gets in the weeds on live deals rather than managing from a dashboard. You'll inherit a strong product and real market momentum, and you'll be expected to add structure, rigor, and urgency — and to own the number.

Key Responsibilities

Professionalize the Team and Maximize Rep Output

• Assess the current team, sales processes, and the marketing-to-sales handoff, then install a consistent sales methodology, ramp plan, and coaching cadence so every rep is measurably progressing against ramp and quota.
• Own team bookings attainment — developing strong performers and making the hard calls to manage out and backfill when needed.
• Build a culture of constant learning that steadily raises effectiveness, conversion rates, forecast accuracy, and quota attainment. Get in the Weeds on Deals
• Join live calls, strategize on stuck deals, and personally engage on high-value and at-risk opportunities.
• Model the way, so more junior reps learn quickly by seeing best practices applied through your leadership and coaching. Install Pipeline and Forecasting Rigor
• Stand up a reliable pipeline review and forecasting cadence, hold reps to their commits, and deliver a leader-level forecast that blends rep commits with a projection of go-get deals to originate and close in period.
• Define stage definitions, qualification criteria, and handoffs across the funnel, and drive the CRM discipline that makes reporting trustworthy. Drive Sales-Led Lead Generation
• Reinvigorate the AE and BDR outbound motions to consistently source qualified pipeline, and partner closely with marketing on ICP, target segments, and lead-quality feedback. Optimize the Expansion Motion
• Refine the playbook for identifying, prioritizing, and converting expansion and add-on opportunities across the installed base, and own expansion targets alongside new-logo bookings. Be a Collaborative GTM Partner
• Work in close partnership with marketing, product, implementation, and partner teams to refine and maintain a predictable go-to-market engine from top-of-funnel through successful transition of closed customers to implementation.
• Bring the voice of the customer and frontline market insights back into the business. Help Shape Growth and GTM Strategy
• Act as an active thought partner to the leadership team on growth strategy and the go-to-market motions that support it, and help build new sales motions over time as the strategy evolves.

Requirements

Required

• A proven, process-driven sales manager with 3+ years directly owning bookings goals and building, coaching, and managing teams of quota-carrying reps.
• A track record of getting directly involved in deals — a true player-coach, not a dashboard manager.
• The ambition and hunger to make a small team great, and the readiness to run a real team.
• Strong B2B SaaS sales experience, including familiarity with the deal sizes and sales cycles typical of a growth-stage company.
• A highly analytical, process-oriented approach — comfortable with data, reporting, and Rev. Ops-adjacent work, while remaining a sales management expert first.
• Good experience driving outbound and sales-led lead generation, and a genuine willingness to partner closely with marketing.
• Experience with higher-velocity, lower-ASP sales motions — balancing consultative selling with transaction volume and turnover. Preferred
• Strong experience with expansion and add-on sales motions, with ownership over cross-sell and upsell targets (a significant plus).
• Direct experience managing BDR teams that reported to you.
• Experience selling into life sciences or quality/regulated markets, or with eQMS or adjacent products.

Benefits

• Health: Employer-offered program through a national carrier with multiple plans; a fully employer-paid option plus employer HSA contribution covering your whole family, with richer plans partially subsidized.
• Dental & vision: Fully employer-paid, covering your whole family.
• 401(k): With a 4% employer match.
• Additional insurance options: Available, employee-funded.
• Time off: 10 company holidays + 3 weeks of PTO.