Sales Leader

Grand Avenue Software Inc.; United States; Remote; USD 150,000 - 210,000; Full time

Benefits offered by this job

Health insurance

Dental & vision coverage

401(k) with employer match

Additional insurance options

10 holidays + 3 weeks PTO

Job summary

Grand Avenue Software is seeking a Head of Sales to lead a small, capable team and professionalize the function. You will optimize structure, methodology, and discipline to ramp reps and consistently hit quota while staying close to deals.

This hands-on, player-coach role reports to the CEO and owns Sales and Sales Development. You will shape GTM strategy, align with marketing, product, and implementations, and own the number.

Qualifications

• Proven, process-driven sales manager with 3+ years owning bookings.
• Hands-on leader with direct deal involvement and coaching.
• Experience in high-growth B2B SaaS with outbound and RevOps familiarity.

Responsibilities

• Professionalize the team with ramp plans and coaching cadence.
• Own bookings attainment and manage reps' performance.
• Lead live deals and guide junior reps by example.
• Install pipeline, forecast rigor, and CRM discipline.
• Collaborate with marketing, product, implementations, and partners.
• Shape growth strategy and GTM motions.

Skills

Player-coach

B2B SaaS sales

Deal involvement

Outbound sales

RevOps/data-driven

Leadership

Analytical/process-oriented

Growth-stage experience

Tools

CRM (Salesforce)

Sales analytics tools

Job description

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.
• 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 RevOps-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.
• 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.