Head of Sales

We're a profitable, 10-year old custom software agency that just hit an inflection point. AI is reshaping our industry and we're positioned at the front of it. We have a documented sales playbook, a content engine already generating inbound leads, and two founders actively creating demand through LinkedIn, a podcast, and an AI workshop series. What we don't have is a dedicated sales leader. You'd be the first. Your job is to turn all of that into aggressive revenue growth. This is a remote, salaried position with performance bonuses and a strong benefits package. You'll report directly to a co-founder, with a clear path to owning the full revenue function as the company scales. Why This Role You're building the function, not inheriting a bureaucracy. No legacy team to manage around. No politics. You get to design how sales works here, with founder-level access and a co-founder/CTO as your technical partner on complex deals. The playbook exists. The pipeline exists. The brand exists. You're not starting from zero. You're taking a working system and making it perform at a higher level. AI is the tailwind. The market for AI implementation services is exploding. Most agencies are scrambling to figure it out. We've already built the methodology, the team, and the positioning. You're selling into demand that's accelerating, not decelerating. The path is real. Prove you can own revenue and you'll own the full Sales and Marketing function as the company scales. This is a leadership team trajectory at a company small enough that your impact is visible from day one. What You'll Own New Business Build and execute an inbound/outbound sales strategy that hits revenue targets Qualify inbound leads and convert them into the right engagement (we have seven service offerings; you'll need to diagnose which one fits each prospect) Generate outbound pipeline through prospecting, networking, and relationship development Develop PE fund relationships where one relationship can unlock multiple portfolio company engagements Present proposals and close deals ranging from discovery engagements to $1M+ builds Leverage the podcast and workshop series as pipeline tools (guests are ICP executives tracked in HubSpot) Client Growth Use our wedge deals and land-and-expand services to convert initial engagements to larger projects. Drive project extensions, renewals, and upsells across all service lines Build referral generation into every client relationship Sales Operations Own pipeline management and deal hygiene in HubSpot Formalize the processes that don't exist yet: referral programs, testimonial collection, lost deal recovery, client lifecycle management Optimize conversion rates at every stage and bring data back to the team Collaborate with the co-founder and fractional CMO on positioning and competitive strategy The Team Around You Sales Architect (co-founder/CTO): Joins qualified calls for technical scoping and solution architecture. Your partner on complex deals. Fractional CMO: Owns brand positioning, content strategy, podcast production, and newsletter. Shapes the narrative that feeds your pipeline. PPC Agency: Manages Google Ads and builds landing pages. Drives paid inbound. Two founders on LinkedIn: Founder-led content is our top awareness channel. You'll inform what they produce based on what you're hearing in sales conversations. What You're Selling We've consolidated our offerings into three Core Solutions that match how prospects describe their problems. AI Strategy & Fluency For non-technical leadership under board pressure to adopt AI without a clear roadmap. Gnar Compass is our flagship advisory engagement, delivering a board-grade strategy doc, a five-dimension opportunity roadmap, and a fully-scoped first build ready to enter development. Compass leads directly into Custom Software Development for the actual build. Immerse is our internal AI fluency training program for client teams. Workshops and the AI Assessment lead magnet anchor the top of funnel. Custom Software Development The core revenue engine. Ideate (discovery and design) flows into Ignite (build), and into ongoing Maintenance retainers. All build work runs on our proprietary Context-Driven Development methodology, backed by the Triple Guarantee. Gnar Forge is the rapid-build variant for large enterprises and PE portfolio companies, designed as a wedge that lands a relationship and expands into adjacent departments and workflows. Legacy Software Modernization For clients running brittle, expensive-to-maintain systems they can't replace overnight. Replatforming, AI-augmented overlays, and integrations that move them off the cliff without ripping everything out. Frequently sold alongside AI Strategy & Fluency when the team also needs upskilling. The Triple Guarantee This is our most powerful differentiator and should be the centerpiece of every sales conversation: Price guarantee: What we quote is what you pay Outcome guarantee: The software works as specified 12-month bug-free warranty: We fix any non-conforming code for a full year after delivery You Are... A strategic thinker who can build a sales plan and execute it personally A consultative, solution-seller with a background in professional services, consulting, or custom software development Someone who builds trust quickly and maintains long-lasting client relationships Motivated by stretch goals. You want to hit quota, not just get close. A diagnostic seller. You figure out which engagement model fits each prospect rather than pushing the biggest deal. Knowledgeable about modern software development and genuinely excited about AI's impact on how companies build products An outstanding communicator who translates technical concepts into business value Resourceful. You don't wait to be told what to do. You Embody Our Core Values (G.N.A.R.) Get to Done: You focus on customer outcomes and execute intentionally. Nurturing: Trust is the foundation of every client relationship. You lead with empathy. Adaptable: Growth mindset. Our industry is evolving fast with AI and you're energized by that. Resourceful: Solution-oriented, self-sufficient, and self-aware. You own your pipeline. You Have... 8+ years of solution sales experience in professional services, consulting, or custom software development A proven track record building pipeline and closing deals in the $100K-$2M range Experience developing and executing a strategic sales plan, not just working one handed to you Comfort selling into C-suite buyers (CEOs, CTOs, CPOs) at mid-market companies Experience selling AI services, technology consulting, or digital transformation engagements Familiarity with HubSpot and a disciplined approach to pipeline management Experience operating within a structured meeting rhythm (we run EOS with weekly L10s, scorecards, and quarterly planning) U.S. citizenship or permanent residency (we are unable to sponsor visas) How You'll Be Measured Weekly scorecard (part of our EOS operating system): New deals created Average closed-won deal amount Close rate Proposals sent Stale deals in pipeline Compensation Compensation includes performance-based incentives aligned with revenue growth. Base Salary: $150,000 On-Target Earnings (OTE): $300,000 - $400,000 (uncapped with accelerated rates above quota) Annual Revenue Quota: $3M Typical Deal Size: $15K - $2M Year 1 targets are prorated for ramp. Year 2 OTE reflects full quota attainment. Uncapped commissions with accelerated rates above quota. Benefits Fully remote work schedule Mandatory vacation policy. We mean it! Generous paid maternity/paternity leave Fully paid phone plan for business and personal use 401K contribution (whether you contribute or not) About The Gnar Company We transform ideas into impact with modern, reliable, and scalable software. Team: 100% U.S.-based team of senior-level engineers, product managers, and leaders. Track record: 100+ projects, $50M+ in product development, 10+ years in business Shift: Core business moving toward AI implementation and agentic development This is a company where your work has a direct, visible impact on growth. No layers. No red tape. Just results. #J-18808-Ljbffr The Gnar Company