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 Linked In, 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.

• 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.

• 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 Hub Spot)

• 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

• Own pipeline management and deal hygiene in Hub Spot
• 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

• 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 Linked In: Founder-led content is our top awareness channel. You'll inform what they produce based on what you're hearing in sales conversations.

We've consolidated our offerings into three Core Solutions that match how prospects describe their problems.

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.

The core revenue engine. Ideate (discovery and design) flows into Ignite (build), and into ongoing Maintenance retainers. All build work runs on our…